Build Customers for Life

The 28-Day Customer Success Program

Turn Customer Relationships Into Long-Term Growth.

The 28-Day Customer Success Program gives you a practical, step-by-step system for building a world-class customer success organization. You’ll learn how to improve onboarding, reduce churn, increase retention, identify expansion opportunities, automate repetitive processes, and build a customer experience that drives lasting loyalty.

By Day 28, you’ll have a scalable Customer Success system designed to create happier customers, stronger relationships, and predictable recurring revenue.
  • 28 Daily Challenges
  • Daily Email Coaching
  • Downloadable Resources
  • Lifetime Resource Library Access
  • Available in Paperback, Digital, Audio, or Daily Email Only
Start My Challenge How It Works

The 28-Day Customer Success Challenge

Starting at $14.99
Choose Your Experience

Program Snapshot

Duration

28 Days

Skill Level

Beginner to Advanced

Format

Paperback, Digital, Audio, or Daily Email

Downloads

Playbooks, Journey Maps, Health Score Templates & Dashboards

Resource Library

Lifetime access

Delivery

Start immediately after purchase

Choose Your Experience
<strong>Paperback Experience</strong>

Paperback Experience

Build your Customer Success strategy while completing practical exercises each day.

$24.99 Includes:
  • Paperback book
  • Daily challenge emails
  • Resource Library
Add to Cart
<strong>Digital Reader Edition</strong>

Digital Reader Edition

Access your Customer Success program anywhere and build your systems at your own pace.

$19.99 Includes:
  • ePub for eReader
  • Daily challenge emails
  • Resource Library
Add to Cart
Most Popular
<strong>Challenge Experience</strong>

Challenge Experience

Receive one focused Customer Success lesson every day and steadily improve retention and customer satisfaction.

$14.99 Perfect for accountability.
  • Daily email delivered to your inbox
  • Resource library
Add to Cart
<strong>Audio Experience</strong>

Audio Experience

Learn while commuting, exercising, or traveling, then immediately apply what you’ve learned.

$29.99 Includes:
  • Audiobook file
  • Daily Challenge Emails
  • Resource Library
Add to Cart

Is This Program Right For You?

Who Should Take This Program?

  • Small business owners
  • Customer Success Managers
  • Customer Success Leaders
  • Customer Experience Professionals
  • SaaS Founders

Probably Not For You If…

  • You believe customer success ends after onboarding.
  • You only focus on acquiring new customers.
  • You’re unwilling to improve your customer experience.
  • You expect retention to improve without building systems.
  • You’re looking for quick fixes instead of long-term growth.

Create Customers Who Want to Stay

Download the first challenge free and start building a stronger customer experience.

Keeping great customers can be just as important as finding new ones. Download the first challenge free and see how the 28-Day Customer Success Challenge helps you create stronger experiences, relationships, and processes throughout the customer journey. Add your free chapter to the cart, complete checkout, and download your sample.

FREE SAMPLE - The 28 Day Customer Success Challenge - First Chapter

What You'll Accomplish

By Day 28 You’ll…

Week 1
Week 1
Built the foundation of a successful Customer Success organization by defining your mission, roles, onboarding process, team skills, and company values.
Week 2
Week 2
Mapped your complete customer journey, identified key touchpoints, segmented customers, developed proactive communication strategies, created health scores, and launched a Voice of the Customer program.
Week 3
Week 3
Audited your technology stack, automated onboarding, built Customer Success playbooks, centralized knowledge management, and created proactive customer alerts.
Week 4
Week 4
Built Customer Success dashboards, defined success metrics, practiced executive business reviews, created customer advocacy programs, developed scaling plans, and established continuous improvement processes.
28 Days
Customers Who Stay Longer.
Paperback
Digital Reader
COMING SOON! Audiobook
Daily Emails Only

Inside the Program

A step-by-step look at the four-week system that turns reactive customer support into a proactive, repeatable Customer Success strategy. Each week builds on the last, helping you strengthen onboarding, improve engagement, increase retention, and turn satisfied customers into loyal advocates.

Lessons

  • Mission & Vision
  • Roles & Responsibilities
  • Hiring Profiles
  • Onboarding Systems
  • Skills Assessments
  • Team Values
  • Weekly Review

Learning outcomes

  • Build a scalable CS organization
  • Create role clarity
  • Hire better people
  • Develop stronger teams

Lessons

  • Customer Journey Mapping
  • Touchpoint Planning
  • Customer Segmentation
  • Communication Strategy
  • Customer Health Scores
  • Voice of the Customer
  • Weekly Review

Learning outcomes

  • Improve customer engagement
  • Reduce churn risk
  • Deliver proactive experiences
  • Understand customer needs

Lessons

  • Technology Audit
  • Customer Success Platforms
  • Automated Onboarding
  • Success Playbooks
  • Knowledge Management
  • Health Score Alerts
  • Testing & Optimization

Learning outcomes

  • Automate repetitive work
  • Standardize customer experiences
  • Improve operational efficiency
  • Scale Customer Success

Lessons

  • North Star Metrics
  • Customer Success Dashboards
  • Quarterly Business Reviews
  • Customer Advocacy
  • Scaling Strategy
  • Cross-Functional Collaboration
  • Long-Term Planning

Learning outcomes

  • Measure business impact
  • Increase customer retention
  • Grow customer advocacy
  • Create sustainable success

Downloadable Resources

Lifetime access to Customer Success resources.

Customer Journey Resources

Customer Journey Resources

Journey Mapping Templates, Touchpoint Worksheets, Customer Lifecycle Maps, Communication Calendars, Onboarding Checklists
Success Resources

Success Resources

Customer Health Score Templates, Success Playbooks, Success Plan Templates, QBR Templates, Risk Assessment Worksheets
Operations Resources

Operations Resources

Workflow Templates, Automation Planning Guides, Knowledge Base Templates, Technology Audit Worksheets, Customer Segmentation Tools
Leadership Resources

Leadership Resources

Customer Success Dashboards, Executive KPI Reports, North Star Metric Trackers, Retention Scorecards, Team Planning Templates
Growth Resources

Growth Resources

Advocacy Program Templates, Renewal Planning Guides, Expansion Opportunity Trackers, Voice of the Customer Templates, Continuous Improvement Worksheets

Meet Your Coach.

Robert M. Coles

Customer Success isn’t customer support.

It’s one of the most important growth functions in your entire organization.

Throughout my career leading operations, customer experience, marketing, and business strategy, I’ve seen organizations invest enormous resources into acquiring customers while giving little attention to keeping them. Sustainable growth comes from creating customers who succeed, stay longer, and become enthusiastic advocates for your business.

This program gives you the same structured framework used by successful Customer Success organizations—broken into manageable daily challenges that help you build systems capable of growing alongside your business. 

 Learn More

What Makes The 28 Day Challenge Different?

Typical Customer Success Books Traditional Training The 28-Day Program
❌ Heavy on theory ❌ Expensive certifications ✅ Daily implementation challenges
❌ Limited practical implementation ❌ One-time learning ✅ Customer Success playbooks
❌ Few reusable templates ❌ Limited customization ✅ Automation frameworks
❌ Difficult to apply immediately ❌ Little day-to-day implementation ✅ Complete Customer Success operating system

Frequently Asked Questions

Find answers to common questions below

Not at all. While Customer Success is often associated with SaaS companies, the principles apply to virtually any business that depends on long-term customer relationships. Whether you sell software, professional services, memberships, subscriptions, consulting, or other products and services, the challenge will help you create a more intentional approach to onboarding, engagement, retention, and customer growth.
Absolutely. You don’t need a large Customer Success department or an enterprise-sized customer base to benefit. In fact, small businesses can often implement Customer Success practices faster because there are fewer layers and processes to navigate. The challenge will help you build practical systems that can grow alongside your business.
That’s one of the primary goals. Throughout the challenge, you’ll learn how to identify potential warning signs, improve customer engagement, strengthen relationships, and proactively address issues before they become reasons to leave. While no program can eliminate churn entirely, you’ll finish with a much stronger framework for improving retention.
Plan on approximately 20–30 minutes per day for most lessons and activities. Some days may take less time, while others may require additional time if you choose to dig deeper or implement a larger process. The challenge is designed to fit into your workday without becoming another overwhelming project on your to-do list.
No. You can complete the challenge whether Customer Success is handled by a dedicated team, an account manager, a salesperson, a support team, or simply you. If you’re building Customer Success from scratch, the challenge can help you establish the foundation. If you already have a team, you can use it to evaluate and strengthen your existing approach.
Yes. You’ll explore how customer health scores can help you identify healthy accounts, customers who may need additional attention, and accounts showing potential signs of churn. You’ll learn how to think about the signals that matter to your business and begin building a practical health-scoring approach rather than relying on a one-size-fits-all formula.
Yes. The challenge includes practical resources, worksheets, and templates designed to help you put what you’re learning into action. Rather than simply reading about Customer Success concepts, you’ll have tools you can customize and begin using within your own organization.
Absolutely. Once you’ve completed the challenge and adapted the frameworks to your organization, many of the concepts and resources can become part of your internal Customer Success playbook. They can help new team members understand your approach to onboarding, customer engagement, health monitoring, retention, and long-term relationship management.
Yes. The core principles of Customer Success apply whether you manage 20 customers or 20,000. Enterprise organizations can use the challenge to evaluate existing processes, identify gaps, improve consistency across teams, and create stronger alignment around the customer journey. The frameworks can be adapted to fit more complex customer segments, teams, and account structures.
Day 28 isn’t the finish line—it’s where you put the system to work. By the end of the challenge, you’ll have built a stronger Customer Success foundation and identified the processes, metrics, and practices that make sense for your organization. From there, you can continue refining your playbooks, monitoring customer health, improving retention, and using what you’ve built as an ongoing Customer Success operating system.

Great Businesses Don’t Just Win Customers.

They Keep Them.

Every successful company understands one simple truth:

The easiest customer to grow is the one who already trusts you.

Over the next 28 days, you’ll build the systems, processes, and strategies that help customers succeed, renew, expand, and become lifelong advocates for your business.

Choose your preferred format and start building a Customer Success organization that creates growth long after the sale.

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