The LeanScale Podcast · Episode 88

Why AI Won't Close Your Biggest Deals

Michael Kiernan on 'Human + Agentic GTM' — where AI belongs in the revenue motion, and where it doesn't

Michael Kiernan · Chief Revenue Officer, Nextdoor · Nextdoor Hosted by Anthony Enrico
Published Updated 00:45:33 39 min read 7,813 words
Executive Summary

The one-paragraph brief, extended

Why this conversation matters — and who should spend the hour.

The market is racing to 'bodify' the sales team — swap sellers for agents and call it the future of go-to-market. Michael Kiernan, Chief Revenue Officer at Nextdoor, named his entire nine-month transformation plan as a deliberate rejection of that idea: Human + Agentic GTM. The plus is the point. Nextdoor is a relationship-based platform connecting more than 110 million verified neighbors across 350,000 neighborhoods — about one in three U.S. homes — and Kiernan's argument is that removing the human from a business built on human connection isn't just distasteful, it's strategically wrong. In this conversation with LeanScale co-founder Anthony Enrico, he lays out a sober, operator-grade framework for exactly where agentic AI belongs in a revenue motion, and where it will quietly cost you the deals that matter most.

Kiernan is an unusual CRO: he openly calls himself an operator first and a sales leader second. He came up through public accounting (where he learned to grind and account for every minute), then ad tech and bizops — campaign management and sales engineering at BrightRoll, operational-turnaround work at Turn — before joining Nextdoor in 2018 and being elevated to CRO. That lineage is the spine of the episode's back half: a practical playbook for the RevOps-to-CRO path built on 'seeing the whole elephant,' feeling the pressure of a number, and staying close to the customer even when it isn't your job.

The intellectual core is a decision framework for AI-in-the-motion. Kiernan describes an inverse relationship between deal size and how much AI belongs in the customer-facing process: in enterprise, agents do research, meeting prep, proposal drafts, and RFP responses — they make the rep sharper, never redundant; in mid-market the motion is AI-enabled but human-last; only in SMB does the agent own outreach, routing, and renewal prompts with a human hitting approve. How much AI is a function of ACV and which product surface the customer is touching — and crucially, new products need more human-in-the-loop, not less, because the fastest way to learn from a new product is to talk to customers, not survey them.

On the org side, Kiernan narrates the centralize-vs-decentralize pendulum: Nextdoor's cross-functional 'Neighbor' AI group started centralized, swung to a decentralized 'let every team run' phase (which produced a surprise $20,000-in-a-month AI bill), and is now settling in the middle with cost-and-tool guardrails while preserving team-level curiosity. Whether you can decentralize at all, he argues, comes down to the strength of your data foundation — a healthy Salesforce-plus-Databricks stack is what let a self-described non-data-scientist 'be my own data scientist.' And the discipline that keeps it honest: measure agentic GTM in the P&L and funnel efficiency — speed to market, meeting volume, conversion rates, revenue per head, ARPU — not the API bill.

The episode closes on time management and monetization: the four-priority, color-coded calendar (a quarter each to core revenue, new monetization, agentic transformation, and team) that a public-company CRO runs his weeks on, and Nextdoor's next act beyond advertising — local services (the neighbor who needs a plumber), peer-to-peer commerce (the neighbor selling a hundred dozen cookies), and the neighborhood data graph as a monetization moat. Who should listen: CROs and revenue executives designing an AI transformation without gutting their teams, RevOps leaders eyeing the C-suite, sales leaders deciding where agents fit by segment, and founders trying to separate real AI leverage from LinkedIn theater. The biggest takeaway is a disciplined mental model: AI should make your humans sharper and your P&L leaner — but it will not carry the relationship, the accountability, or the trust that actually closes your biggest deals.

Key Takeaways

13 things worth stealing

The load-bearing ideas, each with the business implication and who should care.

01

'Human + Agentic GTM' is a deliberate rejection of botifying the sales team

Kiernan named the plan with the 'plus' on purpose. On a relationship-based platform, moving fast to remove humans 'just doesn't feel right,' and positioning a transformation as 'we're going to automate the org' is the wrong way to bring a team through change. The goal is augmentation, not replacement.

Why it matters: Frame your AI transformation as making humans superhuman, not as a headcount story. How you name and position the initiative determines whether the team drives it or resists it.

Revenue ExecutivesSales LeadersFounders
02

You can't put accountability on an agent — especially on a big deal

The episode's thesis: some parts of the sales process can be identified and automated, but others must be done by humans. Buyers want to know a person is on the hook for the deal. Trust and accountability don't transfer to an agent, and that's most acute at the top of the market.

Why it matters: Keep humans owning the relationship and the commitment on high-consideration, high-ACV deals. Use agents to prepare and sharpen the rep, not to be the counterparty the buyer is trusting.

Sales LeadersRevenue ExecutivesFounders
03

There's an inverse relationship between deal size and how much AI you put in the customer-facing motion

As you move upmarket, less AI belongs in the customer interaction. Enterprise: agents power prep, research, proposals, RFPs — the rep still owns the room. Mid-market: AI-enabled but human-last, the rep gets the final word. SMB: the agent can own outreach, routing, and renewal prompts while a human reviews and hits approve.

Why it matters: Don't apply a single AI policy across segments. Map agent autonomy to segment: high human ownership up-market, high automation down the tail, with a human still in the loop.

Sales LeadersRevenue ExecutivesRevOps Leaders
04

How much AI is a function of ACV and product surface

Kiernan's mental model for dialing AI into a motion combines account value (ACV) with which product surface the customer is touching. A mature, well-understood surface like Nextdoor's eight-year-old advertising model can absorb more AI; newer, lower-ACV product experiences need more caution.

Why it matters: Before automating a motion, ask two questions: how big is the deal, and how mature is the product surface. Both must point the same way before you push automation into the customer-facing work.

RevOps LeadersRevenue ExecutivesSales Leaders
05

New products need more human-in-the-loop, not less

When you put a new product in market, the fastest way to learn is to talk to customers, engage, and hear nuance a survey or automated form can't capture. Moving too fast on AI for a new monetization line risks getting the system out ahead of the real work — refining product-market fit.

Why it matters: Resist automating discovery on new products. Put your best human listeners on early adopters and let the feedback flow into product, product marketing, and sales before you scale a motion.

FoundersRevenue ExecutivesSales Leaders
06

The centralize-vs-decentralize AI question is a pendulum, not a permanent choice

Nextdoor's cross-functional 'Neighbor' AI group started centralized, then decentralized so each of ~470–480 people and each department could build its own game plan. That freedom, plus Claude going from competitive to indispensable, swung the pendulum too far — so the group came back to add guardrails. It's now settling in the middle: cost-and-tool guardrails, team-level ownership of process redesign.

Why it matters: Expect several iterations. Centralize to set standards and guardrails, decentralize to capture field ideas and curiosity — and plan to keep re-balancing rather than picking one model forever.

Revenue ExecutivesRevOps LeadersFounders
07

Decentralized AI is only safe if your data foundation is strong

Kiernan credits a hard-won Salesforce cleanup and a healthy Salesforce-plus-Databricks stack for letting a non-data-scientist CRO 'be my own data scientist.' If the underlying data isn't in a good spot, a company should centralize a group to fix the foundation before it decentralizes AI at all.

Why it matters: Audit data cleanliness before you hand AI to every team. Weak foundation → centralize and fix it first; strong foundation → you can safely let functions own their own AI processes.

RevOps LeadersFoundersRevenue Executives
08

Measure agentic GTM in the P&L and the funnel — not the API bill

Success shows up as speed to market (more meetings, faster client turnaround, senior reps prospecting more), better conversion between pipeline stages, and financial efficiency — revenue per head, campaigns per group, ARPU. Many teams run up API bills bigger than the headcount they replaced; if the P&L and funnel metrics aren't moving, reevaluate where and why you're applying AI.

Why it matters: Instrument AI initiatives against revenue and efficiency outcomes from day one. The API bill is a cost input, not a success metric — the scoreboard is the P&L and funnel conversion.

Revenue ExecutivesFoundersRevOps Leaders
09

Guard against the big AI spend mistakes, not the small ones

Kiernan is 'so paranoid' about his team overspending on tools, but says the cost 'is not as bad as we thought it was going to be.' The discipline that matters is avoiding the catastrophic mistakes — like someone trying to catalog the entire internet in a few prompts — rather than micromanaging every prompt.

Why it matters: Set guardrails against runaway, high-blast-radius usage while keeping friction low for everyday experimentation. Cost control is about preventing the $20K surprises, not policing curiosity.

RevOps LeadersRevenue ExecutivesFounders
10

The operator-first path to CRO: see the whole elephant and feel the pressure of a number

Kiernan's edge is operational range — a 'hybrid athlete' good at a couple of things, always raising his hand to take a new initiative from zero to one. His advice for RevOps leaders eyeing the CRO seat: pin-seek new lines of business, international expansion, and reorgs to see the whole business, and go through a period where you genuinely feel the pressure of carrying a number — not for the title, but for the life experience.

Why it matters: Don't run from RevOps to grab an AE badge. Own something strategic end-to-end, get cross-functional exposure, and take a real revenue number when you can — that combination, not a sales title, is what prepares you to lead revenue.

RevOps LeadersRevenue Executives
11

Stay close to the customer — and mine your call data — no matter your role

Customer feedback flows into product, then product marketing, then the sales story; letting yourself get disconnected from what customers actually want is how you don't get a senior leadership job. Nextdoor uses Gong as its primary listening tool, and Kiernan wants everyone in his org digging into it because 'there's some real gold in there.'

Why it matters: Treat conversation data as a strategic asset. Whether you're in finance, RevOps, or sales, build a habit of listening to customer calls — it's the context that makes every downstream decision better.

RevOps LeadersSales LeadersRevenue Executives
12

Run your weeks on a four-priority, color-coded calendar

After a CEO-led priorities exercise, Kiernan runs three pillars plus his team: core revenue (the ads business, down from nearly all his time last year to ~a quarter after hiring a stronger VP of North America), new monetization exploration, agentic transformation, and a fourth quarter for team, skip-levels, and cross-functional partners. He literally color-codes the calendar — a quarter blue, red, green, yellow — as a self-audit.

Why it matters: Make your strategic priorities visible in how your time is actually spent. A color-coded calendar surfaces when you've drifted from customers or neglected your team, and forces you to hire complementary talent so you can shift time to the next horizon.

Revenue ExecutivesSales LeadersFounders
13

Monetization beyond ads: local services, peer-to-peer commerce, and the data graph

Nextdoor's core stays advertising, but Kiernan is exploring additive revenue from organic activity on the platform: helping the neighbor find a plumber (and the plumber find customers), enabling peer-to-peer and gig commerce (the neighbor selling a hundred dozen cookies), and turning the neighborhood data graph into a monetization asset — thoughtfully, without just selling data.

Why it matters: A rich, high-trust data graph opens monetization doors beyond the core model. The discipline is treating new lines as a 'science-fair' portfolio — many ideas, few bets — and protecting user trust as the moat that makes any of it work.

FoundersRevenue ExecutivesMarketing Leaders
Frameworks Discussed

11 named models

Every framework Jimmy names, defined and time-stamped.

Human + Agentic GTM

02:16

A transformation framing in which agentic AI augments the revenue team rather than replacing it — the 'plus' signals that humans stay in the motion, owning relationships and accountability, while agents handle preparation and scale.

Kiernan named his nine-month plan this way as a deliberate rejection of 'botifying' sellers. On a relationship-based platform, positioning a transformation as automation-and-headcount-reduction is the wrong way to bring the team through change; the plus is the whole point.

The AI-in-Motion Spectrum (Inverse to Deal Size)

06:40

The higher the deal value and the more up-market the customer, the less AI belongs in the customer-facing interaction — and the further down the tail (SMB), the more the agent can own the motion with a human reviewing the output.

Enterprise: agents do research, prep, proposals, and RFP responses to make the rep sharper, never redundant. Mid-market: AI-enabled but human-last, rep gets the final word. SMB: agent owns outreach, routing, and renewal prompts while a human hits approve.

ACV + Product Surface Framework

07:22

A two-variable decision model for how much AI to put into any motion: account value (ACV) and which product surface the customer is touching (and how mature that surface is).

A well-understood, eight-year-old surface like Nextdoor's advertising model can absorb more AI in the workflow; newer, lower-ACV product experiences require more caution. Both variables must point the same way before pushing automation into customer-facing work.

Three-Segment Agentic Model

03:54

Split customers into enterprise (large advertisers), mid-market (D2C brands, performance agencies), and SMB, and assign a different agentic role to each based on that segment's customer-service needs and risk tolerance.

It's risky to put too much system-to-human interaction in front of an agency CEO or brand chief strategy officer, so enterprise stays human-led; mid-market is transactional-but-consultative; SMB is where you get comfortable letting the agent take over volume tasks.

New Products Need More Human, Not Less

10:49

The newer and less proven a product, the more human-in-the-loop the motion should be — because the fastest way to learn from customers experiencing something new is to talk to them, not to automate the interaction.

Moving too fast on AI for a new monetization line risks getting the system out ahead of the real work of refining product-market fit; nuance and candid feedback are hard to capture in a survey or automated form.

The Centralize-vs-Decentralize Pendulum

12:19

AI enablement swings between a centralized owning group and fully decentralized team-by-team ownership; the healthy resting point is in the middle — cost-and-tool guardrails set centrally, process redesign owned by the teams.

Nextdoor's 'Neighbor' AI group started centralized (~10 people), decentralized so each department built its own plan, then swung back to add guardrails after usage (and cost) exploded. Expect several iterations to find the balance without killing curiosity.

The Data Foundation Gate

16:11

Whether you can decentralize AI at all is gated by the strength of your underlying data — a clean CRM and a healthy data stack are the precondition for letting functions own their own AI.

A hard-won Salesforce cleanup plus a Salesforce-and-Databricks stack that talks cleanly to AI tools let a non-data-scientist CRO 'be my own data scientist.' If the foundation isn't there, centralize a group to fix it before decentralizing.

Measure Agentic GTM in the P&L, Not the API Bill

18:58

Judge AI initiatives by revenue and efficiency outcomes — speed to market, meeting volume, pipeline-stage conversion, revenue per head, ARPU — rather than by AI spend.

Many teams run up API bills bigger than the headcount they replaced. The prudent test: it should show up in the P&L and funnel efficiency; if those numbers aren't moving, reevaluate where and why you're applying AI.

See the Whole Elephant

27:12

The operator's path to senior leadership: deliberately pursue new lines of business, international expansion, and reorgs so you see and understand the entire business, not just one function.

That breadth improves decision-making and exposes you to company strategy in corners you'd otherwise never touch — the experience that ladders up to a bigger leadership role. Kiernan's advice to RevOps leaders: don't run from RevOps, pin-seek this exposure.

Feel the Pressure of a Number

28:30

The point of 'carrying a bag' isn't the title — it's going through a period where you genuinely feel the pressure of contributing to the top line, a career experience you have to go collect.

Since his turnaround role at Turn, Kiernan has always had 30%+ of comp tied to revenue outcomes. Owning a number just to say you own it misses the point; the pressure is the formative experience aspiring revenue leaders need.

The Four-Priority, Color-Coded Calendar

35:35

Run your weeks against roughly four equal priorities, each assigned a color, and audit your calendar so it's about a quarter of each — a mechanism to keep strategic time allocation honest.

Kiernan's pillars: core revenue (ads), new monetization, agentic transformation, and team/cross-functional partners — a quarter blue, red, green, yellow. Eyeballing the color mix flags when he's drifted from customers or neglected his team.

Best Quotes

16 lines worth clipping

Pulled verbatim. Copy or share any of them.

“Kiernan is a rare breed of CRO. He openly calls himself an operator first and a sales leader second.”
Anthony Enrico 00:00
“To so quickly try and remove human from what we're doing as a business just doesn't feel right. In fact, I think anyone trying to force us to go down that path is actually not thinking about it correctly.”
Michael Kiernan 01:33
“It's very difficult to put the accountability onto AI, onto an agent, especially if you're closing a bigger deal. I want to know that someone's on the hook for that deal when I'm working with them.”
Anthony Enrico 02:18
“Over the past six months to a year, you've gotten a ton of inbound. It's super low quality, the volume's 10x. It's turning me off to this entire experience.”
Michael Kiernan 03:09
“The agent's there to make the rep look good, to make the rep sharper. It's not to make the rep redundant.”
Michael Kiernan 04:35
“As you work more upmarket, there's an inverse relationship to how much AI you're putting into the customer-facing portion of the process.”
Anthony Enrico 06:40
“The fastest way to learn from customers experiencing a new product is to talk to them, to get their feedback, and to engage with them.”
Michael Kiernan 08:41
“The pendulum started way out to the left, then it swung way out to the right, and now it feels like it's starting to settle a little bit more in the middle where it belongs.”
Michael Kiernan 13:29
“It should show up in the P&L, it should show up in the funnel efficiency metrics. And if you're not seeing those numbers move in the right direction, then you should probably reevaluate where you're applying AI and why.”
Anthony Enrico 20:10
“The sales team would tell you I'm not good at sales, and the ops team would tell you I'm not good at ops either.”
Michael Kiernan 21:30
“I get my energy from the plan winning more than I get it from having a great meeting or dazzling someone out in the real world.”
Michael Kiernan 26:29
“One of the most important things you get out of an operational role is the ability to see the whole elephant.”
Michael Kiernan 27:12
“I don't think owning a number so that you can say you own the number is the point. You have to go through a period where you feel the pressure.”
Michael Kiernan 28:30
“Everyone in my organization needs to be digging into what's going on in Gong, because there's some real gold in there.”
Michael Kiernan 31:33
“You want it to be roughly a quarter blue, a quarter red, a quarter green, a quarter yellow. Those are the four colors I use because I like basic colors.”
Michael Kiernan 38:08
“We can't just give or sell our data — that's not what we're doing — but we are thinking about different ways where our neighborhood graph becomes a monetization asset.”
Michael Kiernan 42:39
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Revenue Executives

  • Name and position your AI transformation as augmentation ('Human + Agentic'), not automation-and-layoffs — how you frame it decides whether the team drives or resists it.
  • Set agent autonomy by segment: humans own the relationship and accountability up-market; automate the tail with a human hitting approve.
  • Measure agentic GTM in the P&L and funnel — speed to market, conversion rates, revenue per head, ARPU — and treat the API bill as a cost input, not a scoreboard.
  • Run your weeks against a small set of visible priorities (Kiernan color-codes his calendar to roughly a quarter each) and hire complementary talent so you can shift time to the next horizon.

RevOps Leaders

  • Fix the data foundation before decentralizing AI — a clean CRM plus a healthy data stack is the precondition for letting every team own its own AI; if it's not there, centralize a group to fix it first.
  • Don't run from RevOps to chase an AE title. Own something strategic end-to-end, pin-seek new lines of business, international expansion, and reorgs to 'see the whole elephant,' and take a real revenue number when you can.
  • Build a habit of listening to customer calls (Nextdoor mines Gong) no matter your function — it's the context that makes every downstream decision better.
  • Guard against the catastrophic AI spend mistakes, not the small everyday ones — keep friction low for experimentation while preventing runaway usage.

Sales Leaders

  • Keep humans owning high-ACV, high-consideration deals — buyers want a person on the hook — and use agents for research, prep, proposals, and RFPs to make reps sharper.
  • Put your best human listeners on new products; the nuance you need to find product-market fit doesn't come through a survey or an automated form.
  • Use agentic follow-up and speed to get senior reps prospecting again — turning information around faster should show up as more meetings and better stage-to-stage conversion.
  • Remember the ad-model reality that the sale never ends — the ongoing motion of helping clients get more value is where much of the revenue lives.

Founders

  • Expect the centralize-vs-decentralize question to be a pendulum you re-balance several times, not a one-time decision — and put cost-and-tool guardrails in place before a surprise bill forces them.
  • Move slower on AI for brand-new monetization lines; getting the system out ahead of product-market fit can hurt you long-term.
  • Instrument AI initiatives against revenue and efficiency outcomes from day one so you can tell real leverage from expensive theater.
  • Treat a high-trust data asset (like a neighborhood graph) as a portfolio of monetization options — many ideas, few bets — and protect user trust as the moat.

Marketing Leaders

  • The mature, well-understood surface (a proven ad model) is where you can push more AI into the workflow; new product experiences need a lighter, more human touch.
  • Feed the customer-feedback loop: what customers say on calls flows into product, then product marketing, then the sales story — stay connected to it.
AI Takeaways

How AI actually changes GTM

LeanScale's signature read on the AI-in-GTM question this episode wrestles with.

The thesis

AI belongs in the revenue motion on a sliding scale, not everywhere at once: it should make humans sharper and the P&L leaner, but it cannot carry the relationship, the accountability, or the trust that closes your biggest deals. 'Human + Agentic GTM' — with the plus as the point — is the deliberate rejection of botifying the sales team.

Autonomy scales inversely with deal size

Enterprise: agents prep, research, and draft to make the rep sharper, never redundant. Mid-market: AI-enabled but human-last. SMB: the agent owns the motion while a human reviews and approves. There's no single AI policy across segments.

Accountability can't be automated

Buyers want a person on the hook for a big deal. Trust and commitment don't transfer to an agent — which is exactly why AI won't close your biggest deals, even as it accelerates everything around them.

New products need more human, not less

The fastest way to learn from a new product is to talk to customers, not automate the interaction. Moving too fast on AI for a new monetization line risks getting the system out ahead of product-market fit.

Data foundation is the gate

Decentralizing AI is only safe on a clean CRM and healthy data stack (Salesforce + Databricks). Weak foundation → centralize a group to fix it first; strong foundation → let functions own their AI.

Measure in the P&L, not the API bill

Success is speed to market, conversion, revenue per head, and ARPU — not AI spend. Many teams run bills bigger than the headcount they replaced; if the funnel and P&L aren't moving, reevaluate.

The pendulum keeps swinging

Centralized → decentralized wild-west → guardrails in the middle. Expect several iterations; the goal is standards and cost control without killing team-level curiosity.

Agent & automation ideas

  • Segmented sales-agent tiers: enterprise agents scoped to meeting prep, account research, proposal drafting, and RFP-response consistency (rep owns the room); SMB agents scoped to outreach, lead routing, and renewal prompts with a mandatory human-approve step.
  • A conversation-mining agent over Gong that surfaces customer signal, product feedback, and deal-risk patterns to product, product marketing, and sales — turning 'the gold in Gong' into routed, actionable insight.
  • An AI-spend governance agent that watches API/tool usage against P&L and funnel-efficiency metrics and flags high-blast-radius jobs before they become a $20K-in-a-month surprise.
  • A data-foundation readiness agent that scores CRM cleanliness and Salesforce↔Databricks↔AI-tool integration health to decide whether a team is ready to decentralize AI.
Operations Takeaways

By function

The same conversation, filtered for RevOps, pipeline/marketing ops, and customer ops.

Revenue Operations

  • Data foundation first. A clean Salesforce plus a healthy Databricks stack is the precondition for self-serve, decentralized AI — fix the foundation before handing AI to every team.
  • Centralize-vs-decentralize is a pendulum. Start centralized for standards, decentralize for field ideas, settle in the middle with cost-and-tool guardrails; expect to re-balance repeatedly.
  • Instrument AI against revenue. Judge initiatives by speed to market, conversion, revenue per head, and ARPU — not the API bill.
  • The RevOps-to-CRO path is real. See the whole elephant (new lines of business, international expansion, reorgs), stay close to customers, and feel the pressure of a number — don't run from RevOps.
  • Mine the call data. Everyone should be digging into Gong; conversation data is the context that makes systems, comp, and territory decisions better.

Pipeline & Marketing Ops

  • Speed to market shows in the funnel. Agentic prep and faster client turnaround should produce more meetings and better conversion between pipeline stages.
  • No SDR handoff in the ad model. Nextdoor doesn't run an SDR model or love the handoff; agentic speed is meant to get senior, strategic reps prospecting more themselves.
  • Segment the motion. Enterprise stays human-led and high-touch; mid-market is transactional-but-consultative; SMB automates outreach and routing with human approval.

Customer Operations

  • The sale never ends. Unlike SaaS where a rep hands off to CS after signing, the ad model requires ongoing selling — helping clients change campaigns and get more value every month.
  • Speed to value counts as revenue. Success shows up not just in deals closing but in clients taking recommendations and putting them into the platform faster.
  • Stay connected to customer stories. Getting disconnected from what customers actually want is how you don't get to (or keep) a senior leadership role — build the listening habit regardless of role.
  • Protect trust as the moat. New monetization from the neighborhood data graph must be pursued without simply selling data — user trust is the asset that makes any of it work.
Metrics Mentioned

The numbers, with context

110M+ neighbors · 350,000 neighborhoods
Nextdoor scale

The verified neighbor base across 350,000 neighborhoods — about one in three U.S. homes — and the audience underpinning both advertising and future monetization.

~110 of ~470–480
GTM org size

Kiernan's go-to-market org is about 110 people, a little less than a quarter of Nextdoor's ~470–480-person company — the scope his agentic game plan covers.

$20K in a month
Surprise AI bill

A decentralized 'let every team run' phase produced a roughly $20,000-in-a-month AI bill that forced the 'Neighbor' group to add cost-and-tool guardrails.

9-month plan · 2 months in
Transformation timeline

'Human + Agentic GTM' is a nine-month plan; at recording Kiernan is two months in and already replanning parts of it.

30%+
Comp tied to revenue

Since his turnaround role at Turn, Kiernan has always had 30%+ of compensation tied to revenue outcomes — how he's 'felt the pressure of a number.'

~100% → ~25% on core revenue
Time reallocation

Core revenue (the ads business) consumed nearly all his time last year; after hiring a stronger VP of North America it's now about a quarter of his time.

4 × ~25%
Priority calendar mix

Core revenue, new monetization, agentic transformation, and team — roughly a quarter each, color-coded blue/red/green/yellow as a self-audit.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

People

Tools & software

SalesforceCRM

Nextdoor's CRM; a hard-won cleanup got it into a 'really great spot,' and the way Salesforce talks to Databricks and their AI tools is what makes a decentralized, self-serve data workflow possible.

DatabricksData Platform

Part of Nextdoor's data foundation; a healthy Salesforce-plus-Databricks stack let a non-data-scientist CRO 'be my own data scientist' and is the gate that makes decentralizing AI feasible.

ClaudeAI Assistant

Kiernan's AI assistant of choice — went from competitive with ChatGPT and Gemini to 'the only thing I use,' and he works with Claude to explore new-monetization ideas.

Claude CodeAI Dev Tool

Referenced ('Claude code') as the archetype of the 'let's get it into every person's hands' decentralized approach many companies took with AI.

GongRevenue Intelligence

Nextdoor's primary conversation-listening tool for client meetings; Kiernan wants everyone in his org mining it because 'there's some real gold in there.'

Frequently Asked Questions

Straight answers

Generated from the conversation, marked up for search and AI extraction.

What is 'Human + Agentic GTM'?

'Human + Agentic GTM' is the name Nextdoor CRO Michael Kiernan gave his nine-month AI transformation plan. The 'plus' is deliberate: it embeds agentic AI into the revenue motion to make humans sharper and faster, rather than replacing sellers with agents ('botifying' the team). Humans keep owning relationships and accountability while agents handle preparation, research, and scale.

Why won't AI close your biggest deals?

Because accountability and trust can't be automated. On large, high-consideration deals, buyers want to know a specific human is on the hook for the outcome. AI can prepare the rep, draft proposals, and speed everything up, but it can't carry the relationship or the commitment — so the bigger the deal, the more it stays human-owned.

How much AI should go into each sales motion?

Kiernan uses an inverse relationship to deal size, driven by two variables: ACV and which product surface the customer is touching. Enterprise deals keep humans in front while agents do research, prep, and RFP responses; mid-market is AI-enabled but human-last; SMB lets the agent own outreach, routing, and renewal prompts with a human reviewing and approving the output.

Should AI efforts be centralized or decentralized?

Treat it as a pendulum, not a permanent choice. Nextdoor's cross-functional 'Neighbor' AI group started centralized, decentralized so each team built its own plan, then swung back to add cost-and-tool guardrails after usage spiked. The healthy resting point is in the middle: central standards and guardrails, with teams owning their own process redesign — and you should expect to re-balance several times.

How do you measure whether agentic GTM is working?

Measure it in the P&L and the funnel, not the API bill. Look for speed to market (more meetings, faster client turnaround, senior reps prospecting more), better conversion between pipeline stages, and financial efficiency like revenue per head and ARPU. Many teams run up API bills bigger than the headcount they replaced; if those revenue and efficiency numbers aren't moving, reevaluate where and why you're applying AI.

What did the $20,000 AI bill teach Nextdoor?

When Nextdoor decentralized AI so every team could experiment freely, usage — and a roughly $20,000-in-a-month bill — surprised them. The lesson wasn't to lock everything down; it was to add cost-and-tool guardrails against high-blast-radius mistakes (like trying to catalog the entire internet in a few prompts) while keeping friction low for everyday experimentation.

Can a RevOps leader become a CRO?

Yes, and Kiernan argues you shouldn't run from RevOps to chase an AE title. The preparation is owning something strategic end-to-end, getting cross-functional exposure to new lines of business, international expansion, and reorgs so you 'see the whole elephant,' and going through a period where you genuinely feel the pressure of carrying a revenue number — that combination, not a sales badge, is what readies you to lead revenue.

What is Nextdoor's plan for monetization beyond advertising?

Advertising stays the core, but Kiernan is exploring additive revenue from organic platform activity: local services (helping a neighbor find a plumber and the plumber find customers), peer-to-peer and gig commerce (a neighbor selling homemade cookies), and turning the neighborhood data graph into a monetization asset — pursued thoughtfully, without simply selling user data, with trust as the moat.

Full Transcript

The whole conversation

Broken into chapters, searchable, verbatim from the audio. Speakers inferred (not diarized).

00:00Cold open + intro

0:00 Today, I'm joined by Michael Kiernan, Chief Revenue Officer at Nextdoor, the essential neighborhood network for over 110 million verified neighbors across 350,000 neighborhoods. Kiernan is a rare breed of CRO. He openly calls himself an operator first and a sales leader second, with a background spanning sales engineering, sales ops, and biz ops at X, Turn, Yahoo, and Brightroll before joining Nextdoor in 2018 and being elevated to CRO last year. He's two months into a nine-month plan he's named Human + Agentic GTM, a deliberate rejection of the idea that the future of revenue is just botifying your sellers.

0:49 He's also helping Nextdoor CEO build entirely new monetization systems beyond advertising, all while delivering quarter in, quarter out as a public company exec. In this conversation, we get into the framework he uses to split his attention, where his nine-month plan is already getting replanned, and what most CROs are getting wrong about agents in the GTM motion. Kiernan, you named the project Human + Agentic GTM deliberately, not just Agentic GTM. What were you reacting against when you chose that framing, and what does the plus actually mean in practice? Sure. Thank you for having me, by the way.

1:33 I was reacting to probably two things, and I should say this is a group effort. One, this is sales. This is relationship-based media selling. We are a platform. I work for a platform that connects human beings in the neighborhood to so quickly try and remove human from what we're doing as a business, and what we're doing as an organization just doesn't feel right. In fact, I think anyone trying to force us to go down that path is actually not thinking about it correctly. Two, look, every company out there seemingly, we've got to transform. As a business, we've got to go from maybe being agentic first to agentic enabled to agentic native.

02:16'The plus is the point': rejecting the bodified sales team

2:18 That means we've got to bring people through that and to position it like we're going to automate and modify the organization. I actually don't think that's the right way to get the team on board with that transformation. Yeah, and when I think about it, I feel like there's some components that can be identified of the sales process, and then some that feel like they have to be done by humans. The one thing that comes to mind is it's very difficult to put the accountability onto AI, onto an agent, especially if you're closing a bigger deal. That trust, I want to know that someone's on the hook for that deal when I'm working with them.

3:09 I completely agree. I'd be willing to bet over the past six months to a year, you have gotten a ton of inbound to you as a potential buyer. That inbound, it's super low quality, the volume's 10x for me. As someone on the other side of that, and in particular for me, I'm getting inbound for sales tools, training programs, things to help improve the sales team. It's not that great, it's turning me off to this entire experience, and I agree. We're holding the team accountable to driving revenue and closing deals, and while I would love for automation to play a part in the productivity, in our ability to not just increase

3:53 efficiency but at its core, we're doing more with less over time, I do not think trying to automate the interaction with the customer is the right place to start. For us, one way we've thought about this, next door services, three distinct segments of customers. We have our super large enterprise advertisers, we have direct to consumer brands, performance agencies, we tend to view that as our mid market segmentation. Those are three different segments with three different customer service needs, and the way we're thinking about bringing a Gentic into that, when you think about enterprise,

03:54Accountability, inbound spam, and the three-segment model

4:35 pretty risky to have too much interaction between the system and a CEO at an agency or a chief strategy officer for a brand. For us, we think of it as, a Gentic is powering the sales experience, and so where does a Gentic come into play for our enterprise approach? It's doing things like research before meetings, the meeting prep, proposal drafts, making RFP responses and decks more consistent. It is not owning the relationship or the room or the clothes, the agents there to make the rep look good, to make the rep sharper, it's not to make the rep redundant, then when you

5:17 think about that mid market segment, that's one where we got to start thinking about scale. Not every customer needs a full sales process, or sometimes they don't necessarily want to deal with one of our client partners, which is what we call our reps, and so there, it's a little bit more of a transactional business, there's still solution selling, we still need to get on the phone with our partners and identify the best way to help them leverage next door, and yes, the prep work that goes into that process from an Egentic standpoint can help speed up how our reps prepare for calls, think about putting the right solution

05:30Enterprise vs. mid-market vs. SMB: where agentic fits

5:59 in front of that particular customer, but that's still really an AI enabled human last type of approach, where the rep is still getting in the final word. Now Egentic, how is that different than enterprise, follow up gets lickety split quick because you're doing this at higher volume with customers, getting their accounts onboarded and started, we can start to do things there with a little bit more automation, but that's still like sales in my mind, and then when you move to SMB, that's where you really do get more comfortable allowing the agent to take over the outreach, the lead routing, the follow up prompts for

6:40 renewal, and really what the human is doing in that case is they're the ones reviewing the final output from our agent or from our AI process, and then they're kind of hitting submit or send or approve, and so we still are keeping a human being involved in ensuring the customer experience is strong, but it's down the tail is when you can really take advantage of the skill of AI without completely removing people as part of that process. So it feels like there's a spectrum as you work more upmarket, there's an inverse relationship to how much AI you're putting into the customer facing portion of the process.

7:22 To make this maybe more tangible for somebody listening and thinking, hey, how much AI should I have in each of the motions that I have? What are some mental models or frameworks you use? Is it an average ACV threshold? Is it certain components of the deal that are occurring that unlock needing more human handholding? What's the framework in your mind that you're using to determine how much AI you put in the motion? So I think it's a combination of ACV, right, account value, and it depends on which product surface the customer is touching. For us, our core business today, it is an advertising model.

8:04 We've got a platform that drives so much of that ad revenue through Nextdoor. It's a model we've been working on for eight years, maybe longer now that I think about it. It's something we understand well. It's a well understood industry mechanism. That's an area where I think we should be more comfortable pushing it in terms of building AI into the workflow as you move down to lower ACV customers. For newer product experiences, and I'm sure we'll be touching on that at some point throughout this conversation, we need to be more careful there, right? You're putting a new product in market. You need to learn from that.

8:41 The fastest way to learn from customers experiencing a new product is to talk to them and to get their feedback and to engage with them. That's something while there's always a way, again, to automate what's happening behind the scenes to save people time. We need to be thoughtful in particular our new monetization efforts that we're not moving too fast on the AI side and getting out in front of getting the process and the system out in front of the actual real work, which is refining product market fit, finding our moment where we feel like we've earned the right to start to maybe bend the curve and grow out a new line of business.

08:45The framework: ACV + product surface

9:17 It makes a ton of sense, and I think it's tough to get that feedback in a gentrified way, especially when you're searching for nuance and giving a customer space to open up and share information that it'd be difficult to get in a survey or some type of automated form like that. I think that's a huge nugget for people thinking, "Okay, how much human in the loop do I need?" If it's a new product, you're probably going to want those humans listening and getting as much feedback as they can. That's right, and so much of what I am focused on right now is in exploring new revenue ideas,

10:03 new concepts, new initiatives, trying to keep a good balance between not defocusing what we're doing, but also keeping the aperture open, keeping our mindset open, and that whole area just seems really risky to run too fast on a gentic for the sake of AI transformation when, again, you might actually hurt yourself in the long run if you move too fast there. Couldn't agree more. One question I have about this, and I was at the RevOps AF event. It was in London. It's hosted by RevOps Co-op, really, really good event. AI obviously was a hot topic there. One of the questions that was coming up, and I'm curious how you are doing this, is whether

10:49Why new products need more human, not less

10:52 to centralize or decentralize your AI efforts. A lot of companies, I think, went with, "Hey, let's just get Claude code into the hands of every single person in the company, and let's go see what happens," and now it feels like there's a shift. What's been your thought process of who's leading these AI initiatives? Who's actually implementing them, and then how are you building these at scale and enterprise-wide so you can maintain those standards across the type of team you have at Nextdoor? Great question. It's funny you just brought this up. This has been an internal conversation for a little while.

11:27 Let me give you kind of a quick oral history, because I think it'll maybe set the table correctly. About a year and a half ago, we created an internal group called Neighbor with AI in there instead of EI, and that was our internal cross-functional team to begin to focus on how are we making AI more built into everything we do at the company. I would say that did start as centralized. It was a group of maybe about 10 people cross-functionally trying to identify the different tools to bring into the company to integrate, to get leverage, and continue to make the company run more effectively.

12:05 We made a conscious decision to actually say, "Hey, let's let individual departments put together their own game plan," and Nextdoor's got maybe 470, 480 people today to go to market org, my org is 110, so a little less than a quarter of that. So what did I do? We got with our sales and operational leadership team, and we put together a game plan on what does that mean for us across back-end processes, what are we maybe going to consider building into the product, how do we rethink our roles, and every other department started to do that. And then around that same time, Claude gets hot.

12:19Centralize vs. decentralize: the 'Neighbor' AI group

12:47 There was some moment where Claude went from, I think, in my mind, being competitive to chat GPT and Gemini to it was the only thing I use, and I don't exactly know when that happened personally, but it was maybe six months ago. And so all these teams started doing different things, and so that has caused the neighbor group to come back and rethink how do we have some guardrails around AI tool utilization around the company. But again, we don't want to kill the curiosity, the drive different individuals or teams have to just improve that process. And so Pendulum started kind of way out to the left, then it's one way out to the right,

13:29 and now it feels like it's starting to settle a little bit more in the middle where it belongs, which is some kind of cost and tools-based guardrails, but still allowing the individual teams and process owners to have that kind of final say and redesigning really the processes that make their team successful. Yeah, and then structurally, and I think that makes a ton of sense because it was like Wild West, everybody can use it, and then you don't want to lock it down so much to where you're not getting ideas from the field and things happening that can really drive an impact.

14:03 And then there's also a lot of just personal everyday reasons that you need your own setup to structurally in the company and/or just maybe guidance for other companies, it kind of feels like there's some needs on engineering and product, there's some needs on go-to-market. Do you feel like this can all live under one house and serve it well, or do you need two operation leaders leading that AI efforts for each part of the house? I think it totally depends on the company, so I'll start there. I think some companies are functionally structured. Next door is mostly functionally structured.

14:39The $20K bill and the guardrail pendulum

14:42 We've got president of products, he oversees engineering, product management, data, obviously oversee revenue. We have one of our co-founders overseas marketing, and that I do think kind of lends itself down this path of we'll let the functions own their processes. I think some companies are structured around lines of business or they're in a GM structure where you can probably allow their structures to own their processes. I also think what we're starting to see, and there are roles out there already, are a new department, a new function whose job is to bring the transformation in or at least maybe

15:22 bring some of the outside thinking and outside perspective and then facilitate some of that. I think it depends on the company. I think any company probably needs to go through several iterations to find their way. I think a lot of it also really depends on the strength of the underlying data, and that's something I think we've learned the hard way through our sales force integration that we had a lot of tough ground we had to crawl to get our CRM in a really great spot. Now that I feel like it is, we're realizing that the way Salesforce and Databricks talk to our different AI tools have made the process really easy for people like me, not a data

16:08 scientist, state university. I am my own data scientist, and I'm pretty successful at it because the underlying foundation actually was in a pretty healthy spot. I would say if that's not true, then I do think a company needs to consider this centralized group of people, they go and focus on solving that problem for them. I think for us, again, we feel like we're far enough along there that we don't need to centralize someone to build the foundation. We actually think the foundation's in a pretty good spot. Yeah, I like it, and I like the different models depending on how your company's structured. When human plus agentic GTM is a success. Sure.

16:11One house or two? Structure and the data foundation

16:50 I'm assuming the project's never going to be done and it's going to be iterative after, but I was just going to say that, like never done. Job's not done, but when it gets to the milestone to say like, "Hey, yeah, we did this in a meaningful way," how are you gauging that it was a successful initiative? Are there some NBO-style things? Are you going to see it in your GTM performance metrics? What will make you say you did a good job? So these aren't necessarily in order, but I'll rattle off kind of what we've talked about and what I think we're looking for, especially between now and the end of the year. One, it's speed to market.

17:31 Are we just moving faster? For our field sales account teams, are they getting more meetings because they're able to reply quicker and turn information around through email exchanges and client interactions? So like speed to market, I think we'll see that and you'll see that in a bunch of places. You see that in things like meeting volume, you'll start to see that in conversion rates between pipeline stages. We'll see it in our outbound for sure. We don't have an SDR model. We don't love the handoff and I actually think most advertising models are more like that. And so we'll see it in some of our really senior season strategic reps, you'll see them

18:18 start to move faster on the prospecting side of things when historically, I think the older you get, the less you like to do that kind of work. And we're already starting to see some of that. There's also, you'll see it in response times from clients. We'll see it in some of the solutions or without maybe knowing how much you understand our business model, our core offering is advertising, which means we're constantly helping marketers make changes in our system to maximize the budgets that they're spending to maximize their ROI. And so the job, yeah, there's sales in like finding the new customer, getting them educated

18:57 on next door, getting them over the line, signing the deal and getting them started. But then there's the ongoing sale of like, here's a better way to use our product or you should try this next month or you've got a temple event coming up for your brand. We're going to help you put together a strategy to do that. So the selling never ends. It's very, it's very much unlike maybe SaaS where once, once the rep gets a contract or a license over the line, they tend to hand it to a customer success or an account management team. That's not our business model. And so we see a speed to market, not just in like deals closing, but in clients taking

18:58Measuring agentic GTM: speed to market and the P&L

19:33 our recommendations and putting them on the field and putting them in the platform. We'll see it, you know, the financial metrics, we'll see it in our, like our revenue per head will go up or, you know, our number of campaigns or accounts owned or managed by any one group should increase. It should lead to better ARPU, like all the, all the efficiency metrics you look for, you know, and, you know, when you're evaluating a public company's cost utilization, you should start to see it soon. In fact, we already are, you know, it's something we're really proud of even just through last

20:10 year and into this year, we're like night and day in a better place from like, not just a company profitability standpoint, but on the P&L itself for us, like we already, already seen a lot of that efficiency. There's a lot of people running these initiatives and running up bigger API bills than they had on their headcount. So I think, I think the people that are taking a prudent approach are saying exactly what you're saying. Hey, it should show up in the P&L, it should show up in the funnel efficiency metrics. And if you're not seeing those numbers move in the right direction, then you should probably reevaluate where you're applying AI and why.

20:49 That's right. And yeah, I mean, I'm, don't get me wrong, I'm so paranoid around, you know, our company or people, especially on my team, you spending too much on the tools, but we're, it's not as bad as we thought it was going to be. We just, the trick there is to avoid the big mistakes is the way I kind of do it. Yeah. Someone's trying to catalog the entire internet in a few prompts. I think, I think this comes out in the way you're answering a lot of these questions. And you said it during our prep session for this, that, Hey, you're an operator before you're a salesperson.

21:30 And I'm just curious how you, cause there's a lot of paths to get to that zero title. I'm curious a bit about your background and, and what, what gave you the foundation to approach the role in this way. And what you think makes it unique compared to a typical sales for Sierra. Sure. Um, that's funny. And sales team would tell you I'm not good at sales and the ops team would tell you, I think I'm good at ops. I'm not good at that either. Have you heard the term hybrid athlete? Sure. Of course. I would shoot sports, man. Yeah. Yeah. I feel like I've been called that and it just means I'm kind of good at a couple things. I agree.

22:10 I'm like, all right, I can't tell if it's underhand compliment or not, but sure, I'll, I'll take it. I like compliments. Um, maybe like quick career progression. Cause I think maybe that kind of helps tell the story and I'll get into the mindset. Um, I started working. My first job was for a public accounting firm, very quantitative. They taught you how to grind out 80 hour weeks. I didn't necessarily like the environment or the industry, but it, that was a great place to learn how to find some grit and how to just like get your head down and get good work done. And there was pressure because at the end of the day, those are charge hours.

22:47 Like you've got to account for every minute. And so I would say that was like the beginning of kind of thinking operationally, which is like this mix of quantitative and needing to kind of track your time really, really well. And obviously prove that you're using your time well. Um, I didn't love the industry. I wanted to work for a startup at the time I was living in San Francisco. Ad tech was hot. Video advertising was hot. I found a really hot startup called bright roll, um, got in early and I joined the media team. So my first role there was effectively as a campaign manager, um, at an ad network focused on video.

23:23 But through that, that is, you know, an ad tech, that's a very quantitative, you know, it's a very quantitative. You run the company through numbers. Like they're talking about billions of ad requests and impressions and data points flowing through a platform every day. You have to be good at being quantitative. What happens at a company like bright roll, they grow, they have new needs. Um, I was always, I suppose, sort of there to raise my hand to jump on the next new project. And usually when you're starting something new, you got to operationalize it. Like you got to take it from like zero, which is like, there's nothing to it to how are

23:35Operator-first: from public accounting to CRO

23:57 we going to, you know, where's the spreadsheet that's going to track this thing? How do we get like general, um, you know, communication cadence in line? What do we need to do to get people organized? Like what's the Gantt chart look like? And so my first several years early in my career at a startup, we're doing that kind of work. Only it wasn't an ops job. It was, it was a customer facing job where that just was the need, um, ended up pivoting that into a sales engineering role. So that's where, um, in fact, I led that group there. And so that was, um, that's where you start to like sink your teeth and how to behave

24:31 well in meetings, how to be smart about listening and being a little bit of an empath, the client needs and starting to really put the right solution in front of them from there ended up going to a company turn, which was a DSP at the time they were, they were in the middle of a turnaround. And so I joined, um, a long time mentor, Bruce Falk to help him kind of reorth the company. Like they were, they were bleeding money. They needed to get to profitability. They needed some help, like really rethinking internal operations. And so I went from a job where it had to be operational to know a job where the job was to fix operations at the company.

25:12 Um, I loved it. I thought I was like fairly natural at it was, you know, be the way I described it, um, partly that into, um, ultimately a role at next door, doing the same thing, um, for, um, a long time friend who I'd worked with at turn Lauren Nemeth and kept it going. And at next door, I mean, I've, I've been in the next door eight years. It feels like I've had a hundred roles here. Um, I don't want to like go into all the nitty gritty there, but I would say like at the core is always focusing on what needs to go from zero to one and trying to take it there. And I think that always starts with trying to be organized, looking at the data, um,

25:55 focusing on the communication cadence. And so when I say I'm an operational leader, that's what I mean. I do think you can win, um, by finding the right rhythm, keeping the trains running on the tracks the right way and continuing to pull the right levers and continue to like look for the edge, you know, you're always kind of trying to find a seam or, or where to maybe pull the sticker back. Um, and, and that's what I mean by that. I love clients. I love actually interacting with the team. I know saying I'm not a sales leader sounds like I don't like people, but like I get my energy from the plan winning more.

26:29 So then I get it from, you know, having a great meeting or dazzling someone out in the real world. Yeah. I think that winning edge is the secret ingredient for any really good CRO. And I know a lot of rev ops professionals listen to this podcast, they, they follow what we're doing here at lean scale. And most of them, if you were to ask them where they see their future, especially in a C-suite position, they would say CRO. I know a lot of them have kind of come up through pure operational roles. Is there anything that you think someone sitting in a rev ops role should have as an experience

27:12 that would help prepare them for a CRO type of role or a path they should follow? Yes. Oh man. That's so much of my career and I feel like my, my answers probably changed over time. I think one of the most important things you get out of an operational role is you do get the ability to kind of see the whole elephant. And so for anyone in rev ops, especially at a larger company, like I would be absolutely pin seeking any opportunity you can to work on a new line of business, work on international expansion, work on, you know, sometimes they're painful, but like work on a re-ork and, and

27:53 all of that I actually think is that's seeing the whole elephant I think is incredibly important. I think it helps in decision-making. I think it helps you understand company strategy, maybe in other corners or departments of the company that you otherwise wouldn't engage with or won't be exposed to. And I think all that is what ladders up to, you know, being able to maybe capitalize on the opportunity to step into a bigger leadership role. I think maybe the answer some people seek is, hey, you got to pick your spot where you like own a number, like carry a bag or you got like a number, you know, you got a goal hanging over your head.

28:30 I do think that matters. I think, you know, it, I've since that turn job, I have always had 30% or more of my compensation tied to revenue outcomes. And so I feel like I have always felt the pressure of contributing to, you know, effectively like the top line. And we all know that feeds into the bottom line. And so I don't think owning a number so that you can say you own the number is the point. I think you have to go through a period somehow in some way where you feel the pressure because I actually think that's the thing when people say you got to carry a bag that you actually

29:10 have to, that's a life experience or the career experience that you have to go collect, kind of wrap this thought. I think the more I meet other executives and leaders in our industry, the more I realize they're not just sales leaders, they're incredibly operational. Some of them have like management consulting backgrounds. And, you know, I think probably, you know, my path was more of an ops guy that got comfortable in sales and started to better understand, you know, that world. And I think you go the other way too. You know, I think some people need help like learning the ops side.

29:14The RevOps-to-CRO path

29:47 And so I would say to anyone in like RevOps, like, don't run from RevOps. Don't like tell yourself, okay, this is like, you know, not something that's going to like serve me well in the future. I think it will. I just think it all comes down to getting exposure to new lines of business, something like international expansion. And if you do have an opportunity to like more fully own a number, jump on it. But I don't know that you have to seek it if that makes any sense. It does make sense. I think a lot of people would be sitting in the role thinking, oh, I need to jump out

30:19 and do an AE position or something to have the sales chops to get the respect as a CRO. And I think what you're saying is it's one path potentially, but it's more about did you own something strategic? See it through when the definition of whatever it is. And then I think if you're doing something like international expansion or reorging, and if you're really involved as a RevOps leader, you tend to get involved in the enablement side, which would put you in front of some customers or reviewing calls and seeing how things are going and then using that to create better process. And that might be the exposure you need to get that customer facing side.

31:03 You actually just hit on something I skipped over. I'm glad you brought that up, which is whether you're the one interacting with the customer or not, pay attention to what customers are saying. That is incredibly important, even if it's sort of like not your job because the customer feedback goes into the product team and the product team builds it back into the product. And then the product marketing team builds it back into the story and the sales team tells the story. Allow yourself to get disconnected from customer stories and what customers actually want.

31:33 That's actually how you don't get a CRO job or any senior leadership position on the business side. And so that's something I'd say, seek it out. Whether you guys, whether we use Gong, that's our kind of primary listening tool for most client meetings. I think everyone in my organization needs to be digging into what's going on in Gong because I think there's some real gold in there. And I actually think that's what, if we understand that well and we act on that well, and we make the right executive decisions on that well, that's what actually drives business forward.

32:05 Yeah, because no matter what role you're in, you're there to optimize the customer experience, the value the company is offering, and then you're organizing your go to market resources to maximize that impact too. So having that feedback, whether you're in finance, giving feedback on a comp plan or in RevOps, carving out territories, and figuring out where enterprises versus SMB, really, really understanding the customer is going to give you the context to make really good decisions, I think. Yeah. Well, that was for the RevOps leaders. I think this next part might be a little bit more for the CROs because I'm always interested.

32:45 Everybody has limited time and nobody gets more than 24 hours and I also like to sleep, so maybe I have less than others, and I'm always, always curious how people are spending their time splitting up their day, what their seasons and rhythms look like. Especially you, you're leading the core revenue motion, you're launching new monetization strategies, you're going through GTM redesigns while implementing agentic methods of go to market. There's a lot on your plate. How do you approach having the maximum impact you can in the limited time everybody has? I don't think I've ever nailed this, and I actually think you got to be comfortable with

32:59Stay close to the customer (and mine your call data)

33:25 that in that we're all busy and the trick is to do your best to prioritize and max out your time, but to also not be so particular that you miss opportunities to burn a little bit of time to go learn something or maybe it informs your thinking elsewhere. With Nirov, Nirov Tolia is our CEO at Nextdoor. Beginning of the year, we really, as an executive team, we started to really rethink this idea of priorities. Like we have OKRs as a company, we obviously have a strategy, we have goals, but sometimes in the pursuit of executing, especially given where we are as a public company, it's like two voluminous, there's like too much going on.

34:11 All that stuff gets like a little too short sighted because we're all hungry and we're trying to be world class athletes and we want to go win. He led a conversation with us, a series of conversations where we really focused on longer term priorities and that was for a couple of reasons. One, it was just a healthy thing to do, like you can't go too long before you're sitting down and reevaluating and refreshing long term priorities. Two, when he came back, he was our original co-founder, CEO, he left in 2018, he came back in 2024 and when he came back, he started rebuilding the company, rebuilding the management

34:52 team, transforming the product and there was a lot of people change there. Part of this exercise to focus on long term priorities, we didn't totally get it at the time because he's playing chess like that, but it was for us across the management team to understand where there was either a shared priority with someone else on the team or whether there is, oh crap, there's this moment where, well Kiernan wants to identify his team, great, but he can't do that without buying from Craig who runs our product organization and he actually oversees data and systems.

35:32 As an example, Craig and I have a shared priority around a Gentic transformation and so coming out of that, I came out of there with three priorities, first one was core revenue, got a deliver on the number, all of last year I spent almost all my time on that because I felt like I had to and so coming into this year, it was clear that I had an opportunity to bring in more senior talent to help oversee sales, we hired a new VP of North America, Anthony Demucchio to come in and really take the team to the next level. He's been here like barely three months, it feels like he's been here a year already but

35:35The four-priority, color-coded calendar

36:13 just all the change he's made, it was a good moment for me to like remember like you can actually hire people better than you even if they're in your org and they take things so much further and so for me, we're focusing on core revenue which is our ads business was like nearly all of my time last year, right now this year, I'm trying to make that be maybe about a quarter of my time and so that kind of represents one of my three core pillars and it doesn't mean I don't go to client meetings, you know, we just did an amazing dinner with one of our huge TOCO clients last week, we had a top to top with another

36:45 client earlier in the week, like I'm still going to customer meetings, I'm still meeting with customers but my time spent on the day-to-day part of sales and core revenue, it has gone down a little bit and that's because I hired a complimentary skill set that's way better than me at that part of what we need to do as a company and what does that enable? It's enabled for me to start to really focus on what are we doing next in monetization and that right now, it feels like a little bit like a science fair experiment to be candid like there's way more ideas on the table than we can deliver in, pretty broad range of both

37:26 upside and like super upside of are they going to be easy or impossible? Are they like totally on brand or they like a little bit out there even if they're good business ideas, maybe they don't make sense for next door and so I am spending, you know, again 10-15 hours a week thinking through that, working with Claude on some of that stuff, talking to the team, meeting with partners that, you know, a year or two ago we would have never even fought to meet with and all that is in service of trying to find the next new line of business or the next maybe scaled acquisition strategy when you start to think about some of the

38:08 models out there. The third pillar, we opened our conversation talking about that but that's this idea to combine the human team and what we can what can we do with a Gentec to just take our company further and then the other thing I'll say, I know I said three priorities and then I was like 25%, 25%, 25%. The last 25%, it's for your team, it's a little bit for everything else but it's intentional to focus on, you know, one-to-ones with, you know, people who report directly to you, critical skip levels and cross-functional partners and I color cut my calendar this way to be clear, like I literally stare at it and you

38:51 eyeball it but you try and you want it to be roughly speaking like a quarter blue, a quarter red, a quarter green, a quarter yellow. Those are the four colors I use because I like basic colors and that is a mechanism to kind of keep you on track and you can use it as like a little bit of a self-audit when, you know, maybe you've had a couple weeks where you felt like you haven't interacted with a customer or you can't remember what someone on your team has like said to you and you got to like double back and remember that, you know, there's the relationship side of how you work with your employees is actually just as important.

39:24 Yeah, I think it's really important to intentionally carve that out like you have. Otherwise, you can get lost in all of these things and grow distant from your team, grow distant from just kind of get out of touch if you get lost down these rabbit holes. You brought up new monetization strategies as a classic advertising model. Whatever you can share. I'd love to hear what's in your mind. What's the future of monetization and next door and just understand maybe what's opening up those new opportunities as well. Our core model is advertising. That's not going to change to be clear. So I'm not suggesting

40:12 we're going to pivot. What I'm seeking is additive. We have, you know, we have a platform with 110 million people. Yes, that's an audience for advertising. Yes. In the same way, investing in agentic is going to be a forever project, improving our advertising offering and improving what we give to marketers and agencies. That's a forever experience too. But there are other things that happen on next door that are transactions or potentially commercial in nature that aren't necessarily ad models. Like we have people every day posting saying like, Hey, I need a plumber. Does anyone have a good recommendation? And then you have a neighbor that comes in

40:51 and it's like, talk to this guy. He's great. And then you have another person come in and say, Hey, I actually am a plumber and I'd love to work with you. And so we're thinking through using that as an example of organic activity that's just happening on next door naturally. We're thinking about different ways to help the neighbor find their plumber faster to help the plumber in the neighborhood, find a new customer faster. And so that's like an example of something we're exploring where there's probably a revenue driving mechanism there. In fact, I know there is in there that we're excited to invest in. It's a little

41:25 bit outside of advertising, you know, where there's this whole other area that we're starting to think through, which is what do you do with like peer to peer commerce? For example, there are people who have an amazing chocolate chip cookie recipe and those same people make cookies for their family. And sometimes they make a ton and then they post on a platform like next door, like, Hey, like I've got a hundred dozen cookies available through the weekend, $10 a dozen stop on by. And so like, when you think about the gig economy, when you think about peer to peer transactions, I think it's the early, early innings for

42:04 us to really think through a smarter way to put a business model behind that. Yes, that's promotional in nature in some cases. So like advertising is a part of that, but it's not just pure lower funnel performance advertising that's going to help like build that out. You know, we're also thinking about what do we do with, you know, what do you do with data? We've got, again, we know a lot about our neighbors on next door. We know where they live. We know what they're interested in. We know what their community is like. We know who they engage with. We, we work with partners who can also tell us that, you

42:29What's next: plumbers, cookies, and the data graph

42:39 know, Mike Kiernan at X one one six Pacific street, uh, lives in a brownstone and it definitely doesn't have a pool. So let's not send Kiernan, uh, any sort of marketing related to pool cleaning or, uh, a pool basketball hoop. I'm a huge basketball fan. And so like, when you think about data as this, like, this, this, uh, this nexus of something that, that we feel very well positioned in and it's a big moat for us. There's a lot of interesting business models out there to go evaluate, um, from a revenue standpoint. We need to be thoughtful. We need to be strategic. Like we can't just give or sell our data. That's

43:16 not what we're doing, but we are thinking about different ways where our neighborhood graph, um, becomes a monetization asset on platform or off platform too. I love it. The more just value you're building into the product just opens up all these other potential doors. And absolutely you're sitting on a gold mine oil, well diamond mined of data that I'm sure would be really interesting for all kinds of people. And I also hope, uh, so my sister who also happens to be a go to market architect here at lean scale, she lives in New York. So she, uh, became a Knicks fan right at the right time. She just

43:56 moved there a year ago. I was like, yeah, I was like, do you get to be a fan? You've been there, you know, just bandwagon in on year one, but, um, she survived the, the festivities after two. What a great experience for the city. I, I'm a Warriors fan, but I was pulling for the next because I don't know how you don't in that case, crazy weekend, amazing team. What a run that was fun. Thank you so much for bringing all the insight to the podcast. I love the story. I love the operator trajectory that you've gone on. I think it's really inspiring for a lot of people who are in a rev op seat, go to market operation seat, and just seeing

44:38 what that path could be to get to chief revenue officer role. And I also think you're doing an incredible job with having some real sober approach, how you're going to bring agents into the go to market motions. I think that framework of where it would fit along your go to market life cycle is really, really helpful for those listening. And I am so excited to see what next door is doing next with all of the things that are on your mind and how you can bring more value to advertisers, customers, and help neighbors just get the most out of their experience and networking together. So Kiernan, thank you for being on the show

45:19 and can't wait to follow all you do. Awesome. I had such a blast today. Thank you, Anthony. Thanks for being a great host. And thanks for giving me a chance to catch up with you on this. Thank you.