Vice President of Technology & Innovation

Work for an award-winning company where you will lead transformative innovation while enjoying the flexibility and support you need to succeed. Combine strategy, cutting-edge technology, and leadership in a role that drives the future of real estate operations.

Chestnut Hill Realty has an exciting opportunity for a Vice President of Technology & Innovation. In this newly created role, you will set the strategic vision for technology and innovation across the organization. You will work closely with the executive team to drive digital transformation, enhance IT operations, and lead a forward-thinking team dedicated to operational excellence, cybersecurity, and emerging technologies such as AI and PropTech.

As Vice President of Technology & Innovation, you will:

  • Develop and implement a technology and innovation roadmap that aligns with company goals.
  • Serve as a trusted advisor to executive leadership on emerging tech trends and opportunities.
  • Champion cross-departmental digital transformation and automation initiatives
  • Oversee integration of PropTech solutions and AI platforms to improve resident satisfaction and business operations.
  • Monitor technology KPIs and maximize ROI on digital investments.

Are you the right person for the job?
• Bachelor’s or Master’s degree in Information Systems, Computer Science, or Business Administration
• 10+ years of IT leadership experience, preferably in residential property management or real estate
• Deep understanding of cybersecurity, AI, data analytics, and cloud infrastructure
• Proven ability to lead enterprise-wide technology transformations
• Strong communication and collaboration skills across technical and non-technical audiences
• At least 10 years of experience in managing business information systems such as ERP, CRM, Property Management, etc. with a preference for experience in Residential Property Management. Experience with Yardi Voyager and/or Timberline preferred. 

Some of the benefits to you:
• Excellent benefits package including: medical, dental, vision, 401(k), your birthday off, PTO for volunteer hours
• Chestnut Hill Realty apartment discount
• Hybrid work model (on-site and remote flexibility)
• Opportunity to shape the future of technology in a growing company
• Strong promote-from-within company culture

If you are a strategic thinker with a passion for technology, leadership, and continuous innovation — we want to hear from you!

All job offers contingent upon satisfactory background check.

Chestnut Hill Realty supports individuals in reaching their full potential by supporting equal employment opportunities and an environment that values diversity. Chestnut Hill Realty complies with all applicable laws concerning hiring and employment practices and is firmly committed to fostering and maintaining a workplace free from discrimination. We pledge to hire, train, and promote our employees without regard to race, religion, gender, gender identity, genetic information, age, national origin, sexual orientation, disability, veteran status, or any other category protected by applicable law.