Head of Business Operations

Trail; Palo Alto (CA); On-site; USD 180,000 - 250,000; Full time

Job summary

Trail is seeking an hands-on operations leader to partner with the CEO and run legal, finance, recruiting, and day-to-day business operations from our Palo Alto office.

You will own workflows, systems, coordination, and execution across these areas, collaborating with legal, finance, recruiting, and internal teams to move work forward efficiently and with clear ownership.

Responsibilities

• Legal operations: Keep contracts, reviews, signatures, renewals, and outside counsel moving; establish 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 spending visibility and reduce admin work.
• Recruiting operations: Move hiring from open role through interviews, offers, and onboarding; coordinate hiring managers and recruiters; avoid delays and ensure a good candidate experience.
• Business operations: Make vendors, purchasing, tools, and office operations work efficiently; handle operational problems for a growing company.
• Better systems: Identify recurring friction, simplify processes, and use software/AI to reduce manual work; build workflows people actually use.
• Independent execution: Take substantial operational ownership off the CEO’s plate; turn vague problems into decisions and completed work, bringing in the right people when needed.

Job description

Trail turns company knowledge and processes into context and rules that AI agents can use to get work done.

We’re looking for someone who can bring that same operational discipline to our own business. Someone who sees what needs to happen, takes ownership, and follows through—without needing the CEO to keep things moving.

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 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’ve built and operated in an early-stage startup. 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 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. Any problem give to you and it gets solved without follow up.