Building the systems behind a subscription business

At LEO, I led the move from lifetime desktop-software licences to subscriptions. The work extended beyond pricing: I introduced funnels, automated licensing and renewal reminders, SaaS dashboards and support reporting. This was rule-based workflow automation using tools such as Zapier, not generative AI.

A subscription creates an ongoing customer relationship. Licensing, renewals and support need to work together: customers should know what they have access to, when action is needed and what they are paying for. The team needs that same context without having to piece it together for every request.

1. 01Mapped the customer lifecycle from acquisition through software access and renewal, then introduced funnels and connected the handoffs with rule-based workflows.
2. 02Automated software licensing and renewal reminders so routine lifecycle steps did not depend on someone remembering to follow up.
3. 03Introduced SaaS self-service dashboards that put licence and subscription information in customers’ hands rather than behind a support request.
4. 04Automated support summaries around work performed and hours logged, bringing customer context, service-level agreements and billing information together.
5. 05Introduced Scrum, product analytics, OKRs and remote-first ways of working to support the new operating model.

• –Customers could manage licences and subscriptions through self-service dashboards instead of contacting support for routine account administration.
• –Acquisition funnels, licence automation and renewal reminders formed a connected customer lifecycle rather than a set of manual follow-ups.
• –Support teams had customer summaries and hours worked at hand, making it easier to explain the work delivered against service commitments.
• –Clearer billing connected charges to the work performed, giving customers an understandable record of the service they received.

Moving to subscriptions means designing the ongoing service, not just changing the price. Software access, renewals, support and billing need to work as one customer relationship.