Chief of Staff

About the role

The Chief of Staff at OuterSignal is a senior operating role with broad ownership across the company. Key responsibilities include turning strategy into execution, building the systems and cadence that keep a fast-growing team aligned, and owning the company-building projects that determine how well the company scales.

Opportunity

This is a high-leverage role at an early-stage company. The right person will be the right hand to the VP of Operations — and a trusted partner to the CEO and executive team — taking direct ownership of the highest-stakes initiatives, from company planning to SOC 2 to integrating our recent acquisition.

What You’ll Do

• Be the right hand to the VP of Operations — partner with them day-to-day to turn strategy into execution and own the things that fall between the cracks
• Act as a trusted thought partner and sounding board to the VP of Operations — and, more broadly, to the CEO and executive team — to help think through strategy, pressure-test decisions, and frame the trade-offs that matter
• Protect executive focus — filter and triage what reaches the VP of Operations and CEO, surface bottlenecks early, and keep the team’s attention on the decisions that matter most
• Own company planning — run quarterly and annual goal-setting (OKRs), translate it into an operating plan the team executes against, and define and track the KPIs and dashboards that keep everyone honest about progress
• Partner with finance to work backwards from the model — connecting targets, headcount, and spend to the operating plan and flagging where reality is drifting from plan
• Run the company’s operating cadence: exec meetings, weekly standups, reviews — set agendas, capture decisions, and chase every action to done
• Drive cross-functional initiatives end-to-end, like integrating our recent acquisition (Monocle) into our stack and operations, and standing up consistent company-wide process
• Own relationships with investors, partners, and vendors — own these relationships day-to-day so leadership never becomes the bottleneck, and carry board meetings and fundraises from prep through follow-through
• Take on the big company-building projects ahead of us — starting with SOC 2 certification, a major unlock for enterprise trust and larger deals
• Power our rapid hiring — coordinate interview loops and sharpen the recruiting process as we grow the team fast
• Lead special projects across the operations org — including driving AI adoption across technical and non-technical teams

What We're Looking For

• 3–7+ years in a Chief of Staff, startup operations, business operations, or founder’s-office role at a high-growth company — you’ve done the work, not just advised on it
• A hands-on operator, not a consultant — you build process out of chaos and automate yourself out of the busywork
• Strong business and financial fluency — comfortable in a model, setting targets, and reasoning about the numbers behind the plan
• AI-native: you reach for AI tools to move faster by default, and you can drive that adoption across a team
• Exceptionally organized and systems-minded, with crisp written communication and the presence to run a room of senior people
• Bonus if you’ve integrated an acquisition, stood up SOC 2, or supported a fundraise

How To Apply

Submit your resume along with responses to the application questions. We review applications on a rolling basis and will reach out to qualified candidates to discuss potential opportunities.