Head of Business Operations
About The Position
Trail is building a governed context layer that gives AI agents access to company rules, exceptions, and institutional knowledge so they can make sound decisions across complex business processes. The Head of Business Operations will bring operational discipline to Trail and work directly with the CEO to ensure legal, finance, recruiting, and day-to-day business operations run smoothly. This is a hands-on, full-time role based in Trail’s Palo Alto office, with authority to improve how the company works and responsibility for implementing those improvements. The role owns workflows, systems, coordination, and execution across business operations, partnering with lawyers, finance professionals, recruiters, and internal teams for specialist expertise. The successful candidate will take substantial operational ownership off the CEO’s plate, turn ambiguous problems into decisions and completed work, and improve processes using software and AI. Success means contracts move faster, payments and reporting happen on time, hiring keeps moving, ownership is clear, and fewer tasks fall through the cracks.
Requirements
- 8–16 years of professional experience, including at least 3 years working in the United States.
- A track record of increasing responsibility and ownership.
- Experience building and operating in a venture-backed startup at the Seed–Series D stage, in a team of roughly 20–300 people.
- A track record of improving how a business runs by identifying problems, fixing them, and making improvements stick.
- Comfort working across contracts, spreadsheets, hiring processes, and vendor negotiations, with the judgment to know when specialist expertise is needed.
- Clear communication, speed, and reliable follow-through in a demanding environment.
- Sound judgment and attention to detail, including trustworthiness with sensitive information and important deadlines.
- Enjoyment of both designing better processes and doing the work to implement them.
Nice To Haves
- Former founder or early employee experience; former founders are especially welcome.
- Experience as a business operations leader.
Responsibilities
- Manage legal operations, including contracts, reviews, signatures, renewals, and coordination with outside counsel; establish clear owners, deadlines, and repeatable processes.
- Coordinate finance operations with finance partners, including payments, invoicing, expenses, budgeting, and reporting; improve spending visibility and reduce unnecessary administrative work.
- Manage recruiting operations from open roles through interviews, offers, and onboarding; coordinate hiring managers and recruiting partners, remove delays, and support a consistently good candidate experience.
- Oversee business operations such as vendors, purchasing, tools, and office operations, and handle operational challenges associated with a growing company.
- Identify recurring process friction, simplify workflows, and use software and AI to reduce manual work; build workflows that people will use.
- Take substantial operational ownership off the CEO’s plate by turning ambiguous problems into decisions and completed work, involving the right people when needed.
- Design improved processes and carry out the work needed to put them into operation.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
