Chief of Staff

About the Role

We're looking for an exceptional Chief of Staff to work directly with our COO and founders as we scale Bolto into the default operating system for global employment.

This is not a strategy-only role. You'll be dropped into the company's highest-priority operational problems, often with little context, no existing playbook, and an expectation that you'll figure it out.

One week you might be researching compliance requirements at a state level and designing a product rollout with engineering. The next, you could be untangling a complex customer issue that requires coordinating across payroll, engineering, and support. The week after that, you may own implementation of a new internal system, build an operational process from scratch, or lead a cross-functional initiative that simply needs someone to make it happen.

You'll work side-by-side with our COO and founders, acting as a force multiplier for the executive team. Your job is to take ambiguous, high-impact problems and drive them to completion with minimal oversight.

What You'll Do

• Become the internal expert on whatever the company needs most that week.
• Own critical cross-functional projects from idea through execution.
• Investigate operational, product, and customer problems where there is no obvious answer.
• Design and implement scalable internal processes.
• Coordinate across engineering, product, payroll, operations, and customer success.
• Create order out of chaos while maintaining an exceptionally high bar for execution.

What We're Looking For

• Outstanding executive function and organizational ability.
• Extremely high agency. You don't wait to be told exactly what to do.
• Comfortable operating with ambiguity and incomplete information.
• Strong analytical and research skills. You enjoy becoming an expert in unfamiliar topics quickly.
• Obsession with detail while never losing sight of the bigger picture.
• A builder's mindset. You enjoy creating systems that make organizations better.

You'll Thrive Here If...

• You like solving problems you've never seen before.
• You'd rather own outcomes than follow instructions.
• You enjoy switching contexts quickly and learning new domains.
• You want unusually broad exposure to how a high-growth startup is built.
• You care about speed, but never at the expense of quality.

Career Growth

We view this as one of the best training grounds for future operators. You'll gain exposure to nearly every function of the business, work directly with the founders on the company's highest-priority initiatives, and develop the judgment needed to lead teams and own major business functions. Our hope is that exceptional people who excel in this role grow into long-term leaders at Bolto as the company scales.

Interview Process

Interview Process

We try to keep our hiring process fast and respectful of your time. The process consists of three stages:

1. Preliminary Screen (20 minutes)
A Google Meet conversation with Jake Johnson (Cofounder) to get to know each other, discuss your background, and answer any questions you have about Bolto and the role.

2. Case Study Review (60 minutes)
You'll receive a business case after Round 1. During the interview, you'll walk through your solution with our COO, discussing your assumptions, reasoning, and recommendations.

3. Final Interview (In Person)
A conversation with our CEO and COO at our Chicago office. We'll dive deeper into how you operate, what motivates you, and whether we're a great long-term fit for each other.