Your Carrier Needs Technology Leadership. Hiring It Is Not Always the Answer.

This is not a failure of management. It is a structural reality of the market. Bermuda's insurance sector employs some of the most sophisticated risk and capital minds in global finance. But the technology leadership that enables those minds to operate efficiently — the CTO, the CIO, the CISO — is absent from most carrier org charts. Not because the need isn't recognised, but because the hire is almost impossible to make.

A full-time CTO is among the most expensive hires a carrier makes. On an island of 64,000 people, the pool of senior technologists with both insurance domain expertise and modern technology capability is vanishingly small. A permanent hire requires relocation — which means a housing allowance, a cost-of-living adjustment, and a commitment to an island lifestyle that many candidates with families and established networks are unwilling to make. Bermuda searches for these roles are long, and some never close.

The assumption behind the permanent hire is that a carrier needs a full-time senior technology executive, forty hours a week, fifty weeks a year. For a Class 4 carrier with 500 employees and a complex global technology estate, that assumption is correct. For a Class 3A carrier with 30 people, a single core platform, and an outsourced insurance manager, it is not.

What most Bermuda carriers need from technology leadership is not full-time presence. It is senior judgment at critical moments: when a technology investment is being evaluated, when a transformation programme is being scoped, when a regulatory requirement demands a technology response, when the board needs someone who can translate between technology complexity and business strategy.

Fractional and interim executive models are now established across financial services. But Bermuda's market has three characteristics that make fractional technology leadership not just viable but the practical model.

Three ways. A carrier can buy one, two or all three, and most start with one.

Pieces one and two are Adam Wenham personally, and a carrier buys one of them, not both. Piece three is the bench: named specialists, engaged for a scope, under Garrison’s accountability. Garrison is retained by a small number of carriers at a time for exactly this reason.

On a programme of scale, a delivery lead and programme office sit under Garrison’s accountability and run the day-to-day rhythm. Adam Wenham owns the outcome, chairs the steering group, and is the person your board sees.

1. Fractional technology leadership

A named technology executive in your org chart at four, eight or twelve days a month — CTO, CIO, CISO, or operational and technology risk lead. The role sits in your governance: named in board papers, present at the risk committee, accountable to the COO or CEO, with the authority to make decisions rather than recommend them. Six-month minimum, then rolling monthly. For a carrier that needs the function before it can justify the hire, or that is between hires.

The scope varies, but three engagements are the most common entry points.

2. Programme leadership

Garrison owns the outcome of a large complex technology change, not just the plan: sets the sequence, runs the delivery rhythm, and brings your in-house team, your integrators and your vendor partners onto a single operating model.

Garrison runs the programme under the COO’s delegated authority, and that authority is written into the engagement letter: chair of the programme steering group, sign-off on the delivery plan and the sequence, right of veto on a release that is not ready, and the single point of escalation for every partner on the programme. Your CTO sets technical direction. Garrison does not advise on the programme; Garrison runs it, and is accountable for the dates.

For a carrier whose board has approved change that nobody is sequencing, and where the partners are currently managing themselves.

3. Specialist roles on a defined scope

Specialists are engaged on Garrison’s letter, against a scope agreed in writing, reporting through Adam Wenham. Garrison is paid for a deliverable, not a day rate for a body. This is not staff augmentation and Garrison does not place people and leave.

They come from Garrison’s bench, on-island where it exists, UK and Poland where it does not. Named to you before the letter is signed.

Garrison Technology Leadership is delivered on a Statement of Work basis — not through a staffing agency model and not through a traditional consulting engagement.

A staffing agency places a contractor. The contractor reports to the carrier. The carrier manages the engagement. If the contractor underperforms, the carrier replaces them — and loses the institutional knowledge accumulated during the engagement.

A consulting firm sends a team. The team delivers a report. The report sits on a shelf because the firm that wrote it has no role in delivering it. The consulting firm leaves. The carrier is left with recommendations but no one to implement them.

Garrison scopes the engagement, defines the deliverables, assigns the technology leader or specialist, and takes accountability for the outcome. The fractional leader or specialist works inside the carrier's operations but reports through Garrison's quality framework. The carrier receives defined deliverables — a technology governance framework, a regulatory compliance assessment, a transformation programme plan — not timesheets.

If the gap is leadership — no technology executive, or a hire you are not ready to make — start with fractional. If the gap is delivery — the board has approved change and nobody is sequencing it — start with programme leadership. Specialists come third, against a scope that one of the first two has defined, because a specialist bought before the scope exists is a cost without an outcome.

Most carriers begin with one piece and add the second in the following year.

A manager running several carriers has the same codes landing on every one of them, with no single entity large enough to carry its own technology function. Garrison works at the group level: one assessment methodology applied across the book, one evidence standard, one operational and technology risk lead retained by the manager rather than by each entity, with each carrier’s own accountable officer unchanged, and specialists drawn down against a scope as each carrier needs them. That conversation starts with the manager, not the carrier.

For managers specifically: SOC 1 and SOC 2 readiness and remediation - the attestation itself is performed by your auditor - multi-entity data segregation and the evidence it holds, the outsourcing governance pack each carrier hands the BMA, and PIPA across the book from one methodology.

Garrison acts for a carrier and its insurance manager at the same time only after disclosing it to both and with both parties' written consent, and never rates a carrier's reliance on a manager control that Garrison itself remediated.

The usual first engagement is a control-environment readiness assessment of the shared platform: five weeks, fixed fee, with the findings written for the clients who will ask you for them.

Garrison does not audit you, sell you software, or take vendor commissions. Where a group or a carrier already runs a platform, Garrison’s assessment of it is not a sales conversation about replacing it. The carrier’s own officer stays accountable to the BMA; Garrison does not front with the regulator unless you ask. Garrison acts for a carrier and its insurance manager at the same time only after disclosing it to both and with both parties' written consent, and never rates a carrier's reliance on a manager control that Garrison itself remediated.

Adam Wenham leads every engagement personally, with a named bench of specialists on defined scopes behind him.

A fractional engagement is priced as a stated number of days a month, not a day rate that drifts: three tiers from four to twelve days, six-month minimum, then rolling monthly. Six months because the first quarter is spent building the baseline — the estate, the register, the reporting — and a shorter engagement leaves you with the baseline and nothing built on it. Full detail is in the Technology Leadership summary, available on request.

The comparison is not fractional versus full-time. It is senior technology leadership versus no technology leadership. The carriers that engage fractional are not substituting for a full-time hire they could make. They are filling a gap that would otherwise remain empty — with the COO continuing to own technology alongside every other operational responsibility, and the board continuing to receive generic assurance rather than specific, evidenced reporting.

A fair question: where is the evidence that this model works in Bermuda's insurance market? It is early. The fractional model is proven across financial services globally, but its application to Bermuda's carrier landscape is new. The evidence, for now, is the track record of the practitioner delivering it — the transformation programmes I have led, the regulatory frameworks I have implemented, and the technology estates I have modernised at institutions whose scale and complexity exceed most Bermuda carriers. Carrier-specific case studies will follow. The underlying capability is not new. The delivery model is.

A first meeting, on-island, at your convenience.

The Technology Leadership summary — the three tiers, what the role does, how an engagement starts, and the questions a COO asks — is available on request.