Senior Project Management Jobs in Massachusetts

Benchmark has been a trailblazer in senior living for nearly 30 years, operating 70 communities with 7,400 associates across the Northeast. With $3 billion in assets under management and $700 million in annual revenue, the company is experiencing historic growth, expanding its footprint from Boston to Washington DC. Benchmark offers independent living, assisted living, memory care, and continuing care retirement communities, positioning itself as a leader within this growing real estate sector. Senior housing has consistently ranked among the top three real estate sectors for long-term investment returns, and with the Baby Boomer 80+ population projected to grow over 5% annually through 2030, demand is surging.

Benchmark’s success is deeply rooted in its people. The company’s purpose – Transforming Lives Through Human Connection – is lived daily by associates who embody its core values: Called to Care, Better Together, and Be the Benchmark. Recognized as a Top Place to Work by The Boston Globe for 18 consecutive years and certified as a Great Place to Work for eight years, Benchmark fosters a culture of inclusion, growth, and recognition. It supports employees through initiatives like an associate grant program called One Company Fund, Benchmark University, an Inclusion Advisory Council, and a Cultural Ambassadors program. With over 500 associates boasting 15-plus years of tenure, and an annual gala celebrating excellence, Benchmark continues to be a destination for meaningful careers and compassionate care – setting the standard in senior living.

Benchmark seeks a highly capable and experienced Senior Project Manager (Sr. PM) to independently own and drive complex, cross-functional, enterprise-wide initiatives from initial planning through full implementation. This is a senior-level role, not a coordination role: it requires the judgment, credibility, and communication skills to partner with executive sponsors, and the discipline to see a large-scale initiative through to a successful, sustained outcome. Reports to the Senior Director, Project Management.

Leads initiatives with significant ownership while remaining aligned with and accountable to the Senior Director. Operates under the strategic direction and oversight of the Senior Director, with regular alignment on priorities, risk posture, stakeholder engagement, and executive communications.

This role requires someone who can operate at a strategic level while also engaging in detailed coordination and hands-on execution. The Senior Project Manager is an excellent thinker and an excellent writer — someone who can learn a new business area or technology quickly and apply that understanding with confidence, without needing to sit in a technical role. Equally important is the ability to meet people where they are: to listen closely, ask the right questions, and help executives and frontline associates alike develop and sharpen their own ideas. The Senior Project Manager is empathetic, emotionally intelligent, intellectually nimble, an excellent communicator and presenter, and comfortable shifting between shaping direction and driving day-to-day progress across operational, organizational, IT, and business initiatives.

PRINCIPAL DUTIES AND RESPONSIBILITIES

• Independently plan, lead, and drive complex, enterprise-wide initiatives from strategy through full implementation, with operational and executive visibility
• Partner directly with executive sponsors to define scope, objectives, success measures, and governance approach
• Manage the full project lifecycle including planning, execution, change management, and stabilization
• Navigate cross-functional priorities and drive alignment across multidisciplinary teams, from senior leaders to frontline associates
• Meet stakeholders where they are, asking the right questions to help them shape, refine, and articulate their ideas into actionable plans
• Anticipate risks, organizational impact, and interdependencies; proactively develop mitigation strategies
• Prepare and deliver polished, executive-ready presentations and written communications that distill complex initiatives into clear, actionable narratives
• Facilitate executive-level meetings and provide concise, executive-ready reporting
• Keep the Senior Director appropriately informed on project developments, risks, stakeholder dynamics, and key decisions, ensuring strong alignment.
• Escalate strategic risks and sensitive stakeholder issues to the Senior Director as appropriate
• Oversee multiple high-impact, large-scale initiatives concurrently while maintaining delivery discipline
• Quickly learn new business areas, operating models, and technologies well enough to apply that knowledge and partner effectively with technical and business teams
• Serve as a mentor to junior members of the PMO, supporting skill development and execution consistency
• Contribute to strengthening project management standards and best practices within the PMO
• Support foundational coordination, documentation, and project management activities as needed within a lean team environment

EDUCATION / EXPERIENCE / LICENSURE

• Bachelor’s degree required
• PMP Certification required
• 10–15 years of progressive project management experience preferred, including demonstrated success independently planning, leading, and implementing large-scale, cross-functional initiatives with executive sponsors
• Senior living industry experience preferred
• Experience leading transformation, operational, and systems initiatives preferred
• Experience managing vendor-supported implementations preferred

As a Home Office associate at Benchmark, you will have immediate access to a variety of benefits including, but not limited to, the following:

• 10 paid holidays plus 1 floating holiday
• Vacation and Health & Wellness Paid Time Off
• Tuition Reimbursement Program
• Physical & Mental Health Wellness Programs
• Medical, Vision & Dental Benefits provided by Blue Cross Blue Shield
• 401K Retirement Plan with Company Match
• Long Term Care Insurance
• Company-provided Life Insurance & Long-Term Disability

Benchmark Senior Living is committed to fostering, cultivating, and preserving a culture of diversity, equity, and inclusion.

We embrace and encourage our associates’ differences in age, color, disability, ethnicity, family or marital status, gender identity or expression, language, national origin, physical and mental ability, political affiliation, race, religion, sexual orientation, socio-economic status, veteran status, and other characteristics that make our associates unique.