Senior Software Engineer (Enterprise AI)

• 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
• 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
• 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

Benefits

• Health Insurance: Comprehensive medical , dental, and vision coverage
• Fertility and family forming: Through a partnership, Handshake offers comprehensive family benefits, including infertility treatments and a $15K stipend, to its employees.
• LGTBQ+ coverage: All medical plans cover transgender services.
• Mental health: Discounts on a variety of wellness apps and an Employee Assistance Program with access to five free counseling sessions.
• Tax savings: Tax-advantaged benefits to save money on healthcare, dependent care, and other expenses.
• Life & disability insurance: Essential benefits and automatic coverage with basic life insurance, plus short-term and long-term disability coverage.
• 401k match: Dollar-for-dollar match up to 1% of pay, with a max of $1,200 per year.
• Equity: Our equity program includes grants at hire, refresher grants after two years of tenure, and grants alongside promotions.
• Financial management: Handshake partners to provide free professional financial planning services.
• Learning & development: Employees are provided with an annual stipend to use towards professional development, career development workshops, manager trainings, and 1-on-1 coaching through external partnerships
• Community leader support: Employee Resource Group leaders are compensated with a quarterly bonus for the high-impact work the role requires
• Parental leave: Leaves of 16 weeks for birth-giving parents and 10 weeks for non-birth-giving parents; the policy applies to adoptions as well. Handshake also partners to provide one-on-one coaching on preparing for leave and coming back from leave
• Flexible time off: No accrued time off or waiting period to take vacation. Two paid flexible holiday days off to observe holidays that closely align with religious, cultural, and personal needs
• Sabbatical: Paid six-week sabbatical to recharge and reset beginning at six years of continuous, full-time employment, and every four years thereafter
• Volunteer time off: Two days off for social and civil activism, volunteer work, and/or any related activities, including attending and participating in protests

• 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
• 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
• Strong opinions about product experience, you notice when things feel off and you fix them, regardless of which layer the problem lives in
• 5-6+ years of engineering experience, full-stack with strong backend depth
• Proficiency across the stack: comfortable with modern backend frameworks, APIs, and data modeling, as well as React/TypeScript on the frontend
• Experience at a company where craft was a genuine priority, you’ve helped hold that bar, not just ship features
• Ability to make pragmatic technical decisions that serve the product, not just the architecture
• Product engineering experience with strong fullstack instincts and a high bar for product quality
• Background working in or alongside enterprise deployment environments
• Experience building or integrating AI-powered features in production, customer-facing products
• History of close collaboration with designers, or a background in design yourself
• Experience at a company with a forward-deployed or embedded engineering model