Demo

Director of Learning

Benchmark Senior Living
Benchmark Senior Living Salary
Waltham, MA Full Time
POSTED ON 3/28/2026
AVAILABLE BEFORE 4/26/2026
Benchmark has been a trailblazer in senior living for nearly 30 years, operating 68 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

To meet this demand, senior housing development must nearly double historical levels over the next two decades. Benchmark is outpacing industry growth, backed by prominent investors such as KKR, Prudential Financial, Omega Healthcare Investors, and Ventas, Inc. Its brand strength is reflected in its 62 Best Senior Living Community awards from U.S. News & World Report in 2024, far exceeding industry averages.

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.

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.

The Director of Learning is responsible for developing and implementing training programs that enhance Benchmark associates’ skills and align with organizational goals. This role ensures a culture of continuous learning that advances our purpose of transforming lives through human connection.

Key Responsibilities

  • Strategic Development: By fostering an environment of continuous learning, the Director of Learning ensures that the workforce remains competent and competitive in a rapidly evolving market. Through collaboration with Benchmark communities and departments, the Director of Learning assesses developmental needs, designs and delivers curriculum, and measures the effectiveness of learning initiatives.
  • Training Program Oversight: Oversees the creation, delivery, and evaluation of training programs, ensures they meet the needs of associates at all levels while enhancing associate performance, job satisfaction, and ultimately growth.
  • Needs Assessment: Collaborates with department heads to assess training needs and identifies gaps in skills and knowledge.
  • Leadership Development: Creates, facilitates, and evaluates leadership and career- pathing development programs to prepare high-potential associates for future roles.
  • Continuous Improvement: Evaluates the effectiveness of training programs through feedback and performance metrics, making necessary adjustments to improve outcomes.

Needs Analysis

  • Collaborates with the Talent team and our internal customers to identify skill needs and delivers custom solutions.

Design

  • Aligns training goals and objectives with Benchmark’s purpose and values and industry standards.
  • Ensures that the approach to training design aligns with the Benchmark University philosophy.
  • Aligns training to be state and federally compliant.

Development

  • Develops and delivers training classes using standard in-person, virtual, and self-paced models.
  • Identifies and develops subject matter experts to assist with the development and delivery of specific training programs.
  • Stays current on trends in Learning & Development to ensure that content remains current to how business operates.
  • Conducts coaching and mentoring for associates, peers, and executives.

Implementation

  • Delivers training in communities, on location, in Benchmark home office, and virtually.
  • Expected to travel frequently to deliver training to communities.
  • Works with vendors to implement projects as needed.

Evaluation and ROI

  • Works efficiently with the Training Coordinator to identify reporting needs and delivery of reports to senior leaders.
  • Consistently assesses the quality of training materials to ensure the most accurate and up to date content.
  • Maintains statistics on associate satisfaction and adoption of training content.
  • Assesses and reports associate engagement and adoption of training to measure success and identify new opportunities.
  • Reports on training to ensure communities are in compliance with federal, state, and Benchmark guidelines.

Other Responsibilities

  • Supports other training initiatives and projects as identified by Head of Learning.
  • Assists in all aspects of event planning and speaker vetting.
  • Able to communicate and build exceptional relationships with learners, stakeholders, and leadership.

Education/Experience/Licensure/Certification

  • 8 years training delivery experience
  • 8 years of training design experience
  • Experience/Expertise in developing learning design.
  • Experience / Expertise in effective learning and development methodologies.
  • Elevated level of organization and time management skills; ability to work independently to drive results.
  • Results-oriented leader with excellent decision-making skills, forward-thinking, and a passion for innovation
  • Experience in learning and development, including designing and implementing training programs, is essential.
  • Background in instructional design, e-learning methodologies, and AI preferred.

Required Skills/Abilities

  • Requires familiarity with classroom management such as preparation, set up, platform skills, and training delivery.
  • Ability to influence and collaborate well with internal stakeholders.
  • Excellent communication, leadership, and interpersonal skills.
  • Robust empathy and ability to meet the associates at their level.
  • Passion for learning and promoting a positive culture.
  • Requires working knowledge of Outlook, Teams, SharePoint, and other MS Office suite of products.
  • Strong Project Management skills.
  • Able to be nimble, flexible, and work well with peers.
  • Ability to work in a fast-paced environment and manage multiple projects.

Benefits

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

Salary : $700

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