My Probate Partner

Legal Tech

AI

Product Strategy

Roadmap Development

Turning an ambiguous product brief into a focused delivery plan

Snapshot

Role

Chief Product Officer & Chief Operational Officer

Team

11-13, with 8 directly within the Product team

Timeline

3 months, extended to 1 year 2 months

Context

Context, constraints and goals

A point-of-need legal service with strong customer outcomes, but a growth engine and product operating model that were not yet built to scale with growth.

THE COMPANY

A safer middle ground for a difficult legal process.

My Probate Partner helps people in Scotland obtain Confirmation - the probate equivalent and a legal must-have at a high-stress moment. The market is dominated by two poor options: DIY, which is risky, confusing and full of slow feedback loops; or solicitors, which often take 6–12 months and charge 2–5% of the estate. MPP solves this by sitting between them: guided DIY with expert to review, or fully managed options available to consumers. Cheaper and with higher success rates.

THE MANDATE

Turn strong service delivery into a scalable operating model.

When I joined, MPP already had a dependable, albeit manual, service delivery. I was brought in as the Fractional CPO & COO to create a clear roadmap to growth and improve conversion, while reducing operating dependency on the founder, and to modernise customer support and internal working efficiency.

Market context

Point-of-need. High anxiety. High perceived risk.

Confirmation is not something most people plan for. The emotional and practical context changes how conversion has to work.

01 - In grief or under significant stress

01 - In grief or under significant stress

02 - Arriving with little prior knowledge

02 - Arriving with little prior knowledge

03 - Afraid of getting a legal step wrong

03 - Afraid of getting a legal step wrong

04 - Facing property, wills, IHT and executor complexity

04 - Facing property, wills, IHT and executor complexity

DESIGN IMPLICATION

DESIGN IMPLICATION

A typical SaaS feature-led approach is not appropriate here. Users need orientation, confidence and clear options before they can buy.

Starting state

The service worked. The system around it did not yet scale.

Revenue performance was steady, but growth had plateaued. The team was mostly part-time, important skillsets were missing, and founder involvement had become the dependency between sales, product decisions and delivery.

01 Growth plateau - steady performance, but no repeatable mechanism for scaling beyond the standard level of confirmations we helped achieve.

01 Growth plateau - steady performance, but no repeatable mechanism for scaling beyond the standard level of confirmations we helped achieve.

02 Call dependency - the free, founder-led orientation call had become a crutch in the funnel rather than a deliberate support option.

02 Call dependency - the free, founder-led orientation call had become a crutch in the funnel rather than a deliberate support option.

03 Fragmented follow-through - team ideas were captured, but not systematically prioritised, owned or actioned.

03 Fragmented follow-through - team ideas were captured, but not systematically prioritised, owned or actioned.

04 Misaligned build effort - a backend-heavy portal MVP was underway without sufficient validation.

04 Misaligned build effort - a backend-heavy portal MVP was underway without sufficient validation.

05 Limited capacity - the team was missing design, development and analytics skills and the founder became the bottleneck to scale.

05 Limited capacity - the team was missing design, development and analytics skills and the founder became the bottleneck to scale.

Services

Top Initiatives

Four connected workstreams: acquisition and conversion, AI-enabled support, product operating discipline, and a measurement foundation for faster learning.

01

Funnel & conversion strategy

OBJECTIVE

Reduce overwhelm, increase user confidence, and shift the funnel from “book a call” to “buy online”.

WHAT SHIPPED

Homepage paths for “Ready to buy” and “I’m overwhelmed”; a simplified service-comparison grid; refreshed Confirmation and service-finder tools; and a new education journey covering Understanding Confirmation and Compare your options.

WHY IT MATTERED

It explains the process, compares DIY, MPP and solicitor routes, and makes the case for MPP. Education became a conversion mechanism: users feel safe, informed and in control.

02

AI-enabled customer comms & support

OBJECTIVE

Scale high-quality support, reduce repetitive workload, and enable self-serve confidence around the clock.

WHAT SHIPPED

Moved a scattered omnichannel chat, email and WhatsApp into Intercom; launched a customer Help Centre for self service; created SOPs, edge-case knowledge and reusable templates; and enabled AI-assisted drafting through Intercom co-pilot.

WHAT WE GAINED

FIN, the AI assistant was tested and launched with escalation rules, real user testing and a content-gap feedback loop established.

03

Product operating system & alignment

OBJECTIVE

Turn a fragmented, idea-heavy environment into a measurable execution system.

WHAT I PUT IN PLACE

Made the Atlassian stack the single source of truth across the company: Jira Product Discovery for opportunities and ideas, Jira for delivery, and Confluence for documentation, decisions and living artefacts. Added prioritisation cadence, clearer ownership, documented decisions and follow-ups, and OKR-aligned planning around sales, call dependency and operational load.

OUTCOME

Valuable ideas and priorities assessed and prioritised, guesswork removed from delivery and trade-offs visible to leadership.

04

Measurement foundations

OBJECTIVE

Make performance visible and experimentation possible by being able to accurately and effortlessly measure our impact.

WHAT PROGRESSED

Improved analytics hygiene with event-naming standards and a handbook documenting what fires, where and why. Made conversion and purchase events available at any time (instead of in monthly performance comms), scoped a cross-platform identity approach using unique identifiers, and initiated the move toward Amplitude with execution delegated to the marketing lead.

Key pivot

The decision that changed the trajectory: killing a risky build early

When I joined, an MVP concept was already being pushed forward through a Trello board, feature brainstorms and early estimates. My initial review exposed several classic early-stage risk signals.

Risk signals

Validation was weak - a list of “nice to have” features rather than validated needs. Prioritisation and user journeys were unclear, technical unknowns and dependencies were significant, and the backend-heavy internal workflow scope could be delivered faster with off-the-shelf platforms. Estimates also suggested misalignment on approach and delivery efficiency.

What I did

I ran a rapid product audit across scope versus value, dependency mapping, validation evidence and build-versus-buy options. I explored lighter alternatives, including an AI-assisted build and using existing platforms for internal workflow, then aligned leadership on the opportunity cost: efforts on near-term funnel and conversion improvements mattered more than an expensive internal platform.

Result

We stopped the initiative early, avoided compounding sunk cost, and redirected focus to top-of-funnel improvements and a more scalable support model.

Impact

Growth that shows up in the numbers.

Gross revenue

+50%

February 2026 month-to-date, as of 27 February, compared with January 2026.

Sales month

#2

February 2026 became the second highest-grossing month on record, month-to-date.

Sales calls

↓

Sales increased while calls declined, reducing reliance on one-to-one sales conversations.

Best sales day

+30%

New sales-day record, overtaking the previous high by 30%.

Average order value

£950

Typical order value increased from £760 over 6 months after extensive price sensitivity testing, a usability overhaul and improved user education etc.

Service quality

97% / 100%

97% first-time success rate; 100% overall success for customers.

+50%

+50%

After rebuilding the site with an education-led funnel and shifting towards purchase-first conversion actions, month-to-date gross revenue was 50% above the month before.

Client perspective

The work landed because it felt like partnership.

Mike

Founder & MD, My Probate Partner

“Ryan brought a level of organisation and strategic rigour that we’d been missing. At times he felt like the business partner I never had. He’s strategic by nature, but when we needed momentum on delivery, he stepped up and shipped - often going well beyond what was asked.”

Mike

Founder & MD, My Probate Partner

“Ryan brought a level of organisation and strategic rigour that we’d been missing. At times he felt like the business partner I never had. He’s strategic by nature, but when we needed momentum on delivery, he stepped up and shipped - often going well beyond what was asked.”

Mike

Founder & MD, My Probate Partner

“Ryan brought a level of organisation and strategic rigour that we’d been missing. At times he felt like the business partner I never had. He’s strategic by nature, but when we needed momentum on delivery, he stepped up and shipped - often going well beyond what was asked.”
Tooling

The toolkit behind the work.

A product operating system built around evidence, momentum and clear communication - from discovery through delivery.

Tooling

The toolkit behind the work.

A product operating system built around evidence, momentum and clear communication - from discovery through delivery.

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Better product decisions. Stronger delivery. Flexible senior leadership when you need it.

2026 © All rights reserved.

Better product decisions. Stronger delivery. Flexible senior leadership when you need it.

2026 © All rights reserved.