
How a push-pull learning approach increased Activation Rates by 23%.
Project
Stack Sports is a fast-growing SaaS company that provides management tools for youth sports organizations, including its flagship product, Sports Connect.
As Sports Connect sales continued to rise, activation rates remained flat—particularly among smaller customers that relied on self-service onboarding. Despite strong product adoption at the enterprise level where customers received 1-1 training, many smaller customers struggled to get started, slowing their path to success.
Approach
To uncover the cause, the leadership team asked me to lead a cross-functional research project focused on understanding why some customers were successful and others weren’t. I started by analyzing historical activation data, CSAT and NPS scores, and product usage trends, and by mapping the sales-to-onboarding handoff and customer journey to identify potential friction points and opportunities for improvement.
What we discovered were four key insights that changed our entire approach to customer education:
- Educational materials were spread across multiple platforms and teams, resulting in a disjointed customer experience.
- Unlike traditional SaaS environments where users are motivated by workplace success, nearly 90% of our users were volunteers supporting their children’s sports organizations. Additionally, since many of our users are from volunteer run organizations, there tends to be a lot of turnover.
- While in-app content existed, we found that the content didn’t always align with where the customer was in their onboarding journey resulting in new customers being confused about next steps.
- We found that the longer a customer remained in the onboarding pipeline without taking action the harder it was to reengage them and help them find success.
Solution
Based on what we learned, the decision was made to expand my team to include new customer onboarding (1-1 training, self-service onboarding), live webinars, and digital adoption allowing us to consolidate educational delivery and content development under one team. While we still needed to address content in multiple locations, this change let us create a more consistent experience and guide users to the right content when they needed it.
To accomplish this, I decided to take a phased approach that would allow us to leverage what we were already doing and add to it.
Double-Down on Self-Service Content
We already had a library of training and educational resources, however we needed to do a better job guiding customers to the right content at the right time.
Help Center
Starting with our help center, we worked with our support, success, product, and sales teams to audit, remove, update and add new content to ensure we were addressing the customer’s needs. We focused on bringing content that answered customers’ most frequently asked questions and organized it into check lists, step by step guides, videos, and simple FAQs and articles that aligned with different phases in the customer journey. This allowed users to find a quick answer to a specific problem or question.

Webinars
Next, we looked at our webinars, a great option for one-to-many training and live Q&A. While we were already hosting weekly sessions focused on specific features and best practices, attendance was often low.
Since many of our users were volunteers with limited time and located across multiple timezones, we introduced on-demand access to all webinar recordings, allowing customers to engage with training content when convenient for them. We also added live office hours for direct support from a member of the activation team.
Sports Connect Academy
The final piece of our self-service strategy was the launch of the Sports Connect Academy, a free, on-demand learning platform offering structured courses and learning paths to help customers solve problems independently and to deepen their product knowledge. We built the Academy from the ground up, from concept and LMS setup to course design and launch, creating a scalable program that drives long-term customer success and product adoption.

Meet Customers Where They Are
Again, recognizing that many of our users were volunteers with limited time and subject to high turnover, we couldn’t be passive when it came to education and training. We knew we had to meet customers in the moment and where they were in their customer journey.
Digital Adoption
We had tools in place that allowed us to deliver educational content to users in-app; however, content delivery was time-based rather than outcomes-based, often resulting in customers receiving training content before it was relevant to them.
To allow us to reach customers where they were in their journey, we leaned into product usage data and implemented a product-led onboarding approach where we defined key milestones for customer success (and activation), and automatically tracked those milestones, and delivered content based on users successfully reaching those milestones. If users got stuck, we had automations in place to send nudges along with educational resources reminding users to complete each task.

People Power
Our research showed that the longer customers stayed inactive after purchase, the harder it was to reengage them. To keep momentum high, we introduced proactive milestone tracking that alerted the activation team when users stalled. This allowed us to step in quickly with personalized outreach and 1:1 consultations, helping customers overcome roadblocks and stay on track toward successful activation.
Results
Our “Push-Pull” customer education strategy provided the right balance between proactive, in-product guidance and on-demand self-service learning, ensuring customers were supported at every stage of their journey.
By refining onboarding workflows, adopting a milestone-based, outcomes-driven approach, and introducing blended learning modalities including in-app tutorials and e-learning, we increased activation rates by 23% within 18 months for all customers and 30% among self-service customers.