The GTMnow Podcast

Today marks Aviv Canaani’s 5-year anniversary at Datarails! When he first joined Datarails five years ago, the company was 90% outbound, with analysts emailing inbound leads to SDRs once a week. Today it’s 90% inbound, 30x bigger, $70M Series C, and The Information named it the #1 startup of the year. 

Transcript:
Full interview transcripts can be found by episode at https://gtmnow.com/tag/podcast/ 

What you’ll learn:
- How Datarails flipped from 90% outbound to 90% inbound, and why they doubled down on inbound after the 2022 crash
- The Gong-inspired brand playbook: why “98% of marketing is noise” and how to be the 1% people care about
- Why niche memes for 0.1% of the market work (FP&A vs. accounting in-jokes)
- How to prove brand ROI: the four-way attribution model (HubSpot, open-form website question, SDR ask, Gong calls)
- Why his VP of Brand is the only report with no revenue KPIs, and how he measures brand instead (engagement from the ICP)
- The marketer-to-CRO path, and why he thinks one person owning the whole funnel is the future
- The “revenue architecture” waterfall model: working backward from a number to channels, meetings, and cost
- Why they killed their own category and relaunched as a “Finance OS,” and how to pull off category creation
- How he hires: the “biggest accomplishment” question, and screening for ownership over blame
- Why he automates everything in sales so reps only show up, follow up, and sell

Aviv Canaani, CRO, Datarails
LinkedIn: https://www.linkedin.com/in/avivcanaani
Datarails' website: https://www.datarails.com/
Datarails' career page: https://www.datarails.com/company/careers/

Sophie Buonassisi, Partner at GTMfund
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: Aviv Canaani is the CRO and CMO of Datarails, an FP&A platform the company now positions as a “Finance OS.” He joined roughly five years ago as its first marketing leader (VP of Marketing), later took over sales, and was promoted to CRO, overseeing the full revenue funnel across marketing, sales, growth, and partnerships. Under his tenure Datarails grew about 30x and was named a top startup of the year by The Information.

About GTMnow: The media brand, GTMnow, shares how the best companies get built, told from every perspective: founders, operators and investors, at every stage of company building. GTMnow is owned and operated by VC firm, GTMfund. 

Visit us: https://gtmnow.com
LinkedIn: https://www.linkedin.com/company/gtmnow
X: https://x.com/GTMnow_
IG: https://www.instagram.com/gtmnow_  
Tiktok: https://www.tiktok.com/@gtmnow_
YouTube: https://www.youtube.com/@GTM_now

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

George was a professional poker player, then CEO of a company that sold to Logitech for around $100M, and now he’s the CEO of Monk, an AI company automating accounts receivable.

Monk is an API company solving the other side of the ledger from Ramp: getting B2B invoices paid. George gets candid about the go-to-market mistakes he made (“50 more than I expected”), why vertical companies win on in-person workshops, the proprietary “harness” that he argues is the real moat in applied AI, the extreme-accountability culture he runs with 16 people and almost no meetings, and his sharpest tactical advice on fundraising, websites, and co-founder relationships.

Brought to you by:
Nooks - discover how revenue agents can transform your GTM at https://nooks.ai/gtmfund

Transcript:
Full interview transcripts can be found by episode at https://gtmnow.com/tag/podcast/

What you’ll learn:
- Why sales and marketing is “tier zero,” and why he used to believe the opposite (“if you build it, they will come” is wrong)
- Two lessons from pro poker that transfer to building: stay disciplined through variance, and adapt or get destroyed
- Why go-to-market has never been more nuanced, and why vertical companies are winning with in-person workshops and lunch-and-learns over cold email
- The pre-seed website bet: why spending big on a cohesive visual identity early lifted one company’s close rate ~50%
- The “harness” thesis: why owning your own evals, guardrails, and tests (not just calling the models) is the moat in applied AI
- How to run extreme accountability: everything in Slack, blameless retros, almost no meetings, 16 people
- Why they reverse-engineered into a huge-TAM problem on purpose (recruiting, and not getting disrupted by the frontier labs)
- Why hard ROI (dollars in your pocket) now beats “time savings” as an AI value prop
- Fundraising: compress the process to create FOMO, and why how you run the raise signals how you run the company
- Why the co-founder relationship matters more than the idea, and how to invest in it like a marriage

George, Co-Founder and CEO at Monk
LinkedIn: https://www.linkedin.com/in/georgekurdin
Monk: https://monk.com/

Sophie Buonassisi:
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: George is the co-founder and CEO of Monk, an API company that automates accounts receivable (collections and cash application) for B2B businesses using AI. He was previously CEO of Streamlabs, which sold to Logitech (reported around $100M) in 2019, and before his operating career he was a professional poker player for about five years. Monk is based in New York and has raised roughly $28M, including a Series A. His co-founder is Joe.

About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.

Visit us: https://gtmnow.com
LinkedIn: https://www.linkedin.com/company/gtmnow
X: https://x.com/GTMnow_
IG: https://www.instagram.com/gtmnow_  
Tiktok: https://www.tiktok.com/@gtmnow_
YouTube: https://www.youtube.com/@GTM_now

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

Legora went from $3.5M to over $100M in revenue in about a year, the fastest any company has ever scaled a direct-sales motion from zero to $100M. Then, they doubled revenue in less than 6 months and hit $200M ARR.

Patrick spent seven years at Braze, from the early days through IPO, before joining Legora (a vertical legal-AI company founded by Max, backed by Benchmark and Redpoint) at $3.5M in revenue. He shares the scaling journey. He also gets tactical on the three things he looks for before joining a company, why speed-to-value is the number-one leading indicator of revenue performance, the pilot that lets customers keep everything they build even if they walk, how he structures forward-deploy across legal engineers and traditional FDEs, the Jude Law and Aaron Judge campaigns and whether they paid off, the "8 Mile" objection-handling play, and the shift to consumption pricing.

Brought to you by:
Nooks - discover how revenue agents can transform your GTM at https://nooks.ai/gtmfund 

Transcript:
Full interview transcripts can be found by episode at https://gtmnow.com/tag/podcast/ 

What you'll learn:

• The 3 criteria Patrick uses before joining any company (founder, product, investors)
• Why speed and quality of implementation is the #1 leading indicator of revenue, and why teams over-index on sales and under-index on onboarding
• The pilot design that hands customers the IP, integrations, and workflows to keep (even if they don't buy)
• How to structure forward-deploy: legal engineers for use-case design, FDEs for enterprise integration
• Why he hires roughly 2 post-sale people for every 1 pre-sale
• The Jude Law and Aaron Judge brand campaigns: the real ROI case for B2B brand spend
• The "8 Mile" framework: disarming competitive objections by naming the competitor's move first
• How he screens for real AI fluency in interviews (and why "I summarized my Gong calls" fails)
• Moving the top product to consumption pricing, and what it did to the metrics
• Advice for operators on the fence about joining an AI-native company: bet on yourself, the window won't last

Connect with Patrick Faucher:
LinkedIn: https://www.linkedin.com/in/patrick-forquer-1419a5a

Connect with Host, Sophie Buonassisi:
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: Patrick Faucher is the CRO of Legora. He joined at roughly $3.5M in revenue and helped scale it past $100M in about a year, the fastest any company has taken a direct-sales motion from zero to $100M. Now, they’ve hit $200M ARR. Before Legora he spent seven years at Braze, from the early days through its path to IPO.

About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.

Visit us: https://gtmnow.com
LinkedIn: https://www.linkedin.com/company/gtmnow
X: https://x.com/GTMnow_
IG: https://www.instagram.com/gtmnow_ 
Tiktok: https://www.tiktok.com/@gtmnow_
YouTube: https://www.youtube.com/@GTM_now

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

The CMO of Samsara joins GTMnow to walk through exactly how she ran an AI transformation inside a public company, from a 2.5 week boot camp to 113 agents in production, all while keeping headcount flat and pushing pipeline and revenue up.

Meagan has led teams through platform shifts before (PLG, social, Covid) at MongoDB, DocuSign, Nieman, and now Samsara, and she argues AI is categorically different: not a new channel, but a production shift that changes how the work itself gets done. She gets tactical on the change-management sequence (learn by doing before you cap anything), how agents live in Slack for every function, the ABM pages that went from 2-3 weeks to under 30 minutes, the KPIs she tracks, how she interviews for AI fluency, and her message to anxious operators: this is a chance to leapfrog, not a threat.

What you'll learn:

• Why AI is a production shift, not just a new channel, and what that changes about running a team
• The change-management order that works: let people learn and play before you put cost caps on
• Inside the 2.5-week AI boot camp (vibe-coded LMS, hands-on agent build, present-back) that trained half the org
• Why she democratized agent-building into every function instead of centralizing an AI team
• How 113 agents run in Slack across events, sales, ADR support, and creative
• The rebrand that hit the market in 3.5 weeks instead of six months
• ABM landing pages from 2-3 weeks to under 30 minutes, and content from weekly to 10 a day
• How she keeps headcount flat: backfill differently, raise the bar on output
• How she interviews for AI fluency, and why you can't earn a top calibration score without building agents
• Her advice to anxious operators: build agents to leapfrog leadership, don't wait

Connect with Meagan:
LinkedIn: https://www.linkedin.com/in/meageneisenberg

Host: Sophie Buonassisi, SVP at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

Thank you to our sponsor:
@NooksHQ - discover how revenue agents can transform your GTM at nooks.ai/gtmfund

About the guest: Meagan is the Chief Marketing Officer of Samsara, a public company on the NYSE. She has led marketing through major platform shifts at MongoDB, DocuSign, and Nieman, and has a background in MIS and computer science, starting her career as an IT engineer before moving into marketing.

About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.

Visit us: https://gtmnow.com
LinkedIn: https://www.linkedin.com/company/gtmnow
X: https://x.com/GTMnow_
IG: https://www.instagram.com/gtmnow_ 
Tiktok: https://www.tiktok.com/@gtmnow_
YouTube: https://www.youtube.com/@GTM_now

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

Information has never been more abundant, and trust has never been harder to earn. That's the tension at the heart of LinkedIn's new research, "The Trust Advantage," and Catherine, who leads marketing for LinkedIn's Sales Solutions business (Sales Navigator), joins Sophie Buonassisi on GTMnow to unpack it. The headline gap: 86% of B2B buyers say expertise is what builds trust, but only 45% describe the sellers they meet as trustworthy.

Catherine has spent 25+ years in marketing, including 13 at Meta, and now runs a global team out of Singapore. She argues AI has made "spray and pray" easier than ever, which is exactly why the winning move is doing less, more relevant outreach. She breaks down the four behaviors that separate top sellers, why warm introductions convert so much better, what a seller's LinkedIn profile should actually say, and how putting your expertise out publicly now helps both you and your company rank in AI search.

What you'll learn:
- The trust gap: why 86% of buyers want expertise but only 45% find sellers trustworthy, and how to close it
- Why expertise in a first conversation means leading with their problem, not your product
- The case for less outreach: more signal means you can be far more selective
- The four top-seller behaviors: signal-based selling, early multithreading, timely engagement (hours not weeks), and genuinely personalized outreach
- Why warm intros win: ~3x higher email response and ~2x higher connection-acceptance than cold
- The most underrated entry point: executive sponsors and former customers who moved companies
- What a seller's LinkedIn profile should be (a point of view, not a resume), and why profile views are a top buying signal
- The algorithm and discoverability: how posting even once a week, and engaging on others' posts, compounds
- Why LinkedIn is now the most-cited domain for professional queries in AI search, and what that means for you
- Hiring in the AI era: adaptability and generalists over specialists, and "throw your hat over the wall"

Connect with Catherine:
LinkedIn: https://www.linkedin.com/in/catherineflynn/

Host: Sophie Buonassisi, SVP at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: Catherine leads marketing for LinkedIn's Sales Solutions business, home of Sales Navigator. She has 25+ years in marketing, including consumer and agency roots and roughly 13 years at Meta/Facebook, and is based in Singapore, where much of the Sales Solutions business is being built across APAC.

About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on YouTube: https://www.youtube.com/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.com/gtmnow_/

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

The CMO of Nooks (and former CMO of Jasper) joins GTMnow to explain why buying more agents won't grow revenue unless you rebuild the process underneath, and what the human-plus-agent revenue team truly looks like.

Loreal has had a front-row seat to two AI waves: first at Jasper, where AI reshaped marketing content, and now at Nooks, building toward what she calls the revenue agents category. She breaks down why the tools in today's GTM stack were built for humans to click through, not for agents to execute; why the org chart and the process both have to be rethought from the ground up; and why the real shift isn't reps prompting AI, but AI prompting reps. She also gets into the misconception that agents are easy to build, the CMO-CRO alignment model she runs with her counterpart Hannah, and why the marketing pendulum is swinging back from pure performance to brand.

What you'll learn:
- Why bolting AI tools onto pre-AI processes fails, and what a real revenue operating system requires
- The iceberg model of human vs. agent work, and why the waterline keeps rising
- Why the future flips: AI stops waiting for prompts and starts prompting the rep
- Augmentation over replacement: if an agent makes a rep 10x, you hire more reps, not fewer
- The results some teams see: ~3x meetings booked and ~2x pipeline on the same headcount
- Why "agents are easy to build" is a trap once you need shared data, governance, and calling/email infrastructure at scale
- What stays human: judgment, narrative, and reading the room (the surf-small-talk story)
- The CMO-CRO alignment model: shared pipeline goals instead of fighting over sourced-lead credit
- Why marketing's pendulum is swinging back from performance to brand in the AI era
- Why starting with a wedge (the dialer) and its conversational data beats selling a broad platform

Chapters:
00:00 Cold open: augmentation not replacement, and AI that prompts the rep
01:14 Welcome, and why she left Jasper's AI wave for Nooks
03:26 Seeing AI from every side: customer, board, now operator
04:27 The iceberg: human work above the water, agent work below
05:13 What humans do best vs. what agents do best
07:14 The real question isn't how many agents, it's who prompts whom
07:31 Augmentation over replacement: make a rep 10x, hire more
08:37 The results some teams see, and what's next
09:56 Why bolting AI onto old processes fails|12:06 The misconception that agents are easy to build
13:58 Going AI-native inside her own marketing org
15:10 The framework for what goes to headcount vs. agents
16:19 What stays human: judgment, context, and the naming story
17:32 CMO-CRO alignment: shared systems and shared metrics
19:43 How she and her CRO run pipeline without sourced-lead targets
21:40 What's changed, and what still works: the pendulum back to brand
23:42 What she's excited to build at Nooks
25:10 Who's winning with Nooks: the AI-native early adopters
27:06 Rapid fire: leadership, impact over activity, no time for bad wine
28:25 Who Nooks is hiring, and where to find Loreal

Connect with Loreal Lynch:
LinkedIn: https://www.linkedin.com/in/lorealesque/ 

Host: Sophie Buonassisi, SVP at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: Loreal Lynch is the Chief Marketing Officer of Nooks, a revenue agents platform that started with an AI dialer and expanded across the sales engagement stack. She was previously CMO of Jasper, and earlier held marketing leadership roles at Salesforce, Tableau, and Stripe. Nooks' customers include Cursor, Replicate, Deel, and HubSpot.

About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on YouTube: https://www.youtube.com/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.com/gtmnow_/

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

Chris McDonough has joined four companies right before they exploded. At the first, Motive, he was employee 40 and watched revenue go from $800K to $30M in about 100 days. The VP of Sales at Campfire joins Sophie Buonassisi on GTMnow to break down what he learned riding hypergrowth over and over, and why he thinks AI is about to split the sales profession in two.

Chris gets tactical on the whole arc: how a two-week decision to sign a lease and move to SF changed his trajectory, what a federal mandate taught him about compelling events, why your career growth is tied directly to how fast your company grows, and how he now builds an AI-native sales org from scratch at Campfire (an AI-native ERP taking on the legacy giants). He also makes the contrarian case that AI won't replace reps but will widen the gap between them, why AI outbound is mostly spam for complex B2B, and why a strong SDR bench is existential.

What you'll learn:

• The $800K-to-$30M-in-100-days story, and what a compelling event really looks like
• Why your career trajectory is tied to your company's growth rate ("you can't be a VP if there's no one to be VP of")
• The contrarian AI take: not labor replacement, but a top 30% worth triple and a bottom 20% that's hard to employ
• What he hires for now: not just skill, but whether you can self-learn from AI on day one
• How to build an AI-native sales org with no tech debt (the deal dashboard that grades every call against every win and loss)
• Why AI outbound mostly becomes a spam tool in complex B2B, and why the SDR bench matters more
• Why he leaves once a company is big enough to run Workday, and goes back downmarket
• How to sell into the "real economy," where nobody cares about your hot VC and references are hyper-local
• Regrettable churn: the retention metric behind Samsara's run, and why top reps compound
• One-way vs. two-way doors: how to make fast decisions at 70-80% of the data

Chapters:
00:00 Intro
01:17 Welcome, and a career of joining companies right before they explode
01:51 Employee 40 at Motive, and the two-week decision that changed everything
04:19 The federal mandate, and the hiring class that got promoted in 30 days
05:33 Why career growth is tied to company growth rate
07:12 The mandate story: from selling nothing to 70 demos a week
10:19 Was it the wrong decision? Believing through the objection
10:56 What 800-900 demos in 3 months does to a seller
12:11 Samsara: scaling an office 0 to 100, and 250 interviews in 90 days
13:42 The contrarian hiring philosophy: the 10x seller and the widening gap
15:59 Why he left Verkada for Campfire, and the "Workday rule"
18:41 Building an AI-native sales org with no tech debt
21:14 What Campfire is: AI-native ERP and one of software's last moats
25:25 Expanding the TAM and the recession-proof case
26:12 Selling into the real economy: hyper-local references, not hot logos
28:26 His honest take on AI outbound and AI SDRs
30:49 The SDR org as your existential talent bench
31:56 The metric he obsesses over: regrettable churn
33:45 Who Campfire is hiring, and "will Claude kill this company?"
35:33 Rapid fire: leadership, execution over competitors, one-way vs. two-way doors
40:19 Where to find Chris, and how to actually DM your way into a job

Connect with Chris McDonough:
LinkedIn: https://www.linkedin.com/in/chris-mcdonough-94546626/

Host: Sophie Buonassisi, SVP at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: Chris McDonough is VP of Sales at Campfire, an AI-native ERP company competing with legacy incumbents like NetSuite. He was previously at Verkada, and earlier helped scale Motive (formerly KeepTruckin) from $800K to roughly $100M in revenue and Samsara through hyperscale, opening new-market offices in Nashville and Atlanta.

About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.

Visit us: https://gtmnow.com
LinkedIn: https://www.linkedin.com/company/gtmnow
X: https://x.com/GTMnow_
YouTube: https://www.youtube.com/@GTM_now

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

The founder and CEO of Electric, Ryan Denehy joins GTMnow to explain why and how he rebuilt Electric as an AI-native software company.

Ryan gets specific on why he split the business in half, how the pivot forced a total change in distribution (from direct sales to embedded channel partnerships with payroll platforms), and why a new product doesn't just need a new channel, it can unlock ones that were impossible before. 

He also shares the ADP partnership that put Electric behind 1,700 reps, the near-death moments (including the night he almost wired his seed round back to investors), how to actually get acquired by a public company, and the cold-outreach framework he's used since making extreme-sports videos at 17.

What you'll learn:
- Why he rebuilt a working company AI-native, and the five-step playbook for a "total reinvention"
- Why product-market fit is as much about distribution as the product, and the Sirius XM lesson behind it
- How going AI-native collapsed his unit price and made channel-led growth possible for the first time
- Why the winner-take-all gap between AI companies is so much wider than in classic SaaS
- The embedded-partnership motion behind ADP, Justworks, and TriNet deals (300+ customers onboarded in a day)
- How to actually get acquired by a public company (hint: people buy companies, corp dev doesn't)
- Why the quietest near-death threat is a splashy senior mis-hire, not a market crash
- The cold-outreach framework he's run since cold-emailing pro athletes at 17

Chapters:
00:00 Intro
01:04 A 3x founder who sold two companies to public acquirers
01:33 What Electric is, and why "AI" was in the name in 2016
04:40 What a "wholesale rewrite" meant
06:38 Why go AI-native
08:12 The reinvention playbook
13:08 Why they blew the whole thing up
13:48 Distribution as product-market fit: the Sirius XM lesson
15:37 How AI collapsed the price and unlocked channel sales
18:19 The winner-take-all gap between AI companies
20:35 From direct sales to channel
23:00 The three-year channel payoff
25:17 Rebuilding the product and signing the payroll platforms
26:27 The new-category pitch
29:29 Behind the scenes for ADP, Justworks, and TriNet
30:02 Almost wiring the seed money back
32:00 The day everything changed at once
33:52 The quiet damage of a senior mis-hire
35:48 Two prior companies: go-to-market above all
38:18 How to get acquired by a public company
42:55 Extreme-sports videos at 17, and the outreach framework
44:47 Where to find Ryan and Electric

Connect with Ryan Denehy:
LinkedIn: https://www.linkedin.com/in/ryandenehy/ 
X: https://x.com/DenehyXXL
Electric: https://electric.ai

Host: Sophie Buonassisi, SVP at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: Ryan Denehy is the founder and CEO of Electric, an AI-native IT management platform now embedded in payroll and HR products including ADP Team Management, Justworks, and TriNet. A three-time founder, he previously built and sold companies to USA Today and Groupon. Electric is backed by investors including Notable Capital and Slack.

About GTMnow: GTMnow is the media arm of GTMfund, sharing the strategies, tactics, and stories from the operators and investors building the next generation of go-to-market.

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on YouTube: https://www.youtube.com/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.com/gtmnow_/

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

Ross Rich is the co-founder and CEO of Accord and spent five years leading go-to-market and partnerships at Stripe. He talks to hundreds of CROs and serves thousands of reps, so he has an unusually clear view of what the top performers actually do differently.

His starting point: roughly the top 20%, often closer to 10%, of any sales team drives most of the revenue. Every leader says they want to move the middle 60%, and Ross doesn't think AI is doing it. Tools like Claude and Codex make the people who already have the taste and judgment far more efficient, and the gap widens from there. What closes it is unglamorous and human: a leader with a point of view, a shared language simple enough to stick, a field-friendly process, and only then the technology to reinforce it.

Ross gets specific on what "best" means for a seller (trust and EQ first, then frameworks learned so cold they run subconsciously), the disconnect between what CROs think they're buying and what reps actually receive, the "no-ask note" for multithreading into a CRO, why he sells through his own executives instead of around them, and the biggest lesson of his founder journey: market beats product.

What you'll learn:
- What separates the top 10% of reps from everyone else, and why AI is widening that gap instead of closing it
- The two ingredients of a great seller: the "give a shit factor" you can't fake, then plays run so subconsciously you can get creative
- The waiter analogy that explains great salesmanship in one sentence
- Why the people, process, technology order is the one most teams get backwards in the AI rush
- The disconnect between a CRO's multimillion-dollar investment in the field and what reps actually receive: a 76-page laminate, more Salesforce fields, none of it touching the customer
- Why the best methodology is simply the one that gets used, and why debating how many Ps are in MEDDPICC is optimizing the fringes
- "Unavoidable excellence": how to take what your top performers do organically and make it standard across the team
- The "no-ask note" for multithreading into a CRO by showing respect instead of asking for time
- Why CROs own revenue and not tools, and how to sell through their rev-ops and enablement leaders
- "Show, don't tell": leading with peer references at stage two when everyone can sound the same and ship a surface-level solution
- The founder-led sales handoff mistake Ross has made twice, and the curse of knowledge behind it
- Why market beats product, via April Dunford's positioning and the surfer, surfboard, wave framing

Connect with Ross Rich:
LinkedIn: https://www.linkedin.com/in/rossrich/ 

Host: Sophie Buonassisi, SVP at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About the guest: Ross Rich is the founder and CEO of Accord, a platform that operationalizes value selling (quantified business cases, mutual action plans, stakeholder mapping, account planning) in a field-friendly way. Before founding Accord, he spent over five years at Stripe leading go-to-market and partnerships. Accord's customers include Freshworks and Samsara.

About GTMnow: GTMnow is the media arm of GTMfund, sharing how the best in tech build, scale and invest.

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on YouTube: https://www.youtube.com/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.com/gtmnow_/

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content. 

Is Salesforce the dominant player in the AI platform shift, or the incumbent about to be disrupted? Kris Billmaier, EVP and GM of Agentforce Sales and Growth Products, sat down with Sophie Buonassisi at Salesforce Tower to answer that directly.

Kris runs the business behind Sales Cloud's 26-year run and its rebrand into Agentforce Sales. He makes the case that CRM is becoming "agentic revenue orchestration," that the category needs a new name, and that the future is headless. For Salesforce, that means surfaced inside Slack, ChatGPT, Gemini, and wherever sellers actually work. He also shares the internal numbers, including an engagement agent that worked the leads Salesforce had always ignored and generated over $100M in pipeline in eight months.

What you'll learn:
- Why 60% of a seller's time goes to non-selling work, and which agents remove it
- The case for renaming the category from CRM to agentic revenue orchestration
- What "headless CRM" means, and why Salesforce integrated with ChatGPT and Gemini
- How one leader manages 100 reps plus the equivalent of 400 agents
- Why the Momentum acquisition matters: "memory fragments" that cut an 8,000-word meeting to the 800 words that count
- Why Salesforce is hiring more sellers, not fewer
- How hiring shifted from "what did you do" to "how do you build" (and why a PowerPoint is now a red flag)
- Pricing in the agent era: seats, flex credits, and a coming leads-worked outcome metric
- Why Kris says we're not in a SaaSpocalypse, and how a 70,000-person company still ships weekly

Thank you to our sponsor:
Primer unlocks B2C ad channels for B2B marketers with precision targeting and next-gen measurement. GTMnow Network exclusive offer: Extended 45 day trial and 15% off with code GTM15 - just apply the code when you go to upgrade from the free trial. See who’s really in your funnel: sayprimer.com

Chapters:
00:00 Intro
01:12 Welcome, and the Salesforce platform-shift question
02:25 How Salesforce adapted across cloud, mobile, social, and AI
03:32 Why Sales Cloud became Agentforce Sales
05:17 Renaming the category: from CRM to agentic revenue orchestration
06:56 Will anyone log into a CRM again?
08:09 Agentforce in one line, and the seller's Monday morning
09:08 Build vs. buy, vibe coding, and the context moat
11:01 The Momentum acquisition and memory fragments
13:04 Sellers managing teams of agents, and the $100M pipeline story
15:03 The agent stack: prospecting, engagement, pipeline, quoting
16:27 Efficiency, accuracy, and auto-generated forecasts
18:03 Why Salesforce is hiring more sellers
19:16 What the modern sales role looks like
20:08 Sponsor: Primer
21:34 How AI changed hiring: from "what" to "how"
23:48 The window: shipping weekly, not on three annual releases
25:13 What product-market fit means now
26:05 Software vs. services, and the $10T question
28:10 The complexity problem: easy by default, advanced by choice
30:07 Go-to-market evolution and consolidating the stack
32:07 Leading as a player-coach
33:16 Being "chief repetition officer" and educating the field
35:00 How a 70,000-person company stays agile
36:48 The biggest lesson from Marc Benioff
37:57 Pricing: seats, flex credits, and outcome-based metrics
40:53 Are we in a SaaSpocalypse? The full answer
42:08 Where Kris gets his learnings
43:07 World Cup picks

Kris Billmaier (EVP and GM of Agentforce Sales, Salesforce)
LinkedIn: https://www.linkedin.com/in/krisbillmaier/
Salesforce Agentforce: https://www.salesforce.com/agentforce

Sophie Buonassisi (Host, SVP at GTMnow/GTMfund)
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

About Kris Billmaier:
Kris Billmaier is EVP and GM of Agentforce Sales and Growth Products at Salesforce, where he leads the business formerly known as Sales Cloud. He oversees the company's agentic sales portfolio, including its prospecting, engagement, pipeline, and quoting agents, and the Momentum acquisition that powers its conversational data layer.

About GTMnow: 
GTMnow shares how the best in tech build, scale and invest. The media brand is owned and operated by venture firm, GTMfund.

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on YouTube: https://www.youtube.com/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.com/gtmnow_/

The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.