Chief of Staff

• Own the full OKR cycle: draft templates, run quarterly planning sessions, track weekly check-ins with each function lead, and report progress to the CEO.
• Maintain a single source-of-truth project tracker (Notion / Linear) covering every cross-functional initiative — status, owner, blockers, and ETA.
• Run the weekly leadership sync: set agenda, circulate pre-read, take a decisions log, and distribute action items within 24 hours.
• Design and maintain the hiring operating cadence: pipeline dashboards, interview scheduling, debrief templates, offer timelines, and onboarding checklists.
• Build and own company-wide communication templates: all-hands decks, monthly internal updates, and off-site agendas.

• Build go-to-market frameworks: ICP documentation, segment prioritization matrices, sales motion playbooks, and land-and-expand models for e-commerce verticals.
• Draft and iterate on outbound materials: partnership one-pagers, first-call decks, executive briefing docs, and RFP / POC proposal templates.
• Own the deal-review process — consolidate pipeline data, prepare CEO deal-review memos, and follow up on open next steps post-meeting.
• Research and size target accounts and verticals; synthesize competitive intelligence into concise battle cards.
• Support pricing and packaging analysis: model out scenarios, draft internal memos, and coordinate with product on feature tier decisions.

• Own the monthly investor update: compile ARR, burn, headcount, and milestone data; draft the narrative; route for CEO approval; distribute on schedule.
• Prepare Board meeting materials end-to-end — deck, pre-read, appendix, logistics — and own the follow-up action tracker post-meeting.
• Maintain the advisor CRM: track relationship touchpoints, prompt the CEO on outreach cadence, and send periodic update emails on behalf of leadership.
• Manage the P&L model in collaboration with the COO — maintain the 18-month operating model, flag variances, and prepare budget-vs-actual summaries monthly.
• Support fundraising sprints: build the data room, prepare diligence trackers, manage investor pipeline in a CRM, and coordinate scheduling during active raise periods.

• Act as an extension of the CEO's office — triage inbound requests, draft correspondence, and manage inbox priorities during high-travel or high-stakes periods.
• Pre-brief the CEO before every major external meeting (in support of points 2 & 3): prepare a one-page context sheet with attendee background, goals, suggested talking points, and open action items.
• Track relationship health across key stakeholders (design partners, VCs, strategic advisors, press contacts) and flag when relationships need attention.

The systems thinker

Sees chaos and instinctively builds a process. Can hold 10 parallel workstreams in their head without a checklist going stale. Loves a clean Notion dashboard.

The trusted proxy

The CEO would let them send an email on their behalf without reading it first. Earns trust fast, communicates like a founder, and keeps confidences absolutely.

The force multiplier

Doesn't just execute tasks — asks why, anticipates the next three moves, and flags the thing no one asked about before it becomes a problem.

Compensation

• Base salary: $150,000–$200,000
• Equity: provided as part of the offer, based on experience

Benefits

• 100% health insurance (you + all dependents) via Aetna Gold Plan; option to upgrade to Platinum
• 401K with 4% employer match
• Transit benefit: up to $200 / month
• 20 days paid leave + 5 days sick leave

Perks

• Company on-sites and team events
• Remote flexibility — minimum 3 days / week