Kestrel Work
London · LA · Tallinn

It's time to rebuild how we think. Coaching, AI and Insight: Together.

Book a call Q4 2026
AI Enhanced Team Coaching
Group insights from individual coaching.
$10k/mo for a team of 5 6 months

More cost-effective than executive coaching. Data-backed. Findings that go straight into strategy.

Intro call
Insight

Anonymised team coaching data gives the best insight into how the team are actually functioning. Short-form, AI-enhanced coaching can surface it better than any other process. Mediated by a trusted external colleague, the real data surfaces.

What you get
  • Coaching calls for the designated team, at a cadence that suits them
  • Patterns and approaches made visible from the sessions, mediated back to the team
  • A clear, systemic, data-backed report showing challenges and solutions, feeding directly into strategic goals
Who it's for

Teams who want real feedback on strategy. Who want tension and bottlenecks addressed. Who want optimal working practices.

Examples

Two fintech organisations: turned dozens of coaching conversations into board-legible numbers, trust gaps, time-management overload, restructuring anxiety, and a precise list of what leadership was missing.

A 30-year-old professional services partnership: diagnosed a generational leadership gap and a fear-of-delegation pattern among senior partners directly from coaching-session data. Recommended a scoped, time-boxed intervention rather than a blanket program.

AI Enhanced Individual Coaching
Rewire your thinking architecture
$2.5k/mo 6 months

Coaching, but powered by the latest AI in the experience.

Meet the coach
Insight

It's a tech-rich world. Sometimes our habits haven't caught up, even when you're already running at a level most people don't reach. Cognitive coaching plus AI closes the gap. Put the tools and insight to work for you.

What you get
  • Micro-coaching that fits your week: 15 minutes, or longer. We'll find the right fit on one call.
  • Powerful insights delivered after the call as audio, text, or video.
  • Custom tools, shaped for exactly how you work, built together with you as coaching progresses
Who it's for

Leaders who want to make their systems as sharp as they are.

Examples

A business owner running several ventures at once, each with its own reporting, its own rhythm, held together by memory and habit. Rebuilt his systems around how he actually thinks. Two custom trackers, built in hours, replaced weeks of manual work.

A CEO mid-crisis: frozen accounts, volatile leadership above him, a colleague's job on the line. Solved the operational problem in days, then used the session to decide what mattered next: who to align with, how long to stay.

Personal AI Researcher and Consultant
$1.5k/mo

Tailor your needs and interest, get taught by an AI native, receive regular updates from the frontline.

Start now
Insight

Keeping up with AI is a full-time job most leaders don't have time for. Some ignore it. Some chase the hype. This delivers research and insight, at your pace, built around what actually matters to you.

What you get
  • Insight into what actually matters to your business, at a cadence you set
  • Research and synthesis handled entirely. You stay current without doing the work
  • Delivered how you want it: podcast, video, or a straight call
  • Custom AI tools built when a real use case emerges, transparent from day one
Who it's for

Leaders who want to stay ahead of AI, without doing the tracking themselves.

Examples

An ongoing technical exchange with the founder of a comparable AI-driven leadership tool, benchmarking system design, methodology, and where the technology is actually heading. Delivered as a monthly two-hour call exploring available tools and insight, alongside regular conversations in chat relay pertaining to specific systems architecture.

Three sessions with a CEO, exploring AI data offers and informing a live technology decision. Included ongoing support for his own learning across various commercial GPT tools.

Story, Leadership & AI Workshop
Storytelling is leadership. AI is the new fluency.
$1,100 half day (3 hrs) $2,000 full day

Bring both into the room. A one-day session that sharpens how leaders think, write, and use AI.

Arrange a workshop
Insight

Do the unglamorous work first: clear workflows and explicit judgement. Get the foundations right, then let AI take care of the rest.

What you get
  • A crash course in story fundamentals: structure, clarity, what actually lands
  • Live work on how leaders use AI in their own writing: prompts, emails, comms, marketing copy
  • Real reflection on how the group currently engages with AI, and where it's underused or misused
  • Materials and resources to take back into the organisation
Who it's for

Leadership teams who want their people thinking with more craft before they communicate with it, using AI as a multiplier on clear judgement, not a substitute for it.

Examples

A chamber of commerce leadership group: 15 leaders, three hours, working on how leaders engage AI prompts to create sharper text and copy.

A national energy corporation: 40 leaders, three hours. A story fundamentals crash course, applied directly to comms, conversation, and marketing materials.

FAQ
Who are you?+
I've spent 20 years in leadership and 6 in SaaS & AI. I've coached C-suite leaders through transition and shipped software & AI tools for leadership development. Now I blend coaching & advisory to build leaders' real thinking architecture.
How does this work?+
We start with a short call. If we're a fit, you'll have a proposal the following Monday.
Why hire an outside perspective?+
Inside a company every idea has history and someone attached to it. I show up with neither. I see solutions and challenges with a very different lens and I can see what people often can't.
Who do you work with?+
Fintech, scale-ups, CEO's and public companies that need fresh perspective and want to move even faster.
How flexible are engagements?+
Prices and timelines are fixed so you always know the costs and the dates. We can be flexible on details of cadence and reporting style. These have to be right for you and your organisation.
How fast can we start?+
An intro call, a proposal within 48 hours, and a kickoff the following Monday.
What happens on the intro call?+
30 mins. I identify your needs, I will let you know whether I am the right person. No deck, No questionnaire, you leave knowing what I would do next.
Where are you based, and do you work remotely?+
I am based in the UK and frequently in LA and Tallinn. If you are in London I am always around to grab a coffee.
Why the Kestrel?+
They are energy efficient, highly adaptive with exquisite pattern matching skills.