Head of Business Operations

Trail • Palo Alto, CA

13h • Onsite

About The Position

Trail is building a governed context layer that helps AI agents apply companies’ rules, exceptions, and institutional knowledge to complex business processes. The Head of Business Operations will bring operational discipline to Trail and work directly with the CEO to keep legal, finance, recruiting, and day-to-day business operations running smoothly. This hands-on role owns workflows, systems, coordination, and execution across these areas, partnering with lawyers, finance professionals, recruiters, and internal teams for specialist expertise. The role is based in Trail’s Palo Alto office and has authority to improve how the company works, along with responsibility for implementing those improvements.

Success means contracts move faster, payments and reporting happen on time, hiring continues to move forward, ownership is clear, and fewer tasks fall through the cracks. The role is expected to take ownership of problems and see them through without repeated follow-up.

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, with experience 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 moving between contracts, spreadsheets, hiring processes, and vendor negotiations.
• Ability to recognize when specialist judgment is needed.
• Clear communication, speed, and follow-through in a demanding environment.
• Sound judgment and attention to detail.
• Ability to handle sensitive information and important deadlines responsibly.
• Enjoyment of both designing better processes and doing the work to put them in place.

Nice To Haves

• Former founder, early employee, or business operations leader experience.
• Former founders are especially welcome.

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 role through interviews, offers, and onboarding; coordinate hiring managers and recruiting partners, remove delays, and support a consistently good candidate experience.
• Oversee business operations involving vendors, purchasing, tools, and office operations, and address operational challenges associated with a growing company.
• Identify recurring friction, simplify processes, and use software and AI to reduce manual work; build workflows that people 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed