Senior Director of Engineering, Platform Modernization

Why Work Here

• Headquarters is in Charlotte, NC
• Recently expanded to nearshore
• isolved ranked for SMB Payroll in 2023 Sapient Report
• Voted top places to work in USA 2023

Job Description

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.

Core Job Duties

• 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

Minimum Qualifications 

• 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

About isolved

isolved is a leading provider of human capital management (HCM) solutions that combines modern technology with expert services and support. Purpose-built for People Heroes™, isolved gives HR, payroll and benefits leaders the tools and insights to streamline operations and deliver employee experiences that matter. isolved People Cloud™ is a connected HCM platform with built-in artificial intelligence (AI) and analytics that brings together HR, payroll, benefits, workforce management and talent management in one experience. Built on a legacy of 40 years in the market, isolved is trusted by more than 200,000 employers and used by 9 million U.S. employees, representing about one in 20 American workers. Visit www.isolvedhcm.com.

#LI-KJ1