In the latest *MarTalks* episode, I had the privilege of hosting three enterprise sales powerhouses—Brad Habansky, Chris Sterbenc, and Brian McGlynn—to discuss one of the most daunting challenges for startups: landing that first big deal. These seasoned pros shared their war stories, scars, and hard-earned wisdom on navigating the complexities of enterprise software sales. Here’s what stood out:
Selling Innovation is Hard Work
Brad Habansky recounted his early days at CommerceTools, introducing “composable commerce” to a U.S. market that had no idea what it was. Before he could even pitch flexibility or scalability, he had to convince prospects why they should trust the cloud—a revolutionary concept at the time. His journey was a masterclass in persistence, education, and rapid iteration.
Iteration is Key
Chris Sterbenc shared how selling for startups often requires constant refinement of your pitch. Early on, parts of his presentations fell flat (I hate it when that happens) —but by analyzing what resonated with prospects, he adapted quickly. As he put it,
One bullet point on slide five might eventually become half your deck.” Rapid iteration isn’t just helpful—it’s essential.
The Right Team Makes All the Difference
Brian McGlynn emphasized the importance of hiring entrepreneurial sales talent who can navigate uncharted territory. “Your first hire isn’t just a salesperson—they’re an explorer,” he said. But it doesn’t stop there; investing in marketing and technical support is equally critical to set that salesperson up for success in a competitive market.
Leveraging Accelerators
Chris also highlighted how startup accelerators like Plug and Play and Engage are game-changers for startups looking to break into enterprise accounts. These programs provide access to innovation teams at Fortune 500 companies, opening doors that are often shut to smaller players.
Listen to the full podcast here:
Key Takeaways for Founders
- Educate Your Market: Selling a new concept often starts with teaching prospects why they need it in the first place which requires marketing to prepare the ground for sales
- Iterate Quickly: Be ready to refine your pitch after every meeting until it clicks. Encourage experimentation and celebrate those failures!
- Find the Right Talent: Your first sales hire needs grit, curiosity, and an entrepreneurial mindset to succeed in uncharted waters, like a pirate…😊
- Invest in Marketing:** A strong digital presence is non-negotiable when 70% of the sales cycle happens before a prospect even talks to you.
- Leverage Accelerators:** Programs like Plug and Play can help startups land pilots with major brands and expand into enterprise accounts.
Closing that first deal is tough—it’s a gauntlet of education, iteration, and persistence. But as Brad, Chris, and Brian reminded us, it’s also one of the most rewarding milestones for any startup.
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