YOUR AI COACHING TEAM

Your Coach Is Waiting

Six AI coaching personalities — each designed to push you differently based on how you perform best.

Choose the coach that matches your edge.

Meet the Team

Vishal Sachar

CEO & Visionary

Mahdi Salmanzadeh

CTO & Tech Lead

Get to Know Your Coach

James Caldwell

AI Coach

The Commanding Strategist

Starts every review the same way: 'Show me the numbers.'

What a session actually feels like:

You:“I had a solid week - got through most of my list.”

James:“Most. Walk me through what got cut and why.”

You:“The investor deck. I kept pushing it.”

James:“Third week in a row. That's not procrastination - that's avoidance. Let's deal with it.”

Best for you if:

→You’re a founder, operator, or senior professional who thrives on structure
→Your ambition is outpacing your execution system
→You respect directness and don’t need hand-holding

⚡ Probably not your coach if you need emotional processing before execution.

Start with James →

Claire Ashford

AI Coach

The Precision Catalyst

Will go quiet for 10 seconds after you answer. That silence is the coaching.

What a session actually feels like:

You:“I hit all my targets this week, actually.”

Claire:“Mm. Which one did you hit that you didn't really care about?”

You:“...the networking goal, maybe.”

Claire:“You set it because you thought you should. Not because it matters to you. That's a pattern - and it's costing you energy on the ones that do.”

Best for you if:

→You’re a high-achiever who keeps hitting the same ceilings
→You suspect the thing holding you back isn’t effort — it’s a pattern you can’t see
→You want someone who’ll ask the question no one else will

⚡ Probably not your coach if you want someone to just tell you what to do.

Let Claire coach you →

Aanya Mehta

AI Coach

The Warm Powerhouse

Will ask about your sleep before she asks about your KPIs.

What a session actually feels like:

You:“Work is going well but I'm exhausted all the time.”

Aanya:“When's the last time you did something that wasn't on a to-do list?”

You:“...I don't remember.”

Aanya:“That's not a time management problem. That's a permission problem. Let's talk about that.”

Best for you if:

→You’ve been succeeding at work but something else is slipping — health, relationships, energy
→You need to feel understood before you can be pushed
→You want to build a life that’s ambitious and sustainable

⚡ Probably not your coach if you want to be yelled into action.

Try a session with Aanya →

David Chan

AI Coach

The Quiet Architect

Has been known to spend an entire session on a single question.

What a session actually feels like:

You:“I've got five goals this quarter and I'm behind on all of them.”

David:“If you could only keep one, which would it be?”

You:“I... I don't know. They all matter.”

David:“That's why you're behind on all of them. Let's sit with that question until you do know.”

Best for you if:

→You’re overwhelmed by too many goals and not enough clarity
→You find high-energy coaching exhausting or performative
→You want a thinking partner, not a drill sergeant

⚡ Probably not your coach if you need high energy and fast answers.

Think with David →

Omar Abdullah

AI Coach

The Relentless Believer

Ends every session by telling you what he sees in you that you don't yet.

What a session actually feels like:

You:“I'm not sure I can actually pull this off.”

Omar:“Tell me what 'pulling it off' looks like. Paint the picture.”

You:“I guess... landing the role and actually being good at it.”

Omar:“You said 'I guess.' Say it again like you mean it. Because I already see it - and you're three consistent months away.”

Best for you if:

→You’re setting serious goals for the first time and need momentum
→You’ve been playing it safe and know you’re capable of more
→You’re recovering from a setback and need someone who believes in you

⚡ Probably not your coach if you're skeptical of optimism.

Dream bigger with Omar →

Nia Okafor

AI Coach

The Fire Starter

People say they're slightly nervous before a session with Nia. They always come back.

What a session actually feels like:

You:“I didn't hit my workout goal this week.”

Nia:“How many times is that now?”

You:“Three weeks.”

Nia:“So at what point do we stop calling it a goal and start calling it a wish?”

Best for you if:

→You’ve plateaued and can’t figure out why
→You thrive under pressure and wilt without accountability
→You’re done being comfortable and ready to find your actual ceiling

⚡ Probably not your coach if you need gentleness right now - and that's okay.

Get pushed by Nia →

What Makes AI Coaching Different

Real frameworks. Real accountability. Powered by AI so it’s always available and always affordable.

Always On

Your coach doesn’t cancel, doesn’t take holidays, and doesn’t charge by the hour. Weekly reviews, daily nudges, and monthly deep dives — on your schedule.

Knows Everything

Your coach has full context on every goal, every metric, and every pattern in your data. No catching up, no repeating yourself, no wasted sessions.

Costs a Fraction

Executive coaching costs $500–$1,000 per hour. Your AnnualPlan coach delivers the same frameworks and the same accountability — included in your plan.

Not Sure Who to Pick?

Compare them side by side.

Coach	Style	Energy	In Their Own Words
James	Systems & Execution	Commanding	“I'll treat your year like a business. You'll love it or hate it.”
Claire	Pattern Recognition	Sharp & Warm	“I'll find the pattern you can't see. Then I'll make you see it.”
Aanya	Emotional Intelligence	Grounded & Caring	“I'll push you - but I'll make sure you're okay first.”
David	Clarity & Socratic Method	Calm & Reflective	“I'll slow you down. That's how you speed up.”
Omar	Vision & Belief	Magnetic & Energising	“I'll show you what you're actually capable of. Buckle up.”
Nia	Disruption & Accountability	Bold & Relentless	“I'll say the thing your friends won't. You'll thank me later.”

Your Year Doesn’t Coach Itself

Start your plan and we’ll match you with the right AI coach during onboarding — based on your personality, your goals, and how you like to be held accountable. Or skip straight to the one that already feels right.

Start Your Plan

Not sure? Start with Omar — our most popular coach for first-time users.

You can always switch.

Pick the coach that feels right today. If your needs change — or you just want a different energy — you can switch coaches anytime. No awkward breakup conversation required.