Head of Business Operations

About Us:

Trail is the context layer AI agents run on. We're building the missing layer between your company's rules, exceptions, and institutional knowledge and the agents trying to act on them. It's a governed graph that lets any agent or platform, including Trail agents, make the right call on your most complex business processes. Agents today fail not because models are weak, but because they're never given the judgment a business builds up over years. We're fixing that.

Visit our Website and Youtube to learn more!

About the role

We’re looking for someone who can bring operational discipline to our own business. Someone who sees what needs to happen, takes ownership, and follows through.

You’ll work directly with the CEO to make legal, finance, recruiting, and day-to-day business operations run smoothly. You’ll own the workflows, systems, coordination, and execution across these areas, partnering with lawyers, finance professionals, recruiters, and internal teams for specialist expertise.

This is a hands-on, full-time role based in our Palo Alto office. You’ll have the authority to improve how we work and the responsibility to make those improvements happen.

What you will own

• Legal operations: Keep contracts, reviews, signatures, renewals, and outside counsel moving. Establish clear owners, deadlines, and repeatable processes so requests reach resolution.

• Finance operations: Work with finance partners to make payments, invoicing, expenses, budgeting, and reporting reliable. Improve visibility into spending and eliminate unnecessary administrative work.

• Recruiting operations: Keep hiring moving from an open role through interviews, offers, and onboarding. Coordinate hiring managers and recruiting partners, remove delays, and create a consistently good candidate experience.

• Business operations: Make vendors, purchasing, tools, and office operations work efficiently. Handle the operational problems that come with running a growing company.

• Better systems: Identify recurring friction, simplify processes, and use software and AI to reduce manual work. Build workflows that people actually use.

• Independent execution: Take substantial operational ownership off the CEO’s plate. Turn ambiguous problems into decisions and completed work, bringing in the right people when needed.

Who you are

• You have 8–16 years of professional experience, including at least 3 years working in the United States, with a track record of growing responsibility and ownership.

• You’ve built and operated in a venture-backed startup at the Seed–Series D stage, with experience in a team of roughly 20–300 people. You may be a former founder, an early employee, or a business operations leader. Former founders are especially welcome.

• You have a track record of making a business run better: noticing what’s broken, fixing it, and making the improvement stick.

• You’re comfortable moving between a contract, a spreadsheet, a hiring process, and a vendor negotiation. You know when specialist judgment is needed.

• You communicate clearly, move quickly, and follow through in a demanding environment.

• You combine sound judgment with attention to detail. People trust you with sensitive information and important deadlines.

• You enjoy both designing a better process and doing the work to get it running.

What success looks like

Contracts move faster. Payments and reporting happen on time. Hiring keeps moving. People know who owns what, and fewer things fall through the cracks. You take ownership of a problem and see it through without repeated follow-up.