Edtech.com's Summary

Handshake is hiring a Chief of Staff, President & COO to act as a key multiplier for the President/COO by driving strategic initiatives, operational cadence, and cross-functional alignment. The role involves shaping strategy, analyzing business performance, leading complex projects, and supporting high-level communication and decision-making across multiple teams including Product, Sales, Marketing, and AI.

Highlights

Lead the rhythm of business operations including planning, staff meetings, and operating reviews.
Analyze complex datasets, build financial models, and generate actionable business insights.
Drive strategic project execution in areas such as GTM alignment, AI leverage, and operational improvements.
Develop clear, narrative-driven communication materials for executives and partners.
Work closely with cross-functional leaders across Product, Sales, Marketing, EDU Partnerships, Finance, and Handshake AI.
Required experience: 5+ years in consulting, strategy & operations, product management, or related analytical roles in tech.
Strong analytical skills with comfort handling large datasets; SQL knowledge is a plus.
Exceptional written and verbal communication skills to clarify complex information.
Demonstrated commercial instincts; experience with marketplaces or multi-sided platforms is preferred.
Compensation includes competitive pay, equity ownership, 401(k) match, paid parental leave, health benefits, flexible PTO, and additional wellness and development perks.

Chief of Staff, President & COO Full Description

About Handshake

Handshake is building the career network for the AI economy, backed by the largest and most trusted job network on the internet. As the only three-sided job marketplace connecting 18 million knowledge workers, 1,500 educational institutions, and 1 million employers, Handshake powers career discovery, hiring, and upskilling—from first internships to full-time roles, freelance work to gig work, and beyond.

Founded in 2014, we’ve built the most trusted platform for early talent—owning the college-to-career market and powering nearly every career center. Today we’re building on that foundation to help students and early professionals upskill or reskill for the future.

Now’s a great time to join Handshake. Here’s why:

Category Leader: Over 92% coverage across US universities & 77% of total US university student population.
Proven Market Demand: Deep employer partnerships across Fortune 500s and the world’s leading AI research labs.
World-Class Team: Leadership from Scale AI, Open AI, xAI, Notion, Coinbase, and Palantir, just to name a few.
Capitalized & Scaling: $434M raised with a $175M+ run rate.

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.

Original Job Description