Chief of Staff

About Thoughtly

Thoughtly is a breakout, high-growth SaaS company building the future of GTM through AI-powered voice automation. We work with enterprise customers where reliability, speed, and execution matter—and we’re scaling fast.

The Role

We’re hiring a Chief of Staff to be the CEO’s execution partner and force-multiplier—turning priorities into shipped outcomes, creating clarity across the company, and driving the highest-leverage initiatives that cut across teams. This is a highly cross-functional role: part operator, part strategist, part comms/coordination engine. You’ll build the systems and cadence that keep a fast-growing company aligned while also owning “whatever needs doing” projects that unlock growth.

This role is designed for someone who thrives on ambiguity, moves fast, and can operate comfortably in both board-level work and messy, day-to-day execution.

What You’ll Do

CEO Leverage & Company Cadence

• Translate CEO priorities into crisp plans, owners, timelines, and follow-through; ensure the right work actually ships.

• Drive operating rhythms (weekly reviews, decision logs, cross-functional syncs) to keep the org aligned and accountable.

• Spot misalignment early, surface tradeoffs, and push decisions to closure.

Strategic Initiatives & Special Projects

• Own cross-functional initiatives that don’t fit neatly into one team—new motions, process upgrades, customer-facing readiness, internal tooling, etc.

• Run structured problem-solving: define the problem, frame options, quantify impact, and drive execution end-to-end.

External Polish: Board / Investors / Enterprise

• Help produce sharp, accurate, investor/board-ready materials and updates (metrics, narratives, and progress tracking).

• Support high-stakes enterprise workflows where operational rigor matters: security questionnaires, vendor audits, and compliance documentation.

BizOps Support

• Jump into operational ownership when required—recruiting coordination, vendor onboarding, internal processes, and “make the trains run on time” work.

• Partner with Finance/Ops leadership (or fill gaps temporarily) to keep core business mechanics tight: forecasting inputs, reporting hygiene, and execution follow-through.

What We’re Looking For

• Operator + strategist: you can zoom from board-level narrative to tactical execution without losing the thread.

• High judgment and trustworthiness: you’ll handle sensitive information and represent the CEO in internal/external contexts.

• Exceptional written and verbal communication: crisp, structured, and decision-oriented.

• Strong project leadership: you can drive alignment across teams without formal authority.

• Analytical horsepower: comfortable with metrics, dashboards, and building simple models to inform decisions.

• Startup readiness: thrives in fast-moving environments; low ego; high ownership; resourceful.

Nice to Have

• Experience in high-growth B2B SaaS (especially enterprise), BizOps/Chief of Staff/Strategy & Ops, or investing → operating transitions.

• Familiarity with enterprise procurement/security processes (questionnaires, audits, compliance workflows).

• MBA a plus, especially if paired with hands-on startup execution.

What Success Looks Like (First 90 Days)

• The CEO’s top priorities are translated into an execution plan with clear owners and a reliable cadence.

• Cross-functional initiatives stop “floating” and start landing—fewer surprises, tighter delivery.

• Board/investor and enterprise-facing workflows become smoother, faster, and more polished.

Why Join Now

• Direct seat at the center of the company with massive scope and autonomy.

• High visibility with the CEO and leadership team; opportunity to grow into broader operations leadership over time.

• Build the operating system for a company scaling quickly with enterprise customers.