The Success League

A CS career doesn't have to be accidental. Whitney works with CSMs who are ready to build their skills, define their path, and move toward leadership on their own terms.

Whitney has spent more than 15 years in customer success, including Director and Senior Director roles at Adobe, Optimizely, and UserTesting. She brings deep practical experience across enterprise and mid-market CS to her coaching work with individual CSMs.

What we work on together:

Building the core skills that make you exceptional at your current role
Navigating performance conversations and career development with your manager
Understanding the metrics and business outcomes that matter most at your level
Practicing the high-stakes conversations that actually determine how your career goes
Integrating AI tools into your day-to-day CS work

Let's Talk About the CSM Edge

Russell Bourne | For Managers and Directors

The jump from individual contributor to CS leader is one of the hardest transitions in the profession. Russell coaches managers and directors on building stronger teams, developing their leadership approach, and advancing their careers with intention.

Russell has more than a decade of CS leadership experience, including Director and VP roles, and continues to work as an active practitioner through The Success League's interim leadership practice. He is a Principal at The Success League and a board member of Gain Grow Retain, one of the largest CS communities in the industry.

What we work on together:

Advancing your leadership career and positioning yourself for the next role
Building out your CS program using proven models and methodologies
Navigating senior leadership teams and boards effectively
Driving consistent and measurable performance across your team
Integrating AI into your CS motion without losing sight of what actually drives customer relationships

Let's Start with a Conversation

Kristen Hayer | For VPs, CCOs, CROs and other C-Level Leaders

At the executive level, success isn't about your own performance: it's about what your organization delivers. Kristen works with CS leaders to build the models and frameworks that drive retention, expansion, and customer experience across their teams.

Kristen has spent more than 20 years leading revenue and customer success organizations before founding The Success League in 2015. She is a recognized CS thought leader and co-author of "The Customer Success Talent Playbook."

What we work on together:

Aligning CS, sales, and account management into a cohesive go-to-market motion
Building or rebuilding a CS organization for scale
Improving retention and expansion performance across your team
Navigating growth stages, acquisitions, or major organizational change
Developing the frameworks your team needs to execute consistently

Let's Start with a Conversation

Our Customers Say…

“Working with The Success League helped me advance my career and benefited my company. My coach brought a wealth of industry knowledge to every meeting, and provided tools and insight to help us scale and organize our client success department. The Success League was so helpful I asked them to speak at our annual team retreat where they delivered a wonderful presentation. On a personal note, my coach's career advice helped me become a member of my company's executive team. I would recommend The Success League to anyone working in the customer success field.”

Tim McDonough, Chief Client Officer

“Our coach, Kristen Hayer, spent a week at our office after a growth investment funding round, and we worked on our customer journeys, customer segmentation, s and creating new processes. After our sessions I felt like a new leader! Her experience and knowledge in the Customer Success field has really prepared me for this next stage in our company.”

Will Lopez, Vice President of Client Strategy

“I took on a new role at my company in order to restructure our Client Services and Account Management team into a cohesive Customer Success program. I set up coaching sessions with The Success League. My coach was not only fun to work with, she had a ton of experience and totally understood the challenges of fast growing companies rolling out CS departments. We had struggled with some consultants in the past who were too rigid in 'the way things should be done,' but The Success League took the time to understand the nuances of our industry and helped us to apply best practices of customer success to our business. My coach was always available if something urgent came up during the week, and was the sounding board I needed throughout such a massive change for our team. “

Colleen St. John, Director of Customer Success

What changes when you have the right coach? Everything.

A clearer sense of where you're headed and how to get there. Stronger relationships with your team, your customers, and your peers. Confidence in the decisions that matter most. A career that moves with purpose.

Are you ready to stop guessing and start building?

Let's Start with a Conversation