Job Description

Job Summary

Description

With its intact and picturesque vistas, Cheekwood is distinguished as one of the leading Country Place Era estates in the nation. Formerly the family home of Mabel and Leslie Cheek, the 1930s estate, with its 30,000-square-foot Mansion and 55-acres of gardens, today serves the public as a botanical garden, arboretum, and art museum with furnished period rooms and galleries devoted to American art from the 18th to mid-20th centuries. The property includes 13 distinct gardens including the Blevins Japanese Garden and the Bracken Foundation Children’s Garden, as well as a 1.5-mile woodland trail featuring outdoor monumental sculpture. Each year, Cheekwood hosts seasonal festivals including Cheekwood in Bloom, Summertime at Cheekwood, Cheekwood Harvest and Holiday LIGHTS. Cheekwood is listed on the National Register of Historic Places and is accredited by the American Alliance of Museums and nationally as a Level II Arboretum. It is a three-time voted USA Today Top 10 Botanical Garden, in 2024 and 2025 received a Tripadvisor Travelers’ Choice Award, and in 2021 was named by Fodors as one of the 12 Most Beautiful Gardens in the American South. Cheekwood has a $17M budget and more than 200 full and part-time staff, presenting four seasons of family-oriented festivals, world-class exhibitions, and educational programs for over 380,000 visitors and 17,000 member families annually.

Position Description

Reporting to the Chief Development Officer, the Director of Development, Major and Leadership Gifts is a key member of the institution’s advancement team.

The Director of Development, Major and Leadership Gifts is a goal-oriented major gift development officer, leading the expansion of individual giving to Cheekwood’s annual giving and campaigns. The Director of Development, Major and Leadership Gifts, has strong portfolio management skills and proven frontline major gift fundraising experiences. The Director of Development, Major and Leadership Gifts is responsible for achieving an assigned annual revenue goal through the generation of increased and new major gifts and the continuing cultivation of annual donors and loyal members, which includes significant major gift prospecting efforts from Cheekwood’s pool of members, annual donors and other patrons. This position will use Cheekwood’s database and wealth research tools to identify individuals, foundations, and corporations with the capacity to make 5, 6 and 7 figure gifts and grants, focusing on individual giving.

The Director of Development, Major and Leadership Gifts provides leadership in engaging development committee members and other volunteers, and administrators in identifying, qualifying, and in cultivating, soliciting and closing major outright and planned gifts and pledges. This position will function as a collaborative team member, ensuring the optimization of all giving opportunities.

The Director of Development, Major and Leadership Gifts leads a collaborative team including the Assistant Director, Annual Giving and Event, and the Assistant Director, Corporate and Foundation Giving. Additionally, the Director, Major and Leadership Gifts works collaboratively with Cheekwood’s Director of Membership to identify and target new donor prospects through the organization’s large membership pool and ticket sales.

The Director, Major and Leadership Gifts possesses an appreciation and passion for the arts, with its many complexities, opportunities and challenges in our philanthropic landscape.

 

Job Responsibilities

Essential Responsibilities

• The Director of Development, Major and Leadership Gifts oversees and leads Cheekwood’s major and annual giving program, and the corporate and foundation giving program in collaboration with the CDO and CEO.
• They work collaboratively with the team to identify annual targets to achieve, developing goals, strategies, and specific plans for major and annual gift fundraising objectives.
• Manages a portfolio of 150 – 200 major and planned giving donors and prospects from $25,000 – $100,000 throughout their gift cycle including initiating discovery calls and outreach and developing appropriate cultivation strategies, moving donors and potential donors to close and /or upgrade gifts. Make solo solicitations when appropriate or with the CDO and/or CEO or board members. The Director of Development, Major and Leadership Gifts manages
• Cheekwood Society donors at the $25,000 – $100,000 level in conjunction with the Assistant Director, Annual Giving and Events.
• Helps catalyze a strong major gift pipeline by working collaboratively with the Director of Development Operations and Director of Membership to identify donors with major gift upgrade potential and then designs and implements upgrade strategies to expand the major gifts and the future pipeline.
• Maintains stewardship contacts and forges relationships with new prospects with a particular focus on those with the capacity to make five, six and seven-figure gifts.
• Demonstrates sensitivity to the many aspects of gift stewardship, including planned giving and donation upgrades. Collaborates with the Director of Development Operations in the appropriate and timely acknowledgement and recognition of gifts.
• Leads in developing appropriate planned giving opportunities for donors throughout the giving continuum to Cheekwood, ensuring that development staff have relevant information on planned giving instruments appropriate to their donor pipelines.
• Works with the Director of Development, Annual Giving and Events to integrate planned giving information into routine prospect and donor annual fund outreach appeals.
• Participates in, attends, and evaluates programs and events, donor society events, and other meetings and cultivation programs and activities to develop and encourage further collaborative fundraising partnerships with key partners with a goal of supporting major gifts.
• Help draft compelling letters and fundraising proposals to solicit renewed and new major gifts as well as continual cultivation of annual donor relationships with Cheekwood.
• Manages volunteers as assigned by the Chief Development Officer.
• Meets or exceeds expectations for performance metrics including numbers of visits, and proposals presented and closed.
• Establishes effective working relationships with members of the staff, board members and other volunteers to advance the identification, cultivation, solicitation and stewardship of individual prospects and donors.
• Keeps abreast of and participates in training on tax laws, current fundraising trends and planned giving vehicles.
• May propose and implement office/system procedures that will enhance the efficiency, accuracy, financial and statistical needs and timeliness of the work of the department.

Qualifications

Requirements

• Bachelor’s degree; Master’s preferred.
• A proven, successful, track record of closing five and six figure gifts.
• Five years of portfolio management and major and planned gift solicitation experience.
• Familiarity and experience with planned giving instruments and work with estate and financial professionals.
• Some experience and/or familiarity with cultural or arts organizations is preferred.
• Entrepreneurial spirit with a demonstrated track record of growing revenues through successful and meaningful prospecting efforts.
• Expertise in working with high-net worth individuals including Board members.
• Strong organizational skills and discipline in stewarding donor information and database records.
• Adherence to the highest ethical standards with the ability to act with discretion, self-assurance, and diplomacy.
• Ability to think creatively and entrepreneurially about ways to fundraise for Cheekwood’s many program areas.
• Sound judgment in maintaining strictest of confidentiality of donor information.
• Willingness and desire to attend evening/weekend programming activities in order to cultivate/steward key donors and prospects.
• Demonstrated collegial disposition to achieve required results with the ability to work positively in a flexible team environment.
• Excellent written and oral communication skills.
• Proficiency with Altru or a similar database is preferable.

 

Additional Information

Benefits

Benefits 

The well-being of Cheekwood employees is essential. So, when it comes to our benefits package, we offer one of the best. We offer the following benefits to all full-time employees:

• Health Insurance with an HRA
• Dental
• Vision
• Life Insurance (100% paid by Cheekwood)
• Long Term Disability Insurance (100% paid by Cheekwood)
• Voluntary Life Insurance
• Short Term Disability Insurance
• 403b and Roth 403b with a generous employer match
• Employee Assistance Program
• Paid Time Off and 11 Paid Holidays
• Aflac products are offered.

How to Apply

Please send resume and cover letter to:  https://cheekwood.org/about/join-our-team/

Details

• Date Posted: October 30, 2025
• Type: Full-Time
• Job Function: Fundraising / Revenue Development
• Service Area: Arts / Culture

Job Tags

Full time, Temporary work, Part time, Summer work, Seasonal work, Work at office, Flexible hours, Weekend work, Afternoon shift,

Similar Jobs