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Senior Software Engineer, Enterprise AI

Handshake

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  1. Why do you want to join Handshake?
  2. What is your experience with Data modelling? Tell me one thing you learned the hard way.
  3. How did you know your model was actually good, and not just good on your test set?
  4. Tell me about a time the data was messy or wrong. What did you do?
  5. How would you explain your model's result to someone who is not technical?

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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 a Software Engineer on the Handshake AI Enterprise team, you'll own the product experience layer of AI applications we deploy directly into enterprise customer environments. You'll work closely with customers to deeply understand their workflows, translate ambiguous needs into crisp product decisions, and build end-to-end solutions that are genuinely delightful to use, not just functional. This is not a role for engineers who treat product quality as an afterthought. We believe engineering craft is a meaningful part of what makes AI applications succeed in enterprise environments, and you'll be the person who holds that bar across every deployment. We're looking for engineers across a range of experience — people who've already built high-craft product experiences, and those ready to set the bar for a team from the ground up. This is a unique opportunity to pair direct customer impact with founding-team ownership, helping define what high-craft enterprise AI product looks like from the ground up. Location: San Francisco, CA | 5 days/week in-office What You'll Do Own the product experience of AI applications deployed into enterprise customer environments, from initial discovery through iteration Work directly with customers to understand their workflows, pain points, and what "great" looks like in their context Translate ambiguous customer needs into clear, well-crafted product and technical decisions Build high-quality, full-stack features, from data models and APIs to the interfaces people actually use Collaborate closely with Applied AI and Platform engineers on your deployment team to ship cohesive, production-grade solutions Iterate rapidly based on real usage and customer feedback, with tight feedback loops Establish product engineering standards and reusable patterns that help the team scale quality as we grow Surface insights from customer deployments that inform Handshake's core product direction What We're Looking For 5-6+ years of engineering experience, full-stack with strong backend depth Product engineering experience with strong fullstack instincts and a high bar for product quality Experience at a company where craft was a genuine priority, you've helped hold that bar, not just ship features Proficiency across the stack: comfortable with modern backend frameworks, APIs, and data modeling, as well as React/TypeScript on the frontend Strong opinions about product experience, you notice when things feel off and you fix them, regardless of which layer the problem lives in Ability to make pragmatic technical decisions that serve the product, not just the architecture Comfort working in ambiguous, fast-moving environments with real customers and real stakes Strong communication skills, you'll be in customer conversations regularly and need to translate between business needs and technical decisions Extra Credit Experience building or integrating AI-powered features in production, customer-facing products Background working in or alongside enterprise deployment environments History of close collaboration with designers, or a background in design yourself Experience at a company with a forward-deployed or embedded engineering model 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, $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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Listed on ashby · posted 2026-05-04. ApplySarthi collects openings and links to application pages; the role is advertised by Handshake, not by us.