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Ben is a benefits platform that connects the entire benefits ecosystem for employers, employees, brokers, and providers. As Head of AI Operations, you will lead Ben's internal applied AI transformation, reporting directly to the founders with full budget and authority to reinvent how the company operates across all functions.
Your core mission is to identify and rebuild slow, manual, duct-tape processes across customer operations, finance, commercial, and people functions. You will design and implement end-to-end AI-powered workflows that dramatically increase efficiency—for example, reducing new customer onboarding from weeks to days, or enabling customer operations teams to manage twice as many accounts without quality loss.
Key responsibilities include:
- Partnering with each function to diagnose inefficiencies and co-design AI-native operating systems
- Owning Ben's internal applied AI strategy in close collaboration with founders, separate from product engineering's AI roadmap
- Driving adoption across the company so teams become genuinely AI-native and changes stick
- Establishing standards, guardrails, and quality evaluation frameworks for internal AI systems before they touch live customer, people, or finance data
- Ensuring compliance and trust as AI agents handle sensitive workflows
- Getting hands-on with implementation rather than leading from a distance
You will work at the frontier of a role the market hasn't yet standardized. Success here means writing the playbook that other companies will follow in scaling internal AI operations.
Ben operates in 30+ countries and serves hundreds of thousands of employees through its platform. The company offers a comprehensive benefits package including competitive base salary plus equity, £100 monthly personal allowance (increasing with tenure), 28 days holiday plus bank holidays (30 days after 3 years), enhanced parental leave, private medical insurance, life assurance, and a work-from-abroad scheme.
REQUIREMENTS:
- Proven high-growth B2B SaaS experience with demonstrated track record of driving operational transformation and shifting how teams actually work, with measurable outcomes
- Strong systems thinking: ability to own complex, cross-functional problems and see the bigger picture
- Deep, practical AI fluency: daily hands-on use of Claude, Claude Code, and similar tools; well-formed views on where AI creates real value and where it doesn't; ability to translate that into sticky adoption
- Executive-level influence in a scaling company: can engage and challenge leaders from IC to C-suite, turn ambiguity into aligned action
- Bias for hands-on work: you redesign functions yourself, work proactively with teams to drive change, and can demonstrate building solutions that others assumed required large teams
- Force multiplier mindset: create repeatable systems, develop people around you, know when to coach, co-build, push, or escalate
NICE TO HAVE:
- Prompt and context engineering expertise with a structured approach to optimizing model outputs and teaching others
- Experience building guardrails and evaluation frameworks for internal AI systems, with real evals in place before systems touch live data
