Like me, Lauren McCullough did not begin her career in startups, but she found her way here after getting bored by the bureaucracy and red tape of larger organizations, and asking herself (in her words) “Like, why am I mad all the time?!” This impatience for inertia is also “probably why [she’s] never done enterprise sales”. Instead, she’s been focused on the SMB (Small and Medium Business) segment.Recently, Lauren founded Tromml, a B2B SaaS platform that helps automotive sellers improve their eCommerce performance. Before Tromml, for several years, Lauren was a fractional sales leader at several startups. She found herself coming in to help early-stage founders solve a recurring problem — that the first sales leader they hired just didn’t work out well. At this point, Lauren rode in on her magnificent horse and gallantly saved the day. (That is, she helped get growth going, wrote the sales playbook, hired the first Account Executive, and rode triumphantly off into the sunset.)

On this week's episode, I interview my friend Zack Turner — who's a Vice President of Enterprise Sales at Slack. Me and Zack go way back — we worked together at Kiva.org in San Francisco back in the day, and he was a groomsman at my wedding back in 2010! And he's worked in enterprise sales for almost as long as that — first at Box (he joined back when it was still called Box.net), and more recently at Slack. He's worked both as a Sales Engineer, in "frontline sales", and as a Sales Manager.

My friend Justin leads Revenue Based Financing at Wefunder (where I also work), a platform that helps startup founders raise capital from their customers and community, as well as VCs and millionaires.Me and Justin have known each other for over a decade now. After starting his career in sales at LinkedIn, Justin very quickly got bored, and came to volunteer at Kiva.org in 2012, where I was leading the Kiva U.S. team. Over the next 5 years, we co-led that program together in San Francisco, before Justin left to start his own boat charter business in San Diego — Chill Charters (enter "Closing Time" at checkout for a 20% discount. Not really… Will probably make this dad joke every week. Apologies in advance…). In 2019, we reunited at Wefunder, where we co-lead the BD team. Justin is — literally — the best BD person I have ever worked with. And I've probably worked with hundreds at this point, so that's a large sample size! He has an incredible genuineness and authenticity, that shines forth in everything he does. But even though he's usually decked out in tie-dye, and seems to spend about 97% of his waking minutes playing frisbee golf, he's perhaps the most ruthlessly organized person I've ever met. Although not through a "CRM". He has his own system. Even with systems, Justin is a renegade cowboy :)

My friend Josh is the CEO and Founder of Salesdash, a CRM for the freight and logistics industry. Prior to Salesdash, he worked in sales roles at multiple companies, including becoming one of the top 10 sales reps in North America for Tesla. And now — perhaps the apogee of his career to date — he’s the first guest that I interviewed for this nascent Closing Time podcast :)