Senior Director of Advancement (3870)

The Opportunity

Youth Guidance is seeking an experienced, entrepreneurial, and mission-driven Senior Director of Advancement to serve as the Chief External Affairs Officer's number two and the day-to-day leader of the Development function. This is a pivotal opportunity to help Youth Guidance deliver ambitious private fundraising goals, maximize the Bright Futures Campaign, strengthen fundraising performance across a growing national organization, and build the team and infrastructure required for sustained philanthropic growth.

The Senior Director will inherit a committed team and a strong base of institutional, individual, corporate, and public support. The immediate mandate is to create greater focus, coordination, accountability, and execution across Development: translating strategy into clear plans, strengthening portfolio and pipeline management, coaching fundraisers, improving forecasting, and ensuring that the highest-priority donor and campaign opportunities move forward. Over time, the Senior Director will help shape and build a more specialized Development organization with stronger capacity in institutional giving, major and planned gifts, annual giving, donor experience, grant writing, prospect management, operations, and data analysis.

The ideal candidate is both a fundraising leader and an organizational builder. They can lead the day-to-day work with rigor while keeping sight of the longer-term opportunity; use data and relationships to drive decisions; coach experienced fundraisers; identify and recruit strong fundraising talent; and create the systems, roles, and operating practices that allow talented staff to do their best work. As Youth Guidance begins to expand its frontline fundraising capacity in FY27, the Senior Director will play a central role in identifying, selecting, onboarding, and developing the talent needed to deliver the organization’s philanthropic ambitions.

Position Summary

Reporting to the Chief External Affairs Officer, the Senior Director of Advancement leads Youth Guidance's enterprise Development strategy, execution, team leadership, fundraising performance, and operating discipline. The Senior Director will align fundraising activity with annual revenue goals and the Bright Futures Campaign; oversee portfolio, pipeline, forecasting, moves management, institutional writing, donor engagement, and fundraising operations; and ensure that fundraisers across markets receive the strategy, coaching, tools, and accountability needed to grow revenue and deepen donor relationships.

Essential Duties/Responsibilities:

Development Strategy and Revenue Leadership

• Partner with the Chief External Affairs Officer to translate Youth Guidance's private philanthropy strategy and Bright Futures Campaign goals into actionable annual and multi-year fundraising plans.
• Lead day-to-day execution of the Development strategy across major and principal gifts, corporate and foundation relations, annual giving, donor engagement, institutional writing, and regional fundraising.
• Establish clear revenue ownership, portfolio assignments, quarterly milestones, and performance expectations that roll up to agency-wide fundraising goals.
• Monitor revenue, pipeline health, forecasts, donor retention, renewal and upgrade activity, and fundraising productivity; identify risks early and lead corrective action when results are off track.
• Work with Finance and organizational leaders to strengthen forecasting, revenue planning, and alignment between fundraising commitments, program priorities, and organizational capacity.
• Identify opportunities that span markets or programs and coordinate the right leaders, relationships, and resources to pursue them effectively.

Team Leadership and Organizational Development

• Provide clear direction, coaching, performance management, and accountability to Development leaders and senior fundraising staff across a matrixed, multi-site organization.
• Build a collaborative, high-performing Development culture grounded in trust, shared goals, disciplined execution, learning, and constructive feedback.
• Clarify roles, decision rights, workflows, and handoffs so relationship owners remain close to donors while centralized teams provide effective writing, data, operational, and engagement support.
• Lead the recruitment, selection, onboarding, integration, and development of priority Development hires. Bring a strong eye for fundraising talent and help build a high-performing team capable of delivering increasingly ambitious private revenue goals.
• Assess team capacity and recommend the timing, scope, and design of future roles based on revenue opportunity, fundraiser productivity, organizational readiness, and return on investment.
• Retain and develop strong talent by creating meaningful growth opportunities, equitable expectations, and the support staff need to succeed during periods of change.

Fundraising Performance Systems and Operations

• Lead a consistent operating cadence for portfolio reviews, move management, prospect strategy, pipeline development, revenue forecasting, and performance check-ins.
• Use Salesforce dashboards and other data to assess activity, pipeline quality, next actions, forecasting accuracy, and progress toward individual and enterprise goals.
• Strengthen organization-wide fundraising standards and practices for prospect qualification, relationship management, proposal development, gift processing, stewardship, reporting, and data quality.
• Ensure centralized grant-writing capacity is deployed against the highest-priority opportunities and produces timely, compelling, and consistent proposals and reports.
• Partner with Development Operations and data staff to turn fundraising information into useful insights, stronger decisions, and greater frontline fundraiser capacity.

Campaign Donor and Board Engagement

• Partner with the Chief External Affairs Officer and CEO to advance the Bright Futures Campaign, including prospect strategy, leadership engagement, campaign reporting, stewardship, and execution of priority cultivation opportunities.
• Maintain a selective portfolio of high-priority prospects and donors, and serve as a strategist and closer alongside the Chief External Affairs Officer, CEO, Board members, and other organizational leaders.
• Ensure that leadership donors receive thoughtful, coordinated, and appropriately segmented cultivation and stewardship.
• Equip Board members, campaign leaders, Advisory Councils, and senior staff with clear opportunities, messages, and next steps to open doors and advance relationships.
• Oversee the fundraising strategy and integration of donor experiences, including the Gala, Investor Day, parlor gatherings, Council engagement, and other cultivation and stewardship opportunities, while ensuring strong execution by the appropriate staff.

Enterprise Partnership and Cross Functional Leadership

• Serve as a senior partner to the Chief External Affairs Officer and represent Development in cross-functional planning and decision-making as appropriate.
• Collaborate with Marketing and Communications to strengthen cases for support, donor communications, campaign materials, and storytelling while respecting MarCom's separate reporting line.
• Collaborate with Government Relations and Government Funding and Partnerships to share intelligence, coordinate external relationships, and support integrated funding strategies while respecting their separate reporting lines.
• Partner with regional Executive Directors and Development leaders to balance enterprise standards with local knowledge, relationships, and revenue ownership.
• Develop first-hand knowledge of Youth Guidance programs by engaging with young people, alumni, staff, schools, and community partners and incorporating that understanding into fundraising strategy and donor engagement.

Qualifications

Required Qualifications

• At least 12 years of progressively responsible fundraising experience, including at least five years leading and developing teams in a complex, mission-driven organization.
• Demonstrated success designing and executing comprehensive fundraising strategies and delivering significant private revenue growth.
• Successful experience cultivating, soliciting, and closing major gifts, including six-figure or larger commitments from individuals, corporations, and foundations.
• Experience leading across multiple fundraising channels and functions, including major gifts, institutional giving, campaigns, annual giving, donor engagement, and fundraising operations.
• Demonstrated ability to identify, recruit, develop, and retain strong fundraising talent and to build, restructure, or scale teams and systems while sustaining revenue delivery.
• Experience establishing clear goals, managing portfolios and pipelines, strengthening forecasts, and using CRM data to drive fundraising decisions and accountability.
• Exceptional judgment, communication, relationship-building, and change-leadership skills, with the ability to influence organizational levels and functions.
• Bachelor's degree or equivalent combination of education and relevant experience.

Preferred Qualifications

• Experience in a national or multi-site nonprofit with matrixed reporting relationships and fundraising accountability across markets.
• Experience with a comprehensive or capacity-building campaign and leadership-level Board and volunteer engagement.
• Familiarity with Chicago's philanthropic, corporate, civic, or education communities and experience developing national funding relationships.
• Experience implementing or improving Salesforce and related fundraising systems, dashboards, and operating practices.
• Advanced degree or CFRE credential.

Competencies

• Strategic thinker with strong fundraising instincts
• Exceptional relationship builder
• Executive presence and sound judgment
• Highly organized and results-oriented
• Collaborative and mission-driven
• Resilient, proactive, and entrepreneurial

Skills/Abilities

Demonstrates Youth Guidance Core Competencies:

• Communication: Uses effective written and oral communication with internal staff, teams, and community served; demonstrates empathy and listening
• Equity mindset: Understands and is committed to goals of equity; consistently brings an equity mindset to the organization’s work and workplace
• Growth mindset: Views growth as important for personal and professional development; seeks out opportunities to expand skills, even if change is required; demonstrates curiosity and eagerness to learn
• Supervisory skills: Effectively manages and develops others, ensuring delivery of high-quality work
• Mission driven: Demonstrates commitment to the mission of the organization as a whole and alignment with organizational values

Demonstrates Youth Guidance Leadership Competencies:

• External representation and relationship building: An ability to form and maintain strong, trusting relationships with diverse stakeholders.
• Leads with vision: Has an inspiring vision for the future of the organization, beyond the status quo, and communicates it effectively; leads with courage and willingness to take risks in service of impact.
• Develops and motivates others: Motivates others and supports their development through strong coaching and mentoring. Effectively stewards self and others through both small- and large-scale changes.
• Manages with data: Understands data; analyzes data and identifies insights and implications
• Strategic thinking and resource management: Considers the future of the organization proactively and responsively; weighs diverse inputs to inform strategies; identifies innovative opportunities when relevant; makes and communicates decisions that effectively balance tradeoffs.
• Team building: Builds strong relationships with teams and colleagues; fosters effective teams and collaborative efforts.

Physical Demands

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions

• This position operates in a hybrid professional work environment and requires regular use of computers, mobile devices, video conferencing, collaboration platforms, and other digital tools and technology.
• This position requires the ability to communicate effectively in person, virtually, and via written materials. The role may involve periods of movement, including walking or standing, and the use of hands for typical office tasks such as typing, writing, or handling materials.
• Regular local travel within Chicago and Lake County is required to support local teams, attend events, and engage with external partners.

Benefits

Youth Guidance offers a competitive benefit package for eligible full-time employees including the option to participate in medical, dental, and vision plans as well as short-term disability, life insurance, flex spending accounts, pet insurance, 401k, a wellness program and more. You may also qualify for Public Service Loan Forgiveness (PSLF).

Work Environment

• The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
• Able to spend extended time on a computer in a workstation
• This position operates in a hybrid work environment. The successful candidate is expected to be available for regular in-person meetings with donors, prospects, board members, volunteers, colleagues, and community partners, as well as organizational events and leadership meetings. The schedule should be driven by fundraising priorities and organizational needs.

Youth Guidance is an equal opportunity employer and proudly values diversity. Youth Guidance does not discriminate on the basis of race, color, religion, sex, national origin, disability, veteran status, marital status, sexual orientation, or any other characteristic protected by applicable law and is committed to creating a dynamic work environment that values diversity along all of these lines. People of all backgrounds are encouraged to apply.