Role Overview

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
Be a trusted point of contact for 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

Requirements

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
Most importantly: you want ownership. You like to move fast, solve “figure-it-out” problems, and aren’t afraid of messy early-stage work.

Benefits

Massive upside: Meaningful equity in a venture-backed company defining a new SaaS category
A product that delivers — genuinely memorable customer outcomes, with case studies that speak for themselves.
A team that moves — a leadership group operating with urgency and building toward something significant.

OuterSignal

Open Positions (1)

Management

Chief of Staff