Chief of Staff

Durham, NC // In-office 5 days/week // Up to 25% travel

$75,000–$100,000 base + performance bonus + 0.05–2% equity

What We Do

Every company in America has a marketing compliance problem. They just don’t know it yet.

Right now, billion-dollar brands are getting sued, fined, and shut down because a landing page had the wrong disclaimer. A social post missed a disclosure. An influencer went off-script. The legal review process is broken: weeks of back-and-forth, bottlenecked by overworked compliance teams, while competitors ship faster.

Warrant is the first AI agent for marketing compliance. We give financial services, insurance, consumer goods, and real estate companies instant compliance feedback so they can launch faster, stay audit-ready, and never get caught off guard.

We’re backed by Brickyard, Capitalize VC, Techstars, and Vast Ventures, alongside operators from Brex, Slope, and Mercury. We’re not building a feature. We’re building the category.

Who We Are

Warrant’s pace is not for everyone. We’re in the office five days a week. We routinely put in 10+ hour days. If you need someone to tell you when to start and stop working, this isn’t for you.

Successful team members do not wait for assignments. They internalize a mission, design a strategy, and bring back results that are better, faster, and more creative than anyone could have asked for. Our plans flex to our customers. If you’d rather outwork the competition than complain about work-life balance, you’re our people.

Who We Need

Warrant seeks a Chief of Staff to work directly with the CEO. This is not a behind-the-scenes strategy role. You will be on calls with customers, in the CRM every day, and building the AI-powered systems that make a four-person team operate like a twenty-person one.

This is a unique opportunity for a startup generalist who is obsessed with AI and thrives in fast-paced environments. You’ll gain broad, cross-functional exposure across Go-to-Market, Revenue Operations, Customer Success, and Finance at a category-defining company.

What You'll Do:

• Build AI-powered GTM systems. We practice what we preach. You’ll build and manage our outbound sequences, CRM workflows, pipeline reporting, and lead routing, using Clay, HubSpot, LinkedIn, AI agents, and whatever else gets the job done faster. If a process can be automated, you’ll be the one to automate it. You’ll think in systems, not tasks.
• Get on calls and close deals. This is a customer-facing role. You’ll take demos, follow up with prospects, hop on calls with compliance officers, GCs, and CMOs, and help close business alongside the CEO. You’re not carrying a quota, but you’ll be in the revenue motion every single week and you'll get bonuses to match.
• Manage the pipeline. Keep deals moving through our CRM, make sure follow-ups happen, prep for meetings, and own pipeline hygiene, forecasting, and reporting. Nothing falls through the cracks on your watch.
• Own customer success. Onboard new customers, manage renewals, field questions, and make sure every account gets value from the platform. You’re the person who makes sure no customer is left wondering what happens next.
• Run the business. Payroll, invoicing, contract management, vendor coordination, meeting prep. It’s a small slice of the role, but someone has to keep the lights on. That someone is you.
• Shape the company. Translate customer conversations into product insights. Test new verticals. Inform pricing and positioning. You’ll have more context on our customers and operations than almost anyone, and we expect you to use it.
• Travel. Money20/20, ITC, FINRA conferences, industry dinners, prospect meetings. Up to 25%.
  

What We're Looking For:

• 3–5 years of experience across some combination of operations, business development, customer success, or GTM roles. You’ve worked at a startup or high-growth company and you thrived in the chaos. You don’t need a perfect resume. You need to be resourceful, organized, and relentless.
• You’re AI-native. Not in a “I’ve used ChatGPT” way. In a “I built a 12-step Clay workflow that enriches leads, scores them, writes personalized outreach, and loads them into HubSpot sequences before I finish my coffee” way. You see every manual process as a problem to automate and every tool as something to push to its limits.
• You’re customer-facing and you like it. Some ops people want to hide behind dashboards. Not you. You’re energized by getting on a call with a skeptical compliance officer and walking them through how Warrant solves their problem. You can sell without being salesy.
• You’re comfortable with ambiguity. Your job description will change every quarter and you’ll like it that way. You can context-switch between a customer demo at 10am, a CRM buildout at noon, and a payroll run by end of day.
• You get regulated industries. Maybe you’ve sold into financial services, insurance, or healthcare. Maybe you’ve worked alongside compliance or legal teams. You don’t need to be an expert, but you need to understand why these buyers move carefully and how to earn their trust.
• Bonus points for: Early-stage startup experience (employee #1–15), VC experience, and former founders
• Bachelor's or Master's Degree

What You Get:

• Competitive compensation. $75,000–$100,000 base with performance bonus tied to company milestones for year 1. Salary growth expected.
• Real equity. 0.05–2% ownership in a category-creating company.
• Direct access to the CEO and founding team. Not a suggestion box. You’re in the room for every decision.
• Growth opportunity. A fast growth environment with immediate ownership, a steep learning curve, and travel to top industry conferences.
• A front-row seat to building something that changes how every regulated company in America goes to market.

How to Get An Interview:

• Don’t just apply. Show us how you think. Send a 2-minute Loom walking through how you’d automate one of our processes, pitch our product to a prospect, or build a workflow that would make our GTM 10x more efficient. Reach out to our CEO directly. Creativity encouraged.