Activation & onboarding review

To: Omar | Re: Onboarding review

Recommendation

Activation should mean connecting a bank and categorising 10+ transactions in the first week. Our current definition, completing the setup checklist, barely predicts retention, so the 61% is flat for a reason: we're measuring the wrong thing. I'd fix the path to the real activation event, use the design team's ideas only on that path, and replace next quarter's goal.

Evidence (4,000 August sign-ups, day-60 retention)

Three things stand out:

• The checklist is a weak signal. Checklist completers retain at 30%, against 28% for everyone. The checklist is theme, notifications, account name and goal, so it's mostly cosmetic setup.
• The combination matters, not either step alone. Backing out the overlaps from the CSV:
• Bank only (no categorising): about 920 users, 13% retained.
• Categorised only (no bank): about 300 users, 16% retained.
• Neither: about 1,700 users, 6% retained.
• Both: 78% retained.

Users who connect but never see their spending sorted do worse than average. The value moment is seeing where the money goes, which needs both steps. - Budgets and app opens aren't the answer. Budget creators retain at 33%, close to baseline. Opening the app 4+ days (40%) is engagement, not a lever we can pull in onboarding.

Caveat: this is observational. Motivated users probably do everything, so these numbers show who retains, not what causes it. The recommendations below are therefore tests, not guarantees.

What to change

The funnel is 100% → 50% connect → 27% connect and categorise. There are two leaks:

1. Half of users never connect a bank, and they retain at 8%. Put bank connection first, straight after sign-up. Move theme, notifications and account name out of the critical path (defer or drop them). Look at where the connect flow fails and whether trust copy (read-only access, security) is needed. I can't tell from this data whether the checklist is causing bank drop-off, so I'd A/B test bank-first against the current order.
2. 46% of those who connect (920 of 2,000) never reach 10 categorised transactions. This is the biggest fixable gap, since 78% of those who finish retain. Auto-categorise on connect, pre-fill best guesses, and walk users through their first 10 with one-tap confirmations rather than leaving them to find the feature.

I'd also instrument the funnel by step and by time, so we can see where in the first week people stall.

The design team's proposal

A celebration screen and a progress bar for the checklist would probably raise checklist completion, but that metric barely relates to retention, so we'd likely see a "win" with no change in retained users. I wouldn't ship them as proposed. Both ideas are cheap and sound, though, so I'd redirect them:

• Make the progress bar track the real path (connect bank → categorise 10).
• Put the celebration at the moment of value, such as the 10th categorised transaction, ideally with a first insight ("here's where your money went").

This is a good way to involve design in the work above rather than rejecting their proposal.

Next quarter's goal

Drop "checklist completion 61% → 75%". Pushing it up could even pull effort toward low-value steps.

Replace it with: percentage of sign-ups who connect a bank and categorise 10+ transactions within 7 days. Baseline is 27%. I'd propose a target around 35%, but that is a judgment call until we've sized the effect of the first experiments, so let's set it after a few weeks of data. Guardrail: day-60 retention among those users should hold near its current 78% (if we widen the funnel with less-motivated users, it may dip, and we should watch that). Track the real outcome, overall day-60 retention (28% today), alongside it.

Next steps

• Run the bank-first vs current-order A/B.
• Prototype auto-categorisation and a guided first-10 flow.
• Work with design on the redirected progress bar and celebration.
• Agree the new activation definition and dashboard before the quarter starts.

I'm happy to walk through the numbers if useful.

To Omar — onboarding review

What activation should mean

Activation should mean a new user has reached Tidepool’s core value: connected a bank account and categorized at least 10 transactions within their first seven days. Completing setup tasks is not the same as understanding where your money goes.

What the evidence says

Of 4,000 August sign-ups, 61% completed the checklist, 50% connected a bank, and 34% categorized 10+ transactions. The behavioral data points to which events are most associated with retention at day 60:

• All sign-ups: 28% retained (1,120/4,000)
• Completed the checklist: 30% (742/2,438)
• Connected a bank: 48% (964/2,000)
• Categorized 10+ transactions: 65% (891/1,380)
• Connected a bank and categorized 10+: 78% (842/1,080)

The combined behavior is the strongest signal and represents 27% of all sign-ups today. By contrast, checklist completion is barely above the overall retention rate. Creating a budget is associated with 33% retention, so it is not a better activation milestone on this evidence.

These are associations, not proof that onboarding changes will cause retention to rise: users who connect accounts or categorize transactions may already be more motivated. We should treat the numbers as a strong direction for what value to help users reach, then test changes and track outcomes.

What to change

• Move bank connection earlier. Defer account naming, theme choice, savings goals, and notifications until after users see value. Explain why connection helps, address security concerns, and make the flow as clear and low-friction as possible.
• Guide users to their first insight. After connection, help them review and categorize transactions with sensible suggestions. Measure progress toward 10 categorized transactions, not just completion of onboarding screens.
• Offer budgeting in context. Prompt users to create a budget after they have seen their spending, rather than treating it as a prerequisite.

Design proposal and next-quarter goal

A progress bar could help, but only if it tracks the path to value—connect a bank, review transactions, categorize 10—not the existing checklist. A celebration screen after checklist completion would celebrate the wrong milestone; consider celebrating the first meaningful spending insight instead. Test both against a control, measuring bank connection, 10+ categorization, and retention—not checklist completion alone.

Replace the goal of raising checklist completion from 61% to 75% with a provisional target: raise seven-day activation from 27% to 35% of sign-ups next quarter. Track day-60 retention as a lagging outcome and guardrail. This keeps the goal tied to Tidepool’s promise while making clear that improved activation is a hypothesis to validate, not a guaranteed retention lift.

Onboarding review: activate on financial value, not setup

Recommendation: Replace checklist completion as our activation metric with connecting a bank and categorising at least 10 transactions within seven days of signup. Reorient onboarding around that outcome. The celebration screen and progress bar are secondary; making the current checklist more engaging risks improving the wrong metric.

What activation should mean

For Tidepool, activation should mean a user has taken the first meaningful steps toward understanding their spending—not finished configuring the app.

Bank connection brings their financial data into Tidepool; categorisation makes that data useful. Together, these are our strongest available proxy for experiencing core value. This is a working definition, not proof that exactly 10 categorisations creates a lasting habit. We should validate the threshold and whether users actually understand something useful about their money.

Budget creation can follow that first insight. The evidence does not support making it a mandatory activation requirement today.

What the evidence says

Among August’s 4,000 signups, overall day-60 retention was 28%.

The checklist has weak separation: completers retained at 30.4%, versus 24.2% for non-completers. Its 61% completion rate is therefore a poor headline measure of delivered value.

By contrast, only 27% of signups connected a bank and categorised 10+ transactions, but they accounted for 842 of 1,120 retained users—75% of everyone retained. Users who did not achieve both retained at 9.5%.

These are observational associations. More motivated users may both complete these actions and remain active; we cannot promise 78% retention simply by pushing people through them. Behaviour groups also overlap, so the reported steps should not be treated as a strictly sequential funnel. Before testing, reconcile the rounded onboarding figures with event counts and standardise the day-60 activity definition.

What to change

1. Remove configuration as a gate to value. Defer theme selection and account naming; make savings goals optional. Request notification permission when there is a clear benefit, such as a relevant budget alert—not as checklist work.

1. Bring bank connection forward. Explain why access is needed, what data is used, and how users retain control. Instrument connection starts, provider errors, unsupported banks, abandonment and successful imports. Preserve a skip/retry path rather than forcing consent.

1. Guide users from imported transactions to spending insight. Offer a short, low-effort review of suggested categories. Let users confirm or correct them, then show an understandable spending summary. Do not require ten arbitrary manual edits merely to satisfy the metric.

1. Offer a budget as the next useful action. Use the spending summary to suggest a realistic starting budget, rather than asking users to invent one before seeing their finances.

Test the redesigned flow against today’s onboarding. Measure seven-day activation first, then downstream retention; monitor connection failures, abandonment and user-reported trust and usefulness.

Design proposal and next quarter’s goal

A progress bar is worth testing if it tracks meaningful steps toward understanding spending. It should not encourage completion of low-value setup tasks. A celebration screen belongs after a genuine milestone and should reinforce the insight gained, not interrupt access to it. Neither should take priority over bank-connection and categorisation friction.

Replace the 61% → 75% checklist goal with a goal for the new activation definition. I propose 27% → 35% within seven days, provisionally, subject to instrumentation validation and early experiment results. That is a planning target—not a forecast supported by this dataset.

Keep checklist completion as a diagnostic. Judge success by increased meaningful activation without sacrificing trust or retention, and confirm the retention effect once next quarter’s cohorts mature.