Head of Business Operations
Probook is operating in a greenfield, unsaturated space — defining how GenAI will transform a massive legacy industry. We’re assembling one of the most talent-dense teams in NYC and every early hire has outsized impact on how we scale. We’re looking for a world-class operator - someone who thrives in chaos, brings order to ambiguity, and owns outcomes end-to-end.
As our founding BizOps hire, you’ll touch every corner of the company: from running special projects, negotiating critical contracts, and organizing conferences, to designing internal systems and driving organizational strategy.
This is the ultimate zero-to-one role. You’ll sit at the center of execution, partnering directly with the CEO and leadership team, with the mandate to do whatever it takes to push the business forward. If you’re hungry to build, eager to learn every part of company-building, and want a launchpad into leadership or founding, there’s no higher-leverage seat to take.
What you’ll do
Take on high-priority projects across the business — whatever moves the needle.
Own contracts and vendor negotiations, ensuring speed and precision.
Plan and execute key external events (conferences, dinners, offsites).
Build internal systems and processes that keep the company running at pace.
Partner with leadership to drive organizational strategy and execution.
Be the glue: connect sales, product, recruiting, and finance into one operating system.
What we’re looking for
2-5 years of experience in early-stage operations - building 0-1
Track record of shipping outcomes in ambiguous environments.
World-class operator instincts: organized, resourceful, decisive.
Hungry to build — you want ownership and the chance to shape a company.
Comfortable with intensity: 100% in-office, 6 days/week.
Why join us
Founding-level role at a Sequoia-backed company, working directly with the CEO and leadership.
Build the operating system for one of NYC’s most talent-dense startups.
Exposure to every part of the business: strategy, finance, product, sales, recruiting.
Accelerated path to leadership as the company scales.
Compensation & Perks
$130K – $165K base + Equity
$1K monthly food and wellness stipend
Full Benefits (medical, dental, vision)
Unlimited PTO
Office perks: climbing hang board, office dog, espresso, team lunches/dinners
Average salary estimate
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