In this episode, I sit down with Grey Bradshaw-Mack, GTM at Default, to talk about his unconventional path into tech sales, from starting out in nonprofit work to breaking into software sales through PitchBook and eventually moving into early-stage startup roles. Grey shares how a major skiing accident forced him to relearn how to walk, created a difficult gap in his resume, and ultimately shaped the way he thinks about resilience, discipline, and telling a compelling story in the job market. He also explains what he learned at PitchBook, why that experience gave him such a strong foundation in sales, and why he was drawn to startups over larger, more established companies.

We also get into how Grey landed roles at Sunset and Default, why networking and staying close to people over time mattered more than simply sending cold applications, and what candidates should actually look for when evaluating a startup. Grey breaks down the appeal of joining an early team, the tradeoffs of startup life, and some of the most common reasons startups fail, from founder conflict and poor capital management to losing touch with the customer. He also shares why candidates should backchannel current reps, ask much tougher questions in interviews, and treat the interview process as a two-way vetting process instead of just trying to prove they deserve the job.

TOPICS WE COVER

• Grey’s path from nonprofit work into tech sales and why his career path was anything but linear
• How a major injury and long recovery created a resume gap and changed his perspective on work
• What Grey learned at PitchBook about discovery, product positioning, customer curiosity, and outbound
• Why startup sales appealed to him more than staying at a larger company
• How Sunset first became a prospect and later turned into a career opportunity
• How Grey got his role at Default through networking and relationship-building over time
• Why LinkedIn DMs, networking events, and staying in touch can create real job opportunities
• What to look for when evaluating whether an early-stage startup is actually worth joining
• Common reasons startups fail, including founder disputes, careless spending, and weak customer feedback loops
• Why job seekers should ask harder questions, talk to current reps, and treat interviews like a two-way evaluation

ABOUT THE GUEST

Grey Bradshaw-Mack is on the GTM team at Default, a New York-based startup, and previously worked in sales at Sunset and PitchBook. Before entering tech sales, he worked in the nonprofit world, giving him a nontraditional path into software sales. He's also an investor in Mercor.

LINKS

Connect with me: https://www.linkedin.com/in/carter-armendarez/
Subscribe to the newsletter: https://www.techsaleswithcarter.com/newsletter/
Learn more about Default: https://www.default.com/