Director of Alumni Relations

  • Posted:Oct 29, 2020
  • Apply by:Dec 28, 2020
  • Job Type
  • Full Time
  • Job Level
  • Other
  • Location
  • Whitchurch-Stouffville, ON
  • Impact Area
  • Other
  • Impact Category
  • Other
  • Company Type
  • Other

About this position

Job Summary, Director of Alumni Relations

Trails Youth Initiatives became a registered charity in 1992 and offers a safe haven for youth from the GTA who encounter barriers to success. Our mission is to challenge and equip vulnerable youth to become contributing members of society. We offer participants a feeling of belonging and our Four Seasons, Four Years, For Life outdoor program helps them develop life skills and build confidence through high school credits, bursaries and mentorship. Our vision is to break the cycle of poverty by teaching kids practical skills, fostering a sense of community, developing emotional intelligence and facilitating academic performance, all of which translates to employability. In the process, we forge lasting connections and each child becomes a unique branch on our family tree of graduates. We celebrate together as they reach a turning point and surpass all expectations – society’s as well as their own.

About the Position

Reporting to the President, the Director of Alumni Relations is responsible for overseeing the “For Life” part of the Charity’s “Four Seasons, Four Years, For Life” Program. This area encompasses fostering structured growth of Trails graduates (called “alumni”, from age 15 onwards, ever-present in their adult lives) through the Bursary Fund, Mentorship Program, Career Connections and Alumni Association. This position ensures that our alumni stay connected, receive support throughout their educational and working career and give back to the community as well as to Trails through their time and donations.

The overarching goal of this role is to build on our success of the past 30 years and help take Trails to the next level by overseeing and administering the alumni relations component of the Charity mission. One of the pillars of our Vision 2023 document is to increase the value and impact of the “For Life” program by providing more holistic support to a larger number of people. We want our youth to experience equal access to education and professional connections based on their talent and the content of their character – which we help shape. By impacting one life at a time in a meaningful way, we aim to trigger a multiplier effect across generations and help break the cycle of poverty and systemic racism.

This position carries out its mandate within parameters set by the President. Key requirements include contributing to a positive, healthy and safe work environment, supporting, coaching and inspiring participants and alumni and building long-term relationships with all stakeholders. Crucially, you will be passionate about the Charity’s mission to challenge and equip vulnerable youth to become contributing members of society.

Key Responsibilities


  • Aligns behaviour with mission and policies and procedures in Employee Handbook
  • Consistently arrives to work, appointments and meetings on time
  • Collaborates effectively with team members across departments
  • Identifies, assesses and informs President of issues that may affect organization
  • Ensures that documentation is accessible, traceable and accurate
  • Writes clearly and informatively and edits work for spelling and grammar
  • Strives to expand professional knowledge to enhance impact and innovation
  • Maintains strict confidentiality and security of records and participant information

Bursary Fund

  • Supports Director of Development with creation and roll-out of annual $500,000 fundraising campaign to help cover cost of alumni post-secondary education
  • Develops strong connections with Board of Governors and promotes orderly succession
  • Supports Bursary Committee through management of Trails Dion Bursary Fund
  • Tracks bursary applications and recipients and support them through schooling and career


  • Positions Mentorship Program for deeper and more holistic impact and strives to double Program enrolment by 2023
  • Applies two-tiered approach by having alumni work with alumni first and community members second, outlining concrete benefits to all stakeholders
  • Identifies alumni and community members who may act as mentors to recent graduates
  • Develops and runs mentorship workshops and hosts meetings to enthuse participants for Alumni Association

Career Connections

  • Connects alumni with greater Trails community, links graduates with Trails network and sources volunteer and employment opportunities
  • Pairs alumni with well-connected members of community-at-large who may offer advice and networking and employment opportunities

Alumni Association

  • Identifies, cultivates and stewards Alumni Association to ensure that Trails’ impact is captured and enduring and inspires prospective participants
  • Identifies and manages contact information for 500+ graduates in Salesforce database, capturing biographical and career information via surveys and projects
  • Ensures alumni presence and speakers at signature fundraising events and at youth recruitment presentations
  • Secures spotlight testimonials that demonstrate success of alumni
  • Prepares and disseminates regular correspondence
  • Creates and manages engaging annual alumni socials


  • Continuously builds relations with alumni, mentors and mentees
  • Liaises with Board Alumni Committee, Alumni Association and Bursary Committee
  • Works with President and Committee on making “For Life Program” work
  • Contributes to work culture of high collaboration, productivity and support
  • Represents Charity at community activities, as directed

Qualifications and Requirements

  • Post-secondary degree or equivalent certification in Communication or Education
  • At least 3 years of relevant experience, including relationship management, leveraging on social media for business purposes and corresponding with stakeholders, from C-Suite to teenagers
  • Working knowledge of Microsoft Office products and Salesforce
  • Excellent organizational and administrative skills
  • Track record of success in ideating with others and making youth programs work
  • Outstanding networking, presentation, interpersonal and leadership skills
  • Strong time management skills and keen attention to detail
  • Ability to create insightful reports and recommendations for review by President
  • Ability to connect with people from all backgrounds and varying degrees of experience
  • Ability to switch tasks, respond to shifting priorities and refocus after interruptions
  • Valid Ontario ‘G’ driver’s license free of serious offenses under Highway Traffic Act
  • Willingness to work outside of regular business hours as needed


  • Sincere interest in helping youth
  • Friendly, inviting and charismatic
  • Natural relationship-builder
  • Unfazed under pressure
  • Intellectually curious

Note: as the Charity grows and legal requirements as well as our participants’ needs change, management may change tasks assigned to this role accordingly.

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