Director of Technology Systems

GATEWAY SERVICE GROUP 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.
About Gateway Service Group
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.
Position Overview
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.
Key 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

Who You Are

• Player-coach: you design the plan and execute it personally — equally comfortable presenting a roadmap in the boardroom and configuring a system the next morning in the field at our local branches
• Builder: you have built integrations and reporting systems from scratch, and you know what it takes to go from zero to operational in a resource-constrained environment
• Owner: when something breaks, you find out about it before anyone has to tell you. When a vendor slips or an integration breaks, you own it to resolution rather than relaying the vendor’s excuse, and you surface problems to leadership early rather than after they compound
• Communicator: you explain complex technology decisions in plain language, and you approach non-technical colleagues with patience and clarity — whether they run a branch or sit on the leadership team
• Resourceful: you do not default to needing more headcount when there is a gap — you find a way with what you have, then build the system that prevents the gap from coming back
• Coachable: you will work with a technical operating partner and an executive team who will challenge you, and you get curious rather than defensive when someone tells you that you are wrong
• Dependable and team-first: crews get paid on time because the systems work. You show up the same way for the high-visibility work and the unglamorous implementation detail, you share what you know freely, and you never let the systems live only in your head

Required Qualifications

• 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.

Preferred Qualifications

• 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

Compensation & Benefits
Base salary of $160,000 to $180,000, depending on market and experience. The range reflects differing market baselines between our St. Louis and Washington, D.C. locations. In addition:

• Performance bonus targeted at 20% of base, based on company and individual performance
• Equity participation in Gateway Service Group, subject to plan eligibility and terms
• Medical, dental, and vision insurance
• Retirement plan with company contribution
• Paid time off and company holidays
• Hybrid schedule with flexibility, based from either St. Louis or Washington, D.C.