Deputy Director

The Deputy Director is a key leader on Chicago’s Senior Leadership Team, reporting directly to the Regional Executive Director. This role is responsible for leading both volunteer recruitment strategy and program implementation, ensuring seamless coordination and maximum regional impact. The Deputy Director oversees Program and Mentor Recruitment (2-3 direct reports who supervise layered teams), aligning mentor recruitment, corporate partnerships, and high-quality program execution. Additionally, this leader will drive a strong and inclusive team culture, fostering collaboration across functions and ensuring all staff are working in sync toward shared outcomes.

A critical focus of this role is to oversee the development and implementation of a Chicago-specific recruitment strategy, with a focus on the cultivation of corporate partnerships, to meet ambitious mentor recruitment goals. Additionally, the Deputy Director will be accountable for programmatic outcomes, including student engagement, mentor-mentee relationship quality, and partnership success, ensuring the region delivers on its mission. The ideal candidate will have prior success leading cross-functional teams, a track record of driving shared outcomes in youth development and college access, and experience building and cultivating partnerships. The Chicago region has a budget of $2.5M, partnering with 6 schools in the next academic year, requiring recruitment of 725 mentors.

RESPONSIBILITIES

• Supervise the Director of Volunteer Recruitment in the development and implementation of a data-informed recruitment strategy tailored to Chicago’s specific market needs, ensuring recruitment goals are met.
• Partner with the Executive Director to cultivate and manage corporate partnerships that serve as key recruitment pipelines.
• Direct strategy to identify opportunities to support fundraising by deepening corporate partnerships beyond volunteer mentorship
• Support Director of Volunteer Recruitment in engagement of new and existing corporate partnerships and civic leaders, aligning iMentor partnerships within their CSR goals and organizational missions.
• Represent the organization at corporate, community, and networking events to enhance visibility and engagement.

• Lead and support the Director of Program in ensuring high-quality program implementation, strong school/district partnerships, and achievement of key programmatic outcomes such as student engagement and post-secondary readiness.
• Maintain collaborative, positive relationship with iMentor’s CPS district partner, Office of School Counseling and Postsecondary Advising. (OSCAPA) 

• Ensure seamless coordination between recruitment, program and partner leads/teams to optimize volunteer placement and program success.
• Utilize performance metrics to inform recruitment strategies, program improvements, and resource allocation.
• Monitor and report on key performance indicators, ensuring transparency and accountability in recruitment and program execution.
• Lead programmatic strategy to improve student engagement, mentor retention, and school partnership effectiveness.

• Serve as a key leader on iMentor Chicago’s Leadership Team (CLT), maintaining positive, healthy, collaborative, high performing professional culture, driving all verticals toward meeting and exceeding articulated goals.
• Serve as a regional leader in org-wide spaces - including cross-org collaboration and thought partnership, cross regional leadership collaboration and support, and org-wide leadership and engagement and advocacy.
• Provide coaching and professional development to direct reports, ensuring they have the tools and support needed for success.
• In partnership with CLT, plan and implement quarterly region-wide step-backs and cross-team learning and development opportunities. 
• In partnership with CLT, maximize engagement of Chicago’s Advisory Board to drive cross-vertical success.
• In partnership with CLT, support Annual Planning coordination and execution. 

• Minimum 7+ years of leadership experience, including at least 5 years of managing cross-functional teams to drive shared outcomes.
• Proven ability to develop and execute large-scale volunteer recruitment strategies, or similarly aligned work, such as large-scale fundraising or development, ideally in Chicago or a similar market.
• Strong background in strategic marketing, business development, or sales.
• Experience building, managing, and cultivating corporate partnerships.
• Data-driven decision-maker with experience using analytics and performance tracking to inform strategy.
• Excellent communication and relationship-building skills, with the ability to inspire and motivate diverse stakeholders.
• Prior experience in nonprofit leadership, particularly in youth development, education, or mentorship programs, is strongly preferred.
• After hours, weekends, and in-person work will sometimes be required.
• Demonstrated alignment with iMentor's mission, core values, and commitment to fostering a supportive and collaborative community.
• Recognizes and values the unique backgrounds, experiences, and perspectives of all individuals, and actively contributes to a welcoming and collaborative environment.
• Bachelor’s degree required.
• Our organization works in partnership with district public schools across the country. In doing so we must meet all compliance requirements of those districts including background checks.
• iMentor is committed to ensuring healthy and safe environments for our staff, mentors, and the students we serve. In order to fully comply with the NYC Vaccine mandate, all iMentor employees (regardless of role or region) are required to be fully vaccinated priority to their start date.

• Salary $115-125 commensurate with experience
• Up to 100% employer-funded comprehensive medical and dental coverage
• 18 days paid annual vacation (increasing annually to 21, 23, 25), 13 paid holidays + your birthday + one floating holiday, iMentor closed between Christmas and New Year’s Day, plus 6-7 sick days annually
• 401K match up to 4%
• Hybrid Home/Office/School working arrangement (some evening and weekend hours required)
• Pre-tax commuter benefits
• Dependent care and health care flexible spending plans
• 1 hour of wellness time off per week for wellness activities of your choosing
• Flexible personnel wellness budget for reimbursements or marketplace purchases
• Every staff member is eligible for organization-sponsored professional development annually
• 9 weeks of paid parental leave