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About the role

This role is for an experienced technology operator who has personally led integrations, separations or carve-outs. Most initial assignments will begin before signing or between signing and close. You will help investors understand whether a technology integration or separation is feasible, where value or risk sits, what Day 1 requires and what the plan will cost.

If the transaction completes and Crosslake is selected for follow-on work, you may continue into technology workstream leadership, an Integration Management Office or Separation Management Office role, or interim or fractional CIO leadership. You must be comfortable moving from rapid assessment to accountable execution without losing pace or commercial focus.

This is not a traditional PMO role. Project discipline matters, but plans, dashboards and RAID logs are tools. The value of the practitioner is the ability to challenge a CIO, assess a technology estate, make and defend disposition and sequencing decisions, and convert uncertainty into a credible path to Day 1 and beyond.

Role responsibilities

Pre Sign Assessment and Diligence

• Lead or contribute to technology due diligence with an explicit integration or separation lens, working directly with private equity deal teams, operating partners and target company leaders.
• Assess the technology estate across enterprise applications, infrastructure, cloud, cybersecurity, identity, data, integrations, IT service management, vendors, organisation and operating model.
• Identify technology entanglements, shared services, stranded costs, critical dependencies, key-person risks and constraints that could affect valuation, deal terms, Day 1 or the value creation plan.
• Test the feasibility of the proposed integration, separation or standalone model and identify the decisions that must be made before signing or close.
• Estimate one-time technology costs, recurring standalone costs, investment requirements, potential synergies and realistic timing using the best information available.
• Review draft or proposed technology TSAs and identify gaps in scope, service levels, duration, cost, exit feasibility and Day 1 continuity.
• Produce concise, investment-grade findings that distinguish material deal issues from matters that can be addressed through planning and execution.

Sign to Close Planning

• Turn diligence findings into an executable technology plan with clear decisions, owners, dependencies, costs, milestones and escalation points.
• Define technology Day 1 requirements for applications, infrastructure, access, cybersecurity, data, integrations, service support and vendors.
• Develop or challenge application disposition, infrastructure separation or consolidation, data migration, identity, cybersecurity and vendor transition plans.
• Shape the interim and target technology operating model, including organisation design, leadership needs, sourcing choices and governance.
• Support TSA design and negotiation, build an achievable exit roadmap and test whether the buyer, seller and key suppliers have the capacity to deliver it.
• Establish fit-for-purpose integration or separation governance and management information that gives executives a clear view of readiness and risk.

Post Close Follow On

• Where Crosslake is selected for follow-on work, lead technology integration or separation workstreams through stabilisation, key milestones and TSA exit.
• Take on broader IMO or SMO leadership when the assignment requires an operator who can coordinate business and technology decisions, challenge delivery teams and maintain executive accountability.
• Serve as an interim or fractional CIO or senior technology leader when a portfolio company needs hands-on leadership through transition, integration or standalone build-out.
• Hold internal teams, vendors and implementation partners accountable for outcomes while protecting business continuity and the investment case.

How You Will Work

• Learn Crosslake’s transaction methods, tools and quality standards through an initial apprenticeship on at least two engagements, then lead assignments independently.
• Work in small, senior teams and draw on Crosslake specialists where deeper expertise is required.
• Operate effectively with incomplete data, compressed timelines and changing transaction assumptions.
• Communicate directly and credibly with investment committees, operating partners, boards, CIOs, CTOs, CISOs and technical teams.
• Support engagement scoping and proposals with delivery insight, while remaining primarily accountable for client work and outcomes.

What we’re looking for

Required

• 15+ years of technology experience, including substantial responsibility for enterprise technology strategy, operations, transformation or delivery.
• First-hand accountability for multiple technology integrations, separations or carve-outs. At least one should include meaningful pre-close planning and post-close execution.
• Broad working knowledge across applications, infrastructure, cloud, cybersecurity, identity, data, integrations, IT service management, vendors, organisation and operating model.
• The judgement to assess architecture and dependencies, challenge senior technology leaders and make practical decisions without being the deepest specialist in every domain.
• Experience developing or challenging Day 1 plans, TSAs, application disposition decisions, target operating models, technology roadmaps and execution plans.
• Commercial and financial fluency sufficient to estimate and explain one-time costs, run-rate costs, investment requirements, synergies and key assumptions.
• Strong written and verbal communication, including the ability to turn complex technology facts into clear implications for investment and execution decisions.
• A hands-on, self-directed approach with high accountability for output quality and client outcomes.
• Ability to work remotely, collaborate across time zones and travel to client sites when engagement needs require.

Preferred

• Prior service as a CIO, CTO, Technology Director, Head of IT, Head of Technology Transformation, M and A Technology Lead, Integration or Separation Technology Lead, enterprise architect, or senior leader across enterprise applications, infrastructure or cybersecurity.
• Experience working with private equity investors, operating partners or PE-backed management teams.
• Buy-side and sell-side transaction experience, including corporate divestitures, platform acquisitions and add-ons.
• Experience standing up a standalone technology environment, exiting TSAs, consolidating application or infrastructure estates, or leading complex data and identity transitions.
• Previous advisory or consulting experience is useful, but direct operating experience and personal accountability for delivery are more important.
• Bachelor’s degree in computer science, engineering, information systems, business or a related field is preferred. Equivalent experience is valued more highly than a specific degree.
• Relevant technology, architecture, cybersecurity, cloud or programme leadership certifications are useful but not required.