Engaging (and Re-Engaging) Learners: How to Build Momentum Across Your Education Programs
By Danielle Evans, Director of Customer Education at Sendoso
Customer education drives real business impact. According to Intellum, companies with education programs see higher retention (56%), increased product adoption (38%), and revenue growth (43%).
These data points are impressive, but they only matter if customers actually engage with your programs.
So how do we encourage customers to participate in our programs?
Enrollment is the starting line, not the finish. Sustained engagement requires intentional touchpoints that reinforce progress and build habit over time. Learner engagement is a system, not a moment.
Intentional moments to engage learners
When new customers join
New customers and new employees at existing customer accounts represent a critical moment to build early learning habits. Highlighting educational resources early helps learners reach for digital resources first.
At Sendoso, we launched a four-part email series for new Admins outside of onboarding that introduces our digital programs, key setup steps, and gifting options. The series drives strong engagement and ensures we don’t miss learners who join mid-journey.
Keep in mind: Engagement strategies should welcome learners at any stage.
After strategic learning milestones
94% of learners want additional courses to help them achieve their career goals (Accredible, 2024). This reflects the “first win” effect: once learners complete something, their confidence increases, and when the next step is clear, they’re far more likely to continue.
At Sendoso, this is evident in our certification program. Among learners who complete one certification, 34% go on to earn two or more, and once learners earn two certifications, nearly 47% continue on to complete a third or beyond. Crossing the second-certification milestone is a clear inflection point for long-term engagement.
To reinforce this momentum, we celebrate progress in meaningful ways. After earning their first certification, learners receive a Sendoso University branded tumbler and badge sticker, with each additional certification unlocking a new sticker and a $5 coffee eGift to refill their tumbler.
While gifting isn’t the sole driver of completion, it plays an important role in building a fun, motivating culture of learning.
Keep in mind: The second milestone is the habit-forming moment; optimize for it.
When progress stalls out
We’ve all started projects we didn’t finish—life gets busy, and learning often falls to the back burner. The same thing happens to our learners.
At Sendoso, we use inactivity emails when a course is started but not completed after seven days, encouraging learners to “step back into success” and finish what they started. For higher-value programs, like our New Admin and New Sender certifications, we took this a step further by targeting learners who had begun but not completed the certification.
We paired this outreach with a coffee-themed gifting campaign that teased a celebratory reward, reminding learners that their “growth deserves a latte recognition.” The result: 57 new certifications completed, nearly doubling our original goal.
Keep in mind: Sometimes learners need a friendly reminder and a little motivation to jump back in.
When you have their attention
Driving attendance to webinars and workshops is a common challenge many programs experience. I’ve faced this challenge everywhere I’ve worked, even for paid training. Live learning has to feel worth showing up for.
At Reputation, we built a hands-on webinar series that paired live instruction with interactive, clickable walkthroughs so learners could practice in real time. To make sessions more fun and social, we also ran a live raffle at the end of each session, with one attendee winning a rotating gift. This approach consistently boosted engagement and it’s one I’ve replicated at Sendoso with similar results.
Keep in mind: Attendance improves when learners expect more than just content. When live learning feels fun, social, and rewarding, attendance follows.
When learners are ready to be heard
After completing a meaningful program, learners often feel proud and that makes this an ideal moment to deepen the relationship by sharing their achievement.
I reach out to congratulate learners and invite feedback, framing the ask as a conversation rather than an obligation. When learners feel genuinely seen and appreciated (often paired with a small gift to help celebrate), they’re far more willing to share thoughtful, candid insights. The law of reciprocity works in your favor.
This is also a powerful moment to reinforce professional value through digital badges or certifications learners can showcase beyond your platform. One Sendoso customer shared that completing certifications helped them stand out during a job interview which is a strong reminder that learning doesn’t stop at completion, and its impact extends far beyond your product.
Keep in mind: Feedback and advocacy follow naturally when learners feel valued and proud of their progress.
Engagement tactics for inspiration
At Sendoso, we’re fortunate to use our own product to create moments of surprise and delight throughout the learner journey, but not every program has those resources, and that’s okay! Engagement isn’t about what you give; it’s about when and why you do it.
Below are a few high-impact tactics to inspire your approach regardless of budget:
High-Impact Tactics (When You Have Budget or Tools)
Celebrating milestones with meaningful, well-timed rewards
Reinforcing progress through physical or digital recognition
Using surprise and delight to re-engage learners at key drop-off points
Low- and No-Cost Ways to Drive Engagement
Personalized outreach from a real person
Public recognition in community spaces or live sessions
Badges, certificates, and shareable accomplishments
Clear “next step” guidance immediately after completion
Feedback requests framed as partnership, not obligation
You don’t need a massive budget or complex tools to drive learner engagement, just thoughtful timing and empathy for your learners’ experience. By focusing on moments that matter, celebrating progress, and guiding learners forward with clarity, you can turn one-time participation into long-term engagement.
Pick one idea from this post and try it! You just may be surprised by how much momentum it creates.
Danielle Evans is the Director of Customer Education at Sendoso, where she builds and scales customer and GTM enablement programs that drive adoption and measurable business outcomes.
With a background in Customer Success, she’s passionate about engaging learners across the customer journey, creating meaningful opportunities for practice that drive behavior change, and proving the value of education through metrics executives care about. She’s equally invested in leading and growing high-performing teams, thoughtfully testing AI to free up space for strategic and human connection-driven work, and balancing leadership with life as a hands-on mom to two young boys.
Connect with Danielle on LinkedIn.
