GTM 151: How to Scale Vertical SaaS in 2025 | Dennis Lyandres (Ex-CRO, Procore)

Dennis Lyandres is an Advisor with ICONIQ and a Board Member of Speedchain and CaptivateIQ. Dennis amassed incredible insights through his experience as the Chief Revenue Officer of Procore, where he helped grow the company from $10M to $900M+ in revenue and guided it through a successful IPO. At Procore, he led all customer-facing functions—Sales, Marketing, CS, RevOps, and BD. He’s now an investor, advisor, and board member to iconic B2B SaaS companies, and one of the most respected voices in GTM for vertical SaaS.

Discussed in this Episode:
Why the Best SaaS Companies Align People, Product, and GTM into One Unified Strategy
Using AI as a GTM Advantage Starts with a Crawl-Walk-Run Approach
Scaling Multi-Product in Vertical SaaS Means Following the Money and the Pain
GTM Leaders Win When They Speak Product and Co-Own Strategy with Engineering
Customer Relationships Are Your Most Undervalued Strategic Growth Lever
Your Top 5% of Talent Deserve a Purpose-Built Strategy to Maximize Impact
Lean AI Teams Are Redefining What’s Possible with Just a Handful of Operators

Highlights:
0:00 Intro
3:00 Dennis’s journey as the Chief Revenue Officer at Procore: from $10M to IPO
5:00 The “People, Product, GTM” triad and AI-native orgs
7:00 Why vertical SaaS startups need a talent strategy (and most companies lack one)
9:30 Multi-product GTM strategy explained via Procore and other verticals
13:00 How Go-To-Market teams can show up better for product teams
18:00 Building deep customer strategy across functions in a B2B startup
23:00 Price’s Law and the T30 program for top performers within a revenue organization
24:30 Lean AI startup: what it is and what it isn’t
30:00 Crawl-walk-run AI adoption in Go-To-Market teams

Guest Speaker Links (Dennis Lyandres):
LinkedIn:   / dlyandres  
Speedchain: https://www.speedchain.com/
ICONIQ: https://www.iconiqcapital.com/

Host Speaker Links (Sophie Buonassisi):
LinkedIn:   / sophiebuonassisi  
Newsletter: https://substack.com/@sophiebuonassisi

Where to find GTMnow (GTMfund’s media brand):
Website: https://gtmnow.com/
LinkedIn:   / gtmnow  
Twitter/X: https://x.com/GTMnow_
YouTube: /@gtm_now
The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

Sponsor: TriNet

Every early-stage founder is told to focus on product and growth. But behind every product launch and revenue milestone is a team – and building that team is one of the hardest and important parts of the journey.

“Build the team that builds the company.” – that is part of your go-to-market strategy responsible for growth.

Hiring the right people, keeping them supported, and creating the infrastructure to help them thrive is critical.

TriNet exists to make that easier. TriNet’s full suite of HR solutions is designed to support companies at critical inflection points – from early traction to scale.

Learn more at https://trinet.com/gtmnow

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