Setmore Appointments

Recurring bookings + upfront payments

Overview

Setmore helps service businesses run their calendars and get paid. A recurring appointment workflow was a top customer request because it directly supports retention (standing sessions) and predictable revenue for small businesses. I led the end-to-end effort to ship recurring bookings with an optional “charge later / pay upfront” capability, focusing on edge cases (skips, exceptions, staff changes), pricing strategy, and a flow that felt native to the existing calendar experience.

Role

Senior / Lead Product Designer
Discovery → delivery

Team

Product Manager
4 Engineers
2 Designers

Scope

Customer discovery
Flow + IA design
Prototype & testing
Spec & rollout

Focus

Retention drivers
Payments adoption
Low-friction UX
Discovery
Recurring appointments consistently came up in customer interviews and support requests because service businesses run on repetition: weekly sessions, monthly check-ins, and package-based offerings. The gap wasn’t only scheduling - it was also payments and commitments. Customers wanted to (1) create a standing series quickly, (2) handle exceptions without breaking the series, and (3) optionally collect payment upfront to reduce no-shows and stabilize revenue.
Problem statement
How might we enable recurring bookings with optional upfront payment - without adding complexity to the day-to-day calendar flow?
Solution design
I explored multiple interaction models (single event → “make recurring”, dedicated recurring editor, and template-based scheduling). We chose a calendar-native approach: users create an appointment the way they already do, then turn it into a series with clear frequency rules and an explicit exceptions model (skip, reschedule, edit one vs edit series). This reduced learning cost and made the feature safe for busy operators.
Validation & delivery
I built a high-fidelity prototype and tested it with active Setmore customers to validate comprehension of recurrence rules and exception handling. The biggest risk was “silent mistakes” (editing one event vs the series), so we added explicit confirmation patterns and clearer copy. I partnered with engineering on constraints (payment flows, edge cases, performance) and produced implementation-ready specs to support a staged rollout.
Outcomes
Recurring appointments became a meaningful lever for both customer retention and monetization. We launched the feature behind paid plans and tracked adoption, repeat usage, and support volume to ensure the workflow stayed reliable at scale. Within the first three months, early usage signals showed steady adoption, a meaningful number of recurring series created, and initial paid-plan revenue impact.
$1k

Paid-plan MRR
(first 3 months)

8.1k

Recurring appointments
created

14%

Active accounts using
recurring bookings

Early signals measured after 3 months

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