Chief of Staff, President & COO

About the role

This position supports Handshake's President & COO, Jonathan Stull, who has been instrumental in the company's growth for a decade. You will be a key partner in strategic execution across the organization, particularly focusing on the Handshake Network and its global expansion, as well as the Learning, Recruiting, and International revenue streams. This role offers a direct path to senior leadership within Handshake.

Key facts

What you'll do

• Manage the operational rhythm of the business, including planning, staff meetings, reviews, and board preparations, ensuring all decisions are tracked and completed.
• Proactively develop initial solutions and proposals for emerging issues, aligning with the principal's strategic focus.
• Analyze business performance independently using data, building models, and reporting findings objectively.
• Draft critical communications for the board, executives, and partners, ensuring clarity and conciseness.
• Lead strategic projects that lack a clear owner, navigating challenges and incorporating feedback to drive completion.
• Implement AI-driven workflows to enhance team efficiency, starting with your own tasks.
• Represent the President & COO in various settings with sound judgment and discretion.

Requirements

• 5+ years of experience in roles focused on producing decision-ready materials for senior leaders, such as strategy consulting, banking, investing, corporate development, or C-level strategy and operations.
• Demonstrated rapid career advancement in demanding environments that prioritize quick execution.
• Daily use of AI tools to improve personal productivity.
• Strong alignment with Handshake's mission to broaden career opportunities in the AI economy.
• Proven ability to serve as a right-hand to a senior leader, delivering projects end-to-end.
• Proactive work ethic, consistently initiating tasks without explicit direction.
• Skill in synthesizing complex discussions into clear, concise summaries of decisions and next steps.
• Persistence in advancing projects despite resistance or pushback.
• Self-sufficiency in data analysis, including financial modeling, large datasets, and SQL proficiency (or a rapid learning capability).
• Exceptional written communication skills that require no editing.
• A collaborative approach, building trust through sound judgment and consistent follow-through.

Nice to have

• Experience with marketplace or multi-sided platform business models.
• Involvement in board activities, financing rounds, or public market milestones.
• Familiarity with the AI data, evaluation, or annotation ecosystem.

Skills & tools

• SQL (or ability to learn quickly)
• Financial modeling
• Data analysis
• AI tools

Practical notes

This role is not a standard 9-to-5 position and requires an intense pace with frequent context switching. Handshake offers comprehensive benefits for full-time US employees, including equity, 401(k) match, paid parental leave, medical/dental/vision, mental health support, a $500 wellness stipend, a $2,000 learning stipend, flexible PTO, 15 holidays plus 2 flex days, and team outings. The San Francisco office provides free lunch and gym access.