The Co-Founder & CEO of Merge joins GTMnow to break down how she built a company that now powers integrations for OpenAI, Perplexity, Netflix, Uber, Mistral, and enterprise logos like Mastercard, JP Morgan, and Amex, backed by $75M from Accel and NEA.

Shensi gets tactical on the GTM decisions behind that growth: why she went enterprise-first into greenfield, why she's now layering a self-serve motion back on top (20,000+ self-serve orgs, 400+ enterprise customers), how forward-deployed engineers turned a 1% edge case into 5 to 10x usage growth, and why she rebuilt marketing to run like an engineering team. She also gets candid on founder-led sales, the mercenaries-versus-missionaries hiring trap, the open-source model shift and the China question, and why every founder who started pre-AI should build one product 0-to-1 themselves.

What you'll learn:
- Why she reversed the standard GTM playbook (enterprise first, then PLG) and how to run both motions at once
- How forward-deployed engineers close the 1% edge case that unlocks 5 to 10x enterprise usage
- Why marketing now runs like an engineering function at Merge, and how it took her from 1 to 2 dinners a quarter to 3 to 5 a month
- Why product got fast and go-to-market became the new bottleneck
- How to know when to hire your first salesperson (hint: you should be "dying" first)
- The mercenaries-vs-missionaries test, and the "anti-sell" she uses in hiring
- The 2026 shift away from "token-maxing," and how model routing cuts AI spend
- The truth about open-source (often Chinese) models: where they're built vs. where your data actually lives
- Why founders who started pre-AI should build one product 0-to-1 to understand what's now possible

Chapters:
00:00 Intro
01:14 What Merge does: products, workforce, and three core offerings
02:05 Agent Handler, Gateway, and the new Embedded Routing Stack
04:52 The 2026 shift away from "token-maxing"
07:29 Open-source models, the China question, and where data really lives
10:14 How Merge works with open-source model providers
12:00 What she's learned as a first-time founder: get over your ego
13:22 Reversing the GTM playbook: enterprise-first, then PLG
15:50 Running both motions: 20,000+ self-serve, 400+ enterprise
17:31 Why buyer behavior moved to Twitter and brand
19:06 Founder-led sales, and what a real sales process taught her
22:27 When to hire your first salesperson
23:49 Forward-deployed engineers and 5 to 10x usage growth
27:00 Keeping go-to-market up to speed with product
28:33 Rebuilding marketing as an engineering function
30:45 The dinner agent: 1 to 2 a quarter to 3 to 5 a month
31:24 How AI buying reshaped the marketing org
33:54 Maintaining agents: prompts over legacy builders
35:02 Mercenaries vs. missionaries, and the "anti-sell"
40:25 The market view: from hostility to collaboration
42:06 Is a valuation reckoning coming?
43:07 Why she stayed hands-on building Agent Handler and Gateway
45:18 What's next: training your own models off open-source
46:52 Where to find Shensi and Merge

Connect with Shensi Ding:
LinkedIn: https://www.linkedin.com/in/shensiding/
X: https://x.com/shensi
Merge: https://merge.dev

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

About the guest: Shensi Ding is the co-founder and CEO of Merge, a unified API platform that now spans product integrations, agent tooling, and LLM routing/governance. Merge powers companies including OpenAI, Perplexity, Netflix, Uber, and Mistral, and enterprise customers like Mastercard, JP Morgan, and Amex. The company has raised $75M from Accel and NEA.

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

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. 

Are your sales compensation plans driving the right behaviors or causing your best reps to quit? In this episode of GTMnow, Brian Le (Global Sales Compensation Partner at Notion) breaks down how to build a scalable sales comp operating system.

Brian shares his firsthand experience scaling Notion's sales comp from 80 to over 400 employees and explains why trust is the ultimate currency in revenue operations. If you are a founder, revenue leader, or sales professional, this breakdown covers everything from structuring pay mix to identifying the earliest signs of comp plan degradation. You will even hear what it takes for top AEs to pull in upwards of $1 million in a single quarter.

In this episode, we cover:
00:00 Intro
01:15 Brian Le's journey through Salesforce, Carta, and Notion
04:33 Why sales comp is the operating system for go-to-market
07:07 Phase 1: Building a scalable comp foundation at Notion
13:50 Transitioning from seat-based to usage-based pricing models
18:15 The 3 core pillars of a successful sales commission plan
22:09 Early warning signs your quota and comp structures are breaking
31:41 The real cost of losing sales reps over bad commission payouts
39:35 How to structure compensation for your first early-stage sales hires
42:39 Will AI agents replace SDRs and sales compensation?

Connect with Brian Le, :
LinkedIn: https://www.linkedin.com/in/brianhoangle/

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

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. 

"Investing in companies that OpenAI won't kill." That's Vanessa Larco's thesis, and in this VC bonus episode of GTMnow she breaks down exactly how she decides what survives. Vanessa, founder and GP at Premise (formerly a longtime partner at NEA, where she backed Robinhood from seed to IPO), joins Max to get into the nitty gritty of how AI is rewriting venture, distribution, and the entire go-to-market playbook.

She makes the case for why "it's just a wrapper" got a lot of VCs in trouble, why she only backs technical founding teams, and why the old GTM playbook is breaking fastest exactly where you'd least expect it. She also opens up about leaving a big platform to build a two-person fund from a blank canvas, and why she treats the fund itself like a startup.

What you'll learn:
- The "OpenAI won't kill it" framework for spotting durable AI companies (and why not everything OpenAI ships actually wins)
- Why the "it's just a wrapper" dismissal cost VCs real deals, and the kayak/AWS parallels that explain why
- Why Premise only backs technical founding teams, and the shipping speed that becomes the real early moat
- How the old go-to-market playbook is breaking, especially in DevTools, and what replaces it
- Why someone on the founding team has to "nerd out" on distribution, and why no-playbook moments are where you growth hack
- How to run a conviction-based investment committee, and why big funds drift toward consensus whether they like it or not
- Why running a fund is just running a startup: fundraising, product, and customer success by another name
- The unanswered question Vanessa keeps circling: how to give experienced GTM talent space to rewrite the playbook

Chapters:

00:00 Intro & OpenAI Moats
01:12 GTMnow Intro
01:51 Technical vs. Non-Technical AI Founders
04:37 The Bottleneck of Hiring AI Talent
05:15 Do Old Moats Still Exist?
06:36 Cloud Era Lessons vs. Today's AI Layer
09:18 The Shift to the Distribution Era
11:38 Interview: Vanessa Larco (Premise VC)
12:40 Companies OpenAI Won't Kill
13:37 Consumer Habits vs. Enterprise AI
15:05 Moving Beyond the "Wrapper" Stigma
17:39 Thesis Building vs. Founder Curiosities
20:11 Sourcing & The "Surreal" Community
22:26 Learnings From NEA & Lightspeed
24:06 Rethinking the Investment Memo
26:43 Consensus vs. Conviction Investing
31:26 Running a VC Fund Like a Startup
35:04 Building Internal Automation Tools
37:35 Distribution Moats & DevTools
39:38 Sourcing New GTM Playbooks
41:12 Parallel to the AWS Boom
43:55 Human Psychology vs. AI Tools
47:06 SF's Best Cookie Spots
48:32 Outro

Connect with Vanessa Larco:
About the guest: Vanessa Larco is the founder and GP at Premise. Previously a partner at NEA, she backed consumer and fintech companies including Robinhood from seed through IPO. She started her career in product and engineering, was a computer science undergrad, and founded and sold her own startup before moving into venture.

Connect with Max: 
https://x.com/hackitmax
https://www.linkedin.com/in/maxaltschuler/

Connect with Vanessa:
https://www.linkedin.com/in/vanessalarco/
https://x.com/veelarco

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. This is the VC bonus series, where we host VCs and get into the VC ecosystem.

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. 

A $1.2 billion exit is the dream. Elias Torres calls it his biggest failure. The Drift co-founder joins Sophie Buonassisi on GTMnow to unpack why the headline number felt hollow, what he learned in the quiet stretch afterward, and why he jumped straight back in to build Agency, an AI company that runs your entire customer organization.

Elias gets honest about identity after the exit, the difference between chasing a title and building something enduring, and the operating thesis behind Agency: a billion-dollar company with fewer than 100 people, where 80 to 90% of the team are engineers and everyone talks to customers. He also gets into distribution as the hardest problem in the AI era, why he only takes money from investors who lead with value (Pat Grady and Brian Halligan back the company), and the two decades he's spent building alongside David Cancel.

What you'll learn:
- Why a $1.2B exit can still feel like a failure, and what "enduring" actually means
- How to rebuild your identity when the title goes away
- The Agency thesis: $1B with under 100 people, and how AI agents make it possible
- Why Elias runs the whole company on Agency itself, with no CRM
- Why sales may be the last role AI eliminates, and what that means for GTM
- How to spot investors who lead with value instead of a pitch deck
- Why distribution, not product, is the hardest problem in the AI era
- What 20+ years building with David Cancel (Performable, HubSpot, Drift) taught him about partnership

Chapters:
00:00 Intro
02:25 Time off, slowing down, and losing the title
04:00 The inflection point and what comes after a big exit
07:00 What Agency is and the problem it solves
11:00 Why he brought people he's known for years
11:40 Investors who lead with value (Pat Grady and Brian Halligan)
17:30 Building with David Cancel for 20+ years
23:00 The bold claim: $1B with under 100 people
26:00 The go-to-market motion behind it
28:30 "Sales is the last role AI will eliminate"
36:00 High-agency people and how Agency runs itself
42:00 Building distribution in the AI era
51:00 Where to find Elias and Agency

About the guest: Elias Torres is the founder and CEO of Agency, an AI company that provides agents to run a company's customer organization. He previously co-founded Drift (acquired in a $1.2B deal) and held senior roles at HubSpot and Performable, building alongside David Cancel for over two decades. Agency is backed by Pat Grady (Sequoia) and Brian Halligan.

Connect with Elias Torres:
LinkedIn: https://www.linkedin.com/in/eliast/
X: https://x.com/eliast

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

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 single most expensive sentence in sales is "I'll follow up on that." Adam Liska joins Sophie Buonassisi on GTMnow to break down the "execution gap," the space between knowing what to do in a deal and actually doing it, and why that gap is where most pipeline quietly dies.

Adam left DeepMind's Gemini team in 2022, pre-ChatGPT, to build a native revenue execution platform now serving 200 customers across 20 countries (recently rebranded and fresh off a $20M Series A). In this conversation, he gets specific on what is actually changing in the sales role, what should be automated, and why he thinks this is about to be the golden age for sales reps.

What you'll learn:
- Why "I'll follow up on that" is the most expensive promise in revenue, and how the execution gap compounds from rep to manager to CRO
- What parts of the rep workflow to automate now (research, CRM updates, business cases, follow-ups) and what stays human
- Why AI is squeezing middle management, not reps, and flattening GTM orgs
- How per-rep coaching changes when every call is recorded, shared, and analyzed for patterns
- The "corrective action" approach to coaching deals on the job, in real time
- How to sell globally when borders disappear but local-language talent still matters
- Why in-person events drove 70% of early pipeline, and how that compounds with cold calling
- How to keep your team at the AI frontier by never locking into a single model
- Adam's #1 piece of advice for first-time founders (hint: it starts with your co-founder)

Chapters:
00:00 Why AI won't replace sales reps
00:22 Leaving DeepMind's Gemini team pre-ChatGPT
01:18 What airspeed does and the "execution gap"
02:07 "I'll follow up on that": the most expensive promise in sales
03:28 The $20M Series A and the rebrand from Glyphic
05:30 Why walk away from frontier AI research at DeepMind
07:17 Leading when the frontier models keep changing
08:39 Buy vs. build, and keeping customers at the AI frontier
11:03 Landing the first 200 customers across 20 countries
12:41 Advice for first-time founders
14:04 Selling globally and what AI changes about language
17:07 What the sales rep role looks like in an AI-first world
19:24 How reps and leaders should start automating today
20:51 The channels driving results right now
22:41 How AI makes per-rep coaching actually work
25:14 Building an execution-first culture
27:10 The DeepMind departure story
28:51 Building in London vs. selling in the US
30:43 Adam's favorite AI use case as a busy CEO
31:26 The biggest misconception about AI in sales

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

Guest: Adam Liska, Co-founder and CEO at Airspeed
X: https://x.com/adliska
LinkedIn: https://www.linkedin.com/in/adliska/

About the guest: Adam is the co-founder and CEO of Airspeed (formerly glyph), a native revenue execution platform that closes the gap between knowing what to do in a deal and executing on it. Before founding the company, he worked at DeepMind on the team that became Gemini. 

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. 

Benchmark's Chetan breaks down why the path from $0 to $100M has collapsed from five years to under two, and the one thing that is actually getting harder in the AI era: reaching your first million in revenue. In this VC bonus edition of the GTM Now Podcast, he sits down with Sophie Buonassisi to unpack how AI native companies are compressing 180 day sales cycles into 30 days, why direct sales is here to stay, and how value is shifting away from code toward the last mile of customer service.

Using Legora (legal AI) and Manus as case studies, Chetan explains how Benchmark builds conviction fast, why the marginal cost of code trending to zero changes everything, and what separates the founders who win this window from the ones who miss it.

What you'll learn:
- Why the first $1M now takes longer than the next $99M in the AI era
- How top AI startups compress a 180 day sales cycle into 30 days
- The "trusted vendor" playbook for breaking incumbent distribution advantages
- Why Legora embedded inside a law firm for a year before launching
- How a magical demo plus a tightly scoped pilot collapses six month deals
- Why value is moving from the product build to the service and outcome
- What Benchmark actually looks for: technical insight that creates demand pull
- Why direct sales and forward deployed engineers are exploding in AI
- How buying one AI app triggers an enterprise to buy 100 more

Chapters: 
00:00 Intro
01:13 Why Max + Paul were furious taking notes on this one
02:10 Benchmark's $2B growth fund and the changing strategy
04:57 POC to trial and the power of direct sales in AI
11:33 Meeting Max early: $0 to $100M in 18 months
15:05 Manus: 0 to $100M in eight months through PLG
17:10 Will the AI native window close?
19:09 Sizing the window: $40B software vs $1T services in legal
21:50 How Benchmark picks the winners
25:31 Turning a 180 day sales cycle into 30 days
30:45 The Legora deep dive: research, pilots, legal engineers
41:46 Why $0 to $100M keeps getting faster
42:29 The harder problem: getting to your first $1M
44:04 When code goes to zero, what do customers pay for?
48:46 Sales led vs PLG in the AI era
51:49 How to spot the right founder
55:18 What company Chetan wishes someone would build
56:48 Investors founders should follow
57:40 Working with Jack Altman at Benchmark

Connect with Chetan Puttagunta: 
General Partner at Benchmark
Twitter/X: https://x.com/chetanp
LinkedIn: https://www.linkedin.com/in/chetanputtagunta/

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

About the GTMnow Podcast:
GTMnow is the media brand of GTMfund, sharing the tactics and strategies behind how the best companies go to market. The VC series brings on top investors to break down what is actually working in go to market today.

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. 

LinkedIn CPMs just hit $800. AI is flooding every channel with content. Outbound is dying. So where should B2B marketers actually spend their ad budget right now?

Keith Putnam-Delaney, co-founder & CEO of Primer, joins Sophie to break down the complete state of B2B paid advertising, what's broken, what's working, and where the real opportunities are hiding in 2025.

What you'll learn:
- Why LinkedIn & Google search are hitting a ceiling (and what to do instead)
- How to get 80% match rates on Meta and 70% on Reddit for B2B audiences
- The only moat competitors can't copy: your targeting
- Why you need to feed CRM conversion data back to ad platforms
- Holdout groups, attribution, and what actually proves paid ROI
- The truth about ads in LLMs (ChatGPT, Perplexity, Grok)
- B2B influencer marketing: the most undervalued tactic right now
- Founder lessons from 6 years and 3 pivots building Primer

Chapters:
0:00 – The paid advertising crisis no one's talking about
2:40 – AI's real impact on ad costs
4:06 – Google Search & AI Overviews: what still works
5:04 – LinkedIn CPMs: $20 to $800 in 18 months
6:39 – Why B2B brands need to be on Meta, Reddit & Instagram
7:01 – What Primer does (80% match rates explained)
9:29 – The device fragmentation problem & attribution
11:16 – Holdout groups: the statistically proven approach
13:30 – Which channel to start with (and minimum spend)
22:18 – Paid ad creative: feed the algorithm with variants
25:14 – B2B influencer marketing & thought leadership ads
30:59 – Why you MUST push CRM data back into ad platforms
33:31 – Ads in ChatGPT & LLMs: what's coming
35:53 – Founder lessons, mental health & iteration

Connect with Keith Putnam-Delaney: 
Co-founder, CEO of Primer
Twitter/X: https://x.com/kcpdelaney
LinkedIn: https://www.linkedin.com/in/keithputnamdelaney/

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

About Keith Putnam-Delaney:
Keith is the co-founder and CEO of Primer (https://www.sayprimer.com/), a B2B paid advertising targeting layer that helps brands unlock high match rates on Meta, Google, Reddit, and beyond. Former brand marketer turned data-driven growth leader.

GTMnow is the media brand of GTMfund, sharing go-to-market insights from the top 1% of revenue operators.

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. 

Most sales comp plans are quietly broken, and the people running them have no idea. Siva Rajamani, CEO of Everstage, has visibility into 300+ enterprise comp plans, and he says 90% of companies make the same mistakes. In this episode he breaks down what's going wrong, how to spot it, and what a comp plan that actually drives revenue looks like.

Siva explains why sales compensation is not a back office cost center but the single biggest lever in your go-to-market strategy. It's the glue between what a company intends and what reps actually do. If your reps aren't doing what you want, the answer isn't in a 1-on-1. It's in your comp plan.

We get into the over-complication trap, the hidden math that makes reps refuse your best deals, the base-to-variable ratios that actually work, why your top reps should out-earn almost everyone, and how AI is about to blow open the gap between your best and average sellers.

Chapters:
00:00 Intro
00:30 Siva's RevOps background at Freshworks
04:00 Scaling RevOps from 1 to 25
04:50 Why he left to build Everstage
06:30 Why incentives drive revenue, not tools
08:00 Comp as the glue between intent and action
10:30 The 1 to 2 mistakes almost every team makes
12:00 "If your comp plan needs FAQs, it's a tax code"
14:00 The 60-second test for a broken plan
15:30 Designing comp to retain top talent
16:50 How AI widens the gap between top and average reps
18:00 The $1M sales rep is coming
19:30 Why optimizing for top earners is better on margins
21:30 Quota to OTE ratios that actually work
23:00 Base vs variable: the 50/50 rule and exceptions
24:00 What Everstage does and who it serves
25:30 How Everstage structures its own comp plan
28:00 The rise of the revenue architect
48:00 CPQ and connecting margin to commissions
50:30 When should reps earn commission in the deal cycle
52:30 Six month vs twelve month comp cycles
54:30 The most a sales rep has ever made
55:20 Where to find Siva

Connect with Siva Rajamani: 
Co-founder, CEO of Everstage
Twitter/X: https://x.com/siva_rajamani
LinkedIn: https://www.linkedin.com/in/sivasrajamani/

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

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_/

Subscribe for more conversations with the operators and founders behind today's best go-to-market teams.

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. 

Ben Lerer, Managing Partner and Founder of Lerer Hippeau, has built one of New York's most influential early-stage venture firms across nine funds and nearly $1.5B in AUM. In this VC edition of the GTMnow podcast, Ben sits down with Max and Paul to unpack how he actually picks founders, why he wants to be the "worst investor" at his own fund, and the contrarian belief that backing good, sensible businesses is a mistake.

Ben got his start in media, building Thrillist before it merged into Group Nine, then turned those relationships and that operator empathy into a venture career writing early checks into companies like Warby Parker and Casper. He shares what's changed about winning deals in a more competitive, sharp-elbowed market, how Lerer Hippeau runs its investment committee on conviction rather than consensus, and the process failure behind passing on Peloton.

We also get into the debate every investor is wrestling with right now: the crazy, fast-moving AI-native founder versus the second or third-time operator with deep domain expertise, and why the answer is rarely a silver bullet.

A real venture-nerd conversation on firm building, IC decision-making, founder selection, and what it takes to chase the power law.

Topics covered:
- The "worst investor at my own fund" philosophy
- Conviction vs. consensus in the investment committee
- Why Lerer Hippeau funds "crazy" founders, not good companies
- The Peloton miss and what it revealed about process
- From Thrillist and digital media to venture capital
- AI-native founders vs. domain experts
- How to win competitive deals as a smaller firm

Chapters:
00:00 Intro
00:52 Max and Paul on the episode: IC process and founder selection
14:36 Conversation with Ben Lerer begins
15:02 Nine funds, $1.5B AUM, and the early-stage strategy
23:00 From Thrillist to venture: the media springboard
28:00 What's changed in picking founders and winning deals
33:00 How the investment committee grew and evolved
37:40 The "magic" deal and chasing high-conviction bets
50:43 Why Ben wants to be the worst investor at his fund
53:00 Funding crazy people, not good companies
51:35 Yankees or Mets?

Connect with Ben Lerer: 
https://x.com/BenjLerer
LinkedIn: https://www.linkedin.com/in/benlerer/

Connect with Max: 
https://x.com/hackitmax
linkedin.com/in/maxaltschuler

Listen on Apple and Spotify, and subscribe for more GTMnow VC editions.

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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. 

Maleka Momand, co-founder and CEO of Esper, joins Sophie Buonassisi on GTMnow to break down what it actually takes to build and sell software to government. Esper is the operating system for government policy, serving as the system of record for the regulation and internal policy that shapes daily life, from NYPD procedures to nurse practitioner licensing in rural Tennessee.

Maleka shares hard-won lessons from 8 years in GovTech: why winning trust matters more than winning business, why professional services are a moat (not a cost center), and how Esper turns slow, paper-based policy processes into live digital workflows. She also covers the DOGE effect across red and blue states, why enterprise SaaS still has defensible moats in the age of AI, and her advice to founders entering regulated markets.

Whether you're a founder, GTM leader, or operator selling into complex, slow-moving markets, this conversation is packed with practical playbooks on trust, go-to-market, and building durable enterprise software.

Chapters:
00:00 Intro
00:44 Two types of government policy (regulation vs internal)
02:06 The NYPD 3,000-page policy problem
03:23 Digitizing a paper-based, 20-person workflow
04:12 Why policy is infrastructure
05:23 Real impact: Tennessee healthcare & Arkansas hunting licenses
07:45 Esper's ideal customer: complexity, catalyst, volume
08:18 Going to market in GovTech (and why it's slow)
10:16 Advice for founders entering GovTech: win trust first
11:27 Why professional services are a moat
12:38 In-house vs third-party services
13:49 What DOGE actually looks like on the ground
15:11 Is DOGE a tailwind for Esper?
16:36 The new funding round & enterprise SaaS in the age of AI
19:13 From VC to founder: why Maleka made the shift
22:10 Advice for founders: read fiction, not productivity books
24:14 AI, data quality, and the problem with vibe coding
26:43 How Esper uses AI internally (meet "Poly")
27:27 Building a high-agency culture while scaling
29:00 Closing thoughts

Connect with Maleka Momand: 
Co-founder, CEO of Esper
Twitter/X: @MalekaMomand 
LinkedIn: linkedin.com/in/malekamomand

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

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_/

Subscribe to GTMnow for the latest episodes on AI, founder strategy, fundraising, and go-to-market from the best builders in tech.

#GovTech #GoToMarket #EnterpriseSaaS #StartupAdvice #GTM #SaaS #FounderAdvice #GovernmentTechnology #PolicyTech #AI

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.