The GTMnow Podcast
GTMnow
The GTMnow Podcast interviews well-known tech executive, VC, and founders - the expert operators in the trenches who have ‘been there, done that’ to build some of the fastest-growing software companies. Every week, a guest joins Sophie Buonassisi to dissect their stories, revealing expert insights around what worked, what didn’t, and how things actually went down.This podcast is produced by GTMnow, the media brand of GTMfund - sharing insight on go-to-market from working with hundreds of portfolio companies backed by over 350 of the best go-to-market executives. GTMfund is an early-stage VC fund focused on investing in the most exciting, up-and-coming B2B SaaS companies across the world. The LP network consists of VP and C-level Sales, Marketing, and Customer Success leaders from companies like DocuSign, Salesforce, LinkedIn, Snowflake, Okta, Zoom, and many more.Visit gtmnow.com for more details and to sign up for our newsletter and other content resources.
Episodes
Mentioned books
22 snips
Feb 3, 2026 • 46min
Why Most Founders Build the Wrong Company (And Realize It Too Late), with Lou Shipley, Former CEO and Co-Author of Unlikely Entrepreneurs
Lou Shipley, three-time CEO and Harvard Business School teacher, shares hard-earned lessons on sales, customer pain, and scaling software companies. He explains why founders must sell early to learn, how distribution becomes a competitive edge, why small high-quality teams win, and when churn signals deeper product-market shifts. Practical, blunt, and focused on avoiding the classic founder trap.
22 snips
Jan 28, 2026 • 47min
Why AI Is Killing Your Outbound and Making In-Person GTM Inevitable, with Healey Cypher, CEO at BoomPop
Healey Cypher, CEO and co-founder of BoomPop and multi-time founder, explains why in-person events are a premium growth channel as AI floods digital outreach. He covers using offsites for alignment, designing high-ROI dinners and summits, how events help acquisition and partnerships, and why kindness and team cadence matter for scaling.
13 snips
Jan 22, 2026 • 45min
Why Most Go-To-Market Motions Collapse at Scale, with Jeanne DeWitt Grosser, COO at Vercel
In this engaging discussion, Jeanne DeWitt Grosser, COO at Vercel and former GTM leader at Stripe and Google, delves into the fragility of go-to-market strategies at scale. She advocates treating GTM like a product, emphasizing the importance of clarity in sales decisions and how AI can enhance, but not replace, foundational practices. Jeanne also highlights the role of forward-deployed engineers, the need for effective documentation, and what separates great sales reps in the age of AI. Her insights are invaluable for anyone navigating growth in startups.
20 snips
Jan 20, 2026 • 1h 12min
VC 3: Investing Philosophy for 2026: What Founders Should Know
Mark Goldberg, Managing Partner and Co-Founder at Chemistry, shares insights from his venture capital journey. He discusses why he considers venture the 'liberal arts of jobs' and his transition from Index Ventures to founding Chemistry. Mark reveals his unique fundraising strategy and hiring philosophy, emphasizing network access over traditional methods. He addresses the importance of conviction-based investing, avoiding omissions, and reflects on the challenges of co-founder dynamics, highlighting the value of empathy in leadership.
10 snips
Jan 14, 2026 • 53min
GTM 174: The 7% Rule: How AI Is Rewriting Customer Success Budgets (From 10% to 7%) with Abbas Haider Ali
Abbas Haider Ali, a seasoned VP of Customer Success at GitHub, shares insights from his extensive experience in tech. He discusses the shift in customer success budgets from 10% to 7%, revealing reasons behind this change, including how AI can both enhance and obscure customer retention. Abbas emphasizes the importance of retention costs over customer acquisition in the AI era. He introduces a budget allocation strategy and explains the emergence of AI-powered specialized generalists transforming support frameworks.
17 snips
Jan 7, 2026 • 37min
GTM 173: The PLG→Enterprise Playbook: Turning Product Signals into 9-Figure Revenue with Adam Carr
Adam Carr, Chief Revenue Officer at Apollo, dives into the world of product-led growth (PLG) and enterprise scaling. He shares insights on how to layer sales over a PLG foundation to maximize revenue. Adam emphasizes hiring for long-term talent density, seeking candidates with curiosity and system-thinking abilities. He introduces a bold new model by replacing traditional customer success managers with go-to-market engineers, and discusses how AI can enhance GTM operations. Celebrating customer value realization over mere contracts is his key takeaway.
20 snips
Dec 15, 2025 • 1h 9min
VC 2: How Cassie Young Picks Winners Before They Even Leave Their Jobs
Cassie Young, a General Partner at Primary Venture Partners, shares insights from her career transition from GTM leadership to venture capital. She discusses her innovative approach to sourcing founders before they leave their jobs and the importance of a strong founder outcomes framework. Cassie also emphasizes the difference between real market traction and misleading signals. Her preference for transformative GTM/AI tools over incremental improvements highlights her keen vision for the future of investing. Plus, she offers valuable advice for aspiring VCs.
38 snips
Dec 10, 2025 • 36min
Why Old Playbooks Are Breaking and How AI Assisted GTM Actually Works | Dave Boyce
In a fascinating discussion, Dave Boyce, a seasoned technology executive and author of 'Freemium', highlights the urgent need for B2B companies to ditch outdated sales and marketing playbooks. He unveils how the Bowtie model reveals hidden growth levers and why Product-Led Growth (PLG) thinking is crucial even for traditional sales. Dave explains three core principles of freemium—empathy, generosity, and metrics—while showcasing AI's role in streamlining customer journeys and enhancing self-service experiences. Tune in for insights on reimagining go-to-market strategies.
Dec 3, 2025 • 39min
GTM 171: How to Build a Partner Ecosystem That Sells for You | Brian Weinberger
In this engaging discussion, Brian Weinberger, Chief Revenue Officer at Sisense, unpacks 30 years of partner-selling experience. He explores the evolution of partner ecosystems, emphasizing a delivery-first strategy to drive retention. Brian argues that knowledgeable partners create 'superhuman' sellers and suggests a hybrid approach compared to Salesforce and Microsoft. He also outlines a 90-day playbook for building integrations and highlights the importance of hiring the right talents for successful partnerships.
36 snips
Nov 25, 2025 • 24min
MOMENT: How to Identify Exceptional People Early | Cristina Cordova (Stripe, Notion, Linear)
Cristina Cordova, a seasoned operator and current COO at Linear, shares her insights on identifying exceptional talent early in a startup's journey. She discusses looking for world-class founders who complement each other and how being exceptional aids in spotting talent in unfamiliar domains. Cristina emphasizes finding signs of beloved products through genuine customer conversations, starting with a sharp market wedge, and hiring salespeople skilled in technical sales. Her tactical frameworks provide invaluable guidance for building effective go-to-market strategies.
