Technical Program Manager

Outmarket is building the AI-native platform for the insurance industry — a unified system spanning workflows, policy checking, document generation, analytics, and deep integrations with carrier and agency-management systems. We move fast, ship continuously, and operate across a complex, multi-tenant technical landscape. Headquartered in San Francisco, we’re a team that pairs serious engineering depth with a relentless focus on delivering real value to insurance professionals.

We’re looking for a Technical Program Manager (TPM) to be the connective tissue across our engineering and product organization. You’ll own the planning, coordination, and delivery of cross-functional programs that touch multiple teams, systems, and stakeholders. This is a high-leverage role for someone who thrives on bringing clarity to complex, interdependent work and who can speak fluently with engineers, product managers, and leadership alike.

You won’t just track tasks — you’ll shape how we plan, surface and resolve risks before they become blockers, and create the operating cadence that lets a fast-growing team move quickly without breaking things.

• Own end-to-end program execution for major cross-functional initiatives — from kickoff and scoping through launch and retrospective.

• Build and maintain program plans that map dependencies across engineering, product, design, and data teams, keeping everyone aligned on scope, milestones, and timelines.

• Drive the operating cadence — run planning cycles, standups, reviews, and launch readiness; make meetings sharp, decisions clear, and follow-ups accountable.

• Identify, escalate, and resolve risks and blockers early, proactively unblocking teams and re-sequencing work when priorities shift.

• Translate between technical and non-technical stakeholders, turning complex engineering realities into crisp updates for leadership and clear context for the teams doing the work.

• Improve how we operate — establish lightweight, scalable processes for planning, prioritization, and delivery that reduce friction rather than add it.

• Maintain a single source of truth on program status, dependencies, and decisions, so anyone can understand where things stand at a glance.

• 5+ years in technical program management, engineering program management, or a closely related role at a software/technology company.

• A technical foundation — you can read a system design doc, follow architectural trade-off discussions, and engage credibly with engineers. Prior experience as an engineer, or a CS/technical degree, is a strong plus.

• Proven track record shipping complex, cross-functional software programs on time, with multiple teams and competing priorities.

• Exceptional organizational and communication skills — you write clearly, run a tight meeting, and keep large groups of people aligned.

• Comfort with ambiguity and speed — you create structure where there is none and adapt as priorities evolve in a fast-growing startup.

• Strong judgment on prioritization and risk — you know what matters most, what can wait, and what could derail a launch.

• Experience with modern delivery tooling (e.g., GitHub, Linear/Jira, Notion) and an instinct for using process to enable, not bottleneck, the team.

• Experience in AI/ML, data platforms, or B2B SaaS products.

• Familiarity with the insurance, fintech, or enterprise software domains.

• Experience standing up program-management practices at an early- or growth-stage company.

• High impact, high ownership — you’ll directly shape how a fast-moving company plans and ships.

• Work on hard, meaningful problems at the intersection of AI and a massive, underserved industry.

• A team that values clarity, speed, and craftsmanship in equal measure.

• Competitive compensation, meaningful equity, and the chance to help build the operating backbone of a company in hypergrowth.

Outmarket is an equal opportunity employer. We celebrate diversity and are committed to building an inclusive environment for all employees.