C L A YSEARCH
Coaching

Not ready to hire? Get ready.

1-on-1 coaching for technology leaders navigating AI strategy, org design, and the transition from Foundation to Scale.

The Gap

Most organizations aren't ready for the hire they think they need.

Our assessment data shows 50% of organizations score Foundation or Formation. Coaching bridges the gap between where you are and where you need to be to make a successful leadership hire.

F FOUNDATION F FORMATION A ACCELERATION S SCALE COACHING ACCELERATES THIS
Coaching Tracks

Three paths. Choose the one that fits.

For Executives

AI Strategy & Readiness

For CEOs, CTOs, and founders who need to build their AI operating model before making a leadership hire. We help you define ownership, scope the mandate, and avoid the $2.1M mistake.

  • AI readiness assessment debrief and action plan
  • Org design for AI — structure that matches your maturity
  • Role scoping — define the hire you actually need
  • Decision rights framework across engineering, product, and data
  • 90-day plan creation for the future hire

$3,500

4 sessions over 6 weeks + assessment debrief

For AI Leaders

First 90 Days

For newly hired Heads of AI, VPs of Engineering, or CTOs in their first 90 days. The transition from candidate to operating leader is where most hires fail. We help you land.

  • Stakeholder mapping and political navigation
  • First 30/60/90-day operating plan
  • Building credibility with the CEO and board
  • Team assessment — who to keep, promote, or hire
  • Quick wins vs. structural changes — sequencing decisions

$5,000

6 sessions over 90 days + async support

For Candidates

Career Positioning

For senior technology leaders who want to position themselves for their next leadership role. We help you articulate your edge, target the right opportunities, and navigate the retained search process.

  • Leadership Profile Assessment debrief
  • Positioning narrative — what you've built, not just where you've been
  • Target role definition — CTO vs. VP Eng vs. Head of AI
  • Comp benchmarking and negotiation preparation
  • Network activation strategy

$2,000

3 sessions over 4 weeks + profile review

Who This Is For

Coaching works when the stakes are real.

Good fit

  • You took the assessment and scored Foundation or Formation — you know you're not ready
  • You just made an AI leadership hire and want to maximize the first 90 days
  • You're a senior tech leader exploring CTO or Head of AI roles
  • Your board is pushing for AI and you need to build a credible plan
  • You've had a failed AI hire and want to understand what went wrong

Not a fit

  • You want someone to build your AI product for you — we're coaches, not consultants
  • You need generic career counseling — we specialize in technology leadership
  • You're looking for a recruiter — coaching is separate from our search practice
  • You want a certification or credential — we provide practical guidance, not programs
How It Works

Simple, structured, no fluff.

01

Take the Assessment

Start with the AI Readiness Assessment or Leadership Profile Assessment. This sets the baseline.

02

Book a Session

Pick the track that fits. Your first session is a deep-dive debrief on your assessment results and goals.

03

Build the Plan

Over 4-12 weeks, we work through the frameworks, decisions, and actions that move you forward.

Start with a conversation.

Book a free 30-minute intro call. We'll review your assessment results, discuss which track fits, and decide together if coaching is the right next step.

Book Intro Call Take Assessment First

No commitment. No pitch. If coaching isn't right, we'll tell you.

FAQ

Common questions about coaching.

How is coaching different from your search service?

Search is for when you're ready to hire and need us to find the person. Coaching is for when you're not ready yet — or when you've already hired and need to maximize the outcome. They're complementary but separate services.

Do I need to take the assessment first?

Strongly recommended. The assessment gives us a shared baseline and makes the coaching sessions significantly more productive. It takes 15 minutes and it's free.

What happens in a typical coaching session?

60-minute video call. We work through a specific framework or decision relevant to your situation. You leave with concrete next steps, not just advice. Between sessions, you have async access for quick questions.

Can coaching lead to a search engagement?

Yes, and it often does. About 40% of coaching clients eventually hire through us. But there's no pressure — coaching stands on its own. If you reach Acceleration or Scale readiness, we'll discuss whether a search makes sense.

Who does the coaching?

Senior partners who've built and led technology teams. Not junior associates, not career coaches without operating experience. The same people who run our searches also do the coaching.

What if I'm a candidate, not a company?

The Career Positioning track is designed for you. We help senior technology leaders articulate their edge and navigate the retained search market. You'll also get added to our candidate network for future searches.