Assistant Director of Advancement Strategy & Operations

High-Jump; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Job summary

High Jump is seeking an Assistant Director of Advancement Strategy & Operations to translate fundraising goals into coordinated plans, campaigns, and measurable action. Working with the Chief Advancement Officer and across the Advancement team, this role connects strategy to execution—ensuring that fundraising priorities have clear goals, audiences, timelines, ownership, and measures of success.

This position leads Annual Fund and Sustaining Leaders strategies and oversees the CRM, gift

Qualifications

• 5+ years in nonprofit fundraising or advancement operations.
• Experience planning and executing fundraising campaigns.
• Strong donor segmentation and stewardship knowledge.
• Experience managing a fundraising CRM (Raiser’s Edge preferred).

Responsibilities

• Lead strategy, planning, implementation, and evaluation of key campaigns.
• Lead Annual Fund, Sustaining Leaders Fund, and mid-level giving programs.
• Set clear goals, audiences, segmentation, timelines, responsibilities, and success measures.
• Coordinate campaign execution with Marketing for creative and messaging.
• Develop donor acquisition, retention, upgrades, and recurring giving strategies.
• Manage the annual Board giving and pledge process and related communications.

Skills

Fundraising analytics

Campaign management

Strategic planning

Project management

Tools

Raiser’s Edge

Omatic

Constant Contact

Classy

Job description

• Reports to: Chief Advancement Officer
• Leads: Fundraising campaigns, Annual Fund and mid-level giving, Advancement operations and systems, fundraising analytics, and department planning

Summary

The Assistant Director of Advancement Strategy & Operations translates High Jump's fundraising goals into coordinated plans, campaigns, systems, and measurable action. Working closely with the Chief Advancement Officer and across the Advancement team, this role connects strategy to execution-ensuring fundraising priorities have clear goals, audiences, timelines, ownership, and measures of success.

This position leads High Jump's Annual Fund and Sustaining Leaders (annual major donors) strategies and manages the planning and execution of key fundraising campaigns, including Giving Tuesday, year-end giving, recurring giving, and other targeted donor initiatives. The role also owns the operational infrastructure that supports Advancement, including the CRM, gift processing and donor records, fundraising reporting and analytics, and continuous improvement of department systems and processes.

Ideal candidates are strategic executors who can move comfortably between a fundraising goal and the systems and detailed plans required to achieve it. They are analytical, organized, collaborative, and motivated by a central question: How do we build the fundraising systems and strategies that allow Advancement to raise more?

Core Responsibilities

Fundraising Strategy & Campaigns

• Lead the strategy, planning, implementation, and evaluation of key Advancement campaigns, including Giving Tuesday, year-end giving, recurring giving, and other targeted fundraising initiatives.
• Lead strategy and execution for High Jump's Annual Fund, Sustaining Leaders Fund, and mid-level giving programs.
• Establish clear goals, audiences, segmentation strategies, timelines, responsibilities, and success measures for fundraising campaigns.
• Coordinate campaign execution across Advancement, partnering with Marketing & Communications on creative and messaging and other team members on donor engagement.
• Develop strategies to improve donor acquisition, retention, renewal, upgrades, and recurring giving.
• Analyze campaign results and translate findings into recommendations for future fundraising efforts.
• Manage the annual Board giving and pledge process and Board Customized Letter campaign in partnership with the Chief Advancement Officer, including timelines, participation, tracking, materials, and follow-up.

Advancement Operations, CRM & Data

• Own the day-to-day management and integrity of High Jump's Advancement CRM and related fundraising systems.
• Lead gift and pledge processing, donor record management, acknowledgments, and related Advancement operations, ensuring timely and accurate execution. Partner closely with the Associate Director of Advancement Engagement to maintain appropriate quality-control checks, shared visibility, and backup coverage for these critical functions.
• Serve as the primary Advancement partner to Finance for gift reconciliation, revenue reporting, and alignment between fundraising and financial records, with the Associate Director of Advancement Engagement providing secondary review and cross-checking as appropriate.
• Maintain accurate and comprehensive donor and constituent records, including gifts, pledges, interactions, prospect information, and other relevant activity.
• Establish and maintain clear procedures, documentation, and workflows for Advancement operations.
• Serve as the primary resource for Advancement technology, including Raiser's Edge, Omatic, Constant Contact, Classy, and other fundraising platforms.
• Identify and implement technology and process improvements that increase accuracy, efficiency, and team effectiveness.
• Build lists, segmentation, and data processes needed to support fundraising campaigns and donor strategies.

Fundraising Analytics & Portfolio Support

• Develop and maintain fundraising dashboards, reports, and performance tools that provide visibility into revenue, donor activity, campaign performance, and progress toward goals.
• Analyze fundraising data to identify trends, opportunities, risks, and areas requiring additional attention.
• Use data and fundraising results to inform strategy, forecasting, annual planning, and goal setting.
• Support portfolio management by providing the systems, reporting, and data needed to track donor movement and fundraising activity.
• Partner with the Associate Director of Advancement Engagement on quarterly portfolio reviews and the annual portfolio review and scrub.
• Ensure donor strategies, moves, interactions, and next steps are consistently and accurately documented in the CRM.
• Translate fundraising data into actionable recommendations for the Chief Advancement Officer and Advancement team.

Department Planning & Execution

• Support annual and long-range Advancement planning, translating department priorities into actionable workplans, timelines, and measurable goals.
• Provide project management for key Advancement initiatives, ensuring clear ownership, deadlines, dependencies, and follow-through.
• Coordinate work across fundraising, marketing and communications, operations, events, and constituent engagement when initiatives require multiple team members.
• Support Advancement's role in selected cross-functional organizational initiatives, including Admissions Interviews, Moving Up, the End of Summer Picnic, and other priorities.
• Partner closely with the Associate Director of Advancement Engagement to ensure fundraising strategy, systems, and constituent engagement are aligned.
• Identify opportunities to strengthen department processes, coordination, and effectiveness.

Qualifications

• 5+ years of experience in nonprofit fundraising, advancement operations, annual giving, campaign management, or related work; appropriate experience expectations may be adjusted based on final title.
• Demonstrated experience planning and executing fundraising campaigns.
• Strong understanding of annual giving, donor segmentation, cultivation, solicitation, stewardship, and donor retention strategies.
• Experience managing a fundraising CRM and donor data; Raiser's Edge experience strongly preferred.
• Knowledge of gift processing, donor records, data integrity, and fundraising operations.
• Strong analytical skills and demonstrated ability to use fundraising data to inform strategy and decision-making.
• Exceptional project management skills and ability to move complex initiatives from strategy through execution.
• Strong written and verbal communication skills.
• Highly organized and detail-oriented, with the ability to manage multiple priorities
• Ability to balance strategic thinking, analysis, and hands-on execution.
• Ability to work independently while collaborating effectively across teams.
• Commitment to High Jump's mission and ability to thrive in a dynamic, growing organization.
• Availability for occasional evenings and weekends during key events and campaign periods.