In this episode of Sales Talk for CEOs, Gui Costin, founder and CEO of Dakota, shares his journey of building a thriving business that has raised over $40 billion for investment firms. Hosted by Alice Heiman, the conversation delves into Gui’s approach to leadership, structured sales processes, and fostering a culture that empowers employees while driving results.
Gui begins by outlining Dakota’s dual business model. The first involves providing outsourced sales and marketing services for investment firms, particularly those raising capital for private equity, venture, and credit funds. Dakota’s second business, launched in 2019, offers a subscription-based database of institutional investor information. This tool enables internal sales teams to target investors more effectively, with over 1,100 investment firms now using the platform.
Reflecting on Dakota’s early days, Gui describes the challenges of starting with limited resources. With just himself and a partner, Gui managed both operations and sales, leveraging his network to secure initial clients. This hands-on experience informed his belief that CEOs must own the sales process, especially in a company’s early stages. Gui emphasizes that sales, being the lifeline of any business, should be directly overseen by leadership to ensure alignment and strategic growth.
Central to Dakota’s success is its structured sales methodology, The Dakota Way, implemented in 2012. This system focuses on creating detailed processes, conducting regular check-ins, and ensuring transparency. Gui explains that ambiguity often leads to failure when scaling sales teams. By clearly defining expectations and holding team members accountable, The Dakota Way eliminates guesswork, fostering consistency and scalability. Gui credits this approach with transforming Dakota into a high-performing sales organization.
A key theme in the conversation is Dakota’s emphasis on promoting from within. Gui highlights the importance of training employees in the company’s values and processes, enabling them to grow into leadership roles. This practice ensures cultural alignment and creates a sense of loyalty among team members. Gui also discusses Dakota’s “no ceilings” culture, which encourages employees to continuously develop their skills and advance their careers.
Cold outreach remains a cornerstone of Dakota’s sales strategy. Gui acknowledges that while it can be challenging and emotionally taxing, disciplined outreach efforts drive meaningful connections. The company’s success is built on crafting concise, personalized emails that resonate with potential clients. Gui stresses the importance of avoiding automation and maintaining authenticity in the trust-driven investment industry.
Technology, particularly AI, plays a significant role in Dakota’s operations. The company uses AI to enhance its database product, enabling clients to perform complex queries quickly and efficiently. While AI streamlines administrative tasks, Gui underscores the importance of human interaction in building trust and relationships with clients.
Gui’s leadership philosophy centers on kindness. He believes that treating employees with respect and fostering a positive work environment leads to better employee retention, stronger customer relationships, and long-term success. By focusing on employee well-being and growth, Dakota ensures that its team members are motivated and aligned with the company’s goals.
Gui concludes by recommending resources for CEOs, including The Amazon Management System for its insights into principle-driven success and Category Pirates by Chris Lochhead for its focus on category creation.
This episode offers a comprehensive look at Gui’s approach to leadership, sales, and culture-building, providing valuable lessons for CEOs looking to scale their businesses while fostering a supportive and high-performing workplace.