Engagement Manager

Cacheflow; San Francisco (CA); Hybrid; USD 170,000 - 230,000; Full time

Benefits offered by this job

Equity in fast-growing company

401(k) match

Paid parental leave

Medical, dental, vision

Learning stipend

Remote & Office: SF office perks

Flexible PTO

Team outings & referrals

Job summary

Handshake seeks an Engagement Manager for Handshake AI to own critical Frontier AI lab customer relationships from scope through deployment and renewals. You will coordinate cross-functional teams and manage high-stakes programs with executive-level clients.

The role demands experience in senior stakeholder management, strategic problem solving, and a track record of delivering measurable business outcomes in AI or data-focused environments.

Qualifications

• 6+ years in customer-facing, high-ownership roles in AI or data.
• 4+ years at a top-tier management consulting firm or startup operating experience.
• Proven track record leading complex, multi-stakeholder implementations.
• Experience working with senior stakeholders (VP or C-level).

Responsibilities

• Own a high-impact book of business for Handshake AI.
• Lead the full engagement lifecycle from onboarding to renewals.
• Turn evolving customer goals into clear programs with fast, data-driven decisions.
• Define and report on success metrics and key KPIs.
• Partner with Sales on aggressive expansion and upsell opportunities.

Skills

Customer facing roles

Engagement management

Strategy and operations

Management consulting

Senior stakeholders

Job description

About Handshake

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

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
• Partner hand-in-hand with world‑class AI labs, Fortune 500 partners and the world’s top educational institutions
• Work together with engineers, scientists, operators, and more from Palantir, Meta, Scale AI, and former YC founders
• Build a massive, fast-growing business with billions in revenue

About Handshake AI

Human data is the core infrastructure to AI advancement. Frontier AI labs currently improve model capabilities with various data‑intensive post‑training techniques. We believe that data spend for AI training will increase by 3-5x in the next few years and continue for much longer as models take on new domains. Handshake AI supports all of the frontier AI labs, working on their most complex data at the largest scale.

About the Role

As an Engagement Manager, Handshake AI, you will own our most critical Frontier AI lab customer relationships from first scope through production deployments, expansions, and renewals. You are the person these customers call first, in both high stakes moments and day to day decision making, and you are comfortable operating in environments with high expectations, high visibility, and high pressure.

You will sit at the intersection of customers, operations, product, and engineering, turning ambiguous, high stakes problems into clear programs, making hard tradeoffs at speed, and orchestrating cross functional teams to deliver outsized results while maintaining exceptional, executive level relationships.

You will be responsible for:

• Owning a high impact book of business for Handshake AI, leading strategic implementations for flagship accounts from scope and milestones through on time, successful go live.
• Running the full engagement lifecycle (onboarding, delivery, QBRs, expansions, renewals) as the single threaded owner of value for a portfolio of strategic, often multi million dollar customers.
• Turning messy, evolving customer goals into sharp programs and requirements, pushing back where needed, and influencing product, operations, and roadmap decisions.
• Defining and reporting on success metrics (business KPIs, SLAs, model quality) and using data to make fast, high conviction calls on where to double down, pivot, or sunset.
• Partnering with Sales on aggressive expansion strategies, identifying, shaping, and helping close upsell and cross sell opportunities across your accounts.

What success looks like in the first 6–12 months:

• Multiple high priority implementations are live in production with clear, referenceable wins and expansion in motion.
• Your accounts show deep adoption and material revenue growth, with Handshake AI embedded in core model development and evaluation workflows.
• Sales, Ops, and Product leaders consistently treat you as the owner of outcomes for your accounts and pull you into the most strategic, time sensitive opportunities.

You will work closely with:

• Sales on deal shaping, scoping, handoffs, and expansion strategy.
• Operations on aggressive yet realistic resourcing, training, and quality for Fellows and domain experts.
• Product and Engineering on roadmap, integrations, and new capabilities needed to unlock step function value for your customers.

What You Will Bring

Experience:

• 6+ years in customer facing, high ownership roles (engagement management, management consulting, customer success, strategy and operations, or similar) with AI, data, or complex operational products.
• 4+ years at a top tier management consulting firm (for example McKinsey, BCG, Bain, or equivalent) and/or a mix of that background plus startup operating experience in high intensity environments.
• Proven track record leading complex, multiple stakeholder implementations and driving measurable business outcomes for demanding enterprise customers.
• Experience working directly with senior stakeholders (VP or C level) and navigating complex, political organizations while still getting to an answer fast.

This role works well for people who:

• Want to own a book of business and are comfortable being directly accountable for customer outcomes and revenue
• Can make high judgment decisions with incomplete information and move fast without perfect data
• Enjoy switching between executive level relationship management and detailed project and data reviews
• Are comfortable working directly with senior leaders at Handshake and demanding VP and C level customers

It is not a good fit if you need fixed hours, narrow scope, or heavy structure. There are periods of high intensity, including occasional early or late calls across time zones. Priorities can change quickly and you will often be the person asked to solve the hardest customer problems.

People in this role often come from:

• Management consulting at top tier firms, with significant client leadership and project ownership
• Strategy and operations or bizops roles at early stage or high growth startups
• Customer facing leadership roles in SaaS or AI / data companies (engagement management, customer success, solutions, or similar)
• Investment banking or private equity backgrounds that transitioned into operating or client facing roles
• Prior experience in AI is helpful but not required.

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.