Chief of Staff

Overview

Bolto is building the modern HR stack for globally distributed teams.

We’re hiring a Chief of Staff to work directly with both founders. This is not a calendar-management role. This is a deployment role.

When something high-stakes needs to get done, you step in.

This is a 2-year acceleration track for someone who wants to become a serious operator.

The Role

You will be placed wherever leverage is highest.

That could mean:

• Owning internal ops initiatives
• Taking sales calls with customers
• Conducting deep product research
• Supporting investor conversations
• Hosting/managing events (especially in SF)
• Driving cross-functional execution across teams

You will context switch constantly. You will be trusted with sensitive information. You will see how the company actually works.

Some weeks you’ll feel like an operator.
Some weeks you’ll feel like a founder.
Every week you’ll be pushed.

Who This Is For

You likely have 2 years of experience in:

• Investment banking
• Consulting
• Early-stage startup growth
• Or another high-intensity environment

But pedigree is not what matters. Stamina, judgment, and output do.

You should:

• Be highly organized and extremely execution-oriented
• Have high executive function & intrinsic drive
• Move quickly without losing detail
• Thrive in ambiguity/unblock yourself with ease

If you are optimizing for clear job boundaries, this won’t be a fit.

If you want trust, impact, and rapid growth, it will.

Structure

• Reports directly to both founders
• Mentored by the COO
• In-person only (non-negotiable)
• SF and/or Chicago in person obligations

Round 1: Intro call with CEO

This will be just a 30 minute call to discuss your background & the role.

Round 2: Behavioral screen with President

We will send you some prompts a few hours before your interview. During your interview, you will choose one of those prompts to spend the interview discussing. This is very similar to UChicago’s essay process.

Round 3: Final Round

Will adjust depending on the previous interviews.