Head of Finance

About Prevail and the role

Prevail is a multidisciplinary risk and advisory group that helps governments and businesses navigate the contemporary risk environment as their Complex Mission Partner. We are at an inflexion point, moving from a founder-led, opportunity-driven business into a repeatable, investable platform where the work we deliver today funds the capabilities we are building for tomorrow. The business is currently founder-funded, with no external investors today; over the next twelve months, we intend to raise external investment for the first time with M&A forming a deliberate part of the use of funds - and to roughly double revenue over the following three years through a combination of organic growth and targeted acquisition.

Prevail operates as a group of trading companies, with consolidated reporting currently managed through Xero and Joiin, while financial planning and forecasting remain largely Excel-based. The finance function has a strong operational foundation, overseeing day-to-day finance activity across the group. We are now looking to appoint a Head of Finance to further develop the function into a more strategic capability, with responsibility for financial planning, capital strategy, commercial performance analysis, investor reporting, and supporting the business through its next phase of growth. This role will also lead the continued development of finance systems, processes, and reporting capabilities, including the effective use of modern tooling and AI to improve insight, control, and decision-making as the organisation scales.

As Head of Finance, you will lead the finance function and be accountable for the business's financial direction. The team will continue to run the close, controls, cash operations, project P&Ls and audit. We are looking for an experienced, commercially fluent finance leader who can hold a credible conversation with the Board on capital and strategy, read the economics of a contract alongside the commercial team, coach the finance team, and personally champion the use of modern tooling and AI inside the function so the team works smarter rather than simply harder.

Key responsibilities

• Strategic finance and capital: Develop and recommend a capital strategy to the Executive team and Board: when and how to raise capital (equity, venture debt, revenue-based finance, working capital facilities), treasury approach, FX and reserve policy, framing the options, modelling the trade-offs, and standing behind the numbers. Lead financial scenario planning for the Board including stress tests on pipeline conversion, cost base flex points and external shocks. Lead finance activity across acquisitions, including valuation, diligence, modelling, integration planning, and deal support. Be accountable to the Executive team as the financial voice on strategic decisions.
• Commercial finance and deal economics: Propose the commercial finance framework - pricing principles, bid economics, deal-structuring guardrails and contract margin envelopes for Executive team approval, then own it in operation as the rules of the road for how Prevail prices and structures work. Set the cost-gatekeeping framework: thresholds, trigger points, escalation paths, and principles for spend trade-offs, working with the team on day-to-day operations. Lead a quarterly margin and pricing review across the project portfolio, surfacing loss‑making or thin‑margin projects early and partnering with the Commercial Director on the response. Provide the finance lens- risk‑adjusted return, cash‑curve impact, margin sensitivity on major bids and contract renegotiations led by the Commercial Director. Own the analysis of customer, segment, and contract profitability to identify which opportunities deliver sustainable commercial value and which may negatively impact margins, supporting the Commercial Director in strategic bid/no‑bid and investment decisions.
• Long‑range planning, Board reporting and preparing for first investment: Own and maintain the long‑range financial plan, ensuring alignment and integration with the 12‑month rolling forecast managed by the team, creating a single, consistent financial model that supports both strategic planning and operational decision‑making. Shape the financial story in the Board pack: bridge from operating numbers to strategic narrative, KPI commentary, and forward look. Lead investor‑readiness for the Group's first external raise: equity story, sensitivity narratives, diligence pack and data room, partnering with the Commercial Director on the external narrative and the team on the underlying numbers.
• Finance transformation, innovation and technology: Develop and lead a 12‑24 month finance transformation roadmap covering systems, data, processes, and ways of working, prioritising high‑impact initiatives and providing regular progress updates to the Executive team on initiatives implemented, scaled, refined, or discontinued. Lead the development of the finance technology stack, transitioning from the current Xero, Joiin, and Excel‑based environment to a more modern FP&A platform to support financial planning, rolling forecasts, and cashflow management, while retaining Xero and Joiin as the core systems of record for accounting and consolidation. Improve the scalability and efficiency of the month‑end close process through the implementation of automation, reconciliation tooling, variance analysis, and close‑management processes, with the objective of maintaining a timely and accurate close as the business grows. Drive the practical use of AI, automation, and modern finance tooling across the function to enhance insight, reporting, forecasting, reconciliations, invoice processing, and audit support, ensuring all solutions are implemented in a secure, controlled, and commercially effective manner.
• Finance leadership and team development: Lead the finance function as a whole, with the opportunity to structure and developing the operations and controlling functions in order to scale the business and support planned growth. Partner across the Executive team as a credible, trusted business voice. Represent finance with auditors, tax advisors, bankers and regulators alongside the team.

Essential skills and experience

• Qualified accountant (ACA, ACCA, CIMA or equivalent), with strong technical foundations and credibility in front of auditors and investors.
• 5+ years’ progressive finance experience, including operating at Head of Finance, Finance Director, or emerging CFO level within a scale‑up or high‑growth environment, ideally supporting a business through investment, fundraising, acquisition activity, or other significant capital events.
• Demonstrable experience operating as a strategic finance leader above a Financial Controller with a track record of leading the function, the plan and the capital agenda rather than running the close yourself; ideally in a multi‑entity group with consolidated reporting.
• Strong commercial finance background; fluent in pricing models, bid economics, contract structures and margin management in a project‑or services‑based business, with the judgement to set policy and guardrails rather than run individual deals.
• Experience leading financial scenarios and capital strategy for an Executive team and Board, including direct experience preparing a business for, or executing, an external fundraise (equity, debt or both) and / or buy‑side M&A.
• Track record of finance transformation: implementing or upgrading FP&A tooling, automating close, building self‑serve reporting, and adopting AI/automation in a finance team.
• Excellent communicator; equally comfortable presenting a long‑range plan to the Board, coaching the team, and explaining a bid economics decision to a delivery lead.
• Experience in a regulated B2B or project-based environment; ideally defence, security, government services or an adjacent regulated sector.

Desirable skills and experience

• Experience integrating an acquired business into a finance function (systems, controls, reporting, people).
• Hands‑on familiarity with modern FP&A tools.
• Demonstrable hands‑on experience implementing AI, automation, or modern finance tooling within a finance function to improve efficiency, reporting, controls, or decision‑making.
• Experience supporting international expansion, multi‑entity structures, or partnerships and JVs.

Personal attributes

• Strategic yet operationally grounded, with the ability to elevate the finance function while remaining connected to the practical realities of day‑to‑day delivery.
• Commercially astute, with the confidence and credibility to challenge decisions relating to spend, pricing, investment, and commercial risk.
• Strong interest in technology, automation, and AI, with a proactive approach to improving how finance teams operate and deliver insight.
• Able to remain calm and effective under pressure, particularly during periods of cash management, audit activity, or Board‑level scrutiny.
• Comfortable operating in a fast‑paced, evolving scale‑up environment, balancing immediate operational demands with longer‑term strategic priorities.
• Demonstrates integrity and intellectual honesty, proactively identifying issues early, taking ownership, and presenting practical solutions and recommendations.

At Prevail, we believe in recognising and rewarding our people. Our benefits package is designed to support your wellbeing, financial security, professional development, and life beyond work:

• AXA Private Medical Insurance: Fully funded private healthcare cover through AXA Health.
• Shield Cashback Plan: Claim cashback on everyday healthcare costs including dental, optical, physiotherapy, prescriptions, and more.
• Salary Sacrifice Pension Scheme: A tax‑efficient way to save for your future through pension contributions.
• Employee Assistance Programme: Confidential mental health, legal, financial, and wellbeing support through Health Hero.
• Free Gym Membership & Wellness Perks: Free gym access for London employees at Manor Gym, plus company-sponsored fitness classes each week.
• Enhanced Leave Entitlements: Supporting you through important life moments with flexibility and care.
• Professional Development Days: Dedicated time off to focus on your personal and professional growth through training, courses, or self‑directed learning.
• Cycle to Work Scheme: Tax‑efficient savings on bikes and accessories, available post‑probation.
• Season Ticket Loans: Interest‑free loans to support annual commuting costs.
• Socials & Team Culture: Company socials every other Thursday, regular run club meetups, plus summer and Christmas events that bring the team together.
• Culture & Development: A values‑led culture with collaborative initiatives and meaningful opportunities for personal and professional development.