Chief of Staff

Chief of Staff

Freedom · New York, NY (in-person) · Reports to the CEO

About Freedom

Freedom is an AI-native payroll and benefits platform for startups and small businesses. We're growing fast and hiring, and almost everything we do is still being figured out for the first time.

The role

You'll be the CEO's right hand and the first Chief of Staff at the company. That means owning whatever is most important at any given moment across a wide range of business areas: marketing, customer service, hiring, and more. The job changes month to month. What stays constant is that you'll sit close to every decision and be trusted to run with things.

One thing won't rotate: marketing. We don't have a marketing team, and we need one. You'll own how startups and small businesses find out about Freedom — positioning, content, the website, the acquisition funnel, referral and partner channels, launches. You don't need a marketing background, but you need to want this and be willing to learn it fast.

Concretely, you'll:

• Own marketing end to end: positioning and messaging, content, website and conversion funnel, referral and partner programs, and the metrics behind all of it
• Turn loose priorities into plans, then drive them to done across product, sales, ops, and finance
• Run the operating cadence — goals, metrics, weekly reviews — so the company knows what matters and whether it's on track
• Own special projects end to end, from scoping through execution
• Build the first versions of processes (hiring, onboarding, customer ops, reporting) and know when a process isn't worth building yet
• Prepare the CEO for board meetings, investor conversations, and key customer relationships
• Help recruit the next several hires, and bring your own network to the table

Who we're looking for

We're hiring for drive and intelligence, not for a specific expertise. The right person is someone who learns fast, holds a high bar, and would rather own the outcome than advise on it.

• Roughly 2+ years at a top-tier consulting firm, or comparable experience that taught you to structure ambiguous problems and communicate crisply
• A track record of starting things: a company, a club, a side business, a project nobody asked for — at any stage of your life
• Evidence you've had to hustle for what you've gotten
• Comfortable with numbers, spreadsheets, and building a first-principles model of a problem
• Willing to do unglamorous work and do it well
• Based in NYC or willing to relocate

Nice to have:

• Operating experience at an early-stage startup
• Prior founder experience, especially if technical
• You've grown something before — an audience, a customer base, a community — and have opinions about what worked
• Familiarity with payroll, benefits, HR tech, or fintech (you can learn this; most of us did)

Compensation

• Base salary of $135,000–$150,000, depending on experience
• Meaningful equity, with the option to structure part of the package around milestones you help hit
• Health, dental, and vision (we're a benefits company; ours are good)