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Justin Michael on Why the Series A "Go Enterprise" Decision Blows Up 18 Months Later
The board wants enterprise logos. Eighteen months and five expensive hires later, the pipeline is full and nothing has closed. Justin Michael has watched this movie enough times to tell you exactly where it goes wrong β and what the board should have been looking at instead of the pipeline number. Justin Michael is the author of 12 books on enterprise software sales, including Tech-Powered Sales and Combo Prospecting, and spent 13 years selling in ad tech, MarTech, and mobile before moving into executive coaching. He has trained over 1,000 enterprise sellers across 200+ teams at companies including Salesforce, HubSpot, Matterport, and Proofpoint, working markets from DACH to Australia to Singapore. WHAT YOU WILL LEARN Why the mid-market to enterprise jump fails, and what to keep running while you make it How to spot the "Rolodex myth" before you sign a $600K VP of Sales package When to hire a VP of Sales instead of a CRO, and how much equity the role actually needs Why AI has not yet reduced enterprise headcount, and what that means for a Series A model How to tell when your team's AI-generated outbound is quietly killing your C-level access Which two signals actually predict a private company is ready to buy KEY TOPICS 06:06 The board says "go enterprise" and why it blows up 07:58 What the board sees in pipeline vs. what is actually there 11:19 The three biggest GTM hiring mistakes at Series A and B 17:20 The founder as bottleneck: VP of Sales vs. CRO 20:14 Pilots, tranches, and the dying art of the seven-figure deal 26:01 How to evaluate a go-to-market team in 30 minutes 27:15 The silent sales floor 28:32 Where AI budget actually pays off 31:59 Headcount as the real buying signal 34:07 Does AI mean you hire fewer reps? 35:59 The slop failure mode founders do not catch 46:36 Two tools and two changes to deploy Monday morning GUEST LINKS Justin Michael on LinkedIn: https://www.linkedin.com/in/michaeljustin/ Books and coaching: https://www.amazon.com/gp/product/B0DRPP4Q1T LISTEN AND FOLLOW MARTALKS Apple Podcasts: https://apple.co/4wNap4X Spotify: https://bit.ly/4fF2ukm Darrell Rosenstein on LinkedIn: https://www.linkedin.com/in/darrellrosenstein/ The Rosenstein Group: https://rosensteingroup.com/ Keywords: enterprise sales hiring, Series A go-to-market, VP of Sales vs CRO, AI SDR, outbound prospecting strategy, MarTech sales leadership, sales pipeline qualification Rosenstein Group: martech & ecommerce executive search Rosenstein Group is the only martech-specialist exectutive search firm. For over 20 years, we've been matching leadership talent in sales, marketing and customer success to pioneering startups in ecommerce, supply chain and sales enablement, and for digital agencies. Our experience with recruiting e-commerce technology leaders for companies like SAP Hybris and Demandware has established us as an authoritative and trusted liaison for startups seeking their first sales leader, and scale-ups on their way to IPO. Visit RosensteinGroup.com to find out more.


