About the role

Role Overview

Chief of Staff, President & COO to Jonathan Stull (President & COO) at Handshake. You will operate as his execution partner—driving strategy-through-execution, supporting key leadership forums, and ensuring critical decisions and projects move forward.

Key Responsibilities

Run the business operating rhythm (planning, staff meetings, operating reviews, and board preparation)—ensure owners are named and execution threads don’t drop.
Produce first drafts for high-stakes problems; propose answers aligned with your principal’s thinking and focus.
Provide an independent, data-driven view of performance:
- Interrogate datasets
- Build models
- Communicate what the numbers show, even when uncomfortable
Create executive and market-facing communications:
- Board materials
- Exec memos
- Partner-facing narratives (no filler)
Lead strategic projects with no natural owner, carrying them end-to-end and advancing through resistance.
Accelerate the business with AI leverage:
- Identify and install AI workflows that make teams faster
- Apply improvements first to your own work
Represent your principal in rooms he cannot attend, using judgment, discretion, and calm.

How You Drive Success

Operate in a high-intensity environment (not a 9–5 role) with frequent context switches.
Be able to walk through the decision artifacts (what was decided and what happens next) succinctly.
Stay proactive and execute without waiting for direction.
Keep projects moving through pushback; pausing at the first sign of resistance is the failure mode.
Be analytically self-sufficient (financial models, large datasets, SQL or rapid ability to pick it up).
Have strong writing quality (minimal editing needed), low ego, and high trust.

Requirements

Experience being a “right hand” to a demanding senior leader and carrying work end-to-end.
Ability to produce clear executive artifacts (e.g., one-page decision summaries) in messy, high-debate settings.
Strong analytical skills, including financial modeling and working with large datasets; SQL proficiency or quick ramp.

Nice-to-Haves / Implied Signals

Demonstrated use of AI/workflow automation to improve team speed.
Proven track record stepping into ambiguous projects without clear ownership.

About Handshake

Handshake builds a platform connecting job seekers with employers and educational institutions, aiming to create equitable access to career opportunities. The company powers millions of users and organizations and has expanded into AI-driven data businesses, working with leading AI research labs to create evaluations and benchmarks.

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