Senior Manager of Project Management

Benchmark Senior Living•Waltham, MA

15h•$116,000 - $129,000

About The Position

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.

Requirements

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

Nice To Haves

Senior living industry experience preferred
Experience leading transformation, operational, and systems initiatives preferred
Experience managing vendor-supported implementations preferred

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