Director of Engineering

We're looking for a Director of Engineering, Qualityand Engineering Delivery to lead the functions that ensure our engineering organization delivers high-quality, reliable software at scale. This role owns quality assurance technical support, incident management and release readiness for engineering operations. The opportunity: as a rapidly growing insurance technology company, we rely on high quality reliable systems, predictable delivery, operational discipline, and exceptional customer experiences. As our platform and engineering organization continue to scale, we need a leader who can build the operational foundation that enables teams to move quickly without sacrificing quality or reliability. As a key member of the engineering leadership team, you will establish the processes, tooling, metrics, and organizational practices that drive quality assurance, engineering operational effectiveness, and customer satisfaction across a growing multi-product platform. What You'll Own Team Leadership Build and grow a high-performing engineering team across QA, support and engineering operations. Manage the recruiting, onboarding/offboarding and ongoing team development while fostering technical excellence. Mentor team members through technical challenges, support their continuous growth, and support their career growth. Establish a culture of accountability, continuous improvement, customer focus, and operational excellence. Build strong partnerships across Engineering, Product, Operations, Customer Success, and Business teams, fostering clear communication, alignment, and coordinated execution. Quality Engineering Own the product quality assurance strategy, tooling, frameworks, and quality standards. Lead the QA organization responsible for test automation, release validation, regression testing, and quality governance. Drive a shift-left quality culture across engineering teams. Establish quality KPIs including defect escape rates, test coverage, release quality, and customer-reported issues. Partner with engineering leadership to ensure quality is embedded throughout the SDLC. Technical Support and Incident Management Lead technical support and escalation management functions. Establish support processes, service levels, escalation paths, and operational reporting. Partner with development and product teams to resolve customer-impacting issues quickly and effectively. Drive root cause analysis and remediation efforts that improve platform stability and resilience. Identify recurring customer issues and drive systemic improvements that reduce support burden. Engineering Operations Build data-driven operational reviews that help leadership make informed decisions. Create transparency around engineering performance and improvement opportunities. Leverage metrics such as deployment frequency, lead time, change failure rate, MTTR, incident trends, support volume, customer impact, and engineering productivity. Ensure lessons learned from releases are incorporated into engineering standards, delivery processes, testing strategies, and operational practices. Tech Stack Languages: Python, SQL Frameworks: Selenium, Playwright, Serenity-BDD, Cypress, k6 or Artillery or similar Data Stack: Snowflake, dbt, Apache Airflow (AWS MWAA) Cloud Infrastructure: AWS, Terraform or similar AI/ML: LLM APIs (OpenAI, Anthropic), vector databases, ML frameworks (scikit-learn, PyTorch or equivalent) Tools: GitHub, Jira, Confluence, Jellyfish, Slack Full-Stack Testing: Experience testing mobile, mobile-responsive web applications and APIs (RESTful/GraphQL). DevOps Exposure: Experience configuring GitHub Actions, Jenkins, or similar CI/CD tools. Observability: Datadog, New Relic, Grafana, CloudWatch Operationally Obsessed. You believe reliability, quality, and execution are competitive advantages. You see operational excellence as a force multiplier for engineering teams. Champion Quality Culture: Advocate for "shift-left" testing, testability during the design phase, and modern practices like Behavior-Driven Development (BDD) to create living documentation. Data-Driven. You use metrics to identify problems, validate improvements, and drive accountability. You know which metrics matter and which ones create noise. Customer Focused. You understand that every outage, support ticket, and defect ultimately impacts customers. You use customer experience as a guiding principle for operational decisions. Low Ego, High Impact. You care more about the outcome than the credit. You've hired people better than you in their domains and gotten out of their way. Strong Opinions, Weakly Held. You bring a clear point of view to architecture decisions and update it fast when the data says otherwise. Team First. You win through the team. You hire people better than you in their domains and get out of their way. Required 10+ years of experience in software engineering, quality assurance, Devops, technical operations, or related roles. 5+ years managing engineering teams responsible for QA, support, reliability or engineering operations. Strong understanding of software development lifecycles, Agile methodologies, CI/CD, cloud infrastructure, and modern engineering practices. Experience implementing engineering metrics programs and using data to drive organizational improvements. Proven success leading cross-functional operational initiatives involving engineering, product, infrastructure, and customer-facing teams. Experience building and scaling operational processes within SaaS, enterprise software, or technology organizations. Strong stakeholder communication and management skills. Nice to Have Experience in insurance, fintech, or other data-rich regulated domains Familiarity with DORA metrics, SPACE framework, engineering effectiveness programs, and developer productivity initiatives. Experience implementing observability and operational excellence initiatives at scale. Experience supporting SOC 2, ISO 27001, or other compliance frameworks. For those applying in the US: Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer visa sponsorship at this time Full remote flexibility and asynchronous work culture Unlimited PTO and fully paid sick leave Comprehensive health benefits, including medical, dental, and vision coverage, plus HSA and FSA options Additional financial protection and retirement benefits, including a 401(k), company-paid life insurance, and disability coverage A high degree of ownership, autonomy, and the opportunity to help build and shape a growing company The chance to make a meaningful impact while working alongside an ambitious, high-performing team Exposure to the challenges and opportunities of a fast-growing startup environment Base Salary Range $160,000-$200,000 This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including experience, qualifications, geographic location and other relevant factors. Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.