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 strategyUsing AI as a GTM advantage starts with a crawl-walk-run approachScaling multi-product in vertical SaaS means following the money and the painGTM leaders win when they speak product and co-own strategy with engineeringCustomer relationships are your most undervalued strategic growth leverYour top 5% of talent deserve a purpose-built strategy to maximize impactLean AI teams are redefining what’s possible with just a handful of operatorsHighlights:03:00 Dennis’s journey as the Chief Revenue Officer at Procore: from $10M to IPO05:00 The “People, Product, GTM” triad and AI-native orgs07:00 Why vertical SaaS startups need a talent strategy (and most companies lack one)09:30 Multi-product GTM strategy explained via Procore and other verticals13:00 How Go-To-Market teams can show up better for product teams18:00 Building deep customer strategy across functions in a B2B startup23:00 Price’s Law and the T30 program for top performers within a revenue organization24:30 Lean AI startup: what it is and what it isn’t30:00 Crawl-walk-run AI adoption in Go-To-Market teamsGuest Speaker Links (Dennis Lyandres):LinkedIn: https://www.linkedin.com/in/dlyandres/Speedchain: https://www.speedchain.com/ICONIQ: https://www.iconiqcapital.com/Host Speaker Links (Sophie Buonassisi):LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/Newsletter: https://substack.com/@sophiebuonassisiSponsors: TriNetEvery 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/gtmnowThe 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.