Director Of Engineering - Remote Eligible

Director Of Engineering

Keep Company is on a mission to make human connection an intentional, scalable asset in every workplace. As a venture-backed SaaS platform recognized by Techstars, Forbes, and SHRM, Keep Company blends technology with coaching and mentoring to deliver transformative, measurable employee experiences at leading law and professional services firms. We help organizations accelerate culture, retention, and productivity—especially in moments that matter most.

The Role

Keep Company is seeking a Director Of Engineering to lead and scale the next phase of our platform. This leadership role is both strategic and hands-on, blending technical vision and execution. You'll work closely with the CEO and VP, Product, own product delivery and quality, and help build a high-performing engineering culture as we enter rapid enterprise growth.

Role: Full Time

Location: Primarily remote, with the option to work onsite at our Bethesda, MD headquarters

Compensation: Competitive salary + generous equity

Key Responsibilities

• Lead, manage, and grow Keep Company's engineering organization
• Scale and improve our SaaS platform—owning architecture, performance, and reliability
• Design and evolve Keep Company's architecture to support enterprise integrations and partner ecosystems (e.g., WorkOS, Microsoft Graph, Slack, Teams, Intercom)
• Drive development of RESTful APIs and webhooks that power multi-tenant delivery, data reporting, and client integrations
• Collaborate with product and data teams to ensure external API endpoints reflect internal feature parity and security standards
• Translate product vision into clear roadmaps, sprint plans, and deliverables
• Drive secure, enterprise-grade client launches and oversee delivery for multiple, simultaneous projects
• Mentor and develop engineering team members; foster a culture of growth, inclusion, and innovation
• Establish and track engineering KPIs for velocity, delivery, and quality
• Partner cross-functionally with Product, Customer Success, Sales, and Leadership on priorities, risk management, and go-to-market
• Champion robust documentation and auditable, secure practices

About You

• 7+ years' experience in software engineering, with 3+ years in engineering management or technical leadership in a SaaS or high-growth startup environment
• Strong technical foundation; skilled in modern web architecture (e.g., Next.js, AWS, Vercel, Postgres)
• Experience building and launching secure, scalable B2B software products
• Experience leading B2B SaaS platform delivery for enterprise clients, including HRIS and calendar integrations, data governance, and client-specific configuration frameworks
• Direct experience implementing and maintaining secure development practices, with familiarity in InfoSec standards and enterprise compliance requirements (such as documentation, encryption, access controls, and audit readiness)
• Proven track record managing remote/contract teams and delivering enterprise projects
• Able to balance strategy with hands-on execution; bias for action and accountability
• Excellent communicator, comfortable working cross-functionally and with execs/clients
• Familiarity with modern dev tools (Jira, Notion, Slack, etc.) and a passion for data-driven delivery
• Comfortable leveraging AI-powered coding tools (e.g., GitHub Copilot, Cursor, Lovable) as part of your engineering workflow, and passionate about developing AI-enabled product features
• HR tech or future-of-work experience is a plus

Required Attributes for Success

• Entrepreneurial ownership—ready to shape process as we scale
• Growth mindset—excited to learn, iterate, and improve
• Ability to thrive in ambiguity and bring clarity for others
• Empathy for users, clients, and colleagues

Why Keep Company?

• Play a pivotal leadership role shaping the future of workplace connection and culture
• Be part of a founder-led startup with renowned clients and measurable impact
• Competitive salary, significant equity, medical/dental/vision, 401k, and flexible PTO
• Hybrid work schedule and a highly supportive, mission-driven team
• Regular team events, constant opportunities to grow, and plenty of celebration

How To Apply

Apply by sending your resume and a cover note sharing what excites you about building at the intersection of tech and human connection.

If you're energized by our mission but don't meet every listed qualification, we'd still love to hear from you.