Director of Software Engineering

Gateless is a visionary, remote-first technology company solving impossible problems in mortgage automation. We combine deep industry knowledge with expert systems and next-generation AI to build products that materially improve how lenders and borrowers experience the mortgage process.

Our team is curious, compassionate, and relentless about quality. We value clear thinking, strong judgment, and people who take ownership of complex problems end to end.

The Role

• As Director of Software Engineering, you will lead multiple engineering teams and their managers to deliver Gateless’s core products. You’ll own the intersection of technical execution and business outcomes—translating product strategy into engineering plans, ensuring architectural decisions serve both the technology and the business, and building the teams needed to execute at scale.
• This role requires someone who can reason across the full technical stack without needing to write every line of code. You’ll partner closely with Product, Customer Success, and executive leadership to prioritize work, unblock delivery, and maintain the engineering quality our customers depend on. You’re as comfortable in a sprint planning session as you are in a customer-facing conversation.

What You’ll Do

• Lead Engineering Teams: Manage multiple engineering teams including managers and technical leads, supporting engineers from junior through principal level.
• Drive Delivery: Own the planning and execution of epics, releases, and sprints. Write stories, define scope, and organize work to ensure the team ships on time and at quality.
• Partner on Product Strategy: Work with product and business stakeholders to weigh tradeoffs, refine requirements, and align engineering efforts with company priorities.
• Guide Technical Decisions: Evaluate architectural tradeoffs and work with developers and managers to ensure solutions are sound technically and viable for the business.
• Ensure Problem Resolution: You don’t have to solve every technical problem, but you must ensure they get solved. Drive accountability and remove blockers across teams.
• Engage with Customers: Serve as a credible engineering voice in customer conversations, sharing the right level of detail without getting lost in the weeds.
• Recruit and Build Teams: Attract, hire, and develop strong software development teams that reflect Gateless’s culture and technical standards.

Your Skills

• Technical Breadth: Able to understand and reason about most programming languages, including those in functional and logical paradigms. You think in systems, not just syntax.
• Business-Minded Leader: Comfortable weighing business tradeoffs alongside technical ones. You connect engineering work to customer outcomes and company goals.
• Strong Communicator: Clear and effective across audiences—engineers, executives, and customers. You simplify complexity without losing meaning.
• Delivery-Oriented: Proven ability to organize and execute complex engineering work across multiple teams simultaneously.
• Intellectually Curious: Driven to understand how things work and why. You ask good questions and create environments where your teams do the same.
• Adaptable and Self-Directed: Thrives in a remote-first, fast-moving environment where priorities shift and ownership is expected.

Experience & Qualifications

• 10+ years of software industry experience.
• 5+ years in an engineering leadership role (Engineering Manager, Lead Engineer, or Principal Engineer).
• Experience managing multiple engineering teams with managers and/or technical leads as direct reports.
• Track record of shipping complex software products in collaboration with product and business teams.
• Experience in mortgage, financial services, or similarly regulated industries preferred.
• Familiarity with agile development practices and tools such as JIRA.