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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director of Technology and Innovation - **Company:** GAWLEY COMPANIES, LLC - **Location:** Dupo, IL, United States - **Experience:** Experienced - **Contract:** Permanent contract - **Skills:** Microsoft Windows, Active Directory, Artificial Intelligence, Apple Mac Systems, Microsoft Azure, Business Systems, Software as a Service, Cloud Engineering, Cyber Security, Customer Data Management, Data Migration, Dynamic Host Configuration Protocol, Domain Name System (DNS), Multi-Factor Authentication, Human Resources Information System (HRIS), Identity and Access Management, Virtual Private Networks (VPN), Windows PowerShell, Azure Active Directory, Microsoft Copilot, Systems Integration, TCP/IP, Software Vulnerability Management, Wi-Fi Technology, Software Licensing, Data Classification, Microsoft InTune, National Institute of Standards and Technology Cybersecurity Framework, AI Platforms, Infrastructure Automation Frameworks, Information Technology, Claude, CIS Benchmarks, GPT - **Published:** October 31, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=bbc7e5d91817581c ## About the Role * Bachelor's degree in Information Technology, Computer Science, or a related field, or equivalent professional experience. * 10+ years of progressive information technology experience spanning systems administration, infrastructure, and security, including at least three years in a lead, architect, or ownership role. * Demonstrated ownership of an organization's technology environment rather than execution within one - setting standards, making platform decisions, and being accountable for the result. * Deep hands-on expertise with Microsoft 365, Active Directory, Microsoft Entra ID, Intune or an equivalent endpoint management platform, and both Windows and macOS in a business environment. * Working command of networking across multiple sites: TCP/IP, DNS, DHCP, Wi-Fi, VPN connectivity, segmentation, and troubleshooting. * Demonstrated experience deploying AI tools in a business environment with measurable results - adoption that changed how work actually gets done, not experimentation. * Working knowledge of enterprise AI platforms (Microsoft Copilot, ChatGPT Enterprise, Claude, or equivalent), including licensing, administration, and data-protection configuration. * Practical information security experience - identity and access governance, endpoint hardening, patch and vulnerability management, backup and recovery, and incident response. * Experience managing an outsourced technology partner or Managed Service Provider, including scope, service levels, performance, and escalation. * Experience supporting multiple office locations or a geographically distributed workforce. * Experience owning or materially contributing to a technology budget, including licensing, procurement, and vendor negotiation. * A senior security or Microsoft certification - CISSP, CISM, SC-300, AZ-104, or equivalent - or the willingness to obtain one within the first year, with the cost covered by the company. * Excellent problem-solving, organizational, and prioritization skills, with a demonstrated ability to set your own agenda and work productively without close supervision. * Ability to explain technical trade-offs to executives and non-technical employees, and to translate business priorities into technical direction for internal staff and outside partners. * Ability and willingness to travel regularly to company locations, including occasional overnight travel. * Valid driver's license and ability to lift and install standard IT equipment., * 10+ years of progressive information technology experience, including ownership of security, infrastructure, and business systems for a multi-site organization. * Experience as the most senior technology decision-maker in an organization or business unit, or as a second-in-command prepared to step into that scope. * Experience leading technology due diligence and post-close integration for mergers or acquisitions. * CISSP, CISM, CCSP, CRISC, or an equivalent senior security certification. * Microsoft Expert-level certification (for example, Microsoft 365 Certified: Enterprise Administrator Expert or Azure Solutions Architect Expert), or equivalent. * Experience implementing a recognized security framework (CIS Controls, NIST CSF, SOC 2, or similar) and carrying an organization through customer, insurer, or auditor security review. * Experience owning a technology budget, negotiating vendor contracts, and governing a Managed Service Provider or outsourced partner. * Experience selecting or implementing ERP, HRIS, or industry-specific operational software, and integrating systems across departments. * Experience governing enterprise AI and SaaS adoption - access management, data-protection practices, acceptable-use policy, and end-user security awareness. * Experience building, hiring into, and developing a small internal technology team. * PowerShell scripting or infrastructure automation experience. * Background in construction, contracting, manufacturing, distribution, or another field-based, multi-site industry. * Familiarity with AI risk in a contracting context - customer data, employee data, and confidentiality obligations in bids and contracts. ## Description Technology Strategy & Architecture * Own the multi-year technology roadmap for the company and its operating subsidiaries, translating growth and acquisition plans into architecture, platform, and investment decisions. * Define and maintain the technology standards - endpoint, identity, network, cloud, and application - that every Goley company is brought onto. * Evaluate, select, consolidate, and retire platforms; build the business case for major technology investments and present recommendations to executive leadership. * Own the technology budget: forecast capital and operating spend, track licensing and vendor costs, and tie spend to business outcomes. * Translate technology decisions into plain business language for leadership, and business priorities into technical direction for partners and vendors. Cybersecurity & Risk * Own the company's information security program end to end - policy, controls, access governance, security awareness training, and incident response. * Map the environment to a recognized framework (CIS Controls, NIST CSF, or equivalent), run gap assessments, and drive remediation against a published schedule. * Lead incident response: detection, containment, coordination with forensics and counsel, notification obligations, and post-incident corrective action. * Own cyber-insurance questionnaires, customer and partner security reviews, and third-party vendor risk assessments. * Maintain business continuity and disaster recovery plans, and test restores and failover on a defined cadence rather than assuming they work. Data, AI & Business Systems * Own the company's AI strategy - identify where AI creates measurable leverage across estimating, project documentation, scheduling, safety, back-office, and customer communication, and build the roadmap to capture it. * Run structured pilots with defined success criteria: prove value on a small scale, kill what doesn't work, and operationalize what does with training, documentation, and support. * Build the guardrails that make AI adoption safe at scale - acceptable-use policy, data classification, clear rules on what may and may not be placed into external models, vendor data-handling review, and auditable access control. * Lead AI enablement across the entire workforce, from field supervisors to executives, so adoption isn't limited to the technically curious. * Automate internal processes through scripting, workflow tools, and AI-assisted agents, reducing manual effort in IT, finance, HR, and operations rather than adding headcount to absorb it. * Evaluate AI capability already embedded in the systems we own - Microsoft 365, ERP, project management, estimating - before purchasing new point solutions. * Track the field and brief leadership in plain business terms on what is real, what is hype, and what we should act on this year. * Measure and report on AI outcomes - hours saved, error rates, cycle time - so continued investment is justified by results rather than enthusiasm. Infrastructure, Identity & Endpoint * Own the identity model across the organization - Active Directory, Microsoft Entra ID, conditional access, multi-factor authentication, privileged access, and the joiner/mover/leaver process. * Own the endpoint standard and lifecycle through Intune or an equivalent platform: hardening baselines, patching, compliance, deployment, and secure retirement. * Own network, server, and cloud architecture in partnership with our Managed Service Provider - site connectivity, segmentation, backup, and monitoring. * Maintain accurate inventories of hardware, software licensing, warranties, and technology assets across all company locations, and own lifecycle and refresh planning. Acquisition Integration * Lead technology due diligence on acquisition targets: assess the existing environment, surface security and licensing risk, and estimate integration cost and timeline before close. * Own the post-close integration plan - identity, email, endpoint, applications, and data migration - and the repeatable playbook that makes each next integration faster. * Serve as the technology face of integration to acquired leadership and employees, providing responsive support through the transition. * Inventory inherited hardware, software, licensing, and user environments, and document the infrastructure you are absorbing. Vendor, Partner & MSP Management * Own the relationship with our Managed Service Provider: scope, service levels, performance review, escalation, and the ongoing decision of what stays outsourced versus what comes in-house. * Negotiate contracts, renewals, and licensing with technology vendors, carriers, and service providers. * Hold partners accountable to deliverables and keep the boundary between internal and external responsibility clearly documented. Team Leadership & Hands-On Execution * Build the internal technology function as the organization scales - define the roles, hire, and develop the people who fill them. * Operate as a player-coach: this role still configures, deploys, troubleshoots, and resolves issues directly, particularly during integrations and at sites. * Create the documentation, runbooks, and standards that allow others to execute consistently without you in the room. * Provide senior escalation support for complex technical issues across headquarters and branch locations. Site Presence & Travel * Travel regularly to company locations for hands-on support, equipment and infrastructure projects, office moves, and preventative maintenance. Most sites are drivable day trips from Dupo; some require flights and overnight stays. * Proactively identify technology and security improvements during site visits rather than waiting for requests. * Plan travel based on business priorities, acquisition timelines, refresh cycles, and operational needs. * Support office expansions, workstation deployments, conference room technology, and local infrastructure needs.