Principal Gift Strategist

Principal Gift Strategist

CATEGORY: Administrative

Oregon Shakespeare Festival
Ashland, OR 97520

Job Details


The Oregon Shakespeare Festival is seeking a Principal Gift StrategistThe Principal Gift Strategist leads the creation and execution of integrated communications strategies designed to inspire and engage donors in order to attract, secure, maintain, and increase philanthropic support for OSF. In collaboration with the OSF major gifts fundraising team, the Principal Gift Strategist will advance the scale and scope of financial support to help ensure both the short- and long-term financial success of the organization and its continued pursuit of artistic excellence.

This is a full-time, year-round, exempt position.

The ideal candidate is a strategic thinker and superb writer/storyteller with excellent interpersonal and project management skills and will have a demonstrated understanding of and experience in creating and executing philanthropic communications programs that speak to donor motivations. Prior experience in leading and managing complex communications initiatives in a non-profit environment; coordinating the roles of multiple project contributors (including senior leadership); and setting priorities and schedules is required. 

All OSF employees are expected to understand and embrace our mission statement, in particular how it is reflected in our commitment to respect and represent diverse ideas, races, genders, sexualities, abilities, cultures, religions, and traditions – on-stage and off. OSF company members work in a manner that is consistent with this commitment and work to interrupt behaviors that hinder our diversity and inclusion efforts.

Salary Rate: $34.90

Principal Duties and Responsibilities:

  1. Attend ED&I, sexual harassment and any other anti-bias trainings and workshops as scheduled by the institution.
  2. Model and support the mission and values of OSF.
  3. Be aware of, control, and express one’s emotions, and handle interpersonal relationships judiciously and empathetically.
  4. Lead the development and execution of an integrated suite of communications strategies and tools that rely on demonstrated, specialized understanding of fundraising for the arts. The communications strategies will:
    1. Elevate excitement and engagement among donors for OSF’s artistic mission and core values
    2. Amplify OSF’s strategic fundraising vision to a variety of audiences (both internal and external), articulating the impact of philanthropy and how these fundraising goals advance OSF’s mission
    3. Advance prospects along the cultivation curve
    4. Attract and secure principal gifts
    5. Steward major-gift donors
    6. Promote new or revitalized giving opportunities (e.g. annual fund, transformational gifts)
    7. Bridge individual and institutional giving
    8. Promote understanding among donors of the crucial need for philanthropic support
    9. Embrace and amplify diverse voices
  5. Create strategies and communications tactics that creatively and effectively advance OSF’s fundraising goals, with deliverables to include (but not limited to):
    1. Developing an integrated principal gifts messaging strategy
    2. Telling donor-impact stories
    3. Designing donor communications in the voice of senior leaders
    4. Writing case statements—both internal and external
    5. Writing individual major gift proposals ($25K – multimillion)
    6. Designing Development toolkits (suite of print materials/collateral; digital tools)
    7. Leading Project management/supervision/art direction of creative (print and digital design, photography, videography, etc.) of communication tools
    8. Grant writing and grant reports
    9. Writing stewardship communications and reports
    10. Designing Executive communications (presentations, talking points, ghostwriting, event scripts, correspondence)
    11. Completing Campaign communications research, strategy and tactics
    12. Research prospects
    13. Create principal gift social media strategy
    14. Design and create web content strategy for principal gifts
    15. Integrate brand management into all strategies and communications
  6. Take personal responsibility for reporting metrics to the Director of Development for regular organizational and board reports

Other Duties and Responsibilities:
  1. Active participant in planning and attending Donor Engagement events
  2. Seek out professional development opportunities to understand communications trends and strategies in the field of arts fundraising
  3. Particpate in arts based discussions and presentations at OSF to understand the underlying themes and values being presented in the work

Education: Master’s degree, or equivalent professional experience

Work Experience: 7+ years in communications leadership capacity for a large, complex non-profit organization required. Capital campaign experience is strongly preferred

  • Proven leadership of a communications strategy for a complex fundraising operation (major gifts, grant writing, giving societies, events, annual giving, etc.)
  • Understanding of philanthropy—especially the major gift cultivation cycle—in a large non-profit environment
  • Demonstrated ability to build relationships, trust and confidence with executive leadership, staff, artists, donors, sponsors, grant agencies and other funders
  • Advanced and versatile writing, editing, and proofreading experience
  • Demonstrated ability to manage multiple projects simultaneously, relying on input from various internal stakeholders
  • Successful multiplatform project-management experience: print publications, digital media, video production, web, social media; demonstrated ability to supervise creative contributors (writers, photographers, designers, videographers, printers), negotiate contracts, deliver results on time and on budget
  • Demonstrated sound judgment in situations that require independent decision-making, and handling confidential and sensitive materials.
  • Proficiency in Microsoft Office, Google and Adobe applications
Physical Ability: Comfortable in an office environment and shared workspace that requires frequent use of the telephone and use of a computer 75% of the time

Sick & Vacation Time
Relocation support for eligible employees
Health & Wellness Plan
Flexible Spending Account 
Retirement Plan & Company Match 
Employee Assistance Program 
Long Term Disability
Paid Holidays
Complimentary Tickets to OSF productions and other select events
Discounts at select local businesses

About the Oregon Shakespeare Festival
Located in the beautiful Rogue Valley of Southern Oregon, our Tony Award-Winning company of extraordinary artists present seasons of ten to twelve plays in rotating repertory between the months of February/March and October. A robust and highly dedicated staff of over 500 employees produces these performances each season across three venues: the Allen Elizabethan, Thomas, and Bowmer Theatres. Inspired by Shakespeare's work and the cultural richness of the United States, the productions on our stages reveal our collective humanity through illuminating interpretations of new and classic plays, deepened by the kaleidoscope of rotating repertory and guided by our values of Excellence, Inclusion, Company, and Stewardship. We are also excited to usher in a new creative era this season as recently announced Artistic Director Nataki Garrett takes the helm!

In addition to our main stage plays, we offer an eclectic array of enrichment programs for audiences and staff alike including backstage tours, educational workshops, prefaces, prologues, a lecture series and the Green Show. We also partner with local organizations and community members on a number of immersive events and celebrations including an annual Martin Luther King, Jr Day Celebration, Juneteenth Celebration, OSF Out Weekend, and Daedalus Project.

Why Should I Apply:
Be a part of an industry-leading professional non-profit regional theatre in its 84th season with a rich history and values arts, excellence, and inclusion. OSF is nestled in a scenic mountain valley near the Oregon-California border where the weather is idyllic with mild winters and hot, dry summers. We are one of the only regional theatres of our size and caliber that is not located in a major metropolitan area! Southern Oregonians love the outdoors, and because of our non-urban setting, an abundance of stunning rivers and lakes, nearby state and national parks, hiking trails, outdoor music venues, white-water rafting and hang gliding excursions are just outside the front door. Southern Oregon also offers robust culinary experiences with dozens of top-notch restaurants, local breweries, charming cafes, and award-winning wineries. We care about community, and our region’s dedication to supporting local businesses and agriculture is notable. Our employee benefits are first-rate, too!

At OSF we believe that diverse ideas, cultures and traditions reflect the broad diversity of the nation and enrich our insights into the work we present on stage. We are committed to diversity in all areas of our work, including play selection, casting, marketing and public relation efforts, education programs, strategic recruitment of staff and volunteers, and the composition of the Board of Directors. People of color and members of other underrepresented groups are encouraged to apply. 

If you wish to apply for this position please be prepared to provide:


3 work references (name, email and phone number)

A cover letter is requested but not required.

A professional writing sample is requested but not required (please upload to supplemental materials)

Only complete applications will be considered.





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