Handshake
Chief of Staff, President & COO
SQL
Edtech.com's Summary
Handshake is hiring a Chief of Staff to the President & COO. This role involves driving strategic decision-making, operational cadence, and cross-functional alignment within one of the company’s key marketplace businesses, while providing analytical insights and supporting executive communication to maximize organizational impact.
Highlights
- Lead planning, staff meetings, operating reviews, and ensure organizational alignment.
- Analyze complex datasets, build financial models, and generate actionable business insights.
- Manage strategic projects including GTM alignment, AI leverage, marketplace strategy, and operational improvements.
- Create high-level executive communications such as presentations, memos, and speeches.
- Serve as a trusted partner to senior leaders with discretion and high emotional intelligence.
- Required skills include strong analytical ability, experience with large datasets and financial modeling (SQL a plus), and exceptional communication skills.
- Requires 5+ years in consulting, strategy, operations, or product management at a tech company, with marketplace experience preferred.
- Compensation ranges from $224K to $280K cash plus equity and bonus opportunities.
- Works cross-functionally with Product, Sales, Marketing, EDU Partnerships, Finance, and AI teams.
- Offers comprehensive benefits including equity ownership, 401(k) match, parental leave, medical coverage, learning stipends, and flexible PTO.
Chief of Staff, President & COO Full Description
Chief of Staff, President & COO
San Francisco, CA
Employment Type
Full time
Location Type
On-site
Department
General & Administrative
Compensation
- Cash $224K – $280K • Offers Equity • Offers Bonus
For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above.
Overview
Application
About Handshake
Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.
Why join Handshake now:
- Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel
- Work hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions
- Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others
- Build a massive, fast-growing business with billions in revenue
About the Role
We are looking for a Chief of Staff to serve as a force multiplier to the President / COO. This role is designed as a high-growth platform that prepares exceptional operators for future leadership opportunities within Handshake.
As Chief of Staff, you will sit at the center of decision-making, execution, and analytical insight for one of the company’s most complex and impactful marketplace businesses. You will help shape strategy, improve operating cadence, drive cross-functional alignment, and ensure the President / COO shows up with the highest possible leverage in every room.
This is a rare opportunity to operate at the intersection of marketplaces, analytics, AI, and GTM, working closely with leaders across Product, Sales, Marketing, EDU Partnerships, Finance, and Handshake AI. The pace is fast, expectations are high, and the opportunity to grow is substantial.
Drive operating cadence & cross-functional alignment
- Run the rhythm of the business—planning, staff meetings, operating reviews, and follow-through.
- Surface decisions, clarify priorities, and ensure the organization moves in sync.
- Attend many exec-level discussions; represent Jonathan where needed with calm, maturity, and judgment.
Be the analytical engine behind key decisions
- Develop an independent, data-driven view of business performance and trends.
- Interrogate complex datasets, build models, analyze financials, and distill insights into actionable recommendations.
- Produce crisp, narrative-driven materials for executives, partners, and occasionally external audiences.
Turn ambiguity into structured execution
- Lead strategic projects—GTM alignment, AI leverage, marketplace strategy, operational improvement, forecasting frameworks, etc.
- Bring clarity to ambiguous questions and proactively identify opportunities to elevate execution.
- Support Jonathan’s preparation for high-stakes internal and external moments.
Amplify communication & organizational leverage
- Translate thinking, meetings, and strategy into world-class written communication—presentations, memos, speeches, and narratives.
- Champion the adoption of AI tools and workflows that materially increase speed and quality across the business.
Be a trusted partner
- Build trust across teams; become a reliable sounding board for leaders who need support or clarity.
- Maintain impeccable discretion, judgment, and emotional intelligence.
- Be available when needed—including occasional evenings—as part of supporting a high-velocity operating environment.
Desired Capabilities
- 5+ years in consulting, strategy & operations, product management, business operations, or a similarly analytical role at a tech company
- Strong commercial instincts; experience with marketplaces or multi-sided platforms is a plus
- Exceptional analytical ability; comfortable working with large datasets and financial models (SQL a plus)
- Elite written and verbal communication skills; able to create clarity and narrative from complexity
- High bias to action; anticipates needs and operates proactively
- Thrives in fast-paced, high-expectation environments with frequent context switching
- Low ego, high trust - earns influence through judgment, clarity, and follow-through
Perks
Handshake delivers benefits that help you feel supported—and thrive at work and in life.
The below benefits are for full-time US employees.
🎯 Ownership: Equity in a fast-growing company
💰 Financial Wellness: 401(k) match, competitive compensation, financial coaching
🍼 Family Support: Paid parental leave, fertility benefits, parental coaching
💝 Wellbeing: Medical, dental, and vision, mental health support, wellness stipend
📚 Growth: Learning stipend, ongoing development
💻 Remote & Office: Internet, commuting, and free lunch/gym in our SF office
🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days
🤝 Connection: Team outings & referral bonuses
Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers.
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