About OuterSignal

We are building the customer intelligence layer for commerce. Brands know when an order comes in, but they only see ~5% of the real story. We show them the other 95%: not just who bought, but who that person is — the execs, influencers, journalists, retail buyers, investors, and everyday customers who become a brand’s best evangelists. Our platform enriches every order in real time with professional and personal signals, builds personas, and powers everything from surprise-and-delight outreach to smarter email flows, analytics, and BD leads. We’re a small, high-performing team building the category-defining platform for e-commerce customer intelligence, backed by a world-class investor base.

The Opportunity

OuterSignal is hiring a Chief of Staff. This is a senior operating role with broad ownership across the company: 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 we scale.

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. They’ll build process out of ambiguity, protect executive focus, and define how the whole company runs. The company moves fast, and this person needs to match that pace.

What You’ll Do

Be theright 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 atrusted 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
Owncompany 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 withfinance 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’soperating 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 forinvestors, 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 withSOC 2 certification, a major unlock for enterprise trust and larger deals
Power ourrapid hiring — coordinate interview loops and sharpen the recruiting process as we grow the team fast
Leadspecial projects across the operations org — including drivingAI adoption across technical and non-technical teams

What We're Looking For

3–7+ years in aChief 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-onoperator, not a consultant — you build process out of chaos and automate yourself out of the busywork
Strongbusiness 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
Exceptionallyorganized 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 upSOC 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.

What We Offer

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.

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.

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

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