Raymond Oakley
Focus: Director-level transitions · Based in London
Raymond spent twenty years in senior leadership, including CFO of a listed hospitality group. He now mentors newly promoted directors and heads-of on the specific challenges of first year in role — board relationships, delegation across a wider team, and the language of difficult conversations.
Every session runs inside your Ally cabinet. Requires an Ally account.
Session cadence
Raymond runs 45-minute video sessions from inside the Ally cabinet. Standard clients book four per month; Plus clients book unlimited.
Working languages
English (primary). Ask during intake if you need a bilingual mentor — we may pair you with another mentor for language coverage.
Typical arc
Most executive coach clients work with Raymond for three to six months, then either continue or transition to a lower cadence.
Book your first session with Raymond
Free on Ally Starter. Sign in with a magic link — your cabinet is provisioned on the same page.