Director of Digital Enablement

Progressive Companies (Progressive) is a design-led firm focused on helping clients realize the full potential of their opportunities, by designing and stewarding solutions that support a healthy, inclusive, and sustainable future — transforming spaces, empowering people, and delivering measurable value. As an employee-owned firm, we call on every leader to Design Boldly. Own Fully. Impact what Matters.

The Director of Digital Enablement (Director) is a business-centered digital leader who connects strategy, operations, technology, and innovation across Progressive Companies, helping the firm navigate an increasingly digital and AI-enabled future through alignment, informed decision-making, and technology solutions grounded in business needs.

Combining curiosity, business acumen, influence, and action, the Director translates business and client needs into scalable technology and innovation solutions while anticipating how the market, workforce, and technology landscape are evolving. Rather than prescribing every solution, the Director helps the organization ask better questions, evaluate opportunities thoughtfully, and make practical decisions about where to invest time, energy, and resources.

Reporting to the President and CEO, the Director leads the technology team, the technology R&D cohort and serves as the connector between business needs, technology capabilities, and future possibilities — integral to aligning Progressive's digital capabilities with its brand promise, purpose, and values.

This position owns the strategic direction, execution, and governance of Progressive's digital and technology capabilities — leading the technology team and partnering with firm leadership to translate business needs into scalable digital solutions.

Strategic Connection & Business Translation

• Operate at the intersection of business strategy, client experience, operations, and technology, translating organizational and client challenges into practical digital opportunities.
• Connect technology discussions to business outcomes rather than technical features, acting as a bridge between operational leaders, technical teams, and executive stakeholders.
• Build trust and credibility across diverse stakeholders through relationships, curiosity, and collaboration, facilitating productive dialogue across business, operations, innovation, and technology teams.
• Ensure digital investments are clearly connected to strategic priorities and measurable outcomes, so technology initiatives are viewed as business initiatives, not individual projects.

Action Leadership & Momentum Building

1. Turn ideas into action by challenging assumptions, encouraging thoughtful experimentation, and helping the organization move from discussion to execution.
2. Influence through hands-on demonstration as well as vision and facilitation — modeling possibilities rather than only recommending them.
3. Challenge legacy thinking respectfully, using curiosity and questioning to expand perspectives and improve decision-making.
4. Operate as a player-coach: frame problems, assess options with technical fluency, and selectively prototype early solutions before engaging specialist partners for production build-out.
5. Navigate organizational change and adoption dynamics so new technologies and processes achieve stronger business impact and the organization becomes more adaptive to change.

Digital Architecture & Future Guidance

• Lead the IT team and external service providers toward successful implementation of the firm's technology strategy, identifying the skills, capabilities, and mindset needed to execute it.
• Stay informed on how the AEC industry is evolving — particularly BIM, workflow digitization, collaboration tools, and AI — to help the organization understand emerging opportunities, risks, and trade-offs.
• Engage IT, technology, and innovation teams as an informed owner, translating technical decisions into business outcomes with sufficient technical fluency to evaluate options.
• Establish scalable digital capabilities, governance, and organizational alignment, thinking in systems, workflows, and organizational capabilities rather than individual tools.

QUALIFICATIONS

• 10+ years of progressive experience in technology leadership, digital strategy, or business transformation, ideally within professional services or another complex, multi-office organization.
• Demonstrated experience leading technology or IT teams, including managing external service providers and vendor relationships.
• Proven ability to translate business and client needs into scalable technology solutions, paired with enough hands-on technical fluency to evaluate options and prototype early solutions.
• Experience working within professional services, complex client delivery environments, and multi-office collaboration; direct AEC industry experience preferred but not required.
• Familiarity with BIM, workflow digitization, collaboration tools, and AI as applied to project delivery is a plus.
• Bachelor's degree in business, technology, or a related field required; advanced degree preferred.

COMPETENCIES

• Business Insight — You know how businesses work; you are knowledgeable in current and possible future policies, practices, trends, technology, and information affecting your business or organization; you are aware of business drivers and how strategies and tactics play out in the market to guide action.
• Manages Complexity — You ask the right questions to accurately analyze situations; you acquire data from multiple and diverse sources when solving problems; you uncover root causes to difficult problems; you evaluate pros and cons, risks and benefits of different solution options.
• Cultivates Innovation — You come up with useful ideas that are new, better, or unique; you introduce new ways of looking at problems; you can take a creative idea and put it into practice; you encourage diverse thinking to promote and nurture innovation.
• Drives Results — You act with a clear sense of ownership; you identify and seize new opportunities; you steadily push yourself and others for results; you show tenacity and follow-through, even in the face of resistance or setbacks.