Lead Software Engineer - Hybrid

Crisis Prevention Institute•Milwaukee, WI

3d•Hybrid

About The Position

The Lead Software Engineer is the technical lead of a Product Engineering squad on CPI's Integrated Training and Learning (ITL) platform, the cloud-native learning platform used by CPI's learners, Certified Instructors, and customer administrators worldwide. This is a hands-on, backend-focused role: the Lead spends the majority of their time designing and writing code in C#/.NET microservices built on CQRS and event-driven patterns in Azure, and is comfortable working across the full stack, including the React front end, when the squad's work requires it. As technical lead, the Lead Software Engineer owns the technical direction and delivery health of the squad: translating product outcomes into a sound technical approach, breaking work into small shippable increments, setting engineering standards, and ensuring the services the squad owns are reliable, observable, and easy to change. The Lead is a player-coach, not a manager: they raise the squad's technical bar through design reviews, code reviews, pairing, and mentorship, and they model the culture CPI is building in Product Engineering: curiosity, ownership, drive, experimentation, learning from failure, and relentless improvement.

Requirements

Bachelor's degree in computer engineering, computer science, or a related field, or equivalent practical experience
Seven years or more of professional software engineering experience building and operating production web applications and distributed services
Two years or more of experience as a technical lead, tech lead, or senior engineer responsible for the technical direction and delivery of a team
Five years or more of hands-on experience with C# and .NET (ASP.NET Core, .NET 6+) designing and building backend services and APIs
Deep experience with distributed, event-driven architectures: message brokers (Azure Service Bus or equivalent), idempotency, retries, sagas, and eventual consistency
Experience designing systems using CQRS, event sourcing, and/or domain-driven design, including defining bounded contexts and event contracts
Working experience with React and modern JavaScript/TypeScript sufficient to design, review, and contribute to front-end features
Experience designing relational data models and tuning SQL performance (SQL Server / Azure SQL)
Experience building and operating services in Azure (App Service, Functions, Service Bus, Azure SQL, Azure Monitor / Application Insights, Key Vault) or an equivalent cloud platform
Experience establishing and improving CI/CD pipelines (Azure DevOps or GitHub Actions), automated test strategies, and continuous delivery practices
Experience leading incident response and blameless post-incident reviews for production systems
Experience mentoring engineers and leading technical design and code reviews
Knowledge of observability practices (structured logging, metrics, distributed tracing, SLOs) and security-based design patterns
Experience using AI-assisted development tools daily and guiding others in their effective, responsible use
Yearly personal development demonstrated by successfully completing an accredited software engineering course, acquiring a software engineering-related certification, or presenting a completed learning project to the team
Curiosity: asks why before how, digs into unfamiliar code and systems, and seeks to understand the learner, instructor, and customer problem behind every request
Ownership: treats the services and features they touch as theirs to keep healthy, from design through production support, and does not wait to be assigned a problem before solving it
Drive: a bias toward shipping working software in small, frequent increments and following through until the outcome is achieved, not just the ticket closed
Experimentation: comfortable proposing and running small, time-boxed experiments (spikes, proofs of concept, A/B tests) and letting evidence, not opinion, settle technical debates
Learning from failure: participates openly in blameless retrospectives and incident reviews, shares mistakes as lessons, and turns them into guardrails, tests, or runbooks
Continuous improvement: leaves every codebase, process, and document a little better than they found it
Ability to lead a team technically without formal authority: earn trust, build consensus, and make timely decisions when consensus is not possible
Ability to balance short-term delivery with long-term platform health and to explain those trade-offs to product and business stakeholders
Ability to facilitate evaluation of technologies and achieve consensus on technical standards and solutions among a diverse group of engineers
Excellent verbal and written communication; able to write clear design documents and give direct, constructive feedback
Demonstrated ability to attract, develop, and retain strong engineers

Nice To Haves

Experience on a learning management system, EdTech, or other B2B SaaS product used by end users at scale
Experience decoupling a product platform from an ERP/CRM system of record such as Microsoft Dynamics 365
Experience with infrastructure as code (Bicep, Terraform) and containerized workloads
Experience with web accessibility (WCAG 2.1 AA)
Azure certifications (e.g., Azure Developer Associate, Azure Solutions Architect)

Responsibilities

Own the technical approach for the squad's roadmap: partner with the product owner to shape problems, evaluate options, and choose the simplest design that achieves the customer and business outcome.
Lead technical design for new features and services in the ITL platform: C#/.NET microservices, CQRS command/query handlers, event contracts on Azure Service Bus, Azure SQL data models, and React front-end integration.
Break epics into small, independently deployable increments; drive the squad toward frequent, low-risk production deployments using feature flags, trunk-based development, and automated testing.
Remain hands-on: write production code daily, take on the hardest or most ambiguous technical problems, and unblock the squad when it gets stuck.
Provide task breakdowns, identify dependencies and critical path, and give realistic effort estimates and risk assessments to the product owner and engineering manager.
Demonstrate the squad's work to business stakeholders and clearly connect technical work to customer and business impact.
Own the health of the services the squad is responsible for: define SLOs, ensure meaningful alerting and dashboards exist, participate in and help run the on-call rotation, and lead the response to production incidents.
Lead blameless incident reviews for the squad; ensure follow-up actions are prioritized and completed so the same failure does not recur.
Drive the incremental decoupling of ITL domain data from upstream enterprise systems: for each feature, identify the data ITL should own, design the migration, and ensure it flows to the data warehouse for reporting.
Champion continuous improvement of the codebase: identify and pay down technical debt deliberately, improve build/test/deploy times, and reduce operational toil through automation.
Ensure secure coding practices, accessibility standards (WCAG 2.1 AA), and performance considerations are built into the squad's definition of done.
Lead the squad's adoption of AI-assisted development tools (e.g., GitHub Copilot, Claude, Cursor): establish norms for using them well, including review and testing expectations for AI-generated code, and measure their impact on delivery speed and quality.
Use AI tools daily in your own work for design exploration, code generation, test writing, refactoring, and debugging, and model responsible use for the squad.
Partner with the Principal Software Engineer on the Product Engineering AI strategy; pilot new tools and techniques on the squad and share results across teams.
Identify and champion opportunities to apply AI within the ITL product or internal tooling where it creates measurable value for learners, instructors, and customers.
Set and uphold engineering standards for the squad: code review expectations, testing strategy, documentation, and architectural consistency with the broader ITL platform.
Mentor and coach engineers on the squad through pairing, design reviews, and regular feedback; help each engineer grow their technical skills and sense of ownership.
Create space for experimentation: sponsor time-boxed spikes and proofs of concept, insist on evidence in technical debates, and make it safe to try things that might not work.
Model learning from failure: own mistakes openly, turn them into lessons, guardrails, and runbooks, and lead retrospectives that produce real change.
Collaborate with other squad leads, the Platform team, and the Principal Software Engineer to align on cross-cutting technical decisions and shared standards.
Perform other position-related duties as assigned.