The GTMnow Podcast

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. 

One Person, $10M+ ARR, $30M Raised: How Ben Cera Built Polsia (AI Operating System) Solo

Ben Cera, founder of Polsia, just raised $30M at a $250M valuation while running the entire company alone. His AI agent handles his emails, manages customer support, even led his fundraising calls. This is what a solo founder with an AI operating system looks like at scale.

Polsia is an AI operating system that builds and runs companies autonomously. Give it an idea and it builds the product, writes code, conducts research, creates tweets, sets up company infrastructure, and works 24/7 on your behalf. Users are hitting $10M+ ARR using Polsia to scale their businesses.

In this episode we cover:
00:00 - Intro & The Viral Launch Nobody Forgot
01:24 - How He Raised $30M at $250M Valuation with Himself as the Only Employee
02:15 - The Origin Story: Building Polsia from Scratch
04:13 - Why the Controversial Product Name Became Free Marketing ($Millions in Earned Media)
05:55 - What Polsia Actually Does (AI Operating System for Founders)
06:25 - How He Hit $10M+ ARR Running Solo (No Cofounders, No Hires)
10:30 - Building a Company OS That Works 24/7 on Your Behalf
12:00 - The Psychology of Single Founder Mode (Why It Scales Faster)
14:45 - AI Agents Handling Customer Support, Refunds, & Bug Fixes
16:30 - Email Automation: How Polsia Responds to 100% of His Emails
20:15 - The Viral Fundraising Stunt (Live Dashboard + Agent-Led Investor Calls)
25:00 - Why He Let His AI Agent Handle First Meetings with Investors
28:30 - The Self-Fulfilling Prophecy of Distribution (More Visibility = More Traction)
32:15 - How Distribution Strategy Becomes Your Go-To-Market
35:45 - Building in Public While Running Everything Solo
38:00 - Customer Obsession at Scale (Staying Close When You're Alone)
42:56 - Founder Availability: Direct Phone Access to Customers
44:00 - Manufactured Moments That Feel Authentic
50:13 - Why Distribution Isn't an Afterthought Anymore

Key Insights:
- One founder + AI operating system beats small teams without leverage (speed, decision-making, equity concentration)
- Polsia lets you build multiple products simultaneously without hiring (products work 24/7 on your behalf)
- The more controversial your positioning, the more people talk (free marketing from debate)
- AI agents can handle 80% of founder work: emails, support, customer refunds, even investor screening
- Live dashboards showing real-time growth create self-fulfilling prophecies (transparency = conviction)
- Distribution is how you reach product-market fit faster (not an afterthought)
- AI agents leading first investor meetings works (validates the product claim + generates buzz)
- Customer intimacy at scale = founder still takes direct texts from users
- Retention matters more than naming: customers don't complain about the name, they just use it
- One person with AI tools > 5 people building without leverage

Why This Matters:
This is the playbook for next-generation founders in 2026. Ben shows you how to: scale solo using AI agents, multiply your output without hiring, go viral intentionally, raise capital through distribution, and stay close to customers at scale. If you're a founder thinking about AI leverage, autonomous systems, or scaling lean, this is essential.

Watch This If You're:
- Solo founders scaling without a team
- Founders interested in AI agents and autonomous systems
- Learning about AI-first product development
- Studying modern GTM and distribution strategy
- Raising capital in 2026 (fundraising case study)
- Building products with AI agents doing the work
- Curious about the solo founder + AI agent trend
- Following autonomous company builders

Connect with Ben Cera:
Founder & CEO of Polsia
Twitter/X: @bencera 
LinkedIn: https://www.linkedin.com/in/benbroca/

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.

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. 

AI Infrastructure Spending is Insane: Hyperscalers Betting $575B on the Data Center Race | Tomasz Tunguz

This year's data center infrastructure spending will be the 5th largest infrastructure project in history (bigger than everything except railroads and the two world wars). Tomasz Tunguz breaks down what nobody appreciates about the scale of the AI boom.

Tomasz Tunguz, General Partner at Theory Ventures, and one of the most insightful voices on AI infrastructure, data stacks, and founder strategy.

In this episode we cover:
00:00 - Intro & The Scale Nobody Anticipated
02:13 - Data Center CapEx Could Hit 5-7% of US GDP by 2030
05:21 - For Every $1 AI Companies Make, They Spend $12 on Infrastructure ($575B Bet)
06:20 - Market Share Capture vs. Margin Games: The Chicken Game Big Tech is Playing
09:48 - How the Data Stack & AI/ML Worlds Have Completely Fused
12:33 - Product-Market Fit is No Longer Binary: It's Continuous Now
15:17 - How AI is Changing Venture Capital & Portfolio Management
17:09 - The Future: Image & Video Data is Going to Require MASSIVE Infrastructure
18:25 - Pattern Recognition Across Winning Companies (Domain Expertise is Key)
20:50 - Hot Take: Corporate Org Structure Will Transform in 5 Years
21:00 - Final Advice to Founders: Nobody Knows the Answer

Key Insights:
- Hyperscalers are spending ALL free cash flow + borrowing heavily to fund data center CapEx (Meta, Google, Oracle levered 7:1 on cash flow basis)
- The dominant metric: intelligence per watt of electricity
- Anthropic rumored to have very high gross margins (first wave competition)
- Data teams are now reporting to heads of engineering (huge organizational shift)
- Inference demand is infinite: models are growing 5-10x in size
- Foundation models broke product-market fit: it's now continuous, not static
- Second-time founders win because they understand domain history & distribution
- PR is now a major distribution channel for AI companies (unlike software era)
- Building for images & video is the next frontier (1,000-10,000x larger than text data)

Watch this if you're:
- Founders building AI/data companies
- Investors analyzing the AI infrastructure play
- Product leaders understanding AI's organizational impact
- Anyone following the AI market seriously

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

Connect with Paul:
https://x.com/PaulGTM
https://www.linkedin.com/in/paulsirving/

Guest: Tomasz Tunguz, General Partner
https://www.linkedin.com/in/tomasztunguz/
https://x.com/ttunguz

Host: Sophie Buonassisi, SVP at GTMnow
https://www.linkedin.com/in/sophiebuonassisi/
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_/

Brought to you by: AngelList
From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility, from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com

For inquiries about sponsoring the podcast, email [email protected]

GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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 future of websites isn't a builder problem anymore. It's an agent problem.

In this episode of GTMnow, Sophie Buonassisi sits down with Linda Tong, CEO of Webflow, to unpack how the entire web is being rewritten for a world where humans AND AI agents are your audience.

Linda breaks down why Webflow is no longer "just a website builder" (it's an agentic web marketing platform), what the Vidoso acquisition unlocks for AI-generated brand assets, and how the rise of Answer Engine Optimization (AEO) is forcing marketers to rethink content from the ground up. She also shares the practical playbooks her team uses to "vibe" sites into production with the Webflow MCP server, why human creativity is the only real moat left, and how she built her own personal CRM using Claude Code.

If you run a GTM team, lead marketing, or are trying to figure out what your website should even look like in 2026, this one is essential.

WHAT YOU'LL LEARN
-Why your website is now the #1 source of truth for humans, bots, and agents
-The shift from static sites to continuously optimizing, dynamic experiences
-How "vibe coding" with MCP is changing the way teams build on the web
-Inside the Vidoso acquisition and what "brand-governed AI" actually means
-AppGen: going from prompt to production without losing brand consistency
-Answer Engine Optimization (AEO): the non-obvious mistakes marketers are making
-How to structure a marketing team made of humans plus agent swarms
-The "5 words" exercise every CEO should run inside their company
-Linda's personal CRM built with Claude Code (and how Webflow scales internal AI)
-Why "unlimited credits" and Builder Days unlock real AI productivity

ABOUT THE GUEST
Linda Tong is the CEO of Webflow, the agentic web marketing platform powering some of the most respected brands on the internet. Before stepping into the CEO role, Linda served as President and COO at Webflow, and previously led product at Cisco's AppDynamics and held senior roles at Google.

CHAPTERS 
00:00 Intro 
01:41 From static to dynamic 
03:12 Inside the Vidoso acquisition 
05:38 The human moat 
07:17 Beyond the website builder 
08:55 Structuring human + agent teams 
09:58 AppGen, explained 
10:45 Prompt to production 
12:11 AEO misconceptions 
14:40 Holistic AEO strategy 
16:38 The 5 words exercise 
18:10 Linda's personal CRM 
19:31 Central vs. individual AI 
20:44 Inside Webflow's Builder Days

Guest: Linda Tong, CEO Webflow
https://www.linkedin.com/in/lktong/
https://x.com/YayLT

Host: Sophie Buonassisi, SVP at GTMnow
https://www.linkedin.com/in/sophiebuonassisi/
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_/

Sponsors: 
.Tech - Domains, where the next generation of builders is planting their flag.
Secure your .tech domain today from any registrar of your choice. 

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com

For inquiries about sponsoring the podcast, email [email protected]

GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

#GTMnow #Webflow #AI #LindaTong #AnswerEngineOptimization #AEO #GoToMarket #B2BMarketing #AgenticAI #VibeCoding #AIAgents #FutureOfWeb #MarketingPlatform #SaaS #aimarketing

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. 

AI is rewriting go-to-market and most companies are still operating with a “Frankenstein stack.”

In this episode of GTMnow, we sit down with David, founder & CEO of Reevo, to unpack how AI-native companies will replace legacy GTM systems, why the future of sales teams looks radically different, and how AI agents are becoming the new operating layer for revenue teams.

David shares why Reevo stayed in stealth while building a vertically integrated AI revenue operating system, the problem of institutional knowledge loss in sales organizations, and why the old playbook for SaaS and GTM is breaking in 2026.

We also dive deep into:
- AI-native go-to-market strategy
- The death of the legacy SaaS tech stack
- Revenue operating systems explained
- AI agents for sales, marketing, and customer success
- How founders should think about AI adoption
- Building startups in the age of AI
- Why “failure is the cornerstone of innovation”
- AI-driven sales productivity and revenue efficiency
- Founder-led sales in 2026
- The future of CROs, CMOs, and RevOps
- AI copilots, Jarvis-style workflows, and GTM automation
- Scaling teams without scaling headcount

If you're a founder, CRO, CMO, GTM leader, SaaS operator, AI builder, or investor trying to understand where B2B software and go-to-market are headed next, this episode is for you.

Timestamps:
 00:00 Intro
 01:20 Why Reevo built in stealth
 04:50 Why AI can finally disrupt GTM tech stacks
 09:20 What Reevo actually does
 11:10 AI outcomes vs headcount growth
 15:00 How AI changes leadership & innovation
 19:00 Why legacy GTM teams are vulnerable
 23:00 The future of AI-native GTM organizations
 29:00 Running an AI-native company internally
 34:00 David’s favorite AI workflows & tools
 37:40 Advice for introverted founders & leaders

Host: Sophie Buonassisi, SVP Marketing at GTMnow
https://www.linkedin.com/in/sophiebuonassisi  

Guest: David Zhu, Co-founder and CEO at Reevo
https://www.linkedin.com/in/zhuventures/

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_/

Sponsors: 
.Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice. 

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com

For inquiries about sponsoring the podcast, email [email protected]

GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

#AI #Sales #GTM #SaaS #ArtificialIntelligence #RevenueOperations #Startup #B2B #RevOps #AIAgents #Founder #SalesLeadership #CMO #CRO #GoToMarket #AIStartup #TechPodcast #SalesTech #FutureOfWork #Automation

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. 

Tyler Hogge helped take Divvy from zero to a $2.5B acquisition by Bill.com. Now, as General Partner at Pelion Ventures, he argues that charging for software is dead, per-seat pricing is collapsing, and the next decade of venture-scale companies will be built on outcomes, not subscriptions.

In this episode of the GTMnow VC Podcast, Tyler sits down with Max to break down what comes after SaaS pricing, why founder intensity is the only trait that still matters in 2026, and how Pelion concentrates capital into its biggest winners (Cloudflare alone returned over $1B to the fund). He also shares why most startups won't survive going head-to-head with OpenAI and Anthropic, the "bent the odds" contract he signed with Redo's CEO, and the lesson from raising four kids that changed how he leads.

This is an honest, no-fluff conversation about where venture is going as AI commoditizes software.

Chapters:
00:00 Intro
01:14 Intro
18:48 Tyler joins
23:09 "Sell Jesus, sell anything"
27:42 The $2.5B Divvy exit
34:39 The "bent the odds" contract
38:11 Startups vs. OpenAI and Anthropic
39:05 "Software is worth zero"
40:55 The death of per-seat pricing
43:02 Lessons from raising 4 kids
46:44 "LinkedIn is the trailer park"

Connect with Tyler:
https://x.com/thogge
https://www.linkedin.com/in/thogge/

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

Connect with Paul:
https://x.com/PaulGTM
https://www.linkedin.com/in/paulsirving/

About Tyler Hogge:
Tyler Hogge is a General Partner at Pelion Ventures, Utah's oldest and largest venture fund with $500M AUM across eight funds. Before Pelion, Tyler was VP of Product at Divvy, which sold to Bill.com for $2.5B in 2021. Earlier in his career, he was a product leader at Wealthfront under Andy Rachleff and Adam Nash. He's based in Utah and one of the most active venture capitalists on X.

About GTMnow:
GTMnow is the media arm of GTMfund, a pre-seed and seed-stage B2B SaaS venture firm backed by an LP base of 300+ C-suite and VP-level operators from the best go-to-market organizations in tech. The GTMnow VC Podcast publishes every other week with the investors and operators shaping the next decade of B2B software.

Brought to you by: AngelList
From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund admin infrastructure allowed us to scale without sacrificing agility, from onboarding hundreds of LPs seamlessly to handling compliance, capital calls, and reporting as our fund size evolved.

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com

For inquiries about sponsoring the podcast, email [email protected]

GTMnow is a media brand brought to you by VC firm, GTMfund:
https://gtmfund.com/

Subscribe for new episodes every week

#VentureCapital #VCpodcast #SaaS #AI #B2BSaaS #GTMnow #StartupFunding #TylerHogue #PelionVentures #FounderAdvice

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. 

Boomi was founded in the early 2000s by Rick Nucci, acquired by Dell in 2010, and then spun out to Francisco Partners and TPG Capital in 2021. Today it powers 30,000+ enterprise customers globally and moves more data per second than the entire Visa card network, times two. What started as an integration platform has evolved into something bigger: the leading data activation company, purpose-built for the agentic AI era.

Steve Lucas took over as CEO in early 2023, just as ChatGPT was about to reshape the entire software landscape. A three-time CEO with nearly 30 years in enterprise software, Steve previously led Marketo through its $4.75B acquisition by Adobe (the largest in Adobe's history at the time), scaled iCIMS into the world's leading talent acquisition cloud, and held senior roles at SAP, Salesforce, Adobe, and BusinessObjects. He's also the author of "Digital Impact: The Human Element of AI Driven Transformation," a book arguing that the AI revolution will stall unless companies fix the fragmentation of their data first.

In this episode, Sophie Buonassisi sits down with Steve at HumanX in San Francisco to unpack why 2026 is the year AI moves from pilot to production, the three diagnostic questions every CEO should ask before deploying agentic AI, and why "change only happens at the speed of trust." Steve also gets candid about the internal protest that erupted when Boomi rolled out its first CSM agent, his prediction that AI will go from influencing 20% of executive decisions to making 90% of them within 2 years, and how he picked up Claude Code on an airplane to vibe-code a contracts agent for his sales team.

If you're a founder, operator, or GTM leader trying to figure out whether your business is actually ready for agentic AI (or just chasing the buzzword), this one is for you.

TIMESTAMPS

0:00  Intro

0:58  Welcome to GTMnow at HumanX

1:10  Why 2026 is when AI moves from pilot to production

2:32  Influencing decisions vs. making decisions: the next 2 years

3:18  Digital Impact: why fragmentation will stall the AI revolution

5:01  "Get your data to the gym": the new slogan

5:20  The 3 questions to know if your company is AI-ready

6:47  Change happens at the speed of trust

7:53  The internal protest behind Boomi's CSM agent

9:32  From integration platform to data activation: the strategic shift

10:50 Steve's most transformative AI workflow as a CEO

11:12 Vibe coding with Claude on an airplane

12:20 Where to follow Steve and Boomi

Host: Sophie Buonassisi, SVP Marketing at GTMnow

linkedin.com/in/sophiebuonassisi  

Guest: Steve Lucas, CEO at Boomi

https://www.linkedin.com/in/nstevenlucas/

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_/

Sponsors: 

.Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice. 

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com

For inquiries about sponsoring the podcast, email [email protected]

GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

Keywords: #AI #AgenticAI #Boomi #SteveLucas #GTMnow #DataActivation #HumanX #EnterpriseAI #AIStrategy #B2BSaaS #ClaudeCode #VibeCoding #CEOInterview #DigitalTransformation #futureofwork

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. 

Okta's CRO Jon Addison joins GTMnow host Sophie to break down the full story behind Okta's remarkable revenue turnaround, the launch of Okta for AI Agents, and the go-to-market playbook that's carrying them from $3B toward a $5B ARR target.

From nearly $850M in operating losses to over $760M in operating income, Okta's transformation is one of the most significant turnaround stories in enterprise SaaS. In this episode, Jon pulls back the curtain on exactly how it happened.

In this episode:

- Why 91% of enterprises are already deploying AI agents but only 10% have a security strategy for them

- How Okta's "AI governance gap" insight became the foundation for their biggest product launch in years: Okta for AI Agents

- The GTM restructure around specialization that unlocked productivity and drove 40% higher average contract value on new product deals

- How Okta became a partner-first company: 95% of their top 100 deals in the last fiscal year were partner-led, and what operationally made that possible

- Why the first discovery call no longer exists, and how sellers need to show up differently in the AI era

- Jon's new internal sales methodology, APEX, built on Command of the Message for the AI era

- How Okta is using AI internally to transform their own go-to-market motion, from conversational intelligence to pre-sales assistants

- What the path to $5B ARR actually looks like: enterprise expansion, international growth, public sector, and the massive new TAM unlocked by non-human identity

- Jon's leadership philosophy: why human-centric selling is becoming more critical as AI takes over the repetitive work

Host: Sophie Buonassisi, SVP Marketing at GTMnow

https://www.linkedin.com/in/sophiebuonassisi

Guest: Jon Addison, CRO at Okta

https://www.linkedin.com/in/jon-addison-3399175

Timestamp:

0:00 - Cold open

1:19 - Welcome + Jon's background: from London to Silicon Valley

1:52 - How Jon got into software and identity management

4:08 - Okta for AI Agents launch announcement

5:04 - 90% of customers live with agents, only 10% confident in securing them

6:31 - What's driving the governance gap in the market

7:53 - Speed of agent innovation must be matched by security and governance

8:36 - 40% higher ACV on deals that include new products

9:43 - Why consolidation around a single identity platform is resonating

11:45 - How AI agents unlock a massive new TAM for Okta

13:05 - Okta's turnaround: from $850M operating losses to $760M operating income

13:36 - Key decision 1: GTM specialization drove productivity

15:02 - Key decision 2: becoming a partner-first company

16:14 - What cracking the partner-led model actually looks like

19:08 - How long it takes to see ROI from a partner-led pivot

20:12 - The path from $3B to $5B: enterprise, international, public sector

21:49 - Using AI internally: launching "Apex," the AI-era sales methodology

23:04 - What the Apex sales methodology entails

24:25 - Buyers now show up with strong opinions before the first call

25:44 - How discovery is changing: human-centric selling in the AI era

27:33 - Headcount and AI: what skills matter in the future

29:31 - Why relationships are Okta's core competitive advantage

30:36 - The role of experiences: F1, events, and the 7-touchpoint rule

31:47 - Broad GTM surface area: ABM, ecosystem, brand

33:47 - The future of identity: SaaS disruption, consolidation cycles, and Okta's position

37:06 - Jon's leadership style: coaching reps and unlocking potential

39:01 - Positive vs. negative leadership and the 1-to-10 touchpoints framework

Visit us on: https://gtmnow.com

Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow

Follow us on X (Twitte

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. 

Jennifer Li, Partner at Andreessen Horowitz (a16z), breaks down why the firm allocated $1.7 billion of its latest $15 billion fund specifically toward AI infrastructure, and what she's betting on next.

Jennifer has backed ElevenLabs from Series A all the way through Series D, watching it grow to an $11 billion valuation. In this episode, she explains what she saw in voice AI before anyone else did, what makes a founder worth backing regardless of the tech, and why the next wave of AI infrastructure is being rebuilt from the ground up.

In this episode:

- Why a16z bet $1.7B on AI infrastructure (and why now)

- The shift from cloud to AI-native infrastructure: storage, compute, orchestration, memory

- How ElevenLabs crossed the uncanny valley in synthetic voice

- Voice agents as the first AI category to truly scale in the enterprise

- What "king-making" in AI go-to-market actually looks like

- The traits that made Jennifer write a check for ElevenLabs on founder conviction alone

- Open source vs. frontier models: what 2027 looks like

- Why world models and vision language models are the next unlock

- AI and human creativity: why directors and authors won't be replaced

- How a 1-2 person studio can now make a full movie

Host: Sophie Buonassisi, SVP Marketing at GTMnow

https://www.linkedin.com/in/sophiebuonassisi

Guest: Jennifer Li, General Partner at Andreessen Horowitz

https://www.linkedin.com/in/jenniferhli/

https://x.com/JenniferHli

Connect with Max: 

https://x.com/hackitmax

https://www.linkedin.com/in/maxaltschuler

Connect with Paul:

https://x.com/PaulGTM

https://www.linkedin.com/in/paulsirving

Timestamps:

0:00 - Cold open

1:06 - Max & Paul intro: are we in a bubble?

1:46 - AI vs. dot-com era: the key differences

4:55 - B2B SaaS disruption and value destruction (Thoma Bravo / Medallia)

6:39 - Intercom / Finn: crossing the chasm from legacy to AI-native

8:08 - Introducing Jennifer Lee, a16z General Partner

8:31 - Paul's key takeaway: the distribution era

9:41 - Why speed to default brand has never mattered more

11:33 - The ElevenLabs story: a16z led Series A, B, and C

12:02 - Why the seed strategy still works

13:37 - What the best founders do differently with model capabilities

15:58 - Jennifer Lee joins: why a16z raised $1.7B for infrastructure

16:22 - What existing infrastructure is being rebuilt for AI

19:19 - Specific areas a16z is focused on: models, storage, dev tools, security

20:35 - 90%+ of code now written by agents

21:52 - What Jennifer saw early in the 11 Labs / voice AI space

25:19 - Go-to-market in AI infrastructure: what's working

27:29 - Becoming the default brand: the "Kleenex effect" in AI

28:37 - What makes a founder worth backing on conviction alone

30:48 - Predictions for 2026/2027: open source catching up fast

31:39 - Most exciting new modalities: world models and vision language models

32:07 - AI and human creativity: can they coexist?

34:42 - What's blocking the creative AI future

36:05 - "The best ideas live in the graveyard"

36:57 - Closing advice: make AI tools your friends

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

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Brought to you by: AngelList

From starting as a small, operator-led rolling fund, to evolving to an institutional platform, AngelList has been a core partner in every phase of GTMfund’s growth. Their software-first fund

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. 

Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG).

But the path there was anything but smooth.

In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.

We cover:

- Why Figma refused to discount, even when Microsoft pushed back

- How to hire the right first sales rep as a founder

- The PLG to enterprise transition most companies get wrong

- What the Adobe deal collapse actually felt like from the inside

- How Figma went from 3 products to 8 overnight and launched into an IPO

- What great sales look like in the AI era

Timestamp:

0:00 – Intro

1:02 – Guest intro: Kyle Parrish

1:35 – Joining Figma at $2M ARR in 2018

5:01 – First meeting with Dylan (Figma CEO)

6:13 – How to find your first sales hire

9:05 – Stage alignment in early hiring

11:43 – Early-stage operators need "scar tissue"

13:19 – Northstar metric at Figma

14:13 – Obsessing over customer conversations

16:44 – Building Figma's brand through community

17:31 – Scaling the "unscalable"

20:08 – In-person GTM vs. digital

22:47 – Was there a moment Figma might not make it?

24:48 – Pivoting after the Adobe deal collapsed

28:10 – Figma's no-discount rule

31:05 – Enterprise ELAs replacing discounting

34:47 – What makes a great salesperson in the AI era

36:56 – Missionaries vs. mercenaries in AI-era GTM

39:47 – Spotting the next Dropbox or Figma

43:46 – Kyle's post-Figma investing focus

45:58 – Family, travel & what's next

Guest: Kyle Parrish, former VP Sales at Figma

LinkedIn: https://www.linkedin.com/in/kparrish8/

X: https://x.com/KyleHParrish

Host: Sophie Buonassisi, SVP Marketing 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_/

Sponsors:

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Transcript available under the episode here: https://gtmnow.com/tag/podcast/

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GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.com/

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.