Director of Technology Systems

Shared Services | Hybrid — St. Louis or Washington, D.C., up to 50% travel

Reports to:

VP, Strategy and Corporate Development

$160,000–$180,000 base + 20% target bonus + equity participation

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.

• 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…