JamesJamil
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For Career Transitions · Music, Media & Entertainment

Out, restructured, or ready to leave. Choose your next move well.

Personal advisor and coach to senior leaders in music, media and entertainment. Move on. Move up. Or reshape the role you're in. Whichever, make it the best it can be.

Book a free State of Play Call

30 minutes to understand your situation and share my initial thoughts.

Portrait of James Gillespie

The Moment

You know which one this is.

Maybe the letter came. Maybe you're still in the building and can feel the edge. Maybe you already decided to go. Maybe you're out already. Either way, you're at the point where the next move matters and the old certainty is gone.

I've been exactly where you are. I left a 19-year run at Sony Music, ending as SVP, and I had to work out who I was on the other side.

The Fork

From here, two paths.

A new chapter in your career. Or building something of your own for the first time. You don't have to know which yet. That's the first thing we work out together.

Path Two

Venture Launch.

Build your own for the first time. With someone two years into building his.

How the venture journey works →

How It Works

Clarity of vision first. Then confidence to act.

A real change doesn't happen in a moment. First we get you clear on the right direction. Then we look at what's stopping you - a real block, or just a story you're telling yourself that you can move past. After that, I'm in your corner while you make the moves. Advisory and coaching combined.

I.

Step One

The Compass.

Get clear on the right direction. I read who you are underneath the title, map the real roles and industries you can move into, and we score them against what matters. You leave with a chosen direction and the reasoning.

II.

Step Two

Make the Move.

Picks up exactly where the Compass ends. Six months of active support to land the right role: the plan, the narrative, the interviews and the offer, with you the whole way. You run the search, I advise and keep you on track. The Compass fee credits in full, so nothing is paid twice.

The Approach

The Root Note. Read, define, build.

In music, the root note is the note a chord is built around. Lose it and you can't tell if you're in tune. Nineteen years inside one company quietly detunes the way you judge your own worth. Three reads, in order, put the reference back.

I.

Inward read

Who you are now, and what you actually want. Including whether you want to move at all, or want a different version of where you already are. I listen for the parts of the account that don't ring true, then ask you to justify them. Warmly, without flinching.

II.

Market-reality read

What you bring, who needs it now, and what it's worth today. Most people leave a big company with no calibrated sense of that. This is where I can tell you what a given skill actually pays in this market, so you neither undersell into a sideways step nor over-reach on borrowed confidence.

III.

Fit and readiness

Not "is this a good opportunity". The right question is whether you're the right person in this specific one. A senior role, your own venture, or a deliberate stay and reposition. Every session ends with a named next action and a date.

Ibarra, 2003
People don't find a true self then act. They act their way into knowing, by testing real options.

Lovallo and Kahneman, 2003
Senior people are systematically over-optimistic on big moves. The fix is an outside, experienced view.

Gollwitzer and Sheeran, 2006
A specific when, where and how plan is the most reliable bridge from intention to action.

What You Get

What you walk away holding.

  • A clear read of who you are underneath the role
  • The real options in front of you, scored against what matters
  • A direction chosen with conviction
  • A step-by-step roadmap from decision to done
  • A monthly deep session and text support for six months
  • A former SVP in your corner the whole way

Pricing

One ladder. Three steps.

Small price compared to the cost of the wrong next move.

Step 1 · Free

The State of Play Call

Free

30 minutes, video call

30 min video. A private read and one clear next step. Your written 2-pager within a day, then 20 minutes a few days later to debrief the roadmap and answer your questions.

  • A private read on your situation, right now
  • One clear next step, and the shape of the path from here
  • A written 2-pager sent after the call, summarising what I heard, my initial thoughts, and a personalised roadmap of how I'd work with you
  • You can walk it alone from there, or we walk it together
Book a free State of Play Call
Most start here

Step 2 · Entry

Career Compass

£995

Credits in full toward Make the Move.

Get clear on the right direction. I read who you are underneath the title, map the real roles and industries you can move into, and we score them against what matters. You leave with a chosen direction and the reasoning.

  • Root Note read of who you are now
  • The real roles and industries you can move into
  • A scorecard against what matters to you
  • A chosen direction, with the reasoning written up
  • Fee credits in full toward Make the Move
Book a free State of Play Call

Step 3 · Main

Make the Move

£4,495

6-month engagement. The Compass is month 1. Then 5 more months to land the role.

The Compass is always month 1 of Make the Move. After that, five months of active support to land the role: the plan, the narrative, the interviews and the offer, with me in your corner the whole way. Same room, same person, no restart.

  • The Compass is included as month 1, then 5 more months of execution to land the role
  • Month 1: direction set through the Compass
  • Months 2 to 6: the plan, the narrative and the story that lands
  • CV, LinkedIn and opening lines that stand up in the room
  • Interview and negotiation prep, with live coaching before and after
  • Warm intros into my network where they fit
  • One 2-hour deep session a month (or 2 x 1-hour, whichever suits), plus text support between
  • Optional: a 3-month first-90-days extension, to land well in the new role. Available on request.
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Longer-term advisory is available after the six months, from £500 to £1,000 a month.

Building your own thing instead? See Venture Launch →

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THE FREE PART

What happens when you book.

Two conversations and a written read. All free, and focused on your next career move.

01

The call

30 minutes, video. I listen, ask questions, and audit what's actually going on: your situation, your market value, the options you're weighing, and what's really forcing the move. Then I give you my personal read on where you stand and what a good next step looks like.

02

The 2-pager

Within a day. It says back what I heard about your experience, your constraints, and your best options, then maps a clear career roadmap from here, including where I'd come in, if at all. It's yours to keep and use however you want.

03

20 minutes to debrief

A few days later, once you've read it. We walk the career roadmap together, answer whatever came up, and sharpen the next move.

You leave with a clear read on where you stand and a career roadmap you can use.

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“Possibly the greatest amount of wise words and advice I have ever received.”

Gabriel Rodríguez, former Sony Music Spain

Why James

I've made the exact call you're facing.

19 years inside Sony Music, ending as SVP. I built teams, ran the platform partnerships, and held people through digital, streaming and now AI. Then I walked out with a letter and rebuilt.

I'm two years into building my own practice. I won't sell you a finished playbook I don't have. What I bring is the coaching depth to work out what you actually want, the advisory judgement to shape what makes sense around it, and a partner for positioning and go-to-market when you get there. Plus someone who knows the first steps because he's taking them.

UK relationships with Spotify, Apple Music, Amazon Music and YouTube. Music Week Best Sales Team, 2024. GLG and Coleman expert. ICF Level 2. The credentials resolve at the end, they don't lead.

Straight Answers

The questions people actually ask.

What if I know I need a change, but not what comes next?
That's exactly where the Career Compass starts. We separate what you're good at from the title you've held, map the credible options, and score them against what matters now.
Can I start while I'm still employed?
Yes. It's often the best time. You can test your thinking, understand your market value, and plan the move while you still have solid ground under you.
I've spent years at one company. Will anyone else understand my value?
Yes, but your old title won't do the work for you. I spent 19 years inside Sony Music, ending as SVP. I know how to find the value beneath a long tenure and turn it into a story the market understands.
How is this different from working with a recruiter?
A recruiter starts with an open role. I start with you. We work out which move fits, build the case for it, then approach the market with a clear target and a story that holds up.
What will I have after the first month?
A written read of who you are now, the strongest options in front of you, a scorecard against what matters, and one direction with the reasoning behind it.
Do you know how senior hiring works in this industry?
I hired, led and worked alongside senior people across music and streaming during 19 years at Sony. I also ran UK partnerships with Spotify, Apple Music, Amazon Music and YouTube. I know how the rooms work and what holds weight in them.
What does it cost to find out?
Nothing. A free 30 minutes, your written 2-pager within a day, and 20 minutes a few days later to debrief the roadmap. Paid work starts with the Career Compass.
Is this therapy?
No. This is advisory and coaching, focused on the decision and the move, not on unpacking the past.
“James provided the space for me to own who I am, and who I am is a ruthlessly compassionate and vulnerable leader.”

Sareata Ginda, Course Leader, Music Business MA, University of Westminster

Start with the free 30 minutes.

Free. Thirty minutes. You leave with a straight read on where you are and what the next move looks like, whether or not we work together.

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