November 08, 2024 | 42 MIN

A Modern Leader’s Guide to Sales Success with Gui Costin

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In this episode of The Leadership Habit Podcast, Gui Costin, founder and CEO of Dakota, shares his insights on building successful sales teams, fostering a thriving workplace culture, and adapting to modern sales challenges. Host Jenn DeWall delves into Gui’s leadership philosophies, which prioritize respect, structure, and empathy as the cornerstones of a high-performing organization.

Gui emphasizes the importance of creating a positive workplace culture where employees feel valued and respected. At Dakota, toxic behaviors are not tolerated, even from high performers or clients, as maintaining a supportive and collaborative environment is a top priority. Gui explains that culture is built on clear core principles, and leaders must consistently align their actions with these values. By doing so, employees are empowered to thrive and grow, making work both fulfilling and enjoyable.

Sales, as Gui notes, is one of the most emotionally demanding professions due to constant rejection and the challenges of cold outreach. He stresses the need for a structured process to support salespeople, including daily check-ins, clear expectations, and time-blocking for outreach activities. By focusing on the salesperson’s growth and providing consistent coaching, leaders can help their teams develop resilience and confidence over time. Gui explains that mastering the "cold outreach muscle" is a transformative skill that can take 12–18 months to fully develop but delivers lasting career benefits.

One of Gui’s standout strategies involves addressing follow-ups during the initial meeting by asking tough questions, such as whether a prospect sees potential for a partnership. This approach avoids unnecessary follow-ups and ensures clarity while the relationship is still fresh. He also highlights the importance of clear calls to action in follow-up emails to respect the prospect’s time and facilitate meaningful engagement.

Gui discusses the evolution of sales in the post-pandemic era, emphasizing the need for authenticity and compassion in outreach efforts. He believes that sales success comes from building genuine connections rather than focusing solely on transactions. For leaders, Gui advocates for empathy, self-reflection, and prioritizing the success of their teams, sharing his own journey of personal growth as a leader.

This episode is packed with actionable advice for sales leaders and modern professionals looking to build effective teams, improve sales processes, and create workplace cultures that inspire growth and collaboration.

Podcast Experiences

  • Measure Success: Successful Sales Strategies That Actually Work

  • Mastering Institutional Sales with Allen Gray of Silvercrest

  • Driving Sales and Success with Brad Jung, Russell Investments

  • Democratizing Private Equity with John Bailey, OneFund Investments

  • Guantong (“GT”) Sun on Process-Driven Fundraising at Turning Rock Partners

  • Scaling Private Wealth with Doug Krupa, KKR

  • Michele Colucci on AI-Driven Healthcare at DigitalDx Ventures

  • Driving Distribution with Discipline – Daniel Noonan, Cohen & Steers

  • Earning Trust, One Deal at a Time – Drew Dolan, DXD Capital

  • Joe Grogan on Culture and Consultative Sales at WisdomTree

  • How Stacy Havener Built Havener Capital on Storytelling and Strategy

  • Capital Formation, Not Sales – Inside CAZ with Christopher Zook

  • Fundraising with Precision: Inside Optimizing Sales at LAB Quantitative Strategies with Shane McCarthy

  • Inside the Capital Formation Playbook of RMWC with Michael Rubenstein

  • Educate, Don’t Sell – Danielle Brown’s Fundraising Playbook at Altriarch

  • John Donovan on Building Trust and Transparency at TowerBrook

  • “Thinking Big” with Urban Standard: Seth Weissman’s Approach to Fundraising and Growth

  • Andrew Saunders on Building a Collaborative Sales Culture at Castle Hill Capital

  • Inside 65 Equity: Leon Brujis on Partnering with Founders for Growth

  • Inside Dundas Global Investors: James Curry & Andrew Brown on Hybrid Sales and Service

  • Culture, Content, and the Future of Investment Sales

  • The No Policy, Policy with Gui Costin

  • Sales Confidence, Culture & Connection with Gui Costin

  • Gui Costin On How To Create a High Performing Sales Team

  • How To Win More Deals with Effective Cold Email Techniques with Gui Costin

  • How to Build Unconventional Cultures That Thrive with Gui Costin

  • Leading with Kindness: Building a High-Performance Culture Without Burnout with Gui Costin

  • The Dakota Way

  • Mastering Sales with Data Driven Growth with Gui Costin

  • How Dakota Raised $30 Billion For Their Clients

  • The Dakota Way: Why it Matters with Gui Costin

  • What We’re All Missing to Be Successful at Sales and Like It with Gui Costin

  • A Culture Of Success

  • Words Matter: How Gui Costin Built a Culture of Kindness and ExcellenceNotable Leaders' RadioPlay

  • Mastering the Art of Fundraising: $40 Billion Raised Dakota CEO, Gui Costin

  • Unlocking the Leadership Code: Lessons from the Frontlines

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

  • Helping Investment Firms Thrive – Fastlane Founders with Gui Costin

  • The Power of Kindness

  • Sales Leadership in the Investment Industry with Gui Costin

  • A Modern Leader’s Guide to Sales Success with Gui Costin

  • Gui Costin’s Proven Formula for Coaching Sales Teams to Success

  • Capital Raising Campaign Strategies with Gui Costin

  • Embracing Accountability in Sales with Gui Costin

(610) 764-0539
Gui@dakotaLive.com

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