Flexera saves customers billions of dollars in wasted technology spend. A pioneer in Hybrid ITAM and FinOps, Flexera provides award-winning, data-oriented SaaS solutions for technology value optimization (TVO), enabling IT, finance, procurement and cloud teams to gain deep insights into cost optimization, compliance and risks for each business service. Flexera One solutions are built on a set of definitive customer, supplier and industry data, powered by our Technology Intelligence Platform, that enables organizations to visualize their Enterprise Technology Blueprint™ in hybrid environments—from on-premises to SaaS to containers to cloud.
We’re transforming the software industry. We’re Flexera. With more than 50,000 customers across the world, we’re achieving that goal. But we know we can’t do any of that without our team. Ready to help us re-imagine the industry during a time of substantial growth and ambitious plans? Come and see why we’re consistently recognized by Gartner, Forrester and IDC as a category leader in the marketplace. Learn more at flexera.com
We are building a new model for software engineering: a small, highly autonomous engineering team that combines experienced technical leadership, talented developers, and AI coding agents to deliver high-quality software with exceptional speed.
We are looking for a hands-on Principal Engineer & AI Technical Lead to establish and lead this team. You will be responsible for technical direction, architecture, engineering quality, and delivery outcomes while actively developing software alongside two supporting engineers and AI tools such as Claude Code and OpenAI Codex.
This is not a traditional engineering management position. You will remain deeply involved in design, implementation, code review, debugging, and production delivery. Your leverage will come from making sound technical decisions, decomposing complex problems into manageable work, building effective AI-assisted workflows, and enabling a small team to operate with significant independence.
You will own outcomes rather than simply oversee tasks.
What You'll Do:Technical Leadership and Architecture
- Own the technical architecture, design decisions, and implementation strategy for the team's applications, services, and systems
- Translate business objectives and product requirements into pragmatic, maintainable technical solutions
- Make sound trade-offs between delivery speed, reliability, security, scalability, and long-term maintainability
- Establish lightweight engineering standards, architectural patterns, coding conventions, and documentation practices
- Identify opportunities to simplify systems, eliminate unnecessary complexity, and accelerate delivery
- Ensure the team builds software that can be understood, tested, operated, and evolved by engineers beyond its original authors
- Make AI coding agents a first-class part of the development lifecycle, using tools such as Claude Code, OpenAI Codex, and other appropriate AI engineering tools
- Develop effective workflows for AI-assisted requirements analysis, code generation, test creation, debugging, refactoring, code review, and documentation
- Decompose work into clear, bounded tasks that AI agents can execute independently, in parallel, and with measurable results
- Establish project context, repository instructions, reusable prompts, agent skills, automated checks, and other mechanisms that improve the consistency of AI-generated work
- Evaluate AI-generated code critically, recognizing when to accept, modify, or reject its output
- Continuously improve the team's engineering workflow based on actual delivery results rather than AI usage or code-generation volume
- Take responsibility for delivering production-ready capabilities from problem definition through deployment and operational support
- Collaborate with business stakeholders, product owners, users, and other engineering teams to clarify requirements and prioritize work
- Break larger initiatives into small, independently testable increments that can be delivered frequently
- Identify and resolve technical blockers without introducing unnecessary meetings, dependencies, or handoffs
- Establish appropriate observability, deployment automation, rollback procedures, and operational safeguards
- Monitor production outcomes and use feedback to improve the product and engineering process
- Define a practical quality strategy covering automated testing, code review, integration testing, and production validation
- Ensure AI-generated changes are verified through appropriate tests, static analysis, security checks, and human review
- Establish guardrails for AI access to source code, credentials, production systems, customer data, and other sensitive resources
- Prevent shortcuts that create unacceptable security, reliability, compliance, or maintainability risks
- Make quality controls increasingly automated so that a small team can move quickly without relying on manual inspection for every routine check
- Lead by example through hands-on engineering, thoughtful technical decisions, and disciplined execution
- Mentor two supporting engineers through pairing, code reviews, design discussions, and progressively more challenging assignments
- Build a culture of ownership, experimentation, direct communication, accountability, and continuous learning
- Help engineers develop the judgment to direct AI agents, validate their work, and solve problems independently
- Avoid becoming a bottleneck by delegating meaningful ownership and creating reusable patterns and automated guardrails
- Share successful AI engineering practices with the broader engineering organization
Required Qualifications:
- Significant professional software engineering experience, typically 8+ years, with demonstrated technical leadership appropriate to a Principal or Staff+ engineer
- Strong software design and architecture skills, with the ability to balance simplicity, delivery speed, maintainability, and operational needs
- Demonstrated experience delivering and operating production software end to end
- Strong programming skills in at least one of our primary technology stacks, with the ability to work across application layers when needed
- Deep understanding of testing strategies, CI/CD, version control, observability, application security, and production troubleshooting
- Practical experience using AI coding agents such as Claude Code, OpenAI Codex, or comparable tools in real engineering workflows
- Ability to break ambiguous business problems into well-defined technical tasks and independently drive them to completion
- Excellent technical communication, problem-solving, mentoring, and decision-making skills
- A track record of taking ownership of outcomes rather than limiting responsibility to assigned implementation tasks
Preferred Qualifications:
- Experience building or leading small, autonomous, cross-functional engineering teams
- Experience with agentic coding workflows, parallel AI task execution, repository-level instructions, and automated validation pipelines
- Experience establishing internal developer platforms, reusable engineering templates, or AI-enabled development infrastructure
- Experience in our relevant industry, domain, and technology stack
- Experience improving delivery lead time, software quality, operational reliability, or engineering productivity through measurable changes
#LI-REMOTE
#LI-DL1#LI-Development
Flexera is proud to be an equal opportunity employer. Qualified applicants will be considered for open roles regardless of age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by local/national laws, policies and/or regulations.
Flexera understands the value that results from employing a diverse, equitable, and inclusive workforce. We recognize that equity necessitates acknowledging past exclusion and that inclusion requires intentional effort. Our DEI (Diversity, Equity, and Inclusion) council is the driving force behind our commitment to championing policies and practices that foster a welcoming environment for all.
We encourage candidates requiring accommodations to please let us know by emailing [email protected].
Flexera Itasca, Illinois, USA Office
We are in an area that is easily accessible (about 20 minutes from Chicago/Ohare airport) in a area with plenty of restaurants, a pond, and a walking path.
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