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Engagement and retentionPeople use it once and don’t come back.

People come back when the product keeps doing something for them. When they don’t, it is usually because returning is harder than it should be, the next useful thing isn’t obvious, or the product stopped fitting what they need. I find out which, and work on that.

My strongest measured results are in conversion and pricing. For retention, what I can show is the work I ran at 5 Axis Health and an analysis for Memelord, with the numbers each one produced.

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Where it shows up

What a project covers

A retention diagnosis
One recurring journey, reviewed with usage data and customer feedback. I separate use that means something from activity that only looks like engagement, and find where people stop getting value.
The return visit
Design for picking up where you left off, seeing progress, and finding the next useful thing. That can include account pages, subscriptions, renewal and cancellation.
Lifecycle messages
Which moments a message can help with, what triggers it, and where it sends the user. Every message is tied to something the user did or didn’t do.
The measurement
We define what counts as a meaningful return and a cadence that fits the product, then set up the cohorts and events to track it.

Where I’ve done it

5 Axis Health

Employment, 2024–25. First product hire, then product lead.

I ran subscriptions, retention, fulfillment and the patient portal along with the purchase flow. Reworking the post-booking workflow with the clinical and operations teams cut medication delivery from about two weeks to three days. A reviews program raised the share of positive Trustpilot reviews from 20% to 92% in four months.

Read the 5 Axis Health case

Memelord

Independent consulting, 2026.

I analyzed usage, conversion, subscriptions and churn across web and iOS, compared the behavior of people who stayed with people who left, and delivered a ranked plan for onboarding, upgrades and retention. That engagement was analysis and recommendations.

What the research supports, and what it doesn’t

Holds up

  • People judge an experience mostly by its most intense moment and by how it ends. In a randomized trial with 682 colonoscopy patients, a gentler ending improved how the whole procedure was remembered.

    Kahneman et al., 1993; Redelmeier, Katz & Kahneman, 2003

  • Habits take longer than popular advice says. In the best-known study the median time for a daily behavior to become automatic was 66 days, and individuals ranged from 18 to 254.

    Lally et al., 2010

Doesn’t hold up

  • “It takes 21 days to form a habit.” The figure comes from a 1960 self-help book. No study supports it.

    see Lally et al., 2010

  • “Losses hurt twice as much as gains.” People often weigh a loss more heavily than an equal gain, but estimates of the ratio run from about 1.3 to 2 and depend on the situation. It is not a constant to design around.

    Gal & Rucker, 2018

I don’t design cancellation flows that hide the exit, or messages that guilt people into staying.

References
  • Kahneman, D., Fredrickson, B. L., Schreiber, C. A., & Redelmeier, D. A. (1993). When more pain is preferred to less: Adding a better end. Psychological Science, 4(6), 401–405.
  • Redelmeier, D. A., Katz, J., & Kahneman, D. (2003). Memories of colonoscopy: A randomized trial. Pain, 104(1–2), 187–194.
  • Lally, P., van Jaarsveld, C. H. M., Potts, H. W. W., & Wardle, J. (2010). How are habits formed: Modelling habit formation in the real world. European Journal of Social Psychology, 40(6), 998–1009.
  • Gal, D., & Rucker, D. D. (2018). The loss of loss aversion: Will it loom larger than its gain? Journal of Consumer Psychology, 28(3), 497–516.

Which is easier for you, 1 or 2?

Book a 30-minute callPick a time on my calendar. Bring the journey that is losing people.Write to meA few lines about the product and where it goes wrong is enough to start.

Or email david@heyspiegel.com