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Regional IT Leader

Role at a Glance

•     Title: Regional IT Leader, VP

•     Reports to: Chief Information Officer, with a dotted line to the Regional President.

•     Location: Remote with travel

Core Responsibilities

The Regional IT Leader is the technology owner for the region. The key responsibility is to form strong relationships with the regional operators, understand how technology can enable and enhance their business operations and lead the ideation, creation and deployment of these solutions.

•     Acquisition integration: Own IT diligence, integration planning, PMS migration, provisioning, data onboarding and site launch for every deal in the region, at deal speed.

•     The regional technology agenda: Set it with the Regional President. Decide what gets built, in what order, and what it is worth.

•     Opportunity shaping: Discern the true opportunities that lurk within the region’s list of project ideas and requirements. Dig in to understand the underlying business problem, get to root cause, and use experience and expertise to shape each request for optimal impact. Do this collaboratively with the operators who raised it.

•     The regional technology story: Tell a compelling story of the region’s technology evolution: where the region will be in 1 year, where it will be in 3 years, and why it matters to operators. Use that story to earn buy-in across the region.

•     Analytics and reporting delivery: Lead the regional analysts who build dashboards and answer local operating questions off the shared data platform.

•     AI and automation enablement: Deploy use cases, drive adoption in the field, and build local automations. Train the people who will use them.

•     Local configuration and applications: PMS workflows, custom fields, automations, local integrations and vendor evaluations, inside the enterprise security and data standards.

•     Regional security posture: Own security in the region in partnership with the Corporate Security team. Build security into every acquisition, deployment and local automation from day one, and raise security awareness across the region as it grows.

•     Regional technology budget: Own the regional IT budget with an eye towards cost optimization. Partner with company CIO and other Regional IT Leaders to drive scale efficiencies.

•     Team building: Hire, develop and size the technology team to best service the region’s needs. Anticipate what continued acquisition and growth will demand of the team and build ahead of it, not just to this year’s plan.

•     Program and stakeholder management: Track multiple projects and programs across the region at once, keep them moving, and communicate progress clearly to stakeholders at every level of the organization, from shop teams and brand leaders to the Regional President and the CIO.

•     Escalation and coordination: Serve as the single point of contact for anything technology related in the region, and coordinate with the IT team when something needs to change centrally.

Requirements

Experience

•     10 or more years in technology, including 4 or more years leading teams.

•     Experience scaling teams in a fast growing business. Thinks around corners and plans for where the business will be, not just for in-year capacity.

•     Multi-site or multi-brand operating experience. Hospitality, property management, restaurant, retail, healthcare services or a comparable distributed operation.

•     Direct experience integrating acquisitions.

•     Has owned a technology budget and defended it.

•     Track record of managing multiple projects and programs at once and communicating effectively with stakeholders across multiple levels of the organization.

•     Bachelor’s degree or equivalent experience.

How You Operate

•     Prioritizes by business impact. Able to see the true opportunities within a long list of project ideas and requirements, and to shape requests for optimal impact.

•     Strong root cause analysis and process skills. Digs in, collaboratively, to unpack business problems and opportunities before committing to a solution.

•     Strong influence skills. The company is a very bottoms-up environment with real local autonomy; this role earns adoption through relationships, credibility and results, not authority.

•     Excellent communication skills. Goes beyond project status updates to tell the story of how technology is transforming the region. Forward thinking: develops and conveys a clear vision for how the region should operate 1 year and 3 years from now.

Strongly Preferred

•     Vacation rental or property management systems. Track, Streamline, Guesty or equivalent.

•     Built or led a BI and analytics function working close to operators.

•     Deployed AI or automation tooling to a non-technical field workforce and achieved real adoption.

•     Experience operating in a matrixed structure with both a functional and a business reporting line.