Director of Digital Enablement

Progressive Companies•Grand Rapids, MI

1d•Hybrid

About The Position

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.

Requirements

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.
Bachelor's degree in business, technology, or a related field required; advanced degree preferred.

Nice To Haves

Familiarity with BIM, workflow digitization, collaboration tools, and AI as applied to project delivery is a plus.

Responsibilities

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.
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.
Turn ideas into action by challenging assumptions, encouraging thoughtful experimentation, and helping the organization move from discussion to execution.
Influence through hands-on demonstration as well as vision and facilitation — modeling possibilities rather than only recommending them.
Challenge legacy thinking respectfully, using curiosity and questioning to expand perspectives and improve decision-making.
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.
Navigate organizational change and adoption dynamics so new technologies and processes achieve stronger business impact and the organization becomes more adaptive to change.
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.