Responsible for advancing regional revenue, strengthening iMentor’s presence in the market, and building partnerships that expand opportunity for young people.
Lead the execution of a comprehensive external relations strategy across philanthropy, corporate partnerships, government engagement, and brand visibility.
Serve as a key representative of iMentor in the Chicago region, cultivating relationships with funders, civic leaders, and institutional partners.
Activate the Regional Board as a driver of revenue, engagement, and network expansion.
Collaborate with national philanthropy and marketing & communications teams, and regional leadership to translate enterprise priorities into effective regional strategies and outcomes.

8–10+ years of experience in fundraising, partnerships, or external relations, with increasing scope of responsibility.
Experience leading multi-stream revenue strategies (corporate, foundation, individual, and/or public funding).
Demonstrated success securing and managing high-value gifts and partnerships, including six
and seven-figure investments.
Experience engaging and activating boards or senior volunteer leaders.
Experience working within federated or national–regional organizational structures, with the ability to translate enterprise strategy into locally relevant market strategies.
Demonstrated ability to balance local ownership with national alignment, navigating complexity and influencing across teams and stakeholders.
Mindset of an adaptive leader, with a willingness to build, iterate, and flex as the organization grows and changes, regardless of title or hierarchy.
Strong judgment and decision-making skills, with the ability to navigate complexity without relying on fixed answers or rigid structures.
Experience taking initiative, managing ambiguity, and making sound, high-impact decisions.
Proven ability to operate as an external ambassador and build relationships with senior stakeholders, including executives, board members, and civic leaders.
Strategic thinker who can translate vision into execution and measurable results.
Excellent communication, negotiation, and presentation skills.

Up to 100% employer-funded comprehensive medical and dental coverage.
18 paid days annual vacation (increasing annually to 21, 23, 25).
13 paid holidays, plus your birthday, plus one floating holiday.
iMentor closed between Christmas Eve and New Year’s Day.
Plus 8 sick days annually.
401k match up to 4%.
Flexible Home/Office/School working arrangement.
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

Senior Director, External Relations

Key skills