Director of Business Operations

We're a 20-person cybersecurity company that's grown to double digit million ARR without a dedicated finance or operations person. We've gotten this far by automating aggressively - AI agents, internal tools, systems that handle a lot of the operational work. But someone still needs to own the outcomes and make the judgment calls, and that's been the CEO and VP of Ops. We've reached the point where it needs to be someone's actual job.

We need someone with a finance background who's been running business operations at a startup for a long time and enjoys the work to quickly get up to speed and take things off our plate.

Year one is about taking over what the CEO and VP have been carrying and making it yours. Year two is about owning a function that grows with the company - budget planning, board reporting, procurement, international compliance.

On the finance side, you own the relationship with our accounting firm and handle tax compliance across a US entity, a Swedish entity, and international contractors in Poland and France. You coordinate R&D credit studies, 401k filings, cap table administration in Carta, and 409A valuations. You maintain the cash flow forecast for a business where revenue sometimes comes in big lumps and some months are a fraction of the peaks.

On the people side, you run onboarding and offboarding end to end - Rippling, equipment, Carta grants, background checks, benefits enrollment. You manage the performance review process, pull comp benchmarks, and model budget impact. Benefits renewal, insurance, and the compliance calendar are yours.

There's also the legal and compliance coordination - working with our law firm on contracts, DPAs, and vendor agreements, handling customer redlines and security questionnaires, managing corporate filings and the business side of SOC 2.

And the deal desk: you own the renewal calendar, handle flat renewals end to end, and for strategic renewals you prepare the options so the VP can pick and you can execute.

You sit in our NYC office with the VP of Operations and the CEO. Most of the work comes from conversations - someone mentions a filing deadline or a contract question and you run with it. We've built a lot of internal automation (our own CRM, AI agents, compliance tools) that you'll use daily and help us improve.

You've been the entire finance and operations function at a startup before - not a piece of a large org. You know what it's like when the 401k audit is due and the state tax deadline is the same week. The range here is similar - you might be modeling an equity refresh in the morning and chasing a $150 state tax check after lunch.

Castle is intentionally small and flat, where senior individual contributors own their domain end to end, without the traditional layers of management. The path is VP of Business Operations or VP of Finance, but most likely still as an individual operator.

• 8+ years in business operations, finance, or a combined role at a startup
• Finance background - degree or real experience with accounting firms, tax compliance, cap tables
• You've worked with outside counsel before - contracts, compliance projects
• Comfortable with AI tools