Gui Costin On How To Create a High Performing Sales Team

In this episode of Chasing the Insights, Gui Costin, Founder and CEO of Dakota, joins host Vince Warnock for a wide-ranging discussion on building high-performing sales teams through process-driven leadership, intentional culture, and a clear sales methodology. Known for creating Dakota Marketplace, a widely used database for institutional investors, and authoring The Dakota Way, Gui unpacks what it takes to lead resilient, results-driven teams in the modern sales environment.

Gui kicks off the episode by sharing his early career journey, which included 14 W-2s in 17 years before founding Dakota in 2006. These experiences sparked his mission to build a company where people could thrive long-term, anchored in leadership development and career stability. From the outset, Dakota was built around sales and marketing, with an eye toward developing leaders and keeping the best talent over time.

The heart of the conversation focuses on what makes a high-performing sales team. For Gui, it starts with a leader who not only sets clear expectations but also models the process, brings transparency, and provides consistent accountability. Salespeople are granted autonomy in their daily routines, but with guardrails: everyone knows what success looks like, how progress is tracked, and what steps are required to improve. Without this framework, Gui argues, teams struggle to deliver consistently.

He also emphasizes the importance of hiring the right people – often college athletes, especially lacrosse players, known for their grit and coachability. These reps thrive in Dakota’s structure, which includes daily 7:45 AM check-ins, leaderboards, no quotas, and a culture of compassion and support. Business Development Reps (BDRs) know their expectations down to the city they're booking meetings in, with team leads jumping in to help with email strategy and coaching. Gui listens to almost every call, not to micromanage but to reinforce that performance standards matter and are monitored.

On the Investment Sales side, Gui outlines a simple but powerful playbook: define your total addressable market, know who the buyers are, reach out with structured messaging, and measure progress rigorously. Dakota avoids vague follow-ups by closing each sales meeting with two direct questions: “Do you see our strategy fitting into your model?” and “Will you be doing a search in this asset class in the next 12 months?” This eliminates guesswork and makes the next steps clear.

Gui wraps the episode by reflecting on the core principles of his book The Dakota Way, which include setting expectations, knowing your TAM, mastering the sales story, and leveraging CRM to 10x your follow-up. His leadership philosophy centers on creating low-volatility work environments where people are treated with respect and held to high standards. For entrepreneurs, his advice is simple: start with something people will pay for, hire deliberately, and build a workplace where the best people want to stay.