Software Executive Jobs in Mobile, AL (NOW HIRING)

Chief Technology Officer

Thompson Holdings Inc. - Mobile, AL

Full-Time • Reports to CEO

Thompson Holdings Inc. is a 100% employee-owned (ESOP) holding company headquartered in Mobile, Alabama. Thompson Holdings is the parent company of four subsidiaries:

• Thompson Engineering - Multi-disciplined civil/structural/environmental engineering firm established in 1953
• Watermark Design Group - Architectural and interior design firm serving the Gulf Coast and Southeast
• Thompson Consulting Services - Full-service emergency response, disaster planning/recovery, and grant management
• Sourcetoad - Tampa-based software development, AI, automation, and technology consulting firm (acquired Jan 2026)

This is a newly created enterprise-wide role. The CTO will serve as an executive-level technology leader for Thompson Holdings, working alongside the executive leadership team to set and advance technology strategy across the holding company and all subsidiaries. This position will include evaluating third-party technology solutions, developing enterprise digital solutions, and creating a data strategy and practical governance model across the organization. While the CTO may leverag e Sourcetoad's software, AI, automation, and technology consulting capabilities, this is one component of a broader enterprise technology strategy in an enterprise wide capacity The CTO will build a cohesive technology strategy and position Thompson as a differentiated, technology-enabled competitor in the AEC, disaster recovery, and professional services markets. The CTO will also be tasked with innovating and streamlining process-based tasks for Corporate services including HR, Safety, Legal, IT, Finance, and Communication as Thompson continues to scale. The CTO will have a keen understanding of digital innovation, enterprise data governance, digital solutions delivery, and corporate governance and will serve in a strategic, cross-functional position that requires equal parts vision, credibility, and hands-on execution of technology-enabled solutions.

1. Enterprise-Wide Technology Strategy Across the Portfolio
   • Work with all companies to develop and own a unified technology roadmap
   • Evaluate and prioritize technology capabilities across the enterprise, including Sourcetoad's custom software, AI, automation, and systems modernization expertise can create the highest ROI across all companies
   • Establish technology governance: standards, platforms, and decision frameworks that allow subsidiaries to remain operationally autonomous while benefiting from shared infrastructure
   • Partner with enterprise IT leadership to develop technology roadmaps that balance innovation with operational reliability and risk management
   • Create and lead the enterprise data strategy, including development of a scalable data fabric that connects business, operational, financial, project, client, and other data sources across the enterprise while respecting each company's operational needs.
   • Establish enterprise data governance practices, including data ownership, stewardship, quality, access, security, integration standards, and decision rights needed to support reporting, automation, AI, and digital solutions
2. Enterprise Innovation, Digital Solutions & Sourcetoad Capability Integration
   • Serve as the executive-level technology bridge across Thompson Holdings and all subsidiaries
   • Drive enterprise adoption of technology-enabled tools and solutions, including Sourcetoad-built products where appropriate, from automated debris management systems for disaster recovery to digital project delivery tools for engineering and shared corporate services
   • Lead the design, prioritization, and delivery of enterprise digital solutions that improve project delivery, field operations, disaster recovery workflows, corporate services, client experience, and management visibility
3. AI & Emerging Technology Leadership
   • Define how AI and machine learning are applied responsibly across the enterprise - prioritizing genuine business impact, operational improvement, and scalable adoption over experimentation
   • Partner with subsidiaries to build, evaluate, and scale AI-enabled solutions
   • Keep Thompson ahead of the technology curve in industries (AEC, disaster recovery) that are mid-transformation
   • Lead and Manage technology driven projects from inception to implementation
   • Align emerging technologies, AI solutions, software development efforts, digital transformation projects, and data fabric initiatives with corporate cybersecurity, compliance, data governance, and infrastructure standards across the enterprise
4. Market Differentiation & Client Value
   • Help package and position Thompson's combined engineering + software + AI capabilities and technology tools as a competitive differentiator in the market
   • Partner with subsidiary leaders and business development teams to identify and pursue technology-enabled service opportunities
   • Represent Thompso n's technology vision by partnering with subsidiaries to support clients, partners, and industry associations
5. Change Management & Technology Adoption
   • Lead technology adoption across a workforce that ranges from software engineers to field-based disaster recovery professionals
   • Work within a heterogeneous technology environment: Windows-based enterprise infrastructure across three subsidiaries, Apple/Linux environments at Sourcetoad
   • Build trust with subsidiary leaders and employee-owners so technology is viewed as an enterprise-wide enabler, not an imposition
6. Technology M&A Support
   • Advise on future acquisitions from a technology perspective: assess tech maturity, identify integration risks, and evaluate strategic fit
   • Lead technology integration for new subsidiaries post-acquisition

• 15+ years of progressive technology leadership, including 5+ years in a senior technology executive role (CTO, VP Technology, or equivalent)
• Background in professional services, AEC, engineering, construction, consulting, or government services - or demonstrated experience leading technology transformation in these industries
• Experience managing or closely partnering with software development organizations; sufficient technical depth to earn the respect of engineers
• Proven track record managing technological solutions across multiple business units or entities
• Experience with technology-driven M&A: integration planning, due diligence, or post-acquisition rationalization
• Familiarity with ESOP, employee-owned, or mission-driven organizational cultures is a meaningful plus
• Experience with Management of employees and hands on technology driven solution implementation.

• Strategic thinker who can translate technology vision into tangible business outcomes
• Credible with two very different audiences: enterprise-minded operational leaders and software-native engineering teams
• Strong change management skills; comfortable engaging busy professionals in environments of various technological maturity
• Working knowledge of AI/ML applications, modern software development practices, and cloud infrastructure - not necessarily a practitioner, but informed enough to lead
• Demonstrated ability to shape enterprise data strategy, data governance, and digital solutions roadmaps that turn fragmented systems and data sources into scalable business capabilities
• Practical, ROI-focused mindset consistent with an employee-owned, growth-oriented business

• A pure enterprise IT / infrastructure leader (that is a CIO function, not this role)
• A startup or Silicon Valley background without services-industry grounding or exposure
• A visionary without execution muscle - Thompson Holdings is a builder culture and is looking for a hands on technology leader who can manage and stay on task with project implementation.
• Someone who wants to standardize everything on day one; subsidiaries retain meaningful operational autonomy

Reports to: CEO, Thompson Holdings Inc.

Peer relationships: Subsidiary Leaders (Thompson Engineering, Watermark, Thompson Consulting, Sourcetoad)

Key working relationships: Enterprise wide - including subsidiary leaders, corporate services, enterprise IT, and Sourcetoad leadership as a strategic technology partner.

Location: Flexible / Remote-friendly; Mobile, AL headquarters; Tampa, FL (Sourcetoad HQ) and Southeast travel expected

Employee ownership: Participation in the Thompson Holdings ESOP - every employee earns shares as the company grows