Hilary Aylesworth

‘Hilary is committed to creating tools that empower individuals and organisations alike’

Part of the Tech Women Celebration 50 – a curated list of some of the most inspirational women working at all levels of tech

Hilary Aylesworth is the Chief Product & Technology Officer at CoachHub, a global talent development platform that recently launched its pioneering AI coach, AIMY™.

With a rich blend of scientific expertise and technical know-how, Hilary brings a unique perspective to product innovation in the coaching and learning space. Trained as a neuroscientist, she combines a deep understanding of how people learn, think, and adapt with hands-on experience in coding and technology leadership.

Her career has spanned multiple roles where she has been at the forefront of building products centred on learning and human development, always with a focus on translating academic insights into practical, impactful solutions.

At CoachHub, Hilary oversees the integration of advanced technology, including AI, into scalable coaching solutions designed to democratise access to personal and professional growth. Her approach is grounded in evidence-based methods, ensuring that technology is innovative, effective, and inclusive.

Whether guiding product strategy, fostering cross-functional collaboration, or steering the ethical use of AI, Hilary is committed to creating tools that empower individuals and organisations alike. Her leadership reflects a vision where technology enhances the human connection at the heart of learning and development.

What do you consider the nominees biggest achievement to date?

When Hilary first pitched AIMY™, CoachHub’s AI coaching platform, she was asked, “So… you’re replacing coaches with robots?” In truth, she was reimagining professional development, making it accessible, scalable, and human. Her goal: democratise coaching and bring those “aha” moments to everyone, not just senior leaders.

Over the past year, her team built and launched AIMY™, prototyping three coaching modes: Situational, Goal Setting, and Role Play, tested with 250+ users and refined through rapid feedback. Now, AIMY™ drives daily micro-reflections, boosting engagement by 30%. One reflection, one habit, one win at a time.

Culturally, Hilary built agile, cross-functional squads of curious, coachable learners, prioritising creativity over AI credentials. She also partnered with ethics experts to set new standards for safe, transparent, and effective AI in coaching.

Today, AIMY™ powers structured coaching for hundreds of employees worldwide—many experiencing professional development for the first time.

What is the most significant challenge the nominee has overcome?

Building AIMY™ meant balancing speed with ethics, and scale with nuance. In AI coaching, the real challenge wasn’t just technology. It was trust. Hilary led with a system-first approach: clear guardrails, hand-offs to human coaches and empathy built into the product’s core. She brought in diverse voices, iterated openly, and created a space where users feel seen, not judged.

Another challenge was changing perceptions. Coaching once meant private sessions for executives, not digital access for all. When met with skepticism, Hilary didn’t push—she guided. Through dialogue, consistency, and shared values, she showed that influence isn’t about volume but integrity. Like habits, change grows gradually—through steady presence and belief.

Tell us something about the nominee people would find surprising

Hilary emphasises that effective AI coaching shouldn't diminish critical thinking, instead, it should enhance it and empower people to reach their own insights. In an AI world where the answer is everything, and there's fear it's making us 'dumber', this is a major shift in thinking.

As she puts it, "An AI coach shouldn't allow coachees to become dependent on it for answers; if anything, it should put the responsibility back on coachees to make decisions, think critically, and share ideas on how to solve problems."

Hilary also has a strong strategic vision for CoachHub's AI coach, AIMY™: she ensured it offers personalisation at a deep level by allowing users to choose its voice, gender, coaching style, and language. According to Aylesworth, this helps the experience feel more human, builds trust, and encourages deeper reflection.

In summary, the most interesting aspect is her holistic approach. Hilary combines neuroscience-informed design, ethical AI principles, and thoughtful personalisation to make AI coaching scalable and profoundly human.