• Directly manage up to 20 direct reports, as a single execution unit • Partner with multiple Product Managers to plan roadmaps and sprints • Be accountable for high quality execution on critical and high visibility business objectives • Be responsible for making tradeoffs between feature work and addressing long term technical debt • Be responsible for excellence in software quality, engineering practices and operations • Lead the team through standard Agile processes, such as backlog management, stand ups, retros, etc. • Review and approve engineering designs and be able to set technical direction (in collaboration with a Technical Lead) • Drive cross-org initiatives alongside managing execution responsibilities • Drive career conversations and career plans for your direct reports

The technical challenge: More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, expensive and time-consuming. At Jerry.ai, we are building the first mobile app to manage it all. Our insurance marketplace is our core product today, and our ability to automate the end-to-end shopping experience is our core differentiator. The Core Backend Team owns the most critical part of that, the "last mile", where we orchestrate complex, multi-step transactions with external systems to finalize insurance policy purchases. Because the industry lacks modern APIs, we build custom orchestration layers that navigate internal and external interfaces with precision. It is a high-stakes puzzle of asynchronous state management and real-time system reliability. Your challenge will be to evolve our current automation systems to a robust, fault-tolerant framework that can handle external interface changes gracefully and scale across dozens of new categories with minimal manual intervention. Why you will (or won’t) like working here: - Ownership: You’ll report directly to our co-founder/CTO, who is actively involved in product implementation. There is no red tape, no slow-moving processes, and no layers of approvals needed. If you have an idea, you can pitch it, build it, and see it live in days. - Stellar team: We have a very high bar for talent, as a result, we have a small but mighty team that can move fast and accomplish a lot. You will work with likeminded peers who are equally passionate and who care intensely about what they do. - Hands-on: Many of our TLMs are ex-founders, they like getting their hands dirty and solving difficult problems. You will spend 80% of your time doing hands-on technical work (e.g. transitioning our legacy automation systems into a more decoupled, scalable architecture). - Volume of customer data: We are a consumer-facing business (5M+ customers) and have access to a massive amount of customer data across behaviours like driving/telematics, shopping, payment, etc. which helps guide our product, technical and business decisions. What you’ll own: Our first automation system was built for speed, not scale. Today, it’s a web of tightly coupled business logic and database access that makes changes risky and failures hard to debug. - Phase 1: You’ll be deep in the code, learning both the technical and business sides of our core product (insurance is very complex and every insurance provider uses different logic and behaves differently). Then you will lead incremental refactoring of our existing automation systems: designing and implementing new standards and pairing with engineers to ensure the new system is predictable and testable. - Phase 2: As the architecture stabilizes, you’ll shift towards using an AI-first approach to building the next generation of internal tools that will allow us to grow from 5M to 50M users. Who you are: - A Player Coach: You likely founded a company or were a lead architect at an early stage startup. You are a builder at heart and like being in the trenches alongside your team. - A Detective: You are obsessed with success rates. You love hunting for edge cases in complex business logic and won't stop until you understand exactly why a script failed. - A Systems Thinker: You have a high bar for system design, especially for offline, asynchronous jobs. You understand that async work requires much stricter standards for decoupling, state management, and failure retry logic than synchronous online systems. Our tech Stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda). While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

The technical challenge: More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, expensive and time-consuming. At Jerry.ai, we are building the first mobile app to manage it all. Our insurance marketplace is our core product today, and our ability to automate the end-to-end shopping experience is our core differentiator. The Core Backend Team owns the most critical part of that, the "last mile", where we orchestrate complex, multi-step transactions with external systems to finalize insurance policy purchases. Because the industry lacks modern APIs, we build custom orchestration layers that navigate internal and external interfaces with precision. It is a high-stakes puzzle of asynchronous state management and real-time system reliability. Your challenge will be to evolve our current automation systems to a robust, fault-tolerant framework that can handle external interface changes gracefully and scale across dozens of new categories with minimal manual intervention. Why you will (or won’t) like working here: - Ownership: You’ll report directly to our co-founder/CTO, who is actively involved in product implementation. There is no red tape, no slow-moving processes, and no layers of approvals needed. If you have an idea, you can pitch it, build it, and see it live in days. - Stellar team: We have a very high bar for talent, as a result, we have a small but mighty team that can move fast and accomplish a lot. You will work with likeminded peers who are equally passionate and who care intensely about what they do. - Hands-on: Many of our TLMs are ex-founders, they like getting their hands dirty and solving difficult problems. You will spend 80% of your time doing hands-on technical work (e.g. transitioning our legacy automation systems into a more decoupled, scalable architecture). - Volume of customer data: We are a consumer-facing business (5M+ customers) and have access to a massive amount of customer data across behaviours like driving/telematics, shopping, payment, etc. which helps guide our product, technical and business decisions. What you’ll own: Our first automation system was built for speed, not scale. Today, it’s a web of tightly coupled business logic and database access that makes changes risky and failures hard to debug. - Phase 1: You’ll be deep in the code, learning both the technical and business sides of our core product (insurance is very complex and every insurance provider uses different logic and behaves differently). Then you will lead incremental refactoring of our existing automation systems: designing and implementing new standards and pairing with engineers to ensure the new system is predictable and testable. - Phase 2: As the architecture stabilizes, you’ll shift towards using an AI-first approach to building the next generation of internal tools that will allow us to grow from 5M to 50M users. Who you are: - A Player Coach: You likely founded a company or were a lead architect at an early stage startup. You are a builder at heart and like being in the trenches alongside your team. - A Detective: You are obsessed with success rates. You love hunting for edge cases in complex business logic and won't stop until you understand exactly why a script failed. - A Systems Thinker: You have a high bar for system design, especially for offline, asynchronous jobs. You understand that async work requires much stricter standards for decoupling, state management, and failure retry logic than synchronous online systems. Our tech Stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda). While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

The Development Lead is responsible for overseeing multiple product teams that develop, operate, and maintain mission-critical products. This position is accountable for the quality and timely delivery of all technical deliverables and leads overall projects or critical workstreams involving web development, code deployment, version control, build and release management, and requirements execution in accordance with acceptance criteria. This role: - Leads and drives the vision for the technology workstream, encompassing architecture, development, testing, integration, and deployment. - Leads teams of software developers, testers, and business analysts through requirements gathering, development execution, and delivery milestones. - Collaborates closely with stakeholders to define product direction and works directly with development teams to guide execution and remove impediments that may impact deliverable timelines. - Leads risk mitigation efforts as needed and ensures product teams understand future strategic direction while serving as a servant leader to promote team success. - Manages resource allocation, including staffing, budgeting, and project prioritization, in accordance with customer guidance. - Remains current on industry trends and emerging technologies to drive continuous improvement within the IT development landscape. - Ensures all development efforts prioritize cybersecurity and align with applicable customer standards, policies, and mandates. - Collaborates with cross-functional teams to gather and analyze requirements to ensure alignment with business objectives. - Reviews task orders associated with products and provide estimates for delivering required features and capabilities. - Establishes individual performance objectives, conducting regular performance evaluations, and providing ongoing feedback. - Develop and maintains software architecture technical specifications and ensures development activities conform to architectural standards. - Leads multi-functional software development teams through coding, integration, testing, migration, and deployment of all system components, and assist leadership and project teams with planning and technical strategy discussions. Job Responsibilities - Lead and oversee multiple product teams responsible for developing, operating, and maintaining mission-critical systems and enterprise applications. - Define and drive the technology vision across architecture, development, testing, integration, deployment, and sustainment activities. - Ensure quality, timely delivery of all technical deliverables, including web development, code deployment, version control, build and release management, and requirements execution aligned with acceptance criteria. - Lead software and cloud workstreams supporting program architecture, including restricted web presence, development environments, and portals. - Develop and maintain enterprise dashboards and analytics solutions that provide real-time performance visibility to support risk management and executive decision-making. - Enforce configuration management and change control processes through participation in Configuration Management Boards (CMB) and other governance forums. - Ensure development activities align with cybersecurity standards, DevSecOps practices, and customer requirements, including implementation and continuous monitoring of NIST 800-53 controls and ATO support activities. - Maintain secure development and production environments to ensure compliance with security and regulatory standards. - Collaborate with cybersecurity teams to drive delivery and sustainment of secure, compliant software solutions. - Monitor system health and performance of program applications and lead troubleshooting and remediation efforts when issues arise. - Guide cross-functional teams through requirements gathering, solution design, development execution, integration, and deployment milestones. - Manage staffing, resource allocation, and project prioritization in alignment with program objectives and contractual requirements. - Lead Agile planning events and collaborate with Government stakeholders to align development activities with evolving program goals. - Serve as a servant leader by removing impediments, mentoring technical staff, fostering collaboration, and promoting continuous improvement across teams. - Stay current on emerging technologies and industry trends to drive innovation and modernization initiatives. - Perform additional duties as assigned. Basic Qualifications - BS degree and 12 – 15 years of prior relevant experience or Masters with 10 – 13 years of prior relevant experience serving as a technical lead or servant leader overseeing multiple product teams. - Minimum of ten years of software development experience within an Agile and DevOps environment, with demonstrated ability to deliver on commitments. - Proven experience leading enterprise-level software solutions from development through deployment and sustainment. - Certified Agile Professional/CSM Certification/ Professional Scrum Master level II or better required. - Strong understanding of PHI and PMI protection requirements, Risk Management Framework (RMF) processes, and secure development within a DevSecOps framework. - Extensive knowledge of NIST 800-53 controls and ATO processes. - Demonstrated leadership and management experience overseeing technical teams of ten or more personnel. - Strong ability to work across matrixed and geographically dispersed teams. - Excellent written, verbal, and presentation communication skills, with the ability to translate technical data and reports into business-focused language for non-technical stakeholders. - Strong strategic thinking skills with the ability to balance technical execution and business objectives. - Demonstrated ability to lead change, manage risk, and drive continuous improvement initiatives. - U.S. citizenship and fluency in English required. - Ability to successfully pass criminal history, fingerprint background checks, and credential verification required. - Ability to maintain and retain suitability investigation and clearance as required. - Proficient in navigating electronic systems, computer programs, and virtual service platforms. - This position requires a separate, quiet, private, confidential space to work from, as well as having access to your own reliable high-speed internet hard wired to your home (coax or fiber from the Internet Service Provider (ISP) to your home.) Using a hot spot from a mobile device (tethering) or wireless ISP is not acceptable. If you're looking for comfort, keep scrolling. At Leidos, we outthink, outbuild, and outpace the status quo — because the mission demands it. We're not hiring followers. We're recruiting the ones who disrupt, provoke, and refuse to fail. Step 10 is ancient history. We're already at step 30 — and moving faster than anyone else dares. Original Posting: April 3, 2026 For U.S. Positions: While subject to change based on business needs, Leidos reasonably anticipates that this job requisition will remain open for at least 3 days with an anticipated close date of no earlier than 3 days after the original posting date as listed above. Pay Range: Pay Range $131,300.00 - $237,350.00 The Leidos pay range for this job level is a general guideline only and not a guarantee of compensation or salary. Additional factors considered in extending an offer include (but are not limited to) responsibilities of the job, education, experience, knowledge, skills, and abilities, as well as internal equity, alignment with market data, applicable bargaining agreement (if any), or other law.