Technical Program Manager

Outmarket AI

2d•Remote

About The Position

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. The Role 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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.