The $40 Billion Secret: Gui Costin on Trust, Leadership, and Redefining Sales

In this episode of the Manage 2 Win Podcast, Gui Costin, founder and CEO of Dakota, shares his journey of building a high-performing sales organization and the leadership principles that have fueled Dakota’s growth — including raising over $40 billion for investment clients. While Gui is quick to credit luck and timing, he emphasizes the essential role of a clearly defined sales process and values-based leadership in scaling a business.

A core message throughout the conversation is Gui’s belief that CEOs must own the sales process. He explains that early in Dakota’s history, outsourcing sales without clear expectations led to failure. In response, Gui meticulously documented his own approach to sales, eventually formalizing it into “The Dakota Way” — a company-wide sales methodology that ensures consistency, accountability, and measurable outcomes. Dakota’s software business now relies heavily on this system, with a particular focus on cold outreach and booking high-quality demos.

Gui also dives deep into Dakota’s unique organizational structure and culture. The company has no middle management and instead operates with small, agile teams led by engaged team leads. Daily check-ins and end-of-day reviews promote alignment and real-time course correction. This structure, Gui explains, helps eliminate bureaucracy and ensures every team member remains focused on what matters most. For example, inside sales reps must always be targeting five cities for outreach — a simple, repeatable structure that ensures momentum.

Another distinctive aspect of Dakota’s culture is its focus on hiring Division I athletes and other high-performers who thrive in competitive, team-driven environments. Gui seeks individuals who are used to being coached hard, handling rejection, and performing under pressure — particularly for sales and BDR roles. But while the standards are high, the environment is built on kindness, trust, and compassion. Gui differentiates between “kind” and “nice,” explaining that kindness involves honest feedback and clear expectations delivered with respect.

Leadership at Dakota is intentionally flat and transparent. Gui emphasizes treating people like adults, offering flexibility and autonomy — no vacation policy, no travel expense scrutiny — which, in turn, builds trust and loyalty. He shares how cultivating a positive environment, removing bureaucracy, and investing in wellness (such as company-paid gym memberships) have led to high employee retention.

Feedback and learning are central to Dakota’s operations. Monthly “W Days” (short for “What’s Working, What’s Not”) allow teams to meet, identify blockers, and suggest improvements in real time — a practice Gui says has significantly boosted morale and efficiency. He also warns against outdated processes, borrowing a lesson from Amazon: regularly reevaluate and ask “why” to avoid stale habits.

Ultimately, Gui believes that great leadership is about humility, constant self-evaluation, and a commitment to helping others grow. His leadership style balances high expectations with human empathy, making Dakota not only successful but also a place people are proud to work.