Founding Strategy & Ops Lead

Rockstar is recruiting for a company built for the backbone of a $600B industry: freight brokers. This organization provides the technology and support that independent brokers need to compete with large brokerages, replacing manual work with AI-powered leverage. They are a small, senior team working to give independent freight brokers better tools, better support, and a true growth partner.

The Problem

Freight brokers are the backbone of a $600B industry. They're the person a shipper trusts to move their goods. But the technology available to them was built for large brokerages with IT departments, not for independent operators running $2M-$50M books of business out of a home office.

These brokers are drowning in manual work: quoting loads by gut feel instead of data, making dozens of carrier phone calls per shipment, toggling between five tabs to track a single load. The best ones succeed despite their tools, not because of them.

AI changes this. It doesn't replace the broker — it gives them leverage that lets them cover more loads, win more freight, and run at higher margins. That's what this company is building.

The Role

We're looking for a Founding Strategy & Ops Lead to own every touchpoint between the company and the independent freight brokers building their businesses on the platform.

Our agents are experienced operators. They chose this platform because they want better tools, better support, and a partner that helps them grow. Your job is to make that promise real — to define what exceptional service looks like and then deliver it, personally, across every interaction.

This means you own the full agent experience: onboarding new agents, running business reviews, providing sales and growth support, troubleshooting live issues, and making sure every service we offer is genuinely excellent. You'll be the person our agents call when something matters.

You'll also need to understand the back-office operations well enough to step in when needed. The Operations Lead owns that domain day-to-day, but you should be capable of covering it — and that cross-functional fluency will make you better at your own job.

This is an IC role on a small, senior team. You'll shape how the company works with its agents, not manage a team doing it.

What You'll Actually Do

• Own the agent relationship. You're the primary point of contact for our agents on everything that isn't pure back-office execution. That means onboarding, regular check-ins, escalations, and being genuinely responsive when they need help.
• Define and deliver our services. Design and run the touchpoints that make agents successful: weekly and monthly business reviews, sales support, growth enablement, and anything else that helps agents win more freight and run better businesses. You'll figure out what's worth doing, build it, and iterate.
• Drive agent performance. Track how agents are doing — revenue, margin, load volume, growth trajectory — and use that data to coach, support, and spot problems early. You're accountable for agent outcomes, not just agent satisfaction.
• Support agent recruiting and onboarding. Work with the CEO on go-to-market for new agents. Design the onboarding experience so new agents ramp quickly and feel supported from day one.
• Be the fallback on operations. Understand how the back-office works — AP, AR, carrier vetting, claims — well enough to step in and cover when needed. You don't own it, but you can do it.
• Feed insights back into product. You'll have the deepest understanding of what agents actually need. Translate that into clear input for the product team — what's working, what's broken, what's missing.

What We're Looking For

• Service orientation. You genuinely care about making customers successful. You build trust, follow through, and take ownership of outcomes.
• Operational chops. You can manage multiple agents, multiple workstreams, and a lot of context without dropping balls. You're organized and reliable.
• Communication skills. You're clear and direct in how you communicate — with agents, with teammates, and in writing. You can run a business review and make it valuable, not performative.
• Analytical ability. You're comfortable with data — reading dashboards, pulling reports, spotting trends in agent performance. You use numbers to drive decisions, not just tell stories.
• Builder mentality. You're not waiting for a playbook. You'll design our services, build the templates, set up the cadences, and improve them over time.
• AI-native. You use AI tools in your daily work. You see opportunities to automate or improve processes with AI and you act on them.
• Comfort with ambiguity. This role doesn't come with a manual. You'll figure out what agents need, what 'great' looks like, and how to get there.
• Ownership orientation. You treat the business like it's yours. You don't wait to be told what to do.

Background That Might Fit

• Operations or biz ops role with customer-facing responsibility
• Former management consultant
• Nice to have: freight brokerage experience
• Former founder or early startup generalist

Location

The team is building a small, senior team that works primarily from an office in Brooklyn. Right now, the team works in person 4 days/week.