About the Role
Stakeholders VR is a PE-backed vacation rental management company that acquires and consolidates property management companies across the US. We're closing our first tranche of 20 acquisitions — and with them, we're inheriting 20 different IT environments with no unified standards, no centralized security, and no visibility into what's running where.
We're hiring a Director of IT Operations to build our IT function from the ground up. You'll stand up Mission Control's internal IT, then turn your attention to the bigger challenge: assessing, standardizing, and securing IT infrastructure across a rapidly growing portfolio of acquired companies. You'll do this with a small team, a lot of autonomy, and an expectation that AI is your default tool — not an afterthought.
What You'll Own
Mission Control IT. You'll select the tool stack for a fully remote corporate team — productivity suite, video conferencing, password management, device management, onboarding/offboarding — and roll it out. This is a finite project that you'll knock out in your first 60–90 days, not an ongoing timesink.
IT assessment across the portfolio. You'll gain access to every acquired company's IT systems and run a structured audit of their infrastructure — DNS, email, identity management, security, devices, networking. You'll figure out what's working, what's a risk, and what needs to change. Then you'll do it again, faster, as each new tranche of acquisitions closes.
IT standards and remediation. You'll define the portfolio-wide standards for IT infrastructure and build remediation plans to bring acquired companies into compliance. You own the roadmap for how we eventually centralize — but you'll drive adoption through influence and partnership with PMC leaders, not top-down mandates.
Vendor consolidation. You'll establish preferred vendors across common IT functions and migrate companies over where it makes sense. We're not dictating every tool, but when 20 companies are using 15 different solutions for the same problem, you'll bring that to a manageable number.
Audit readiness. You'll be the IT point person for PE and 3rd party audits, ensuring the portfolio meets compliance requirements as we scale.
What We're Looking For
Must-haves:
- 10+ years of IT operations experience.
- You've managed teams of 3–10 people and know how to get a lot done with a lean group.
- You've worked in a diverse, multi-site, multi-brand environment — a rollup, franchise, or distributed company where you couldn't assume consistency across locations.
- You have a demonstrated AI-native approach to IT operations. You've already automated help desk functions, used AI for auditing or compliance, or fundamentally rethought how an IT team operates with AI at the center. We'll ask you about this in detail.
- You know how to drive standardization across teams you don't directly control. You build relationships, earn trust, and make people want to adopt your standards — not resent them.
Nice-to-haves:
- M&A or rollup experience — you've been through the chaos of integrating acquired companies before.
- Experience in a PE-backed company and comfort with the audit cadence and pace that comes with it.
- Hands-on familiarity with Google Workspace, Microsoft 365, MDM platforms, and identity management tools like Okta.
- You've built IT playbooks and runbooks from scratch rather than inheriting someone else's.
- Experience supporting a fully remote workforce.
- Hospitality industry background.
Why Join Us
You'd be building IT operations from scratch at a company doing $38M in EBITDA with plans to 10x over five years. Every acquisition adds scope to your role. The team at Mission Control is small — you'll work directly with the CTO and alongside PMC founders who built and sold their own businesses. This is a greenfield opportunity to define how IT works across a growing portfolio with an AI-first philosophy, equity upside, and a clear path to VP as the company scales.