The Problem

When I first met the Chief Product Officer, the US$50M ARR business had reached an inflection point. Back to back years of rapid growth led by a very ‘hands-on’ founder/engineer with a first-in-market product, momentum had slowed dramatically just as the company was preparing to invest heavily in AI and new products.

New competitors with bigger marketing budgets and dedicated product design teams were now popping up offering better solutions for less and the sales team were finding it harder and harder to close multi year deals.

To complicate matters further, the business was increasingly agreeing to prioritise building new or modifying existing features at the request of individual customers in order to close deals. The business was being sales led when it needed to be design-led.

Strategy

I quickly learned from our early conversations that up until this point, the founding partners had owned product strategy, making product decisions and prioritising features based on hunches and gut feel. There was no dedicated product design or user experience team capable of getting close to users to understand what they needed from the software and to advocate for them and influence/shape product strategy at the highest level. The CPO was essentially flying blind.

I could already see from our early conversations that the solution would need to involve establishing a product design function. I was also beginning to see how the structure of the current product organisation would also need to change.

So first cab off the rank, the CPO and I got to work restructuring the product org and hiring new roles where required. Once the new structure was in place we established the company's first product design function, I recruited and coached a high-performing team, embedded design practices into cross-functional product squads, and introduced customer-centred ways of working that positioned design as a strategic partner in product development.

Key Achievements

1. Established a balanced product operating model

Partnered with the CPO to redesign the product organisation and shift toward a more outcome-focused model.

• Evolved the “two-in-a-box” (Product Owner + Engineering) into a “three-in-a-box” model (Product Management, Product Design, Engineering)

• Positioned design as an equal partner in shaping product direction and delivery

• Transitioned existing Product Owners into a dedicated Product Delivery function

• Introduced Product Managers to drive strategy and customer outcomes

• Temporarily led Product Management while establishing the function and preparing for future leadership

2. Building design and product capability

• Defined new roles, created job descriptions and hired Product Designers and Product Managers

• Established design practices, rituals and ways of working

• Introduced more structured discovery and user-centred design approaches

3. Connecting customer insight to decision-making

• Partnered with Customer Experience and Support teams to strengthen feedback loops

• Improved visibility and accessibility of customer insight across product teams

• Explored tools (e.g. Twine) to transform large volumes of customer conversations into more usable, scalable insight

4. Introducing AI into the product experience

• Led design of AI-powered product experiences (including Archie)

• Explored how AI could support customer workflows and improve productivity

• Balanced opportunity with the realities of delivery, adoption and team capacity

5. Aligning cross-functional teams

Over time, aligned:

• Product Design

• Engineering

• Product Delivery

• Product Marketing

• Customer Experience

• Customer Support

Creating more integrated, end-to-end ways of working across the organisation.

Key Challenges

• Navigating team change while maintaining trust.

• Shifting from feature-led to insight-driven ways of working.

• Elevating design as an equal partner.

• Balancing transformation with delivery while building the team.

My Role

Outcomes

Within two years, product design had become a trusted strategic capability at the heart of the product organisation. The team delivered the organisations first design system, led the UX for its redesigned web platform, and played a central role in launching a suite of AI-powered products. Solid foundations had been laid for the next phase of growth.

Embedding design, product and engineering as equal partners, supported by real customer insight, is critical to delivering consistent, high-quality experiences.