Senior Director of Engineering, Platform Modernization
About The Position
isolved is executing a multi-year decomposition of a 7M+ line HCM monolith into modern, domain-isolated microservices, and we're looking for the person to lead it. This is a hands-on technical leadership role reporting directly to the CTO, responsible for both running the program and staying close enough to the work to make good decisions about it. You'll lead a program of approximately 20 engineers organized into domain teams (Tax, Benefits, Time, Payroll, Shared Logic), with two Engineering Managers and a Data Architect. You're not just managing delivery - you're a technical voice in how the work gets done, an escalation point when teams hit hard problems, and the person accountable to the CTO for outcomes.
Requirements
- 10+ years of engineering experience, with at least 3–5 years in a senior engineering leadership role
- Direct experience leading a large-scale modernization, re-platforming, or decomposition program - you understand what makes these programs succeed and fail
- Strong enough technical depth to engage credibly with principal engineers on architecture, data modeling, and distributed systems tradeoffs - you don't need to write all the code, but you need to understand it
- Experience managing engineering managers and leading through them at scale
- Track record of delivering complex, multi-team programs with cross-cutting dependencies in a production environment
- Clear, direct communication style - comfortable presenting to executives and working through ambiguity without needing complete information
- Familiarity with the Azure ecosystem and modern distributed systems patterns (event-driven architecture, microservices, IaC)
- HCM, payroll, benefits, or tax domain experience
- Hands-on background with .NET / C#, Cosmos DB, or Azure Service Bus
- Experience building or scaling engineering teams from the ground up
Responsibilities
- Own the modernization program end-to-end - roadmap, sequencing, dependencies, risks, and delivery outcomes across all five workstreams
- Drive extraction sequencing decisions in partnership with the Lead Architect, balancing technical risk, business continuity, and team capacity
- Maintain visibility across all domain teams and surface issues before they become blockers
- Represent the modernization program to senior leadership and the CTO, with clear, data-grounded communication on progress, risks, and tradeoffs
- Stay close enough to the architecture and implementation to make informed decisions, challenge assumptions, and support teams when they hit difficult problems
- Partner with the Lead Architect on technical direction - event schema strategy, infrastructure standards, paved road compliance, cross-workstream data dependencies
- Understand the full technology stack well enough to assess quality, identify risk, and have credible technical conversations with principal-level engineers
- Ensure AI-assisted development practices are embedded across teams and delivering real productivity gains
- Directly manage two Engineering Managers, each supporting approximately 10 engineers
- Build and maintain a high-performance team culture in a remote, distributed environment
- Own hiring for the program in partnership with the CTO - identifying, recruiting, and closing principal-level engineers and architects
- Support career development for EMs and, through them, the broader engineering team
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
