Remote Flight Operations Manager Jobs in Chicago, IL

Prelim is growing 2-3x annually and our platform powers account opening and onboarding for banks across the country. Our team is at a turning point: the informal systems that got us here won't scale with where we're headed next.

Today, the work of coordinating across teams, tracking delivery, and keeping the company’s operational rhythm falls on the founder — who is also our head of product — and on the leads themselves. That’s not sustainable and we know it.

As our first Business Operations hire, you’ll build the operational infrastructure Prelim runs on. There’s no playbook and no predecessor. You’ll decide what to systematize first, build processes that scale, and manage our two technical account managers.

What You'll Own

• The company operating system. You'll build and run the lightweight systems that give leadership a weekly view of who's working on what, team load, and delivery risk across product and implementations. When a new bank comes in, you're the person who looks at current allocation, identifies who has capacity, and presents staffing options — not the founder doing it from memory in a Slack DM. You surface stalled projects, overloaded teams, and unanswered customer concerns before they become emergencies.

• Our technical account management team. Our two TAMs report to you. You'll hold regular 1:1s, track goals, provide feedback, and develop them. You own their workload and development; the founders retain executive ownership of bank relationships and account strategy.

• Staffing and project coordination. When projects need to be reassigned, when someone goes out of office, when a customer issue needs routing to the right lead, you make sure the handoff happens and nothing gets dropped. You maintain the map of who covers what. And when an implementation goes sideways, the lead who owns it runs the recovery. Your job is making sure every client concern has an owner, a plan, and a next check-in date, and that nothing quietly goes dark. If a project stalls or has no owner, you flag it before the client does.

• Operational rhythm. Lead syncs have agendas. Cycle kickoffs happen on a schedule. Commitments from meetings get tracked and followed up on. You own the cadence that keeps the company running smoothly.

• Vendor and logistics management. You’ll collaborate with People Operations on software contracts, offsites, and team meetups.

What You Won't Own

You won't recover client projects yourself — our leads own recovery on their accounts; you own making sure recovery is happening. You won't own client strategy or the executive relationship with our banks — account health, expansion, and voice-of-customer stay with the founder. You're not making product decisions — the founder and product leads own the roadmap, though what you see in the operating data should shape it. And beyond our two TAMs, you're not a people manager — team leads manage their own reports.

What We're Looking For

• 4-6 years spanning delivery leadership and business operations, including a leadership role at a B2B software company or a smaller group in a larger tech company.

• You've personally done the work at least once. You've run complex enterprise implementations or owned technical accounts yourself, recently enough that your teams will trust your judgment in an client-facing communications.

• You're a strong writer and communicator. The operational documentation, staffing plans, and status rhythms don't exist yet; you'll create them, and they'll only work if they're clear and concise.

• You're relentlessly organized without being bureaucratic. You add just enough structure that things don't fall through cracks, and you know the difference between useful process and process for its own sake.

• You're direct and unintimidated. You'll tell a lead their team is overloaded, and you'll tell the founder he committed to something we don't have capacity for.

Nice to Have, Not Required

• Experience in fintech or selling into banks

• Familiarity with tools like Linear, Notion, Pylon, Mixpanel

• Experience supporting a technical team (engineering, design, implementations)

What You Won't Find in This Role

A mature org to administer. You'll work directly with the founder daily, interim structures, and make the org-design decisions a founder has been making from memory. The decisions you make will directly determine the reach and scope of our mission.

How You'll Know It's Working

A month in, the founder stops being the person asking "who's covering this." Three months in, there's a weekly load-and-risk snapshot leadership relies on, and every implementation has a clear owner and status. Six months in, a new bank's staffing conversation takes fifteen minutes, client concerns have an owner who isn't the founder.

About Prelim

Prelim is a San Francisco and New York City-based startup that operates with fully remote positions across the US, helping banks onboard their customers. Our platform is designed to streamline the account opening process for both consumers and businesses, accelerating speed-to-market and enhancing the customer experience for financial institutions. If you’re excited to help shape the future of the banking industry, we encourage you to apply and join our team at Prelim. We are seeking individuals who are driven, ambitious, and eager to make a real impact in a traditional industry ready for technological innovation.

We offer equity, a sponsored 401K, parental leave, and fully paid health, vision, and dental insurance. Additional benefits include unlimited PTO, a remote work stipend, a life-style stipend, and twice-yearly company retreats. This role would also attend periodic team meetups in NYC and SF.

Prelim values diversity and inclusion; people of all backgrounds are welcome to join our mission to transform banking.

Compensation Range: $240K - $260K