Manager, Software Development

Company Description

Trupanion is a leading provider of medical insurance for cats and dogs in North America. Our mission is to help loving, responsible pet owners budget and care for their pets. At Trupanion, we offer a collaborative, casual, and pet-friendly environment where everyone is encouraged to be themselves.

Job Description

We are seeking a highly hands-on Software Engineering Manager to lead teams building and operating mission-critical systems. This role is for a leader who is deeply technical, personally engaged in code and architecture, and accountable for production outcomes. You will actively troubleshoot live issues, lead incident resolution, and ensure the team consistently delivers reliable, high-quality software while continuously raising the performance bar.

This is not a purely managerial role. Success requires strong technical judgment, direct involvement in engineering work, the ability to attract and retain top-tier engineering talent, and the capability to operate effectively across diverse teams with competing priorities and directives.

This position is open to candidates in the Seattle, WA area. You will have a hybrid remote/in-office schedule where you will work from our casual, pet-friendly office at least 3 days a week.

Key Responsibilities

Hands-On Technical Leadership

• Serve as a hands-on technical leader, actively involved in system design, architecture, code reviews, and troubleshooting.
• Bring deep expertise in the Microsoft stack, including .NET, C#, and Azure, and apply it directly to real production systems.
• Personally dive into complex technical problems, including debugging and diagnosing issues in live production environments.
• Lead technical discussions and decisions, clearly articulating technical and business trade-offs across performance, scalability, reliability, security, cost, and delivery speed.
• Partner with senior engineers and architects to evolve systems while maintaining stability and operational excellence.

Production Ownership & Incident Management

• Own the health, reliability, and operational readiness of production systems.
• Lead and personally contribute to the resolution of urgent production incidents, including hands-on investigation and troubleshooting.
• Drive structured incident response / RCA’s, clear communication, and rapid mitigation.
• Lead post-incident reviews, root-cause analysis, and execution of preventative actions.
• Establish strong operational practices, monitoring, and on-call readiness.

Execution & Delivery

• Drive flawless execution by ensuring work is well-scoped, well-designed, and delivered predictably.
• Hold teams accountable for engineering quality, operational excellence, and long-term maintainability.
• Make timely, pragmatic decisions when trade-offs are required to meet business objectives.
• Proactively drive innovation with new ideas and options made available by new technologies.
• Maintain and actively contribute to a list of innovation & research projects.
• Assist by offering strategic and technical advice for anyone working on these projects.
• Drive a shift-left culture into development from QA and DevOps.

Best Practices, Standards and Compliance

• Define and enforce development and coding standards and other Software Development Best Practices.
• Ensure Trupanion and its developers are compliant with all relevant security and compliance standards ( ISO, SOX, etc).
• Design and implement development policies and procedures and ensure they are followed, including (but not limited to) ISO, PCI DSS and Trupanion test/release processes.
• Stay aware of the latest data protection and security threats, update team members accordingly, and mitigate against known industry standards.
• Ensure your knowledge of software development is kept up to date and relevant by networking/researching/reading blogs and news sources/training courses.

Cross-Team Leadership & Synthesis

• Work effectively across varied and diverse teams, including engineering, product, operations, and business stakeholders.
• Navigate differing priorities, incentives, motivators, and directives
  across teams.
• Synthesize multiple perspectives and approaches into clear, actionable paths forward.
• Provide decisive leadership when alignment is unclear, ambiguity is high, or trade-offs are required.
• Influence without authority by building trust, credibility, and shared understanding.

Talent Leadership: Hiring, Retention, Performance, Mentorship

• Recruit, hire, and retain top-notch technical talent, maintaining a consistently high bar for engineering excellence.
• Personally assess technical depth, judgment, and ownership during hiring.
• Create an environment where strong engineers want to stay: meaningful problems, high standards, autonomy, and growth.
• Actively performance manage underperforming employees, including improvement plans and termination when necessary.
• Build and sustain a culture of accountability, ownership, and continuous improvement.
• Mentor engineers at all levels with a strong focus on technical depth, system thinking, and operational ownership.
• Develop senior engineers into future technical and organizational leaders.
• Continuously raise the technical and performance bar of the team.

Communication & Executive Engagement

• Demonstrate top-notch communication skills, both written and verbal.
• Synthesize complex technical and business scenarios into clear, concise, and actionable communication.
• Communicate risks, trade-offs, and production impacts effectively to senior and executive leadership.
• Provide clarity during high-pressure situations such as production incidents or shifting priorities.
• Ensure alignment and transparency across technical and non-technical
  stakeholders.
• Ensure deep understanding of issues and root causes and be able to speak both to technical and business impacts of issues in a clear, accurate, and timely fashion.
• Proactively provide status updates frequently and accurately to management and stakeholders.

Qualifications

Required

• 3+ years working as a Software Development Tech Lead or Software Development Manager
• Bachelor’s degree preferred, ideally in Computer Science or other technical discipline.
• Proven experience as a Software Engineering Lead or Manager with significant hands-on technical involvement.
• Deep, practical experience building and operating production systems using .NET, C#, and Azure.
• Experience leading a team of in-house and remote developers across different time zones
• Demonstrated ability to personally troubleshoot and resolve complex production issues.
• Strong system design and architectural skills.
• Proven ability to recruit, hire, and retain high-performing engineers.
• Experience working across multiple teams with differing goals and constraints.
• Exceptional ability to communicate complex technical and business concepts clearly.
• Comfort with direct performance management, including difficult conversations and termination decisions.
• Ability to collaborate effectively with the business analysts, program managers, business leaders, and SMEs to ensure solutions meet business needs
• Proficient with the Agile methodology

Preferred

• Experience in the insurance industry or other regulated, mission-critical domains (bonus, not required).
• Experience operating high-availability systems and on-call rotations in Azure-based environments.

Additional Information

Compensation:

• The pay range for this position is $155,000 to $160,000, on a full-time schedule.
• Along with base salary, Trupanion employees may be eligible for monthly bonuses.
• We want all employees to be invested in Trupanion’s success, so we grant Restricted Stock Units to all new team members. Our new hire grants vest over 4 years.

Benefits and Perks:

• Full medical, dental, and vision benefits at no cost to the employee
• Four weeks of paid time off and 9 paid float holidays (you can decide which days are most important to you!)
• Five-week sabbatical after five years of employment
• Open, casual, pet-friendly, and fun office environment
• Free medical health insurance for your pet (1 dog or cat)
• Paid time off to volunteer at nonprofit organizations
• Seattle Office Amenities: Free on-site gym, free dog walking services for office pets during business hours, free parking, and paid ORCA cards.