Job Description
iMentor is seeking a strategic, externally oriented leader to serve as Senior Director of External Relations in Chicago. This role is responsible for advancing regional revenue, strengthening iMentor’s presence in the market, and building partnerships that expand opportunity for young people.
Reporting to iMentor’s VP of Philanthropy and Strategic Partnerships, the Senior Director will lead the execution of a comprehensive external relations strategy across philanthropy, corporate partnerships, government engagement, and brand visibility. They will serve as a key representative of iMentor in the Chicago region, cultivating relationships with funders, civic leaders, and institutional partners, and activating the Regional Board as a driver of revenue, engagement, and network expansion.
This role operates at the intersection of national strategy and execution, working in close partnership with national philanthropy and marketing & communications teams, as well as regional leadership, to translate enterprise priorities into effective regional strategies and outcomes.
Revenue Strategy and Execution
- Set and lead the regional revenue strategy in alignment with organizational priorities and local market opportunity
- Build and manage a growing portfolio with a trajectory toward overseeing $2–$3M in annual philanthropic revenue across corporate, foundation, and individual giving
- Cultivate, secure, and steward five- and six-figure investments through strategic relationship management and donor engagement
- Drive new pipeline development by identifying and advancing priority prospects in partnership with national leadership
- Support accurate forecasting and portfolio management to drive consistent revenue performance
Regional Board Leadership
- Activate the Regional Board as a driver of fundraising, engagement, and network-building
- Partner with regional leadership to support board recruitment, engagement, and participation in revenue-generating activities
- Lead the planning and execution of board strategy, including meetings, communications, and engagement opportunities
Market Presence & Partnerships
- Represent iMentor in the Chicago market, strengthening the organization’s visibility and positioning through events, convenings, and partnerships
- Build and steward relationships with corporate, community, and cross-sector partners to expand iMentor’s reach and impact
- Lead local activation of national campaigns and initiatives, ensuring strong local resonance and engagement
- Identify and pursue partnership opportunities that integrate mentor recruitment, funding, and brand visibility
Government & Civic Relationships
- Build and maintain relationships with government, civic, and education stakeholders to support iMentor’s presence and growth in the region
- Partner with national and regional staff leadership to identify and pursue public funding opportunities
Cross-Functional Collaboration
- Serve as a key connector across national and regional teams, ensuring alignment between fundraising, partnerships, communications, and program priorities
- Contribute to regional strategy and planning in partnership with leadership
- Foster a culture of collaboration, accountability, and shared ownership across teams
- Partner closely with Chicago’s recruitment leadership to manage and grow the local corporate partnerships portfolio, ensuring strong alignment between mentor recruitment goals and philanthropic investment
- Serve as a key member of the Chicago Leadership Team, supporting healthy effective cross-team communication, coordination and a cohesive regional presence
Qualifications
- 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
Compensation and Benefits
- Salary $135,000 to $145,000 annually commensurate with experience.
- 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
$135,000 - $145,000 a year
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
