Executive Partner / Chief of Staff

Scratchpad — Minneapolis (US)

At Scratchpad, we’re building the AI workspace for sellers — designed to remove admin work and help every seller drive better deal strategy and execution. Our users love what we’ve built (see why on G2), and we’re proud to be backed by leading investors like Craft Ventures and Accel. Hundreds of the world’s best companies — including Brex, Dialpad, Autodesk, Headway, and Clio — run their sales teams on Scratchpad.

About the Role

We’re looking for an Executive Partner / Chief of Staff to work directly with our founders (CEO and CTO). This is a high-trust, high-impact role designed to multiply founder leverage. You’ll turn ideas into motion, manage critical priorities, and extend founder presence across customers, investors, and the market. You’ll operate as part builder, part consigliere, part operator — helping the founders stay focused on what matters most while keeping the company moving fast and aligned. If you love the idea of helping build a company from the inside — sitting next to the founders, solving real problems, and seeing your work directly impact how the business grows — this role is for you. The role is based in Minneapolis, MN, with at least three days per week in office.

What You’ll Do

• Create founder leverage: Ruthlessly protect founder time and attention by prioritizing what matters most, managing key workflows, and anticipating needs before they arise. This includes being comfortable pushing back on and holding founders accountable.

• Turn ideas into motion: Take messy, unstructured ideas and turn them into plans, projects, and outcomes.

• Extend founder presence: Represent the founders in internal and external meetings, capture and circulate insights, and follow through on commitments with precision.

• Keep founders close to customers: Build systems that deepen customer relationships, ensuring founders stay connected to the market and our users.

• Lead special projects: Run the high-impact initiatives that don’t have a home elsewhere — customer councils, experiments, process redesigns.

• Use AI to create scale: Use and experiment with AI tools to streamline workflows, capture insights, and increase team velocity.

About You

• Builder mindset: You thrive in ambiguity, spot leverage points quickly, and build systems that make things move faster.

• Sharp judgment: You understand how founders think — and can make calls that reflect their intent, even before being asked.

• Strategic executor: You’re equally comfortable writing a board memo, leading a customer meeting, or managing a critical internal project.

• Customer fluent: You understand how to engage with executives and customers, helping translate their insights into company action.

• Direct and trusted: You communicate clearly, handle sensitive information with care, and offer candid feedback with empathy.

• Tech-forward: You design and optimize workflows using modern tools (including AI) to multiply output.

• Hands-on: You’re not afraid to get into the details when it matters — and you know when to zoom out.

Qualifications

• 3-7 years of experience in operations, strategy, consulting, or a Chief of Staff role (startup experience preferred).

• A track record of making things happen — from start to finish.

• Exceptional written and verbal communication skills.

• Strong systems thinking and comfort with AI and productivity tools.

• High EQ, maturity, and discretion — with the confidence to push back when needed.

What Success Looks Like

• Founders spend the majority of their time on the most strategic, high-leverage work.

• Critical projects and customer relationships move faster and with greater clarity.

• Company communication and decision-making are sharper, faster, and better aligned.

• Systems are in place that make the leadership team — and the company — more scalable.

Why Scratchpad?

You’ll be joining a venture-backed startup with a bold vision: to transform how sales teams work. In this role, you’ll get a front-row seat to the founder journey and play a pivotal role in shaping the company’s trajectory. If you thrive in fast-paced environments, love building systems that create clarity and speed, and want to multiply the impact of a high-performing leadership team — this role is for you. This is a role designed to accelerate your career — many who thrive in positions like this go on to lead product, strategy, or operations teams, or start their own companies.