Program Director

Boots2Roots | Portland, ME, United States

Posted Date 9/07/2021

Job description


The Mission

Boots2Roots is seeking a dynamic people-oriented, mission-focused leader to serve as Program Director.

Boots2Roots provides personalized and proactive workforce and transition services to active duty military members and their families who are planning to live and work in Maine. Critical to successful transition is starting work with new "Teammates" up to a year before they leave military service. Boots2Roots was built on the hypothesis that early, personalized preparation and networking will enable Maine’s newest active duty veterans to hit the ground running and find meaningful work quickly. As Maine's workforce shortage has become more acute, we have also committed to being part of Maine's workforce shortage solution. .

Boots2Roots’ Goals:

1) That transitioning active duty members will find fulfilling, good paying employment within two months of arriving in Maine

2) That transitioning active duty members will remain in their first post-military job for at least one year

3) That Boots2Roots will provide Maine employers with a growing pipeline of quality veteran workforce talent as an important contributor to Maine’s workforce development effort


In our first four years, Boots2Roots has provided services to over 200 Teammates (clients) while providing new workforce talent to over 80 employers. Over 90% of Teammates were hired within two months of arriving in Maine, and 92% have remained in their first civilian job for more than a year.

Your Opportunity

As Program Director, you will fill a critical role in continuing this record of success.

You will be responsible for the day to day operations of the organization and report directly to the Executive Director (ED).The ideal candidate is capable and willing to do the work necessary to meet program goals while growing the organization and developing and implementing program efficiencies.

Job Description

The Program Director is responsible for all personalized interaction with Teammates (clients) and their families. This includes coordinating and administering self-assessment, resume assistance, interview preparation, community integration, networking, peer mentoring, and program continuity. The Program Director is responsible for building and maintaining collaborative relationships with various community partners including businesses and other employers, educational institutions, and state agencies. Additional responsibilities include primary management of volunteer and paid staff acting as peer mentors, resume & interview coaches, and other program-related functions.


  • Manage all aspects of the day-to-day Boots2Roots program including the supervision of up to 5 subordinate employees
  • Recruit, train, and manage volunteers and employees to meet Teammate transition needs and assist in the hiring of additional employees
  • Develop and implement program improvements
  • Maintain the Customer Relationship Management (CRM) database, train staff and volunteers on CRM systems, run CRM system reports
  • Grow and maintain relationships with Maine community partners
  • Grow and maintain relationships with the B2R network of businesses and other employers
  • Attend local Maine-based community events in order to promote the Boots2Roots mission and positively and professionally represent the organization
  • Other duties as assigned

Required Qualifications and Skills

  • Exceptional interpersonal skills- relationship building is a key part of this job
  • Excellent organization
  • Exceptional written and verbal skills
  • Critical thinking and problem-solving
  • Experience with performance appraisals (military or civilian) and editing resumes (preferred)
  • Proactive problem solver and an initiative taker
  • Comfortable working with minimal supervision
  • Efficient while juggling multiple competing demands and excellent time management skills
  • Supervisory experience
  • Training experience
  • Skilled at planning and running efficient meetings
  • Willingness and ability to work outside typical working hours- frequent evening community and organization events
  • Comfortable communicating by phone and internet
  • Computer literate and proficient in Microsoft office suite
  • Proficiency using social media, including Facebook and LinkedIn

Required Education and Experience

  • Veteran of the active component of the U.S. Armed Forces who separated or retired from active duty in the past 10 years (related experience; e.g. military spouses) will also be considered
  • Undergraduate degree required (or military senior leadership experience)
  • Five or more years of supervisory experience (preferred)
  • Have completed at least one post-military job successfully (preferred)

Compensation and benefits:

  • Flexible work schedule
  • Healthcare available
  • Competitive non-profit salary


Job Type
Geographic Region
Greater Portland/Casco Bay
Town (optional)
Portland Maine

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