Opportunity is here


Senior Director, People Strategy



People & HR, Sales & Business Development
Boston, MA, USA
Posted on Tuesday, September 5, 2023

The Organization: MassChallenge

The Role: Sr. Director, People Strategy

Location: Boston, MA

Reports to: Chief Operating Officer
Compensation: $140,000-$150,000

MassChallenge is the global network for innovators who are working to solve massive challenges. We connect startups, experts, corporations, and communities to grow and transform businesses and economies. Our mission is to equip bold entrepreneurs to disrupt the status quo and create meaningful change. Our mission is BIG, and thus we are a team that gives 100% every day. Our guiding principles ensure we stay true to our mission and our core beliefs.

MassChallenge is currently seeking a Senior Director of People Strategy to join our HQ People Strategy Team and join our Boston-based offices.

Position Summary

The Senior Director of People Strategy reports to the COO and is a key member of the Leadership Team. Responsible for leading all aspects of the People Strategy (PS) function, including but not limited to training and development, change management, succession planning, compensation & benefits, talent management, culture, diversity, equity & inclusion, and organizational development. The Senior Director, People Strategy develops and executes the human resource strategy in support of the overall business plan, and strategic direction of the organization, including understanding future trends and workforce needs.

Providing insightful and credible leadership to the COO, CEO, and the Senior Leadership Team, the Senior Director, People Strategy also partners with staff to provide support, direction, and solutions that are creative and forward-looking.

This role is hybrid and will be expected to work from the Boston office for at least two days per week, typically Tuesday and Thursday. This position also supports a team located in Texas as well as several fully remote employees. This role currently manages one PS team member.

What You'll Do

Lead and Direct:

  • Provide leadership and guidance on all PS functions including, but not limited to:
  • Talent acquisition; onboarding, retention, and offboarding
  • Career development, growth and advancement
  • Team Structure and succession planning
  • Performance management
  • Training and development
  • Compensation and benefits.
  • Evaluate People Strategy structure, processes, and team plan for continuous improvement of the efficiency and effectiveness and support to all MassChallenge employees.
  • Work with leaders on a clear process of organizational planning that evaluates team structure, job design, and staffing forecasting throughout the organization.
  • Understand, advise, and lead on all federal and state-specific guidelines about employment law, leave procedures, etc.

Develop and Implement:

  • Establish and implement People Strategy efforts that effectively communicate and support business operations objectives, culture, and strategic vision.
  • Develop and manage the annual budget for People Strategy
  • Develop comprehensive strategic recruiting and retention plans to meet the human capital needs of the organization.
  • Create and implement a comprehensive long-term vision for learning & development and ensure staff are engaged, productive, and prepared for future growth.
  • Collaborate and Influence:
  • Act as an employee champion and change agent by anticipating People Strategy-related needs and delivering value added services for the benefit of the employees.
  • Actively engage with HR professional organizations and build strong relationships with other HR professionals in order to identify best practices and incorporate innovative thinking into MC’s HR strategies.


  • Advise the COO and the Senior Leadership Team on organizational plans and company policies.
  • Ensure MC is meeting government reporting requirements, including: EEO, ERISA, Wage & Hour regulations, etc
  • Guide managers and employees in resolving employee relations issues by providing effective conflict resolution and coaching.

Your Leadership Competencies

Innovative and Agile:

  • Ability to innovate and approach situations in new ways.
  • Thinks broadly and creatively, beyond immediate details and issues and conventional thinking, to encourage forward-thinking ideas and approaches.
  • Anticipates crises and problems. Entrepreneurial, displays curiosity, passion for continuous learning.


  • Seeks to proactively identify trends and opportunities impacting the organization.
  • Has an outstanding analytical mind.
  • Has a proven ability to prioritize and manage competing and sometimes conflicting priorities.
  • Prudent risk taker and experienced with change management concepts.


  • Ability to build support for recommendations, solutions, or ideas that improve PS and DEI practices within MC.
  • Draw on wide-ranging sources of information and networks of relationships to develop and carry out complex business strategies and initiatives.

What You Bring

Education & Experience Requirements

  • Bachelor's degree required (preferably in Human Resources, Business Administration or related field). Advanced degree preferred in Human Resources and or certification is preferred.
  • Experience in all core areas including benefits, compensation, training, employee relations, and compliance.
  • Minimum 5 years of HR leadership experience.
  • Experience working in a not-for-profit a plus but not essential
  • Proven track record of success in positions that required a strong mix of business skills, leadership abilities, strategic thinking, and sound judgment in driving organizational effectiveness is required.
  • Deep experience implementing overall HR best practices, including directing talent management and leading all aspects of culture, diversity, change management and organizational development, employee engagement, training approaches, and career pathways.
  • Demonstrated success leading change with employees at all levels.

Who You Are:

  • Authentic leader and manager with a collaborative and inclusive approach in assessing
  • Individual/organizational challenges, problem-solving, and developing partnerships.
  • Thoughtful, energetic, and diplomatic change ambassador; an experienced professional in understanding organizational dynamics, guiding individuals and teams through complex and changing environments.
  • Facilitative and accessible style, approachable manager, strong advisor to the COO and Senior Leadership Team.
  • Excellent communication skills, both written and verbal
  • Exceptional coach and mentor; demonstrated experience in influencing and supporting senior leaders.
  • Demonstrated commitment to the values of diversity, equity, and inclusion.
  • Able to establish credibility throughout the organization to be an effective listener and problem solver of people issues.


  • MassChallenge offers competitive salaries, excellent benefits, and a supportive working environment.
  • Salary is based on a nonprofit scale and commensurate with skills and experience.
  • For this position, the base salary range is $140,000-$150,000
  • Internal equity considerations and the average salary of the peer range will be reviewed before making a final offer.


MassChallenge is proud to be an Equal Opportunity Employer. We seek individuals from a broad variety of backgrounds with varying levels of experience who have a desire to do meaningful work. We recruit, employ, train, compensate, and promote regardless of race, color, gender, gender identity, religion, national origin, ancestry, disability, age, veteran status, sexual orientation, or any other characteristic protected by law.