Position Description – VP, Engineering

Stakeholders VR is a first-of-its-kind alliance of best-in-class vacation rental property management companies, united by a shared vision: to redefine hospitality, drive innovation, deliver magical guest experiences, and unlock premium value through strategic collaboration and shared ownership. We’re building a movement of local operators who believe that exceptional guest & owner experiences and community-driven service can scale nationally.

𝗪𝗛𝗔𝗧 𝗪𝗘 𝗗𝗢 We bring together the top-performing PMCs in the country, hand-selected for their operational excellence, integrity, and local market leadership, and empower them through shared ownership, best-in-class technology, operational support, and group-level advantages in marketing and purchasing. Together, we’re raising the standard of vacation rental hospitality and delivering amazing experiences for our guests and homeowners.

𝗢𝗨𝗥 𝗠𝗜𝗦𝗦𝗜𝗢𝗡 To empower the best local operators by giving them the resources, reach, and capital to thrive in a competitive landscape. We believe that true hospitality and local excellence are superpowers in the right hands. Stakeholders VR exists to make sure those hands stay in control, yet go further, and faster, together.

We believe the future of travel belongs to the bold, the united, and the hospitality-obsessed.

The Role

We are seeking a strategic and execution-oriented VP of Engineering to lead the central engineering function for Stakeholders VR. This role is responsible for building and scaling a lean, high-impact engineering organization that delivers shared platforms, integrations, and data capabilities across a rapidly growing, multi-entity portfolio.

The VP of Engineering will play a critical role in translating the CTO’s technology strategy into executable roadmaps, scalable architecture, and reliable systems that support integration, operational leverage, and value creation in a PE-backed roll-up environment.

This position requires close collaboration with executive leadership, finance, operations, and portfolio company stakeholders. The ideal candidate brings instant credibility, can operate effectively in ambiguity, and can balance architectural rigor with pragmatic delivery.

Key Competencies

Engineering Leadership & Organization Design

  • Build, lead, and mentor a lean, senior engineering team focused on platforms, integrations, and data.
  • Establish clear engineering operating models, decision rights, and accountability frameworks.
  • Create career paths, performance expectations, and feedback mechanisms for engineers.
  • Foster a culture of ownership, technical excellence, velocity, and disciplined execution.
  • Partner closely with Product, Data, IT Operations, Finance, and Operations leadership.

Platform, Architecture & Delivery

  • Translate business strategy and CTO roadmap into executable engineering plans and technical architecture.
  • Own the design and delivery of central platforms, shared services, APIs, integrations, and data pipelines.
  • Ensure systems are scalable, reliable, secure, and fit for a multi-entity operating model.
  • Implement lightweight but effective engineering processes that scale with growth.
  • Balance build vs. buy decisions with a strong bias toward leverage and reuse.

Integration & M&A Enablement

  • Lead technical diligence for acquisitions, assessing systems, data quality, risks, and integration pathways.
  • Define and execute post-acquisition technical integration strategies aligned with value creation plans.
  • Develop repeatable integration patterns, tooling, and standards to reduce marginal integration cost.
  • Provide architectural guidance to portfolio companies while respecting operational autonomy.
  • Drive rationalization of overlapping systems and reduction of long-term technical debt.

Data Strategy & Governance

  • Partner with data and analytics leaders to deliver a unified, governed data foundation.
  • Oversee engineering work related to data ingestion, modeling, master data, and identity resolution.
  • Ensure data quality, security, and consistency across systems and entities.
  • Enable BI, operational reporting, risk analysis, and acquisition intelligence through robust data pipelines.

Operational Excellence & Risk Management

  • Establish engineering SLAs, SLOs, and delivery metrics aligned with business outcomes.
  • Ensure strong security, reliability, and observability across platforms and integrations.
  • Implement disciplined release management, incident response, and technical risk controls.
  • Reduce portfolio-level technology risk through standards, shared infrastructure, and governance.

Executive Leadership & Communication

  • Serve as a trusted partner to the CTO on long-term technology vision and investment planning.
  • Clearly communicate engineering priorities, trade-offs, and progress to executive leadership.
  • Influence portfolio company leaders through credible technical guidance and structured change management.
  • Represent engineering perspectives in executive and board-level discussions when appropriate.

The Successful Applicant

  • 12+ years of software engineering experience, with 7+ years in senior engineering leadership roles (Director, Head of Engineering, VP).
  • Proven track record building and scaling lean engineering teams in complex environments.
  • Strong architectural expertise across cloud platforms, SaaS ecosystems, integrations, and data systems.
  • Experience in multi-entity, roll-up, or private-equity-backed environments strongly preferred.
  • Demonstrated success leading platform unification, system consolidation, or integration programs.
  • Excellent communication skills with ability to engage technical and non-technical stakeholders.
  • Comfortable operating in ambiguity and creating structure where none exists.
  • Pragmatic, outcome-oriented mindset with a bias toward execution and accountability.

What we Offer 

  • Opportunity to build and lead a people organization from the platform level with significant autonomy 
  • Competitive base salary with performance-based bonus structure 
  • Comprehensive benefits package including health, dental, vision, 401(k) with match 
  • Chance to make a transformative impact on a fast-growing organization

Location

Remote / Hybrid (U.S.)

Email careers@stakeholdersvr.com with the role of interest, a brief introduction, and your background.

Stakeholders VR. is proud to be an affirmative action / equal opportunity employer. All qualified applicants will receive consideration without regard to race, creed, gender, marital status, sexual orientation, citizenship status, color, religion, national origin, age, disability, veteran status, or any other status protected under local, state, or federal laws.