Rebuilding from the data up: how Itinerist fixed a broken onboarding and finally understood their users

The situation

Itinerist had onboarding in place. That was part of the problem. The flows were live, the emails were sending — but the data underneath was dirty, triggers were misfiring, and nobody could tell what was actually working. The team was making product decisions based on signals they couldn’t trust, and users were moving through an onboarding experience that wasn’t designed around any clear goal.

Pam, Itinerist’s founder and CEO, knew something was wrong. What she didn’t have was the visibility to know where — or the bandwidth to find out while running the company at the same time.

The approach

Before touching a single flow or rewriting a single email, we started with the data. We audited Itinerist’s product analytics to understand what was being tracked, what was missing, and what was unreliable. We cleaned the data, established a reliable baseline, and produced a full user journey map in Figjam — a multi-stage visual document mapping every touchpoint from first visit through activation, annotated with the specific friction points, misfiring triggers, and confidence gaps we identified along the way.

What we built

Data cleanup and tracking foundation

We audited the existing tracking setup, identified events that were misfiring or missing entirely, and rebuilt the data structure so that every meaningful user action through the onboarding flow was captured reliably. The output was a clean event taxonomy and a KPI framework the team could use to measure onboarding performance going forward — something that hadn’t existed before.

User journey mapping

The journey map covered six stages from acquisition through activation, with each stage broken down by what users saw, what they were expected to do, and where they were actually dropping off. Each friction point was annotated with the likely cause and a recommended fix — giving Pam and the team not just a diagnosis but a prioritised action list. The map became the reference document for everything built after it.

In-app onboarding rebuild — Userpilot

We rebuilt the onboarding flows in Userpilot from the ground up — with clear activation goals, triggers based on actual user behaviour rather than time delays, and a structure designed to get users to their first meaningful moment in the product as directly as possible. This included a multi-step onboarding checklist with contextual modals at each stage, designed to surface the right guidance at the right moment without overwhelming new users. Each step was mapped to a specific activation milestone and configured with completion tracking so the team could see exactly how far users were getting.

Lifecycle email campaigns — ActiveCampaign

We redesigned and rebuilt Itinerist’s onboarding email campaigns in ActiveCampaign to complement the in-app experience. The sequence was built with branching logic based on user engagement — contacts who opened and clicked moved through a shorter path, while those who didn’t received follow-up emails designed to re-engage them before they went cold. Each email was written around a specific activation goal, not just a content topic, and the full sequence was configured with open rate and click tracking to give the team ongoing visibility into performance.

The result

Itinerist now has a reliable data foundation, an onboarding experience with clear goals and measurable outcomes, and an email sequence that works in tandem with what users experience in the product. More importantly, Pam has visibility into what’s working — and a structure she can keep improving as the product evolves.

“Tovana has a great way of understanding my needs and thinking creatively about how to map customer journeys and engage with them to improve product adoption. Mel doesn’t just give you a doc with suggestions — she gets her hands dirty and implements and tests for you. A true partner.”

— Pam, Founder and CEO — Itinerist

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