The 28-Day Customer Success Challenge
Transform your team from a reactive support function into a proactive, data-driven, and indispensable growth engine.
Purchase Your Challenge & Build a Proactive Customer Success Plan
Are you tired of living in a constant state of reactive firefighting? This challenge is the definitive, hands-on sprint designed to break that cycle. Over four weeks, you will stop juggling at-risk accounts and battling escalations, and start building the foundations, strategies, workflows, and measurement systems of a modern CS organization. It's time to build a customer success plan that empowers you to become a strategic partner for your customers.
What You'll Learn
This is not another book of abstract theories. It is a practical, day-by-day "gym" where you will actively build the systems that drive world-class customer outcomes and prove your team's value to the entire business.
- Week 1 (Foundation): Forge your team's core identity by defining its mission, values, roles, and a world-class onboarding plan.
- Week 2 (Strategy): Architect a sophisticated, data-driven customer experience by mapping the journey, building a predictive health score, and creating powerful customer retention strategies.
- Week 3 (Execution): Translate strategy into action by building automated onboarding sequences, risk/expansion playbooks, and a centralized team wiki—your core CSM playbook.
- Week 4 (Measurement): Prove your impact by defining North Star metrics like NRR, building performance dashboards, and delivering value-focused QBRs.
Read the First Challenge for Free!
Ready to break the cycle of reactive firefighting? Take the first step today. Get Day 1 of The 28-Day Customer Success Challenge delivered to your inbox and forge the powerful mission statement that will become your team's North Star.
Challenge Resources
Every challenge is packed with free, downloadable resources to bring your systems to life. Gain instant access to templates for role descriptions, customer journey maps, health score calculators, QBR decks, and your first CSM playbook outline.
From the Blog
Explore our latest articles on customer success, retention strategies, and scaling your post-sales organization to become an undeniable driver of business growth and profitability.
Why is this challenge different?
This challenge was born from the reality of the daily grind. It’s for the CS leader buried in day-to-day chaos, the ambitious CSM ready to level up, and the founder building a CS function from scratch. We skip the abstract theory and provide a concrete, day-by-day blueprint for building a proactive customer success engine from the ground up.
This is the ultimate customer success manager training because it’s based on action, not just theory. It's designed for the entire CS ecosystem—Leaders, CSMs, Founders, and CS Ops professionals. By the end of 28 days, your team won't just feel more strategic; it will have the documented systems, playbooks, and metrics to prove it, elevating its role to an essential driver of business growth.
Ready to become a growth engine? Purchase the challenge today.
What to Expect During the Challenge
Each day, you will receive a focused lesson and a single, critical task that builds upon the last, guiding you from core principles to a fully operational, proactive Customer Success organization.
- A daily email with your CS lesson and your single, achievable building-block task.
- Guided exercises to define your team's mission and core values in Week 1.
- Practical frameworks for mapping the customer journey and building a health score in Week 2.
- Step-by-step instructions for creating risk, expansion, and onboarding playbooks in Week 3.
- Templates for building your first KPI dashboard and preparing a value-focused QBR in Week 4.
- The confidence that you are finally building the systems for true proactive customer success.
- A tangible, documented, and professional CS program at the end of 28 days.
How to Get the Most Out of the Challenge
This challenge is most powerful when it becomes your team's shared project for one month. Gather your team—CSMs, Ops, and leadership. Commit to completing the daily tasks together. Use the exercises to spark strategic conversations, challenge old assumptions, and build universal alignment on the path forward. By building together, you’ll not only end up with a world-class CS program but a more unified and energized team to run it.
Start building your world-class CS organization by purchasing the challenge now.
About Your Guide
Robert M. Coles is a business strategist and author who understands that acquiring a customer is only the beginning of the story. True, sustainable growth is born from the ability to retain and expand that customer base, a mission that lives and dies with the Customer Success team.
After years of building systems that drive marketing and sales growth, he saw that even the best pre-sales engines falter without an equally powerful post-sales counterpart. He created The 28-Day Customer Success Challenge to provide a clear, actionable blueprint for the often-overlooked post-sales journey, giving teams the tools they need to transform from a cost center into a powerful and recognized profit center.