Director of Software Engineering

The Equity Management team is looking for a seasoned Director of Software Engineering to take on one of the most consequential roles in the organization  — leading the Platform & Architecture vertical.  Reporting to the Senior Director of Engineering, you will be responsible for greenfield development as well as the core existing application with a mature enterprise customer base and multiple Fortune 100 broker relationships.

You will own the success of a true 0-to-1 platform modernization — a ground-up greenfield project to build an equity platform as an Azure cloud-native application. You will join the initiative in its early phase and drive the teams through MVP and GA on an aggressive timeline.   insightsoftware is an AI-first organization, and this initiative is utilizing pure AI Spec-Driven Development (SDD) with GitHub SpecKit and Claude Code in the Azure stack (Azure SQL, Data Lake, Fabric, AKS, Entra, .NET, Angular). This is the single-most strategically important initiative in the organization. You'll partner directly with Solution Architecture, Engineering, Product Management, and UX in achieving cross-functional success. Technical direction for the modernization sits with the Solution Architect, functional direction sits with the Product team, execution sits with the Engineering Manager — your role owns the program delivery and holds every contributing team accountable. 

You will also own the existing application ecosystem running the business today — the core CEM platform and all broker integrations that 1,200+ customers depend on every day, top to bottom, from front-end to database. You'll own the stability, health, and delivery of the legacy application, and migration to the new platform when it is ready. 

You are the right person for this role if you thrive in leaning into ambiguity and forging the path ahead, are not afraid to fail fast, and recognize that sometimes it's better to proceed without all the facts rather than standing at the fork in the road waiting for the perfect circumstances. Extreme accountability, cross-team collaboration & leadership, client-facing, strong communication — these are a few of the traits that describe the ideal candidate. You'll lead these initiatives with somewhere between 4-6 teams, all with Managers and Senior Managers reporting directly to you. 

Modernization Initiative - Ownership & Delivery Accountability 

• Own overall delivery accountability for the modernization initiative — defining the plan, sequencing execution, and driving it to completion. 

• Partner closely with the Solution Architect, who owns technical direction and architecture decisions for the initiative; this role owns translating that direction into a resourced, sequenced, accountable delivery plan. 

• Continue to push boundaries in Spec-Driven Development (SDD), encouraging Lean and fail-fast experimentation. Grow the usage and adoption of modern AI development practices.   

• Own Engineering and QA/Automation directly for the modernization initiative, while driving Product and UI/UX as a matrixed, non-reporting partner toward the same outcome. 

• Establish and enforce delivery standards and definition-of-done discipline consistently across Engineering, Product, and UX/Design. 

• Proactively identify misalignment, blockers, and undecided cross-functional questions before they surface on their own - engineering, product, and design each report through different leaders, and this role is accountable for the seams between them. 

• Hold Engineering, Product, and UX/Design equally accountable for delivery commitments. This is a cross-functional accountability role - success requires driving outcomes with partners outside your direct reporting line, not just within it. 

• Communicate program status with complete candor to the Sr Director, VP, and executive stakeholders — including surfacing bad news early rather than smoothing it over in status reporting. 

Broker & Core CEM Portfolio Delivery 

• Own end-to-end delivery accountability for insightsoftware's broker integration programs. 

• Own delivery accountability for the core Certent Equity Management (CEM) platform serving 1,200+ global customers, ensuring committed roadmap items and client-critical fixes are delivered on schedule. 

• Balance capacity and prioritization across the initiative, broker programs, and core CEM delivery; escalate tradeoffs to the Sr Director directly and early when competing demands threaten committed dates. 

• Serve as the single point of delivery accountability across this full portfolio — executive leadership should get one clear, consistent narrative regardless of which program they're asking about. 

Team Leadership & People Management 

• Own people leadership across 4-6 teams, each led by a Manager or Senior Manager, spanning platform modernization, Broker Applications & Broker Integrations, Core CEM Application, and Platform Services. 

• Coach and develop the managers and senior managers reporting to you — including calibrating what kind of leadership a given team or program actually needs, and adjusting staffing decisions as needed. 

• Own hiring, onboarding, performance management, and retention across your organization; partner with the Sr Director on headcount and org design for the vertical. 

• Shield your teams' capacity from competing delivery pulls; escalate conflicts when external demands threaten committed delivery. 

• Build a high-trust, high-accountability culture — explicitly encouraging fast, reversible decisions over prolonged research cycles, and rewarding people who proactively surface risk. 

Required 

• 12+ years of software engineering experience in enterprise SaaS environments, including 5+ years leading multiple managers or senior managers at Director level or equivalent scope. 

• Demonstrated track record driving large, ambiguous, cross-functional programs to completion — defining the plan, sequencing execution, and holding every contributing team accountable, regardless of reporting line. 

• Demonstrated pattern of proactively surfacing organizational risk or misalignment that nobody asked you to look for — not just responding quickly to problems once they're visible, but actively investigating whether the plan everyone believes is true actually is. 

• Bias toward the smallest end-to-end slice that proves a concept works, over fully building out any one piece in isolation — comfortable shipping something rough and connected rather than something polished and disconnected. 

• Skilled at continually measuring progress against the next most important priority, and realigning the team and plan as that priority shifts — rather than executing a fixed plan on inertia. 

• Structures deliverables and sequencing to proactively avoid blockers and dependency conflicts before they occur — rather than resolving blockers reactively after they've already stalled a team. 

• Technical fluency in modern software architecture and Azure cloud-native platforms to partner credibly with a Solution Architect and translate technical direction into a delivery plan. This role is not expected to make architecture decisions. 

• Experience in data architecture — Azure SQL, Cosmos DB, Data Lake & medallion architecture with temporal tables. 

• Experience managing a portfolio with real external/customer stakes — client-facing programs, SLAs, or regulated delivery commitments, including direct customer-facing communication. 

• Strong executive communication skills — able to deliver complete, candid status to senior leadership, including surfacing problems early. 

• Demonstrated comfort operating in ambiguity — able to forge a path forward without a fully-defined plan handed down in advance. 

• Experience with modern software delivery practices: Agile/Scrum, CI/CD pipelines, code review standards, and definition-of-done discipline. 

• Experience managing distributed, global teams across multiple time zones. 

• Bachelor's degree in Computer Science, Engineering, Business, or equivalent work experience. 

• Proven track record in spec-driven or AI-assisted development methodologies. 

Preferred 

• Background in financial services, equity compensation, banking/brokerage integrations, or adjacent regulated domains. 

• Direct experience delivering enterprise SaaS programs serving 1,000+ clients.