Sales Confidence, Culture & Connection with Gui Costin

In this episode of Transition to Sales, Gui Costin, Founder and CEO of Dakota, joins host Heather Javier for an inspiring and tactical conversation on how to lead with values, build resilient sales organizations, and create company cultures rooted in kindness, structure, and belief. Gui, author of The Dakota Way and creator of Dakota Marketplace, shares how his unconventional path through 14 jobs in 17 years shaped his vision for a better way to lead, sell, and grow.

Gui opens the episode with a candid look at his early career, bouncing between roles before launching Dakota in 2006. Those experiences, while difficult, became the foundation of his mission to build a company where people could grow long-term and thrive in an environment of mentorship, respect, and high performance. Today, Dakota is known not just for raising over $40 billion, but for creating a work culture that people genuinely want to be a part of.

The episode dives deep into Dakota’s values-driven approach to sales and leadership. Gui explains that at the heart of every deal is how you treat people. At Dakota, that means no passive-aggressive behavior, no “corporate weirdness,” and a clear distinction between being nice and being kind. He believes leaders must be hyper-aware of how their words and actions impact others, and must lead with intention and integrity every day.

For those transitioning into sales, Gui offers practical, battle-tested advice: start with a defined sales process, get comfortable with cold outreach, and track every interaction in a CRM. He outlines his four-part framework from The Dakota Way: 1) setting a clear plan with expectations, 2) identifying your ideal buyer, 3) running structured meetings, and 4) leveraging CRM for follow-up – as essential for avoiding the "law of 18 months" that plagues many sales professionals.

Gui also speaks directly to women and newcomers in sales who may feel sales is inherently confrontational. His approach is consultative, centered on asking two key questions at the end of every meeting to clarify next steps: “Do you see this fitting into your model?” and “Will there be a search in this category in the next year?” This removes ambiguity, eliminates ghosting, and respects both parties’ time.

The conversation wraps with a preview of Gui’s forthcoming leadership book Be Kind, which shares lessons learned from nearly two decades of building a high-performance company with empathy at its core. He also teases exciting developments at Dakota, including software enhancements, new data sets, and a growing conference business designed to bring the investment community together.

For anyone thinking about transitioning to sales, or leading a team through growth, this episode is a masterclass in building a business that scales through trust, process, and purpose.