Fractional CTO

• The company provides the data and intelligence layer for large-scale litigation: the platform supports case management, document and medical-record workflows, and portfolio valuation. Production systems handle protected health information (PHI).
• Role: Fractional CTO for a 6–9 month embedded engagement to build and hand off a repeatable, audit-ready engineering organization. This is a delivery- and transfer-focused mandate: leave behind a Head of Product who can lead engineering, a hired and calibrated team, and an engineering operation that runs without heroics.
• Location / cadence: Remote with US Eastern overlap; part-time embedded commitment (initially heavier, ~3 days/week, then reduced to ~2 days/week). Initial term about 6 months (extendable to ~9). Conversion to a permanent role is possible if both sides agree.
• Engagement start: begins with a paid one-week assessment (access, systems, team, hiring pipeline) that ends in a written ~90-day plan — the trial for both sides. A Business Associate Agreement is required before any access to production data. Monthly retainer; no equity in the fractional engagement.

Responsibilities

• Make the Head of Product technically decisive
• Weekly working sessions (practical, collaborative coaching; not lectures).
• Sit in on architecture decisions with the Head of Product; the Head of Product drafts decision records for review.
• Run technical interview loops with the Head of Product scoring alongside; by month three the Head of Product runs them independently.
• By the end of the engagement the Head of Product can hold his own in system design, data architecture, security posture, and AI-system quality — and understands limitations.
• Hire the team (own the hiring machine end-to-end)
• Recruit and close roughly a dozen roles over ~3 months: product engineers (full-stack across multiple products and one domain-specific product), data engineers (mix of full-time and contractor bridge), analytics engineer for valuation, systems/security engineer, product managers, an implementation lead, and product operations support.
• Define levels and scorecards, design technical working-session interview fixtures, calibrate interviewers, and own offer decisions with the Head of Product.
• Own first-90-days onboarding plans for each hire. Work with engaged recruiters; take ownership of the technical funnel and candidate evaluation.
• Stand up the engineering operation (make production safe, repeatable, and auditable)
• Create organization-held access and secrets (remove single-person ownership of core accounts).
• Inventory and transfer single-person credentials to organization-held accounts.
• Produce a written map of every production system, its owner, and its risk.
• Define and enforce: definition of ready/accepted, release gates per product (including evaluation sets for ML/AI systems and reconciliation for data systems), a single delivery cadence across in-house and partner work, and an on-call rota with named owners.
• Produce runbooks for every production component and require an exit test (runbook exercised by someone who did not build it).
• Implement security controls an audit (e.g., HIPAA / SOC 2) would sample.
• Deliver the following ~90-day milestones
• Within the first month: access inventory complete and credentials transferred; written map of production systems and owners; hiring machine live (levels, scorecards, fixtures, interviewer calibration); Head of Product has drafted initial architecture decision records.
• Within the first two months: definitions and release gates in force; on-call rota with named owners; first wave of hires closed or with signed offers; partner delivery aligned to the same cadence/acceptance rules as in-house.
• Within the first three months: every production component has a runbook that passed an exit test by someone who did not build it; subsequent hiring wave in flight; a written technical roadmap the Head of Product can present to leadership; a written recommendation on whether the organization needs a permanent CTO, a VP of Engineering, or neither — and by when.
• Operate as an embedded, hands-on leader (not a monthly advisor)
• Be present and active in day-to-day work required to meet priorities; transfer ownership rather than accumulate it.
• Ensure work and decisions are documented and communicated plainly to lawyers and non-native English speakers.

Qualifications

• Proven interim/fractional CTO or VP of Engineering experience.
• Has served as CTO or VP Engineering of a company of roughly 15–60 people through a hiring wave — and has done this at least once as a fractional or interim leader, with clear examples of transferred ownership.
• Regulated-data, PHI production experience.
• Has carried PHI or another regulated data class in production and faced auditors (HIPAA / SOC 2 experience strongly preferred).
• Hiring and process evidence.
• Has hired 10+ senior engineers within a year with a written process and can show scorecards and interviewer calibration artifacts.
• Coaching and transfer skills.
• Has coached a non-engineering executive into technical leadership and can describe the person and outcome.
• Modern AI-assisted engineering fluency.
• Fluent in agentic coding tools used in daily team practice, LLM systems with evaluation sets as release gates, and the judgment to know where AI output cannot be trusted.
• Communication and documentation.
• Communicates plainly with lawyers and non-native English speakers; habitually writes decisions down and produces decision records.
• Practical constraints.
• This is not a permanent CTO hire (the staffing recommendation is a deliverable). This is not a long-term hands-on individual-contributor role on a single product. This is not an advisor who meets monthly — the initial period is embedded work.
• Screening expectations.
• Engagement begins with a paid one-week assessment (no assessment, no engagement). A Business Associate Agreement is required before any access to production data. References will include the CEO the candidate last served and the executive they coached.