Head of Operations & People

Sanity Check

1. This role is in-person in San Francisco. Not hybrid. Not "mostly in office." In person.
2. We can sponsor a TN Visa if you are a Canadian citizen relocating to San Francisco. We do not sponsor any other visa categories.
3. If you are not legally authorized to work in the U.S. and not eligible for a TN, this isn't the role.

About the Role

This isn't a "we'll hire ops when we're bigger" role. We're 10 people, growing ridiculously fast, and the things that keep a fintech company alive — bookkeeping, AP, vendor and customer contracts, partnership follow-through, hiring, insurance, banking relationships, the boring-but-fatal-if-you-miss-them parts of regulated finance — currently land on the founder's desk. They shouldn't.

We're hiring a Head of Operations & People to run the company day-to-day so the founder can stay heads-down on product and our Series A raise. You'll be the operator the rest of the company routes through. When something needs to get done that doesn't have an obvious owner, you own it.

We're not looking for a functional specialist. We're looking for the kind of person who has run ops in a small fintech before, who reads contracts without flinching, who keeps a bookkeeper honest, who can push a partnership across the finish line, who can hire a payroll provider and not just have opinions about it. A senior Swiss Army knife. The person who quietly keeps the company running while everyone else gets to focus on their job.

If you've only ever worked inside a function at a 500-person company, this isn't your role.

What You'll Actually Do

• Run finance ops day-to-day. Manage the relationship with our bookkeeper and fractional accounting partners. Own the close cadence, AP, bill pay, expense workflows, and corporate card admin. Make sure nothing fails because nobody paid for it.
• Own contracts end-to-end. Vendor agreements, customer agreements, NDAs, employment paperwork, partnership contracts. You'll route to outside counsel where it matters, but you'll be the one driving the document, redlining the boilerplate, and getting it signed.
• Push partnerships across the finish line. Founder opens the door, you do the follow-through. Diligence packets, KYB requests, integration paperwork, scheduling, status tracking. Partnerships die in inboxes; not ours.
• Build the people function from the basics up. Hiring ops, offers, onboarding, payroll, benefits, equity admin, compliance training. Pick the tools, set the rhythms, write the first versions of the policies, and make sure the team has what they need without making it bureaucratic.
• Own compliance and admin. Business insurance, state registrations, banking relationships, SOC 2 program support alongside engineering, audit prep, regulatory inquiries.
• Be the founder's force multiplier during the Series A. Investor scheduling, data room hygiene, diligence response coordination, closing checklist. Keep the company running so the raise doesn't slow product down.
• Catch what falls. At 10 people things slip through. You're the net.

What We're Looking For

• 7+ years of operating experience in fintech, payments, or banking — non-negotiable. You've worked inside a regulated financial environment. You know what KYB, OFAC, BSA, and SOC 2 mean without Googling them. You've seen what a bank partner's compliance team asks for and you can produce it.
• You've run ops at a small or early-stage company, not just held a seat at a big one. You know what it feels like to own five functions at once and you prefer it to specializing.
• Strong with contracts — vendor, customer, employment, partnership. You can read them, redline them, push back on the bad ones, and get the rest signed. You know when to loop in outside counsel and when to just close it.
• Direct experience working with bookkeepers, controllers, or fractional CFOs. You can keep the books clean, the close on schedule, and the AP queue empty. You don't need to be the accountant, but you can tell when one isn't doing their job.
• You've built or shaped early-stage people operations — hiring pipelines, offer process, onboarding, payroll, benefits, basic policies — without turning the place into a corporate HR shop.
• A bias to action and total ownership. You close loops. You don't wait to be told twice. If you said you'd do it, it gets done.
• Fluent with modern AI tooling as a daily operator's tool — drafting, summarizing, pulling structure out of documents, automating the boring parts. We're an AI-first company end-to-end, ops included.
• Comfortable in Linear (or willing to be). The whole company runs on it.
• Discretion. You'll see compensation, performance, legal matters, and investor conversations. That stays where it belongs.
• Must be legally authorized to work in the U.S. (or eligible for TN status as a Canadian citizen) and willing to be in our San Francisco office in person.

Bonus Points

• You've helped take a company through a Series A or later raise from the operating side — data rooms, diligence, closing logistics
• You've owned a SOC 2 or PCI-DSS program from the ops/compliance side
• You've negotiated bank partner agreements, sponsor bank arrangements, or payment processor contracts
• You've built a people function from zero — recruiting pipeline, offer process, onboarding, perf cycle — at a sub-50-person company
• You've worked directly with a founder or CEO before in a Chief of Staff or operator capacity
• You have an opinion about the right cap table admin tool, the right benefits broker, and the right payroll provider, and you can defend it

What We Offer

• Competitive salary and equity — you're joining early, and your compensation reflects that
• A seat next to the founder, on the company's most important problems, every day
• A small, sharp team where what you ship is immediately visible and immediately matters
• The chance to actually run a company, not a function inside one
• The boring stuff: medical/dental/vision, reasonable PTO, equipment, the usual

How to Apply

Send us:

1. Your resume and LinkedIn.
2. A short note — no more than a page — covering: the smallest company you've run operations at, the messiest contract or compliance problem you've solved end-to-end, and what you'd want to dig into in your first 30 days at Truss.
3. Two references we can call: one founder/CEO you've worked directly for, and one person you've hired or managed.

If your application reads like it was written by ChatGPT to sound impressive, we'll know. Be specific.

About the Interview

• 30-minute phone call with the founder
• 90-minute working session with the founder (we'll walk through a real, live operational problem together — bring opinions)
• Conversation with two team members on the things you'd be working with them on
• Reference calls

About Truss

Truss is a YC-backed, fast-growing fintech startup, an all-in-one banking and payment automation platform for construction businesses. With Truss, construction companies can manage bill payments, receivables, and corporate cards in one place. They can save time on manual data entry by integrating Truss with their existing tools and automating the full billing cycle, from invoicing and reconciliation.

We started by building a B2B payment platform in Canada called MazumaGo — and discovered that most of our customers were construction companies. We took everything we learned and pivoted to the U.S. to build a banking and payments engine purpose-built for SMB construction, with a built-in network effect. We soft-launched a beta in 2023, fully launched in 2024, and have been growing rapidly ever since.