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Vice President of Technology & Innovation - Job Opportunity at Chestnut Hill Realty

Chestnut Hill, United States
Full-time
Executive
Posted: July 14, 2025
Hybrid
USD 175,000+ per year

Benefits

Comprehensive healthcare coverage including medical, dental, and vision insurance providing full family protection and wellness support
Robust retirement planning with 401(k) plan and company matching to accelerate long-term financial security
Unique personal time benefits including paid birthday off and volunteer PTO hours reflecting company culture values
Employee housing discount program providing direct cost savings on residential accommodations
Flexible spending account enabling pre-tax allocation for healthcare and dependent care expenses
Complete life insurance coverage ensuring family financial protection
Professional development assistance supporting continuous learning and career advancement opportunities
Comprehensive parental leave policy supporting work-life balance during family transitions
Employee assistance program providing confidential counseling and support services
Flexible hybrid work arrangement combining remote productivity with collaborative on-site engagement

Key Responsibilities

Architect and execute comprehensive technology and innovation roadmap that directly drives organizational strategic objectives and competitive positioning
Function as primary technology strategist and trusted advisor to C-suite executives on emerging technology trends and digital transformation opportunities
Lead enterprise-wide digital transformation initiatives across all departments to optimize operational efficiency and enhance competitive advantage
Spearhead integration of cutting-edge PropTech solutions and AI platforms to revolutionize resident experience and streamline business operations
Establish and monitor critical technology KPIs while maximizing return on investment for all digital infrastructure and innovation investments
Build and lead high-performing technology team focused on operational excellence, cybersecurity leadership, and emerging technology adoption
Drive cross-functional collaboration to ensure technology initiatives align with business objectives and deliver measurable impact

Requirements

Education

Bachelor's or Master's degree in Information Systems, Computer Science, or Business Administration

Experience

10+ years of IT leadership experience, preferably in residential property management or real estate

Required Skills

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
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Sauge AI Market Intelligence

Industry Trends

The real estate industry is experiencing unprecedented digital transformation with PropTech investments reaching record levels as companies seek to differentiate through technology-enabled resident experiences and operational efficiency. This trend is driving demand for senior technology leaders who can bridge traditional real estate operations with cutting-edge digital solutions. Artificial intelligence and machine learning are becoming critical differentiators in property management, with applications ranging from predictive maintenance and energy optimization to resident service automation and market analysis. Companies are prioritizing leaders who can effectively implement and scale these technologies. Cybersecurity has become a paramount concern in real estate technology as companies digitize operations and manage sensitive resident data. The increasing frequency of cyber attacks on real estate firms is driving demand for technology executives with deep security expertise. Cloud infrastructure adoption is accelerating in real estate as companies seek scalability, cost efficiency, and enhanced collaboration capabilities. This shift requires leaders who can orchestrate complex cloud migrations while maintaining operational continuity.

Salary Evaluation

The $175,000+ salary range is competitive for VP-level technology roles in the Boston metropolitan area, particularly given the specialized real estate technology focus. Similar positions in the region typically range from $170,000 to $250,000 depending on company size and specific responsibilities. The salary appears positioned at the lower end of market range, suggesting potential for negotiation or additional equity compensation.

Role Significance

Typical technology teams for this role in mid-sized real estate companies range from 8-15 professionals including IT infrastructure specialists, software developers, cybersecurity professionals, and business analysts. The role likely involves both direct management and matrix leadership across multiple technology functions.
This is a senior executive position reporting directly to C-suite leadership with significant strategic influence over organizational technology direction. The role carries substantial responsibility for driving digital transformation initiatives that directly impact business performance and competitive positioning in the real estate market.

Key Projects

Implementation of integrated PropTech platform to enhance resident experience and operational efficiency Enterprise-wide digital transformation initiative spanning all business units and operational processes AI and machine learning platform deployment for predictive analytics and operational optimization Cybersecurity infrastructure modernization and compliance program implementation Cloud infrastructure migration and optimization project to improve scalability and cost efficiency

Success Factors

Ability to translate complex technical concepts into business value propositions that resonate with executive leadership and drive strategic decision-making across the organization Strong change management capabilities to guide enterprise-wide digital transformation while maintaining operational continuity and employee engagement throughout the transition process Deep understanding of real estate industry dynamics combined with technology expertise to identify and implement solutions that address specific sector challenges and opportunities Exceptional relationship-building skills to foster collaboration between technical teams and business stakeholders while driving adoption of new technologies and processes Strategic vision for emerging technologies with practical implementation experience to ensure successful deployment and measurable business impact from innovation initiatives

Market Demand

High demand exists for technology executives with real estate industry experience as the sector undergoes rapid digital transformation. The combination of PropTech expertise, AI implementation capabilities, and property management system knowledge creates a specialized skill set that is highly sought after in the current market.

Important Skills

Critical Skills

PropTech and real estate technology expertise is absolutely essential given the industry-specific nature of the role and the need to understand how technology can address unique real estate operational challenges and resident experience requirements AI and machine learning implementation capabilities are crucial as these technologies become fundamental differentiators in property management efficiency, predictive maintenance, and resident service delivery Enterprise digital transformation leadership is vital for successfully orchestrating complex organizational change while maintaining operational continuity and achieving measurable business outcomes Cybersecurity expertise is critical given the sensitive nature of resident data and the increasing frequency of cyber attacks targeting real estate companies and property management systems

Beneficial Skills

Yardi Voyager and Timberline experience would provide immediate operational value and reduce learning curve for property management system optimization and integration initiatives Cloud infrastructure architecture knowledge would support scalability planning and cost optimization as the company grows and modernizes its technology infrastructure Data analytics and business intelligence capabilities would enable development of insights-driven decision making and performance optimization across all business functions Vendor management and technology procurement expertise would be valuable for evaluating and implementing PropTech solutions while managing costs and ensuring successful implementations

Unique Aspects

This is a newly created role, indicating the company's strategic commitment to technology leadership and digital transformation, providing opportunity to build technology strategy from the ground up
The position combines traditional IT operations with innovation leadership, requiring both operational excellence and strategic vision for emerging technologies
Focus on PropTech and AI implementation in residential property management represents a specialized niche with significant growth potential and competitive advantage opportunities
Hybrid work model for an executive-level position demonstrates progressive approach to leadership and recognition of changing work preferences in the technology sector
Direct involvement in shaping technology KPIs and ROI measurement provides opportunity to establish metrics and demonstrate quantifiable business impact from technology investments

Career Growth

Typical progression to next-level roles occurs within 3-5 years based on successful delivery of digital transformation initiatives and demonstrable business impact from technology investments and innovation programs.

Potential Next Roles

Chief Technology Officer (CTO) at larger real estate organizations or PropTech companies seeking to scale their technology leadership Chief Digital Officer (CDO) roles focused on comprehensive digital transformation across real estate enterprises Technology consulting leadership positions specializing in real estate and PropTech implementations Executive roles at PropTech startups or venture capital firms focusing on real estate technology investments

Company Overview

Chestnut Hill Realty

Chestnut Hill Realty operates as an established residential property management company in the Greater Boston area, focusing on providing comprehensive real estate services and residential property management solutions. The company has demonstrated commitment to innovation and employee development, as evidenced by their creation of this new executive technology role.

The company appears to be a mid-sized regional player in the competitive Boston real estate market, with sufficient resources and growth ambition to invest in senior technology leadership. Their award-winning recognition and promote-from-within culture suggest strong market reputation and operational excellence.
Based in Chestnut Hill, Massachusetts, the company operates in one of the most competitive and technology-forward real estate markets in the United States. The Boston area's concentration of technology talent and innovation resources provides significant advantages for technology recruitment and implementation.
The company culture emphasizes innovation, flexibility, and employee development with unique benefits like birthday time off and volunteer PTO hours. The hybrid work model and promote-from-within philosophy suggest a progressive, employee-centric environment that values work-life balance and career growth.
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