Coaching Services

Most people are promoted into leadership roles without being taught how to lead.

This is where that gets fixed.

I work with commercial operators who are trying to move into leadership—or who recently got there and realize the job is different than they expected.

This is practical, real-world coaching focused on career strategy, leadership skills, real-time situations, and positioning.

This is for you If...

  • You’re performing, but not getting promoted

  • You just became a manager and feel behind

  • You’re in leadership meetings but not influencing decisions

  • You’re doing the work, but not getting recognized for it

  • You feel stuck and don’t know why

How we work together

This isn't theoretical.

We focus on what you're actually dealing with in real time:

  • Breaking down real situations you’re navigating right now

  • Preparing for high-stakes conversations

  • Interpreting leadership signals ("what did my CRO actually mean?"

  • Reviewing deals, org dynamics, and decision-making

  • Establishing your leadership cadence and style

  • Translating what’s actually happening inside your company

  • Building your leadership narrative and positioning

Who I Typically Work With

High-performing individual contributors trying to become:

  • Manager

  • Director

  • VP

First-time leaders struggling with:

  • Managing people

  • Unclear expectations

  • Operating in ambiguity

Mid-level leaders who are stuck:

  • Not advancing and don’t know why

  • Need help seeing the patterns holding them back

What We Can Work On

Career Strategy

  • Should I take this role?

  • How do I position myself for VP?

  • Am I under-leveled / underpaid?

  • How do I get recognized for my best work?

Real-Time Solutions

  • I have a tough conversation tomorrow - how should I handle it?

  • My CRO just said this - what does it mean?

  • This deal is sideways - what do I do?

Skill Development

  • Running pipeline reviews

  • Developing a Sales Process

  • Identification of your ICP

  • Leading Teams

  • Handling Underperformance

  • Communicating Up and Communicating Down

Interviewing / Positioning

  • resume refinement

  • narrative building

  • interview prep

  • offer negotiation

Options & Pricing

Ongoing Coaching (steady-state support)

  • 2 calls/month

  • async support

  • $1,500 / month

High-Touch Advisory (weekly + deeper involvement)

  • weekly calls

  • async support

  • document review

  • $3,500 / month

Promotion / Transition Sprint

  • 4-weeks

  • focused on: narrative, positioning, interviews

  • $4,000 flat

If you're trying to move into leadership - or you're already there and realizing no one trained you for it - this is exactly the kind of work we'll do together.

Reach out if you want to discuss fit.

About Carter Cathey

Carter Cathey is a sales and revenue leader with more than 20 years of experience helping market research, technology, and private-equity-backed businesses scale revenue, improve operations, and build predictable growth systems.

Throughout his career, he has led sales transformation initiatives, pricing strategy projects, subscription business model transitions, operational redesign efforts, and commercial growth programs.

He writes about leadership, organizational design, business systems, data-driven decision making, and the challenges companies face as they scale.

Learn more about Carter Cathey