Shownotes
When was the last time a salesperson helped you make a truly confident decision? In this episode of the Sell by Being Human podcast, Alex Smith sits down with Mark Kosoglow, Chief Revenue Officer at Deutsche Bank and former CRO at Catalyst Software, to talk about what selling actually looks like when you strip away the scripts. From selling shoes as a teenager to helping scale Outreach to $250M, Mark’s journey is anything but typical, but his core idea has stayed the same: great salespeople help others make confident decisions.
They get into what that looks like in practice. Mark shares why letting passion lead often creates better conversations than trying to sound polished, how his early experience with consultative selling shaped the way he works today, and why honesty and vulnerability matter more than most people think, especially when you’re asking teams or customers to embrace change.
They also dive into storytelling, the role of metaphors in making ideas stick, and the problems that come from unclear expectations. Throughout the conversation, Mark makes a strong case for being yourself, not as a slogan, but as a real advantage in both sales and leadership.
If you’ve ever felt like selling forces you to be someone you’re not, this episode will change how you approach every conversation.
Key Takeaways
- Help people make confident decisions, not just hit numbers
- Let passion show instead of hiding behind professionalism
- Treat “no” as a step that moves you closer to yes
- Focus on understanding the problem before offering solutions
- Build trust by being transparent about intentions and mistakes
- Give direction, but avoid control to unlock creativity
- Act, learn, and adjust instead of over-planning
- Prioritize clarity and ask questions instead of assuming
In This Episode:
- [00:00] Mark’s core motivation for selling
- [01:00] Welcome & introduction to Mark Kosoglow
- [02:05] Dan Pink’s To Sell Is Human and personal connections
- [05:05] What “sell by being human” means to Mark
- [06:03] Helping people make confident decisions (the 2-out-of-3 rule)
- [08:15] Early days: Selling shoes at The Athlete’s Foot & learning consultative selling
- [11:45] Telemarketing lessons and embracing “no”
- [14:21] Leading through change and the weight of asking people to shift how they work
- [16:05] Balancing control with freedom and creativity
- [18:46] Admitting failures and iterating quickly (self-sourcing example)
- [22:28] Revenue Kickoff reflections and the power of in-person connection
- [25:32] Using metaphors and storytelling (the Boeing story)
- [29:38] What Mark looks for in a CEO/leader above him
- [33:29] Clear communication and avoiding misinterpretation
- [36:08] Lessons for his kids
- [39:06] Signature question: What makes Mark totally Mark?
- [40:36] Where to find Mark
- [40:59] Closing
Notable Quotes
- [05:11] “Let your passion overcome your professionalism.” — Mark Kosoglow
- [05:55] “My personal motivation and the motivation I like my sales teams to have is to help people make confident decisions.” — Mark Kosoglow
- [10:32] “People love learning about their problem enough to understand why you’re suggesting a solution, and then they’re super confident in making the decision of that solution.” — Mark Kosoglow
- [12:27] “The faster they say no, the more I can move on to the next call that could say yes.” — Mark Kosoglow
- [36:42] “Who you are is who you are, and it’s probably pretty awesome” — Mark Kosoglow
- [24:27] “ I just really want to have fun and I want to work hard and I want to kick ass and win. And I don’t think that I have to be an asshole to do that.” — Mark Kosoglow
- [36:54] “Work ethic is like a trump card for success.” — Mark Kosoglow
- [38:22] “Expectations are the number one thing that kill parent-child relationships.” — Mark Kosoglow
Our Guest
Mark Kosoglow is Chief Revenue Officer at Deutsche Bank and a seasoned sales leader with decades of experience scaling revenue organizations. Previously, as CRO at Outreach, he helped scale the company to $250 million in revenue. Mark's career began at a shoe store called The Athlete's Foot, where he learned consultative selling at 16 years old, a philosophy that has shaped his leadership style ever since. Known for his storytelling, metaphors, and unconventional communication style, Mark believes that great sales leadership comes down to trust, transparency, and helping people make confident decisions.
Resources and Links
Sell by Being Human
Mark Kosoglow
Alex Smith
