Jon Rogers

Director | Executive Search

What I Do at Pioneer

I lead the Executive Search division at Pioneer Search, partnering with Specialty Insurers and Lloyd's Market organisations on discreet senior mandates, direct reports, and strategic hires.

I am fully immersed in the London Market, building strong networks of industry-specific professionals and advising on transformational, technological, and personnel change with tailored, confidential consultation.

I am also a Community Ambassador for Nexus Connect, a community hub that connects, educates, and inspires the talented professionals that make up the London Market.

Typical Roles I Recruit For

I work closely with clients on senior leadership appointments, including:

• Chief Information Officer (CIO)
• Chief Technology Officer (CTO)
• Chief Data Officer (CDO)
• Transformation & Change Directors
• Heads of IT, Data & Architecture
• Other C-suite and senior executive roles across Technology, Operations, and Strategic Functions

Executive Search Solutions

Our on-demand Executive Search solution is designed for businesses where leadership decisions shape the future. We combine in-depth consultation, discreet search, and market insight to ensure the right leadership appointment every time.

What clients can expect:

• Retained & exclusive search for critical executive hires
• Bespoke talent mapping & market analysis
• Shortlists built from deep industry networks and off-market talent
• End-to-end management of the search process, from brief through to appointment
• Ongoing consultation and market intelligence beyond the hire

Recent Projects

I recently led a retained CIO search for a Specialty Insurer, managing the full process end-to-end:

• Consultation to define requirements and shape the brief
• Full market mapping and analysis
• Delivery of a high-quality shortlist
• Screening of both internal and external candidates
• Managing first stage interviews
• Coordinating the entire process with transparent, ongoing communication

Executive Market Outlook | London & Lloyd's Insurance

In my recent Executive Talent Insights Report, I explore the challenges and opportunities facing executive leaders across the London Specialty Insurance market.

The piece highlights the growing demand for executives who can integrate AI responsibly, lead through complexity, drive sustainable growth, and what organisations must do to attract and retain them.