Chief of Staff, President & COO

About the role

In this position, you will work closely with Handshake's President & COO, Jonathan Stull, who has played a crucial role in the company's development over the past ten years. Your primary responsibility will be to facilitate strategic initiatives throughout the organization, with a particular emphasis on the Handshake Network's global growth, as well as the Learning, Recruiting, and International revenue streams. This role is designed to provide a clear trajectory towards senior leadership within Handshake.

Key facts

What you'll do

• Oversee the operational cadence of the organization, which includes planning sessions, staff meetings, performance reviews, and board meeting preparations, ensuring that all decisions are documented and executed effectively.
• Proactively identify and propose initial solutions for emerging challenges, ensuring alignment with the strategic priorities set by the President & COO.
• Independently assess business performance through data analysis, constructing models, and presenting findings in an objective manner.
• Craft essential communications for the board, executive team, and partners, ensuring that messages are clear and concise.
• Lead strategic initiatives that do not have a designated owner, effectively navigating obstacles and incorporating feedback to ensure successful completion.
• Integrate AI-driven workflows to boost team productivity, beginning with your own responsibilities.
• Act as a representative for the President & COO in various contexts, exercising sound judgment and discretion.
• Collaborate with cross-functional teams to ensure alignment on strategic goals and initiatives.
• Monitor industry trends and competitive landscape to inform strategic decision-making.
• Develop and maintain relationships with key stakeholders, both internal and external, to facilitate collaboration and communication.
• Prepare detailed reports and presentations for executive meetings, ensuring all materials are ready and impactful.
• Drive a culture of accountability and performance excellence within the organization.

Requirements

• A minimum of 5 years of experience in roles that require the creation of decision-ready materials for senior executives, such as in strategy consulting, investment banking, corporate development, or C-level strategy and operations.
• A track record of rapid career progression in high-pressure environments that demand swift execution.
• Regular use of AI tools to enhance personal productivity and efficiency.
• A strong commitment to Handshake's mission of expanding career opportunities within the AI-driven economy.
• Proven experience acting as a trusted advisor to senior leaders, managing projects from inception to completion.
• A proactive mindset, consistently taking the initiative to start tasks without needing explicit instructions.
• Ability to distill complex discussions into clear, actionable summaries that outline decisions and next steps.
• Resilience in pushing projects forward despite encountering resistance or challenges.
• Proficiency in data analysis, including financial modeling and working with large datasets, with a strong capability in SQL or the willingness to learn quickly.
• Exceptional writing skills that require minimal to no editing.
• A collaborative spirit, fostering trust through sound judgment and consistent follow-through on commitments.

Nice to have

• Experience with marketplace or multi-sided platform business models.
• Participation in board activities, financing rounds, or milestones related to public markets.
• Familiarity with the AI data ecosystem, including evaluation and annotation processes.

Skills & tools

• SQL (or a strong ability to learn quickly)
• Financial modeling expertise
• Proficient in data analysis
• Familiarity with AI tools

Practical notes

This position is not a conventional 9-to-5 role and demands a fast-paced environment with frequent shifts in focus. Handshake provides a comprehensive benefits package for full-time employees in the U.S., which includes equity options, a 401(k) matching program, paid parental leave, medical, dental, and vision coverage, mental health support, a wellness stipend of $500, a learning stipend of $2,000, flexible paid time off, 15 holidays plus 2 additional flex days, and opportunities for team outings. The San Francisco office also offers complimentary lunch and access to gym facilities.