Headway’s CRM Triumph: Zero to Winner with Epic Lifecycle Marketing

If you’re not embarrassed by your MVP, you launched too late. The best strategy is to experiment as you go.

Headway, a global EdTech company with Ukrainian roots, rapidly went from startup to industry leader. Within a year of launching, the company outpaced industry giants like Blinkist. At the heart of its success story lies a powerful growth engine: a flexible, experimental, and deeply data-driven lifecycle marketing strategy.

In this blog podcast recap, we dive into a conversation with Olena Zarubina, CRM Marketing Lead at Headway. We’ll explore how her team builds retention loops, activates trial users, and turns CRM efforts into a strategic force that keeps the business running.

From Generalist to CRM Trailblazer

Olena’s journey into CRM is a case study in curiosity and adaptability. Before joining Headway, she cut her marketing teeth at EVO, a Ukrainian company behind marketplaces like Prom and Kabanchik. It was an experience that taught Olena versatility, but left her craving a deeper product focus.

The turning point came at Genesis’s product school, where she sought a community of like-minders and a chance to dive into product scaling. “I didn’t realize products could grow so fast,” she said, recalling how Genesis’s approach to rapid iteration opened her eyes.

After graduating, she landed at Headway, first as a user acquisition specialist, then moving into customer engagement and eventually leading the CRM team. Today, Olena drives Headway's user lifecycle strategy across the company’s ever-growing ecosystem.

App Ecosystem Redefining EdTech

Headway started under the Genesis umbrella as a book summary app, but has since expanded into a five-app ecosystem. Each app targets a specific aspect of personal development.

1. Headway – the flagship, providing bite-sized book summaries for time-strapped learners.
2. Impulse – brain-training app for adults.
3. Nibble – interactive lessons in STEM, art, history, biology, and more.
4. AddMile – a coaching platform for career and personal growth.
5. Skillsta – a soft skills training app (still in its early stages).

Since its launch in January 2019, Headway has disrupted the market, overtaking the niche leader - Blinkist - in its first year. Today, Headway is eyeing Duolingo, attracted by shared gamification tactics and user behavior patterns.

Headway’s Lifecycle Playbook

Headway’s CRM approach is a calibrated balance of acquisition, conversion, and retention. Here’s how Olena and her team keep users engaged across the subscriber lifecycle.

Starting with Conversion-First Campaigns

For new apps like Skillsta, the priority is converting users into subscribers. “The first touchpoint is critical,” Olena explains. “Users are excited, and we can’t lose them.” . With 10,000 users, she believes there’s enough data to start A/B testing trial sign-up and purchase campaigns. For a 7-day trial, Headway sends an email and 1-2 push notifications a day, tailored to actions like reading a summary. At this stage, the goal is to hook users before interest fades.

Winning Back Cancellers

A surprising strength is Headway’s cancellation flow. First implemented for the flagship app, it was later adapted for Nibble. The campaign targets users who unsubscribe, and achieves reactivation rates of up to 10%, far exceeding Olena's initial expectations of 2-3%. “We segment [users] by cancellation day and past offers,” she said. Then, the team sends personalized nudges – like discounts or content highlights. It’s a resource-intensive tactic, but the payoff is worth it.

Building Habits with Reminders

For active users, reminders are the retention engine. “People who form habits are more likely to renew. That’s where CRM really drives long-term revenue,” Olena noted. If a user starts reading a summary but doesn’t finish, a nudge follows. If they ignore it, a new recommendation comes next. Frequency caps at 1 email and 1-2 pushes a day, with a 60-90 day cutoff for inactive users. A/B testing refines these flows, measuring incremental daily active users (DAUs) or purchases to evaluate success.

Testing Nonstop

Headway's CRM thrives on experimentation. It runs hundreds of A/B tests weekly. But there's a notable misstep: over-segmenting testers by onboarding goals (e.g., “art expert”) flopped compared to a simpler mix. But successful experiments, such as matching visuals to ad creative, boosted conversions by 30-40%. “Ideas come from product testing or gamification collabs,” Olena shared, emphasizing a hypothesis-driven approach tied to metrics like purchases or retention.

Gamification = Retention Booster

A dedicated gamification team sets Headway apart, embedding timelines, challenges, and AI-driven messaging into the experience. “It’s a big focus. It keeps users coming back,” Olena commented, nodding to Duolingo’s influence. This synergy between CRM and product teams strengthens engagement across the ecosystem.

Actionable Tips from Headway’s CRM Lead

Olena’s insights offer some practical takeaways for any app-driven business:

• Don’t overbuild, launch with a minimum viable product (MVP) ASAP. Speed beats perfection early on.
• Focus on conversions first. Start with campaigns that quickly produce tangible results before tackling retention. These are usually trials or purchases.
• Tailor trialist communications. One email and 1-2 pushes per day based on user in-app actions is the right balance.
• Win back drop-offs. Segment your target audience by behavior and offer personalized incentives to drive up to 10% reactivation.
• Test smart and at scale. Pair each test with a clear hypothesis and metric. Avoid over-segmentation without data to back it up.
• Add gamification. Game-like elements build habits and improve retention. And they work just fine with adults.

The Future of Retention at Headway

Today, Headway’s CRM engine is firing on all cylinders, successfully blending agility, data, and user-centric design. Small but mighty, Olena’s team handles hundreds of scenarios across five apps, with plans to expand as the ecosystem grows. With a culture of never-ending testing, Headway is definitely rewriting the EdTech playbook.