Edtech.com's Summary

Handshake is hiring a Chief of Staff to the CEO to serve as the CEO's closest partner in driving strategic initiatives, managing the operating cadence, and ensuring cross-functional alignment throughout the company. The role involves leading high-stakes projects, building analytical foundations for key decisions, and producing executive-level communications to support Handshake's growth and impact in the AI economy.

Highlights

Drive CEO's operating rhythm including board preparation, executive meetings, and annual planning.
Lead critical cross-functional initiatives such as go-to-market alignment, organizational design, and IPO readiness.
Analyze complex datasets and model financials to provide actionable insights and recommendations for executive decisions.
Create high-quality communications like board decks, investor memos, and company-wide narratives representing the CEO's vision.
Require 8+ years experience in consulting, strategy & operations, investment banking, or senior technical roles.
Experience with scaled organizations of 500+ employees and familiarity with late-stage growth complexities.
Strong analytical skills including financial modeling; knowledge of SQL is a plus.
Exceptional written communication skills with ability to produce polished executive materials.
Proven ability to influence senior leadership and drive alignment across executive teams in ambiguous environments.
Benefits include equity ownership, competitive compensation, 401(k) match, paid parental leave, wellness stipend, learning stipend, flexible PTO, and more.

Chief of Staff, CEO Full Description

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

The Role

The Chief of Staff to the CEO is one of the highest-leverage roles at Handshake — a seat at the center of our most consequential decisions as we our next phase of growth. You'll be the CEO's closest partner: driving operating cadence, leading strategic initiatives, and ensuring the company moves in sync across every function.

This is a pivotal moment at Handshake. We've tripled ARR at scale, launched a new AI business, and are building fast in one of the most consequential markets in tech. The Chief of Staff to the CEO will be a key partner in shaping how we grow — bringing structure to ambiguity, alignment across teams, and leverage to every high-stakes decision the CEO faces.

Drive the CEO's operating rhythm — from board prep and executive staff meetings to annual planning — so decisions get made and priorities stay clear across the company
Lead high-stakes cross-functional initiatives (GTM alignment, org design, IPO readiness) from ambiguous idea to structured execution with clear owners and measurable outcomes
Build the analytical foundation behind key decisions by interrogating complex datasets, modeling financials, and distilling insights into crisp, actionable recommendations for the CEO and board
Produce world-class communications — board decks, investor memos, all-hands narratives — that represent the CEO's thinking with precision and reflect Handshake's strategy externally

You Have

8+ years in consulting, strategy & operations, investment banking, or a senior operating role at a technology company
Experience inside scaled organizations (500+ employees), with exposure to the complexity of late-stage growth — board dynamics, cross-functional alignment, and high-stakes external relationships
Exceptional analytical ability: you build the analytical foundation that shapes exec-level decisions, including financial models and business cases that influence board-level strategy (SQL a plus)
Elite written communication skills — board-quality decks, executive memos, and all-hands messaging that don't need much editing
High bias to action and low ego: you anticipate needs, act before being asked, and measure success entirely by the outcomes of the people you support
Track record of influencing senior leaders and driving alignment across an executive team without direct authority, in fast-moving, ambiguous environments
Track record of driving complex, cross-functional projects from ambiguity to execution in fast-moving environments

Bonus Points:

Background in business operations, strategy & operations, or strategic finance — with experience moving from insight to execution across a fast-moving org
Experience operating across company stages — from early-stage, high-growth environments to scaled organizations — and the ability to adapt your operating style accordingly
Familiarity with marketplace businesses, multi-sided platforms, or AI/SaaS go-to-market motions

We Offer

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, $500 wellness stipend

📚 Growth: $2,000 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

About Handshake

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

The Role

Drive the CEO's operating rhythm — from board prep and executive staff meetings to annual planning — so decisions get made and priorities stay clear across the company
Lead high-stakes cross-functional initiatives (GTM alignment, org design, IPO readiness) from ambiguous idea to structured execution with clear owners and measurable outcomes
Build the analytical foundation behind key decisions by interrogating complex datasets, modeling financials, and distilling insights into crisp, actionable recommendations for the CEO and board
Produce world-class communications — board decks, investor memos, all-hands narratives — that represent the CEO's thinking with precision and reflect Handshake's strategy externally

You Have

8+ years in consulting, strategy & operations, investment banking, or a senior operating role at a technology company
Experience inside scaled organizations (500+ employees), with exposure to the complexity of late-stage growth — board dynamics, cross-functional alignment, and high-stakes external relationships
Exceptional analytical ability: you build the analytical foundation that shapes exec-level decisions, including financial models and business cases that influence board-level strategy (SQL a plus)
Elite written communication skills — board-quality decks, executive memos, and all-hands messaging that don't need much editing
High bias to action and low ego: you anticipate needs, act before being asked, and measure success entirely by the outcomes of the people you support
Track record of influencing senior leaders and driving alignment across an executive team without direct authority, in fast-moving, ambiguous environments
Track record of driving complex, cross-functional projects from ambiguity to execution in fast-moving environments

Bonus Points:

Background in business operations, strategy & operations, or strategic finance — with experience moving from insight to execution across a fast-moving org
Experience operating across company stages — from early-stage, high-growth environments to scaled organizations — and the ability to adapt your operating style accordingly
Familiarity with marketplace businesses, multi-sided platforms, or AI/SaaS go-to-market motions

We Offer

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, $500 wellness stipend

📚 Growth: $2,000 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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Chief of Staff, CEO

Edtech.com's Summary

Chief of Staff, CEO Full Description

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