ABOUT
James Gillespie.
I spent 19 years inside Sony Music, ending as an SVP. Now I advise leaders and founders of digital media and entertainment with career and company advancement.
CHAPTER 01 · 2005 to 2024
Inside Sony.
I joined Sony Music in 2005. Digital was considered fringe. CDs were still the serious money. It wasn't fringe for long.
Over 19 years I climbed through manager, senior manager, head of, director, senior director, VP. The last three years I was an SVP, first in Digital in 2021, then Commercial Partnerships from 2022 to 2024, running the UK relationships with Spotify, Apple, Amazon and YouTube. Three paradigm shifts, lived from inside. Digital. Streaming. Now AI.
The hardest part was never the strategy. It was holding a team together when nobody knew what came next, including me. If there's one thing I did well across the whole run, it's building people who ended up better than me at the parts of the job they took on. Music Week gave the team the Best Sales Team award in 2024. That was theirs, honestly, not mine.
CHAPTER 02 · 2024
The letter.
I went in one day thinking I was signing a new deal. I walked out with a letter in my hand. Redundancy. The clean version of a story that was neither clean nor rare that year. The labels were cutting headcount, and I was expensive senior management with a highly accomplished team. My role sat across both frontline and catalogue; my last project was part of landing the Pink Floyd deal. So it wasn't a simple reallocation from people to catalogue. It was a senior role being removed.
What I hadn't prepared for was the Tuesday that came after. The diary went quiet. Someone asked me "so what do you do?" at a dinner and for the first time in two decades there wasn't a clean sentence for it. Twenty years of who I was, built on top of a title, and the title was gone. That was the room I now work in for other people.
CHAPTER 03 · 2024 to present
The rebuild -
still in it.
I retrained. ICF Level 2 through Barefoot. Consulting work through GLG and Coleman. Westminster MA guest lecturing. Building a music-adjacent AI tool. Paid advisor to an early-stage AI venture in the personal-brand space (artists, athletes, actors).
And I launched my practice, James Jamil, personal advisor to people and companies in digital media and entertainment. Not because I have the answers. Because I'm inside the rebuild I hold for others.
I spent 19 years building and governing new things inside a legacy music giant and holding people through three industry shifts. Now I do the same for the leaders and founders standing where I stood.
WHAT I ACTUALLY DO
Three things.
· I advise senior leaders through the moment growth or change forces the next big call.
· I come in beside founders as chief of staff and personal advisor, building the layer that lets a company scale without flattening the people inside it.
· I write and I lecture, because the read only stays current if the reading keeps happening.
If any of this reads like your Tuesday, let's talk.
30 minutes. Just a proper sounding board for the moment you're in.