Director, Annual Giving (Direct Response Fundraising Strategy)

Advancement Worcester, Massachusetts


Job Summary

The Director, Annual Giving (Direct Response Fundraising Strategy) serves as a strategic and operational partner to the Director of Annual Giving and Volunteer Engagement to meet annual fundraising goals and increase alumni participation. This position is accountable for donor participation and responsible for providing leadership, strategic direction and oversight of an integrated solicitation plan for the Annual Giving team. The Director will lead and execute a best in class, multi-channel direct response effort for our nationally ranked annual giving program. This position also oversees the Associate Director of Annual Giving Communications.

Major Areas of Responsibility

 Annual Giving Strategic Planning and Management 

  • Work with the Annual Giving directors to facilitate aggressive and rigorous participation, goals. Work across all channels and constituencies, with a special emphasis on sustaining and growing donor participation in the Holy Cross Fund and Crusader Athletics Fund. Ensure ongoing monitoring and evaluation of results to ensure success in meeting goals.
  • Develops the Annual Giving integrated solicitation strategy  to meet donor acquisition, reactivation and retention goals and benchmarks. The strategic plan should convey the case for support through a combination of channels, including direct mail, email, texting, our digital fundraising platform, and additional materials such as President’s Council, class, reunion and sport-based communications.
  • Oversees the tracking and analysis of all Annual Giving solicitation results against progress toward participation goals. If necessary, make recommendations to pivot messaging, segmentation and channels to achieve Annual Giving benchmarks.
  • Studies current and innovative annual giving strategies and best practices, recommending and implementing new methods and activities to improve overall Annual Giving results and to increase average annual gifts.
  • Partners with Advancement Communications and College Marketing and Communications teams to create marketing strategies, multi-channel solicitations, websites and other collateral for the Annual Giving program.
  • Collaborate with Advancement Operations colleagues to develop tools to support and track annual giving programs.


  • Manage Annual Giving appeal codes, analysis, and other key functions that support the Annual Giving multi-channel solicitation/marketing plan.
  • Oversee the tracking and analysis of all direct mail solicitation results, and report periodic (monthly, annual, and campaign-specific) progress to goals and/or adverse trends. Study trends and ensure appropriate responses to trends are happening. Recommend ways to enhance the effectiveness and success of solicitations strategies and communications, as well as targeted Annual Giving campaigns.
  • Partner with internal staff to ensure systems and reports are in place to meet and track and meet strategic goals of unrestricted giving to Holy Cross. Build and analyze fundraising reports that provide progress toward goals, appeals, and fundraising projects.

 Communications and Solicitations 

  • Utilize digital analytics tools, predictive modeling, segmentation, and other data-driven techniques to ensure communications are personalized, timely and consistent and Annual Giving goals are achieved.
  • Work closely with Advancement Communications and College Marketing and Communications offices to ensure messaging is aligned with department and College best practices.
  • Serve as the key communications contact for Annual Giving electronic communications and solicitations.
  • Work with internal marketing partners to create, edit, and review integrated communication materials, including strategic print materials, e-mail content, volunteer materials and online giving pages.
  • Deliver timely and strategic messaging recommendations and feedback to compliment integrated campaigns and make decisions on communications assets.
  • Participate in promoting positive and effective communications.

 Marketing and Multi-Media Strategies 

  • Collaborate closely to develop and orchestrate an integrated marketing and communications strategy and operating plan to convey the case for support of the Annual Giving program through a combination of direct mail, email, print and electronic advertising to increase dollars and donors.
  • In partnership with internal partners, prepare a detailed operating plan and calendar each year to execute the communications efforts for the Annual Giving program.
  • Develop segmentation strategy to maximize the impact of campaigns.
  • Solve advanced marketing challenges through segmentation strategy, testing packages and initiatives, and partner on the implementation of A/B testing protocol and procedures.
  • Provide strategy for dashboard analysis and analyze back-end results and responses.
  • Partner with internal alumni relations, communications, and marketing staff to create communications strategies, solicitations, emails, websites and other collateral and media solicitations for the Annual Giving program.
  • Recommend marketing techniques to improve overall annual giving results and to increase average annual non-reunion gifts.
  • Partner with internal stakeholders to creatively utilize, implement and manage tools (crowdfunding, texting, volunteer platform, email, etc.) to ensure success.
  • Implement ongoing dialogue mechanisms with constituents/stakeholders (surveys, interviews, forums, focus groups) to improve the effectiveness of Annual Giving efforts.
  • Maintain knowledge of industry trends and standards in fundraising, identifying market and competitive trends, understanding potential business opportunities and impacts, and proactively communicate findings to staff to inform decision-making and strategies.
  • Serve as premier Annual Giving donor participation business analyst/consultant to staff, guiding them in the development of workable solutions, and maintaining staff focus and motivation in an environment with shifting priorities and unanticipated changes based on environmental factors.
  • Recruit, hire, train and manage direct reports.  Complete appropriate performance management program to ensure goals, objectives and expectations are communicated and completed in alignment with the overall College mission, division and department.
  • Other duties as assigned. 

Minimum Qualifications

  • Bachelor’s Degree required.
  • 7+ years of experience working in higher education fundraising administration or a complex development operation; or the equivalent.
  • Extensive experience managing projects, programs, budgets, and financial reports, working with various technologies including advanced knowledge and experience with Microsoft Office Suite, database and project management software, and CRM systems.
  • Experience in developing annual giving, marketing or communications strategies
  • Strong knowledge of information systems, and business analysis of complex information systems experience preferred
  • Market intelligence/market research and analytic experience
  • Broad knowledge of the relative value of all communications channels
  • Experience with digital marketing and direct mail
  • Demonstrated ability to seek and strategically employ new technology to achieve goals

Additional Information:

This is a full time, exempt level position. The College is committed to providing competitive market pay for its employees.  The College also offers a competitive benefits package for full-time staff, including:

  • 10% College contribution to the 403(b) Retirement Plan (1 year wait waiver available)
  • This position may be eligible for a hybrid work arrangement
  • Condensed summer 4-day work week
  • Tuition benefits
  • Wellness programs & ongoing Training and Development opportunities
  • Generous paid time off

The College is an Equal Employment Opportunity Employer and complies with all Federal and Massachusetts laws concerning Equal Opportunity and Affirmative Action in the workplace.

To review our Employee Benefit Options, please go to:


Please upload a resume (CV) and cover letter.

In your cover letter please address how your work might support the College's mission as a Jesuit, undergraduate liberal arts college (see and its core commitment to diversity and inclusion. Please provide examples of any past work that illuminate your commitments in these areas. For more information, please visit

Review of applications will begin as received and continue until the position has been filled.