Handshake

• Own both new business acquisition and the growth of an existing portfolio of federal agency customers • Develop and nurture relationships with key stakeholders, identify opportunities, and drive the sales process from prospecting to close across your named book of accounts • Manage and grow an existing portfolio of federal agency customers while continuously pipelining new, relevant opportunities • Meet or exceed annual quota across both a customer retention number and a new business target • Understand a department or agency's business drivers, challenges, and pain points • Navigate federal acquisition processes and contracting, including sole source justification • Schedule, manage and run meetings with senior economic buyers within the federal government • Create proposals, executive briefings, and seasonal business reviews for HR and business leaders at federal agencies • Generate scalable pipeline and revenue to achieve 100% of annual quota attainment • Partner closely with Customer Success and Program Management teammates to ensure strong customer outcomes post-sale • Utilize Salesforce.com on a daily basis to manage activity, leads, follow-up and pipeline

• Support the growing team by matching Fellows to project opportunities • Review resumes and assess candidate qualifications and overall fit • Ensure alignment with client and project needs • Work closely with internal stakeholders to evaluate experience, skills, and transferable strengths • Maintain a high level of accuracy and attention to detail throughout the screening process

• Design and evaluate high-difficulty Mechanical Engineering prompts that probe the limits of AI models • Identify reasoning errors, weaknesses, and failure modes in model outputs • Apply adversarial prompting techniques to surface gaps in model understanding • Provide expert-level feedback on model responses for Mechanical Engineering • Collaborate with project leads to maintain high quality and consistency standards

• Design and evaluate high-difficulty Computer Engineering prompts that probe the limits of AI models • Identify reasoning errors, weaknesses, and failure modes in model outputs • Apply adversarial prompting techniques to surface gaps in model understanding • Provide expert-level feedback on model responses for Computer Engineering • Collaborate with project leads to maintain high quality and consistency standards

• Design and evaluate high-difficulty Civil Engineering prompts that probe the limits of AI models. • Identify reasoning errors, weaknesses, and failure modes in model outputs. • Apply adversarial prompting techniques to surface gaps in model understanding. • Provide expert-level feedback on model responses for Civil Engineering. • Collaborate with project leads to maintain high quality and consistency standards.

Senior Product Designer II, Handshake AI Location: San Francisco, CA Full time Hybrid Compensation - $170K – $215K • Offers Equity 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. 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. Your role Handshake AI powers expert-labeled data collection at scale, matching domain experts with leading AI companies to train frontier models. We're hiring a Senior Product Designer II to lead significant, high-impact design initiatives — someone who can navigate ambiguity with confidence, bring rigor and data-informed thinking to complex problems, and raise the bar for the design org around them. In this role, you'll own meaningful chunks of our product strategy, driving design end-to-end across complicated, often loosely-defined projects. You'll be a go-to resource for your teammates, proactively mentoring and improving quality beyond your own work — while staying close to customers, operators, and the full business to keep your decisions well-grounded. - Lead end-to-end design on significant, high-impact projects, from discovery through production and iteration, often with minimal definition and little precedent to work from. - Bring a data-informed mindset to every aspect of your work — articulating when data is incomplete or biased, keeping the user at the center of every solution, and holding a high bar for quality and craft before sharing your work. - Contribute to prioritization, strategy, and process — breaking big ambiguous problems into actionable steps and building clarity for your team and cross-functional partners. - Use business goals, data, patterns, and industry context to arrive at quick, iterative solutions — avoiding getting stuck in the abstract. - Proactively identify opportunities to inform, influence, and collaborate across the design org, creating workflow efficiencies and sharing learnings with teammates. - Serve as a helpful mentor for teammates at earlier career levels, improving craft, communication, and design quality beyond your own area. Your experience - 6+ years of product design experience, with a track record of designing and shipping products that customers love. - Proven ability to lead complicated, ambiguous projects with little direction, driving them forward and creating clarity for those around you. - Strong data-informed thinking. You roll business goals, research, technical constraints, and user needs into well-crafted solutions (mocks, prototypes, flows), and you iterate fast. - Experience mentoring or coaching peers, and a track record of improving quality beyond your own work. - Strong communicator who manages stakeholders well — you understand the nuance of upward and cross-functional communication and proactively keep the right people informed. - Deep visual and interaction design craft, with attention to detail across flows, states, and edge cases. - Humble, collaborative, and curious. Energized by a complex, evolving product and motivated to keep learning and help others grow. - Bonus if you have experience designing LLM or AI-powered products, or working on enterprise or operations tooling. 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.

Title: Staff Product Designer, Handshake AI Location: San Francisco, CA; New York, NY Hybrid Full-time Compensation - $190K – $240K 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. 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. Your role - Partner with product, engineering, data, research, and operations to define and build the vision for operator independence and self-serve tooling. - Develop strategic product visions and collaborate with partners to sequence them into pragmatic phases. - Collaborate closely with Model Enablement and Fellow Experience squads—your work enables theirs. - Partner with operations leaders and stay close to operators’ workflows. Run pilots, shadow users, uncover pain points, and translate insights into prioritized investments. - Tackle complex, ambiguous human-centered problems and translate them into clear, simple solutions. - Own design end-to-end—from concept through production—iterating quickly through research, user journeys, wireframes, prototypes, and high-fidelity designs with a strong point of view on craft. - Raise the bar for design culture and execution through systems thinking, product reasoning, pixel-level precision, facilitation, and mentoring. Your experience - 7+ years of product design experience, ideally working on enterprise products, operations tooling, or internal platforms. - Strong communicator who clearly articulates design decisions, tradeoffs, and the thinking behind them to partners and leadership. - Deep visual and interaction design expertise, with a proven track record of shipped work and measurable impact. - Experience designing complex systems, workflows, or platforms with many moving parts and stakeholders. - Highly collaborative, valuing diverse perspectives and incorporating them into the design process to achieve better outcomes. - Design-led thinker who raises the bar by embedding design thinking into day-to-day work and helping others grow. - Impact-driven, with the ability to prioritize ruthlessly and focus on the work that matters most. - Hands-on, willing to roll up your sleeves and take ownership—nothing is “someone else’s problem”. - Deeply motivated by Handshake’s mission. Humble, kind, and curious, with a desire to keep learning and help others grow. - Bonus if you have experience in operator or driver management, workflow or task management systems, or building internal tools for operations teams at a high-growth company. 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.

Title: Senior Security Engineer, Application Security Location: San Francisco, CA Department: Engineering Employment Type Full time Compensation - $176K – $220K 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. Job Description: Senior Application Security Engineer At Handshake, we believe security should be built into the product, not layered on after the fact. We're looking for a Senior Application Security Engineer who’s excited to shape how security shows up in the developer experience, and enable our engineering teams to ship secure code without compromising on velocity. About the Role As a Senior Application Security Engineer, you'll play a critical role in protecting Handshake’s users and their data. You'll work closely with our engineering, platform, and cloud teams to make the secure way the easy way and embed security directly into how software gets designed, written, and shipped. This role is on our Cloud Security squad on our Infra & Platform team and is an engineering forward role. You’ll be building systems, tools, and automation that make secure development the default. You’ll bring a modern, opinionated perspective on how application security should work in a cloud-native, AI-enabled environment. What You'll Do - Own and grow key areas of our Secure Software Development Lifecycle (SDLC) like threat modeling, security reviews, and vulnerability management. - Work collaboratively with and be a trusted partner for engineering teams. - Eliminate whole classes of vulnerabilities by building secure by default libraries and tools into our platform. - Raise the bar for security awareness by teaching others and sharing your knowledge through - Design and build developer facing tooling to help engineers identify and fix security issues before they make it to production. - Scale your impact and security knowledge by teaching others, automating processes, and leveraging AI and agentic tooling. - Balance security and speed by using your judgement and expertise to add the right amount of security to our SDLC. - Help respond to potential security incidents as a member of the security on-call rotation. What We're Looking For - A builder mindset and experience working on large codebases and safely shipping code to production. - Strong understanding of common application security risks (OWASP Top 10) and how to mitigate them. - A pragmatic and empathetic approach to security controls that favors guidance over blocking and influence over mandates. - Strong communication skills and the ability to communicate security risks and tradeoffs to both technical and non-technical audiences. - Experience with threat modeling and risk assessments. - Familiarity with securing and running software in a major cloud provider. - Curiosity and a desire to use AI and agenting tooling to scale your and the security team’s impact. Nice to Haves - Experience working in Google Cloud (GCP) - Experience writing production code in the most popular languages at Handshake: Ruby, Typescript and Go. - Experience building agentic systems to solve security problems. Why This Role You’ll have real ownership over how application security is built and scaled at Handshake. This role sits at the intersection of security, developer experience, and AI, with the opportunity to define how all three come together. As part of a fast paced and growing business you will regularly get to work on new and interesting problems. If you care about building systems (not just processes), enjoy working closely with engineers, and want to rethink what modern application security looks like, we’d love to hear from you. 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

• Join the Strategic Customer team focused on retaining, growing, and deepening Handshake’s partnerships with Fortune 500 and Fortune 100 employers • Inherit and own a book of Handshake’s most strategic customer relationships • Lead overall commercial partnership post-sale alongside the Client Success Manager • Responsible for executive alignment, renewal strategy, contract negotiations, account planning, and identifying whitespace opportunities • Ensure customers realize value from their partnership while uncovering opportunities to expand Handshake’s footprint and impact • Operate with high autonomy and engage customers in person to strengthen relationships

• Create and evaluate complex chemistry prompts across organic chemistry, polymer chemistry, NMR spectroscopy, and molecular analytical characterization • Apply adversarial prompting strategies to induce and document model reasoning errors • Critically assess the accuracy, depth, and scientific validity of AI-generated responses • Contribute to quality standards and provide calibrated feedback to the broader team