Chief of Staff

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 CEO — and a trusted partner to the VP of Operations and executive team — taking direct ownership of the highest-stakes initiatives. 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 the right hand to the CEO — 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 CEO — and, more broadly, to the VP of Operations 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 CEO, surface bottlenecks early, and keep the team’s attention on the decisions that matter most

• 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

• Lead special projects across the 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

• 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.