Coaching
The Success League’s coaching program offers tailored advice to CS leaders facing a variety of challenges. Our coaching team can help both emerging and experienced leaders drive performance and effectively manage their CS organizations. We also provide insight and support throughout projects, ensuring they continue in the right direction while driving accountability for major milestones. Our CEO, Kristen Hayer, focuses on supporting C-level leaders as they add or grow their customer success programs, and assists investors with the development of CS discipline within their portfolios.
Scaling Teams
Using proven models and frameworks, leaders learn how to grow customer success while scaling their company. In learning how to build out their CS organization, leaders cultivate skills they will use for the rest of their career.
Emerging Leaders
Coaching helps leaders with valuable experience further develop important leadership skills in order to drive strong performance while effectively managing a CS organization.
Project Accountability
Leaders who have the basic skills to tackle CS projects still sometimes need expert advice throughout the project. Coaching helps keep the project going in the right direction while providing accountability for major project landmarks.
"I had the privilege to work with Kristen at The Success League during some private coaching sessions. When we started our sessions, I thought I knew the primary areas to focus on. After a few sessions with Kristen, I had reprioritized a few things, and left with a solid path to move the team forward in a big way. We drilled down to a tactical level (to get) tangible examples of not just why I should do something, but how I could actually operationalize it. I would highly recommend The Success League to anyone who wants to up their game in the Customer Success arena."
-Reanna Dempsey, Director of Customer Success
Our Coaches
Russell Bourne
Russell has primarily worked with growth-stage companies who are building or refining their customer success organization. His professional background is in compliant verticals including data protection, medical, and financial, and he's especially interested in furthering the career trajectory of directors and VPs. Russell employs a listen-first, problem-solving coaching style, effective whether the client needs to build or react.
Whitney Littlewood
Whitney has helped a wide range of companies—from growth-stage startups to industry leaders like Adobe and UserTesting—scale successfully and build high-impact customer success organizations. Whitney is known as a strategic powerhouse who brings both creativity and practical problem-solving to the table. Her coaching style is focused, down-to-earth, and action-oriented. She helps clients cut through complexity to find clear, simple paths forward. Taking a holistic view of career development, Whitney works with individuals not just on securing the next promotion, but on aligning their professional growth with their bigger life goals and personal needs. Whitney enjoys working with new managers, emerging leaders and CSMs looking to take the leap into leadership.
Kristen Hayer
Kristen has been leading Sales, Success and Marketing teams at the executive level for the past 15 years. She has a background in HR, Marketing and Event Management verticals, and has completed a significant amount of consulting work with HealthTech, FinTech and EdTech organizations. Kristen enjoys working with emerging executives, CEOs and Investors, and focuses on building strong CS programs that drive revenue.
Kristen has limited availability for coaching, and focuses on C-level executives and investors.