Director of Technology Systems

Gateway Service Group•Herndon, VA

4d•$160,000 - $180,000•Hybrid

About The Position

Gateway Service Group is one of the fastest-growing commercial property services platforms in the country. We have already chosen the systems that will run this company. What we need now is the person who makes them work together — and who holds the vendors delivering them to the standard we set. This is not a strategy role looking for someone to pick a stack. It is an ownership role for someone who wants to build one. Gateway Service Group is a growing, private equity-backed commercial property services platform operating across lot sweeping, day porter, power washing, construction sweeping, and other exterior property service lines, with branches serving St. Louis, Atlanta, Washington, D.C., Dayton, Philadelphia, and Kansas City. The Director of Technology Systems owns how our technology platform performs: making the systems we have chosen work together, holding the vendors who deliver them accountable, and turning what comes out of them into visibility the business actually runs on. You are not joining a blank page. Our platform decisions are made and several systems are already live; your job is to finish the build, connect it, and get our systems adopted and talking to each other across every branch and every business we acquire. It is also a role that reaches across the whole company. Operations, finance, sales, and HR all depend on these systems, and none of them report to you. Credibility does the work that authority cannot — you earn it by making things work, and you keep it by being straight about what is not working yet. You will work closely with our sponsor’s technical operating partner, who continues to lead long-range architecture and cybersecurity, so you are not carrying the strategy alone. And there is room to grow here: we are hiring at Director level for someone who will own more over time as the platform scales.

Requirements

Eight or more years of progressive enterprise technology, business systems, or technical program management experience, with increasing ownership over time
At least one ERP or field service management implementation where you were the internal accountability owner on the company side — through configuration, integration, go-live, and adoption
Demonstrated experience rolling one platform out across multiple sites or business units and achieving real user adoption, including the data cleanup and migration work that goes with it
Direct experience holding an implementation partner, managed service provider, or platform vendor to scope, schedule, or SLA
Practical working knowledge of business system integration — able to read an integration design, run the data mapping, and hold an integrator accountable to it
Experience delivering operational and executive reporting off enterprise systems that operators actually used
Hands-on configuration experience within the last two years
Willingness to travel to our branch locations as rollouts require — up to 50%
A note on titles: we do not require that you have held a Director title. We care what you personally owned, not what your business card said or how many people reported to you. A manager or team lead who did this work is exactly who we are looking for.

Nice To Haves

A strong data and analytics background, including Power BI or comparable business intelligence tooling
Familiarity with the platforms in our stack or close equivalents — NetSuite and SuiteBilling, a field service management platform, HubSpot, Samsara, Fleetio, and telecom expense management
Multi-site services, field services, fleet, or facilities environments — ideally in a business growing through acquisition, and the systems work that comes with it
Experience with systems where failure has immediate consequence — payroll, billing, or dispatch
Access governance, segregation-of-duties remediation, or IT controls work
Bachelor’s degree in information technology, computer science, data science, engineering, or a related field — or equivalent practical experience

Responsibilities

Own the integration program — serve as the internal accountability owner for the integration between our ERP and our field service platform — holding milestones, vendor performance, and cross-functional coordination on schedule, with a 12-month execution plan approved by executive leadership within 90 days of start
Drive the selected stack into every branch — complete our ERP, billing, and field service rollouts across all locations, and carry the HRIS implementation — already well in flight by the time you arrive — through go-live and adoption
Deliver the reporting layer — the three to five executive KPIs the business runs on, plus recurring versus non-recurring revenue and gross margin by service line by location, built off the operating platforms where the data already lives
Own vendor and MSP relationships — contract oversight, SLA accountability, and licensing across the technology portfolio — including handling first-level triage internally before escalating outward, and holding implementation partners to the dates they committed to
Execute IT controls and access governance — including segregation-of-duties remediation, working through our managed service provider and alongside finance
Support systems work on acquisitions — our integrations team runs each deal; your job is to make sure no integration milestone waits on systems, vendor scheduling, or data capacity
Support compliance-driven technology needs — including fleet telematics and DOT reporting, contractor prequalification portals, and payroll and HRIS data integrity
Put AI to practical use — identify and implement AI-powered tools that automate real workflows, along with the governance and usage standards to deploy them responsibly
Manage the technology budget — report rollout progress and vendor performance to executive leadership regularly, and build institutional capability so that no system depends on one person’s knowledge — including your own