Vice President, Strategic Initiatives & Technology Enablement

Hirenexus; Chicago (IL); Remote; USD 225,000 - 275,000; Full time

Job summary

Hirenexus seeks a Vice President of Strategic Initiatives & Technology Enablement to run the executive operating rhythm while leading regional technology enablement in a fast-moving, private equity-backed environment. You will collaborate with the CEO and regional teams to shape AI-driven tech strategies, oversee budgets, and drive complex integrations across brands.

Ideal candidates bring deep technology change experience, strong leadership, and the ability to navigate multi-site, acquisitive

Qualifications

• 7+ years of progressive experience with clear career progression and people leadership.
• Experience leading technology initiatives through to adoption, including AI and automation.
• Experience guiding technology diligence, system migrations or integrations in acquisitive settings.
• Strong process mapping, requirements gathering and business-case development skills.
• Experience running executive operating cadences and preparing board materials.
• Experience managing a budget and influencing cross-functional teams.
• Willingness to travel 20–30%.
• Bachelor's degree required; MBA preferred.

Responsibilities

• Own the executive operating cadence, including weekly leadership meetings, monthly business reviews and quarterly planning.
• Prepare board and investor materials and shape the narrative for the executive team.
• Act as the CEO's extension on cross-functional issues and drive decisions to closure.
• Lead executive communications and change management for organizational changes and initiatives.
• Set the technology agenda for the region and prioritize initiatives with regional leadership.
• Spend time with local brands to understand system usage and opportunities for improvement.
• Identify friction and turn it into defined use cases with a clear business case.
• Shape requests, define problems, and architect solutions with operators who raised them.
• Drive technology diligence and integration planning for regional acquisitions.
• Lead migrations and implementations and manage regional technology budgets.

Education

Bachelor's degree

MBA preferred

Job description

Vice President, Strategic Initiatives & Technology Enablement

Category

Location

$225,000 - $275,000

Job Reference

252335

Job Description

Vice President, Strategic Initiatives & Technology Enablement

Location: Remote (United States) with regular travel

The Opportunity

A private equity-backed, multi-brand services platform is seeking a Vice President of Strategic Initiatives & Technology Enablement who will also serve as Chief of Staff to the CEO. The company has more than tripled its footprint through acquisition and now operates dozens of locally led brands across the country, each keeping its own identity and customer relationships. To support that growth, the business is moving to a two-region operating model backed by a central Continuous Improvement function, and leadership believes the next phase of value creation will be driven heavily by technology and AI.

This role carries two connected mandates, with time split roughly evenly between them. On the strategic side, you will report to the CEO and run the operating rhythm of the executive team. On the technology side, you will have a dotted line to the SVP of Continuous Improvement and lead technology enablement for one of the company's two regions, partnering closely with a regional technology counterpart who covers the other. You will spend real time in the field learning how local teams use their systems, set the technology agenda for your region, and lead the projects that move it forward, working with the central technology and integration teams who handle hands‑on execution.

The ideal candidate is a business athlete who has spent their career close to technology change. You can sit with a team, map how work really gets done across a handful of tools, come back with a sharp point of view on what to fix first and what it is worth, and then lead the plan to get it done.

What You'll Do

Strategic Initiatives and Chief of Staff to the CEO

• Own the executive operating cadence, including weekly leadership meetings, monthly business reviews and quarterly planning
• Prepare board and investor materials and help shape the narrative for the executive team
• Act as the CEO's extension on cross-functional issues that lack a clear owner, and drive decisions to closure
• Lead executive communications and change management for organizational changes and company-wide initiatives
• Connect the dots across regions and functions to spot duplicated effort, downstream impacts and problems before they grow
• Set the technology agenda for your region with regional operating leadership and Continuous Improvement, deciding what gets prioritized, in what order and what it is worth
• Spend time inside the local brands with front‑line and support teams to understand how they use, and move between, their systems day to day
• Identify friction, manual workarounds and duplicate entry, and turn them into well‑defined use cases with a clear business case
• Shape requests rather than take orders: dig into the business problem behind each idea and shape the solution with the operators who raised it
• Drive technology diligence and integration planning for acquisitions in your region, working alongside the integration team
• Identify when systems need to change, build the plan with local teams and the central technology organization, and lead migrations and implementations through to launch
• Own the regional technology budget, partnering with your regional counterpart to capture scale efficiencies
• Lead AI and automation adoption in the field, including training and change management for non‑technical teams
• Own a clear one‑year and three‑year technology story for your region and use it to earn buy‑in from operators
• Lead or support third‑party vendor evaluations and selection

Who We're Looking For

We are looking for an operator who is fluent in technology. You lead technology programs from the front without needing to be hands‑on technical, and you have spent enough time around enterprise technology change to know what good looks like, ask the right questions and earn credibility with both operators and technical teams. You have the confidence and presence to hold your own in board and executive conversations, balanced with the humility to earn trust with local teams. Candidates typically come from backgrounds such as:

• Big Four, Accenture or similar firms with a focus on technology transformation, enterprise system implementation, AI adoption or post‑merger technology integration
• Strategy or management consulting with M&A, integration or digital work, often followed by an operating role in a private equity‑backed company
• Chief of Staff, strategy or transformation leadership in a multi‑site, acquisitive business, with meaningful technology change on your record

Qualifications

• 7+ years of progressive experience with clear career progression and people leadership
• Track record of leading technology, automation or AI initiatives through to real adoption, from either a consulting or operating seat
• Experience leading technology diligence, system migrations or integration programs in an acquisitive environment
• Strong process mapping, requirements and business case skills; able to get to the root cause behind a request
• Experience running executive operating cadences, board materials or a portfolio of strategic initiatives
• Experience managing a budget
• Ability to influence without authority in a decentralized environment with real local autonomy
• Comfort in a fast‑growing business where priorities and scope evolve quickly
• Willingness to travel 20 to 30 percent
• Bachelor's degree required; MBA preferred

Why This Opportunity

This is a rare chance to hold two senior mandates at once in a company that is scaling quickly and reorganizing for its next stage of growth. You will work directly with the CEO and the executive team, see the full picture of where the business is headed, and help decide how technology and AI reshape the way dozens of local businesses operate. The role offers unusual breadth, real visibility with ownership, and a clear path to broader leadership as the company grows.