

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

18 snips
Mar 25, 2025 • 59min
GTM 139: AI Agents Are Changing Everything — Microsoft’s VP of AI Agents on the New Era of Work and Software | Ray Smith
Ray Smith, Microsoft’s VP of AI Agents and former CEO of DataHug, explores the revolutionary impact of AI agents on business. He explains how these agents differ from traditional bots and automation, driving ROI and reshaping team structures. Ray discusses the challenges of adapting SaaS pricing models to fit an agent-first world and shares real-world applications of AI at Microsoft. He also highlights essential skills in this new era, emphasizing the importance of customer relationships and strategic thinking for business success.

26 snips
Mar 18, 2025 • 54min
GTM 138: The AI Advantage, Solving Sales & Marketing Alignment for Better GTM Execution with Jaleh Rezaei
Jaleh Rezaei, CEO & Co-founder of Mutiny, is transforming the B2B buying landscape with AI-powered personalization. She discusses how AI is revolutionizing sales and marketing, highlighting that personalized experiences can lead to 14x higher conversion rates. Jaleh shares insights on effective lead scoring, overcoming sales objections in real-time, and the importance of aligning sales and marketing teams. She also warns against common pitfalls in AI-driven strategies, emphasizing the need for genuine customer relationships in today's digital age.

Mar 11, 2025 • 56min
GTM 137: The Biggest Business Turnaround You've Never Heard Of & The Growth Levers to Pull When Things Go Wrong | Cassie Young
Cassie Young, General Partner at Primary Venture Partners, shares her extensive experience in turning around businesses, moving from Chief Customer and Commercial Officer to investor. She dives into the impressive turnaround at Sailthru, emphasizing the importance of rebuilding customer trust after failures. The conversation covers crucial themes like leveraging Net Promoter Scores for insights, the effectiveness of Customer Advisory Boards in driving growth, and innovative engagement strategies that foster strong customer relationships.

15 snips
Mar 4, 2025 • 59min
GTM 136: How Asana & Calendly Scaled: PLG to SLG Playbooks That Work | Jessica Gilmartin
In a captivating discussion, Jessica Gilmartin, a seasoned go-to-market leader and former CRO/CMO at Calendly, shares her journey through tech giants like Asana, Google, and Microsoft. She dives into the challenges of transitioning from product-led to sales-led growth and emphasizes the need for clear ideal customer profiles. Jessica also highlights the importance of fostering a culture of experimentation, building trust within teams, and the strategic role of marketing in startup growth. Her insights on hiring and nurturing creativity are invaluable for aspiring leaders.

Feb 25, 2025 • 55min
GTM 135: How Marketing Creates Million-Dollar Exits: 6 SaaS Success Stories | Katrina Wong
Katrina Wong is the CMO of New Relic and a top marketing leader. She specializes in launching products, entering new markets, and scaling companies to the enterprise. With 15 years of experience at Twilio, Zuora, Salesforce, and SAP, she has led award-winning campaigns and helped six companies exit successfully.Discussed in this Episode:Why you should be using "marketing sprints"Importance of operational excellence and agility in marketingThe role of marketing in preparing for a successful exitIs 'fire fast' the right approach for managing your teamsHighlights: 07:08 Secrets to picking winners09:30 Attaining operational excellence in startups15:43 Marketing's role in successful exits29:12 Transforming PIP programs for successful employees31:26 Challenging the 'fire fast' mentality35:20 The importance of team dynamics40:24 Navigating getting acquired successfully48:58 Tactics for modern marketingGuest Speaker Links (Katrina Wong):LinkedIn: https://www.linkedin.com/in/katrinawong11/New Relic Website: https://newrelic.com/Host Speaker Links (Scott Barker):LinkedIn: https://www.linkedin.com/in/ssbarker/Newsletter: https://thegtmnewsletter.substack.com/Where to find GTMnow (GTMfund’s media brand):Website: https://gtmnow.com/LinkedIn: https://www.linkedin.com/company/gtmnow/Twitter/X: https://x.com/GTMnow_YouTube: / @gtm_now Sponsor: PursuitThe best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.If you're hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.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.

Feb 18, 2025 • 57min
GTM 134: When to Hire Your First Sales Reps (And How to Get It Right) with Joe DiMento
Joe DiMento, Head of Go-To-Market & Industry Partnerships at Bain Capital Ventures, shares his wealth of experience in sales strategies. He discusses the critical timing for hiring your first sales reps and what traits to look for, such as grit and adaptability. Joe emphasizes structuring simple yet effective compensation plans and the value of hiring multiple account executives simultaneously. He also delves into the importance of aligning candidates with company mission and highlights how AI is transforming sales and revenue generation.

15 snips
Feb 11, 2025 • 1h 6min
GTM 133: Build your AI Outbound Machine with ChatGPT | Jordan Crawford
Jordan Crawford, Founder of Blueprint and a go-to-market innovator, dives into the transformative power of AI in sales and marketing. He reveals how to create targeted outreach messages using tools like ChatGPT and the FIND process for effective go-to-market strategies. Highlights include revolutionizing personalized sales outreach, enhancing operational efficiency, and mastering prompt engineering. Jordan emphasizes the importance of process over mere prompts and shares insights on utilizing Deep Research AI for better customer insights and messaging.

Feb 4, 2025 • 49min
GTM 132: The Rise of the Operator with Casey Woo + Special Announcement
Join Casey Woo, Founder & CEO of Operators Guild and seasoned finance operator, as he dives into the rise of operators in business. He discusses how to effectively communicate with CFOs and cross-functional teams, highlighting the crucial dynamics of trust and collaboration. Casey emphasizes what truly matters to CEOs and founders, and shares insights on recruiting top operators in a world where funding and technology have become commoditized. He also underlines the power of community and in-person events in today’s digital age.

20 snips
Jan 28, 2025 • 56min
GTM 131: Being CMO Under Marc Benioff of Salesforce, the Innovator's Dilemma and AI SDRs
Kraig Swensrud, Founder & CEO of Qualified and former CMO of Salesforce, shares insights from his entrepreneurial journey. He discusses how SaaS and AI disrupt markets and reshaping pricing strategies. Kraig emphasizes customer obsession as vital for startup growth and addresses the risks of hasty hiring practices. He also delves into the role of AI in transforming business dynamics and the importance of effective frameworks like V2MOM for team alignment. A thought-provoking conversation for tech enthusiasts!

11 snips
Jan 21, 2025 • 1h
GTM 130: Scaling to Billions: How DocuSign, HubSpot & Canva Built Winning GTM Strategies with Rob Giglio, Canva’s CCO
Rob Giglio, Chief Customer Officer at Canva with over 20 years in tech leadership roles, shares invaluable insights from his experiences at HubSpot and DocuSign. He discusses the importance of concept testing in B2B marketing and how to apply consumer product strategies to enhance engagement. The conversation also emphasizes cultivating loyalty, the power of simplicity in messaging, and the challenges of leading remote teams. Rob's take on transitioning enterprise customers reveals the need for authentic, human-centered marketing in the evolving landscape.


