VP, Technical Operations

Insurance underwriting runs on human judgment, manual workflows, and knowledge locked in someone's head. It breaks when that person leaves and doesn't scale when the book doubles. Sixfold is building AI agents that understand risk the way a 20-year veteran underwriter does. Not summaries or flags, but systems that make real decisions on billions in premium for some of the world's largest carriers. AI is the product and the workflow. The Customer Success Manager is the person carriers trust to make sure it all delivers. At Sixfold, being our Staff Technical Program Manager means owning the infrastructure that lets AI systems make real decisions on billions in premium and knowing exactly why something breaks when it does. Who We Are Sixfold is the AI brain for underwriting. Our platform handles submissions at scale, assessing risk against appetite, surfacing cited insights, and deploying AI agents to handle research, referrals, and triage so underwriters can focus on building profitable portfolios. The Team A focused team of insurance operators, AI researchers, and engineers who love hard problems. We're pushing the boundaries of AI adoption across every function, from how we build, to how we sell and to how we support customers. We ship fast and stay close. Traction Processing billions in premium for some of the world's largest carriers. We know AI. We know underwriting. We're building what comes next. About the Role Orchestrate the full product delivery for our largest and highest-value initiatives. Own end-to-end program management across the entire organization. Work directly with engineering, product, and design leads and ICs to understand product direction and technical architecture, participate in project and capacity planning, review product and technical specs, and identify dependencies and risks early. Be an active unblocker when issues arise. Align engineering, product, and go‑to‑market teams. Serve as the connective tissue between Engineering, Product, Customer Success, and Sales. Translate technical realities into language each team can act on. Make sure no important decision falls through the cracks and risks are owned and mitigated. Run program governance with discipline and minimal overhead. Own weekly program reviews, cross‑functional working sessions, and executive status updates — keeping each meeting focused on the specific items that require leadership attention. Build lightweight, durable program infrastructure. Design and own the minimum‑viable set of processes, tools, and tracking systems that keep programs running: roadmap and backlog planning, milestone tracking, dependency maps, risk registers, and executive dashboards. Processes should be owned and evolvable by teams, not dependent on you. Drive operational programs within Tech and across the company. This could include managing the corporate and tech OKR processes, supporting 3‑6 month planning horizons, continuing the organization’s broader push toward agentic ways of working, etc. In general, staying plugged in and jumping in where you can add the most value. Become an active, valuable member of the Senior Technical Leadership Team. Report to the CTO and work closely with technical leadership to understand what's happening across the company and provide support and input to key technical decisions. What Success Looks Like 30 days: Mapped the full program landscape for the most urgent initiatives — understood key dependencies and where the delivery risks are. You've sat in every recurring meeting, read the critical specs, and have a clear point of view on how to manage the program going forward. You’re a hands‑on user of the products you are managing. 60 days: For your key programs, you’ve built the minimum‑viable program infrastructure to be successful. Risks surface early, nothing falls through the cracks, and executive updates are crisp. You’re seen as a source of truth by leadership. Engineering and Product trust you to represent their work accurately upward. You have a solid understanding of the Sixfold product suite. You’ve also taken on full ownership of the Tech OKR process. 90 days: Your processes are team‑owned, your automations are documented, and you've visibly moved the needle on at least one high‑value initiative. You’ve explored other priority work outside of your primary programs and have started to engage in operational improvements within Tech and across the company. You’ve become a trusted member of the Tech leadership team actively contributing to key decisions. About You 8+ years in technical program management, engineering program management, or a closely related role, with meaningful time at a startup or high‑growth company. You've seen what good program management looks like at scale and what breaks down when a company grows faster than its processes. Experience driving complex cross‑functional programs through alpha, beta, and GA, coordinating engineering, product, and go‑to‑market teams simultaneously. You are equally at home in an architecture review and a board‑level status update, translating ambiguity into structured plans and turning cross‑functional chaos into predictable delivery. A demonstrable technical foundation. Prior software engineering experience, a CS or technical degree, or equivalent hands‑on exposure to systems design, distributed architectures, and the SDLC. You can read a technical spec, understand a system diagram, and have an opinion on areas of risk. Demonstrated habit of reaching for AI tools and agents as a first instinct — actively incorporates LLM‑based workflows, automation, or AI‑assisted tooling into day‑to‑day program management work. Nice to Have Experience in insurance, fintech, or another regulated industry. Experience managing or integrating external consulting or nearshore delivery partners into an internal engineering roadmap. Experience building OKR and roadmap processes for a scaling technical organization. Prior work supporting a Field Delivery or Customer Success team during a B2B SaaS go‑to‑market motion. Compensation Expected full‑time salary range between $175,000 to $205,000 + equity + benefits. Advertised and actual salary ranges may differ by geographic area, work experience, education, and/or skill level. Comprehensive benefits, 401(k) with employer match, parental leave, unlimited PTO, and birthday off. This position does not include visa sponsorship. Moments We're Proud Of Forbes: AI Is Starting to Close Deals on Its Own — Here's Where Sixfold Fits Sixfold Named One of the 100 Most Promising AI Companies in the World Backed by Salesforce Ventures — Here's How It Started Sixfold Hit 100 Billion Tokens — Here's What That Actually Means How Zurich Went From Pilot to Companywide Rollout in Under a Year Watch Our CEO Explain Sixfold's "Holy Grail" Metric Equal Opportunity & Accessibility Sixfold is committed to accessibility and provides reasonable accommodations for qualified individuals with disabilities and disabled veterans throughout our recruitment process. If you have any difficulty using our online system and you need accommodation due to a disability, please reach out to us directly at (646) 847‑8824. #J-18808-Ljbffr Sixfold