Senior Software Engineer (Operator Tooling)

• As a Senior Software Engineer on Operating Tooling, you’ll build internal products and automation that help Handshake’s operators run the business at high quality and speed
• This team functions like an embedded/consulting engineering group: you’ll partner directly with operators, learn their workflows deeply, and deliver pragmatic solutions that remove friction, improve quality, and enable new operational capabilities
• This role is highly collaborative and communication-heavy
• Success requires strong technical fundamentals plus high EQ—someone who can translate ambiguous operational needs into reliable systems, and iteratively ship improvements that stick
• Embed with operators to understand processes, pain points, and success metrics; translate them into clear technical requirements and deliverables
• Architect and build internal tools, automations, and workflows that improve operational throughput, accuracy, and visibility
• Lead projects end-to-end: discovery, scoping, technical design, implementation, rollout, and iteration
• Balance speed and quality by making thoughtful tradeoffs, ensuring maintainability, and building with operational reliability in mind
• Collaborate closely with cross-functional partners (operators, engineering, product) to drive adoption and measurable impact
• Mentor other engineers and help establish strong engineering practices for an internal-tools environment

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

• 5+ years of software engineering experience, with comfort owning systems end-to-end (from requirements through production support)
• Strong engineering judgment: can design scalable systems, pick the right level of abstraction, and avoid over-building
• Track record of delivering iterative, high-leverage improvements in ambiguous environments
• Strong communication skills and stakeholder management; able to partner deeply with non-engineering teams and operate with high empathy/EQ
• Experience building internal tools, workflow systems, or automation for operations-heavy teams (or analogous customer-embedded roles like FDE / solutions engineering)
• Experience with workflow/backlog systems, intake processes, and operational analytics (instrumentation, dashboards, QA)
• Background building tooling for knowledge-work operations (e.g., case management, review/approval flows, data quality tooling)
• Comfort operating in a “player-coach” environment (mix of hands-on building plus lightweight coordination/mentorship as the team grows)