Job DescriptionXactimate is the industry-standard platform for property claims estimating, and Xactimate Desktop is its primary client application: a large, actively modernized Windows desktop product with a substantial engineering footprint.
We're hiring a Software Development Manager to lead this team through its next phase of new feature delivery and platform modernization. You'll own delivery, technical direction, and people leadership across the team.
This is a hands-on leadership role for someone who wants to run a substantial, high-visibility desktop product. We're looking for strong technical judgment, problem-solving, and the ability to synthesize across technical, product, and business context.
ResponsibilitiesPeople Management- Manage 4 team leads and 3 principal engineers directly, providing coaching, career development, and performance management.
- Create clarity and accountability for individual and team goals across a ~30-person org.
- Drive hiring, onboarding, performance reviews, and compensation input for your reports.
- Support the growth of leads and engineers through regular feedback and mentoring, regardless of location or time zone.
Delivery & Execution- Own reliable, high-quality delivery across the team's active initiatives.
- Collaborate with Product, QA, and architecture to scope, prioritize, and plan work against committed deadlines, and own outcomes in partnership with them rather than just executing assigned scope.
- Remove delivery impediments and own escalation paths for the team.
- Own production support, monitoring, and incident response for a widely used desktop client.
Technical Leadership & Modernization- Provide direction on technical decisions in partnership with principal engineers and architects across a large modular monorepo (shared business, data, database, and UI libraries), grounded in technical judgment and systems thinking, not necessarily prior hands-on time in this exact stack.
- Own CI/CD pipeline health for the team: build, test, and release automation across the monorepo, evolving it as the codebase and delivery cadence grow.
- Own release and deployment engineering, ensuring build, packaging, and update processes stay reliable as the platform evolves.
- Lead the team's legacy-to-modern technology transitions, balancing continued feature delivery against migration debt and sequencing risk.
- Ensure code quality, scalability, and maintainability across a mix of modernized and legacy .NET targets.
- Champion engineering best practices, including testing, secure development, and technical documentation.
- Use delivery and quality data to inform decisions and communicate status to stakeholders.
- Serve as a point of technical continuity for a product deeply integrated into the broader insurance claims ecosystem: assignment/intake workflows, estimate synchronization, pricing, policy/coverage context, compliance validation, and partner data exchange.
Org & Culture- Model hands-on leadership in AI-assisted engineering practices, at the individual, team, and organizational level, rather than delegating AI adoption to others.
- Drive engagement and inclusion across the team.
- Influence engineering-wide practices as scope expands; participate in org-wide initiatives and guilds.
The Technical Environment You'll LeadYou don't need pre-existing expertise in this exact stack to succeed here. You need the technical judgment and ability to ramp quickly, including with AI-assisted tools, into:
- C#/.NET Windows desktop application development; WPF as the primary UI framework with some WinForms; MVVM-oriented architecture.
- SQLite-backed local data and storage.
- Large modular monorepo with shared business, data, database, and UI libraries; MSBuild, Visual Studio, NuGet.
Qualifications- Proven experience managing software engineering teams of comparable scale, including managing other people-managers (e.g., Team Leads), not only individual contributors.
- Strong technical judgment and systems thinking: able to evaluate architecture, tradeoffs, and risk, and engage directly and credibly in technical decisions, even outside your own prior stack experience.
- Demonstrated problem-solving ability: a track record of diagnosing and resolving complex technical and organizational problems, not just managing others who solve them.
- Ability to synthesize across technical, product, and business context: connecting delivery data, incidents, stakeholder input, and strategic priorities into clear decisions and direction.
- Demonstrated ability to rapidly build technical fluency in unfamiliar domains, including using AI-assisted tools to accelerate ramp-up and decision-making. This is core to how the role operates, not a nice-to-have.
- Direct experience owning or significantly evolving CI/CD pipelines for a production codebase.
- Direct experience leading a legacy-to-modern technology migration (framework, platform, or architecture upgrade) while maintaining active delivery commitments.
- Demonstrated ownership of production delivery, incident response, and operational excellence for a widely used software product.
- Track record of coaching and developing engineering leads and senior engineers.
- Effective communicator able to engage both technical and non-technical, cross-functional stakeholders (Product, QA, architecture).
Preferred Qualifications- Prior experience with desktop or native client application engineering (e.g., C#/.NET, WPF, WinForms, or a comparable native UI framework): a plus, not required.
- Experience with Windows installer and release engineering.
- Experience leading distributed teams across US and international (particularly India) time zones.
- Hands-on experience with AI-assisted engineering tools and practices.
- Familiarity with cloud-hosted services that a desktop application integrates with (this role does not own cloud infrastructure directly).
- Experience in an insurance, claims, or similarly regulated/data-sensitive domain.
Success Measures- Consistent, predictable delivery against committed timelines.
- Stable production health: incident frequency, severity, and time-to-resolution trending favorably for the desktop client.
- Demonstrated coaching impact: growth and retention of team leads and senior engineers under your leadership.
- Successful, low-disruption execution of platform modernization work, including measurable CI/CD pipeline improvements.
- Effective cross-functional partnership with Product and QA reflected in delivery predictability and stakeholder confidence.
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