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Toucanberry
Legal & HR 1h ago

Fractional Head of People (HR) - Contractor-to-Perm Transition

Toucanberry
United KingdomUnited Kingdom
Contract
Not Disclosed
Senior-Level

Job Description

Key Skills Required

Master these to land this role

Contractor WorkforceHR ManagerTalent AcquisitionIR35 CompliancePromotion Framework Design

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We are a boutique tech consultancy specializing in building AI and data engineering solutions for global reinsurers. With five years of experience, we help rebuild systems and processes with deep industry domain knowledge, setting us apart from generalist consultancies.

As the business scales rapidly, the founders are establishing a Senior Leadership Team (SLT) to improve delivery quality and transition senior contractors to permanent roles. We seek an experienced, pragmatic Fractional Head of People to manage these transitions fairly and efficiently.

The Role & Engagement Structure

We are looking for a Fractional Head of People with hands-on experience negotiating compensation, titles, and performance frameworks for a contractor-heavy workforce. This role is initially focused on assessing team capacity, advising on contractor-to-permanent transitions, and designing performance management systems that align with project-based outcomes.

Key Responsibilities:

  • Capability & Capacity Assessment: Conduct an objective review of current team capacity and contractor-to-permanent mix to determine role conversions and identify gaps.
  • Contractor vs. Permanent Composition: Advise on balancing workforce flexibility with stability and institutional knowledge.
  • Contractor-to-Perm Hiring Negotiation: Lead negotiations for role titles and compensation, acting as an intermediary between founders and contractors to avoid direct founder involvement.
  • Contractor Performance Management: Design and advise on performance frameworks for contractors, focusing on Statement of Work (SOW) ownership and output rather than traditional line management to avoid employment-status risks.
  • Advice on Titles & Promotion Criteria: Develop fair, defensible promotion criteria for the first cohort of permanent hires, ensuring precedent-setting decisions are well-justified and scalable.

About You & Requirements

  • Consultancy Experience: Prior experience in professional services or consultancy environments, understanding billable utilization, project-based teams, and contractor-heavy workforces where value is tied to client outcomes.
  • Pragmatic Approach: Ability to distinguish between legal requirements and operational preferences, advocating for practical solutions over overly cautious defaults.
  • Contractor Workforce Experience: Deep understanding of contractor-heavy models, including IR35 implications for performance management and communication.
  • Direct Negotiation Experience: Comfortable conducting one-on-one compensation and title discussions with contractors, not just designing frameworks for others.
  • Promotion Framework Design: Experience building or advising on career progression criteria, particularly in environments where title inflation and precedent-setting are risks.

Benefits

Fully Remote

Outside IR35

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Toucanberry (operating at toucanberry.com) is a boutique software consultancy engineered for reinsurance firms seeking operational efficiency. Specializing in reinsurance, the company transforms manual processes and fragmented systems into streamlined, data-driven workflows. Founded by Alexander Page Bhishma, who leads AI strategy and product development, Toucanberry combines deep technical expertise with industry-specific insights. Under the hood, their solutions integrate AI and data engineering to rebuild legacy systems, ensuring scalability and real-time analytics. This empowers reinsurers to optimize underwriting, claims management, and risk assessment while reducing operational friction. Backed by a total funding of $121.9B (as per Crunchbase), Toucanberry positions itself as a niche yet impactful player in the reinsurance tech landscape.

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Fractional Head of People (HR) - Contractor-to-Perm Transition at Toucanberry | HireSkys