Development Director

The Development Director is responsible for developing and executing a comprehensive fundraising strategy, including identifying, cultivating, soliciting, and recognizing donors, sponsors, and grantors. This multifaceted role is essential to sustaining and advancing both the organization’s mission and financial stability.

The ideal candidate will be an outgoing relationship-builder that is responsible for all partnerships and fundraising related to the organization. You will identify prospects and build a pipeline of talent that will help accelerate the company’s financial growth.  Reporting directly to Dare2tri’s Executive Director, the Development Director is an integral part of our small, dedicated, and hardworking team.

This role is perfect for you if.. 
You thrive in a tight-knit, collaborative team environment. You are motivated to make a significant impact and change lives for para athletes. You have a desire to be a key advocate for Dare2tri’s mission and vision, playing a crucial role in securing the essential funds needed to support our initiatives. You are a dynamic and compelling communicator who can seamlessly integrate a wide range of skills and functions to create and communicate engaging opportunities for support.

Benefits: Dare2tri provides a benefits compensation package that includes health insurance, dental insurance, vision insurance, a simple IRA retirement plan, and a flexible work environment.


Fundraising Strategy:

  • Create and refine an annual development plan, encompassing strategies and tactics for individual donors, foundations, corporations, sponsors, and in-kind contributions.
  • Develop annual development budgets and income projections, diligently tracking progress toward set objectives.
  • Cultivate and maintain relationships with funders and donors to stimulate growth.
  • Collaborate with the Director of Communications on the execution of fundraising campaigns, including but not limited to the year-end appeal and monthly giving program, “Pacesetters.”

Prospect Engagement:

  • Spearhead fundraising efforts, covering the complete spectrum of donor engagement, from identification and cultivation to solicitation, acknowledgment, and stewardship.
  • Collaborate with the Director of Communications to craft development-related marketing materials, such as brochures, emails, newsletters, social media content, and website updates.
  • Conduct thorough prospect research, coordinating and preparing materials for meetings with potential donors and supporters.

Partnerships and Fundraising Events:

  • Establish and nurture relationships with prospective sponsors, individuals, corporations, and foundations, with a focus on securing long-term financial support.
  • Collaborate with team to plan and manage all aspects of Dare2tri’s annual gala, “Victory Lap,” including donor solicitation, sponsorship activities, and event execution
  • Oversee peer-to-peer fundraising campaigns, like “Race2Raise,” covering promotion, solicitation, tracking, communication, and follow-up.
  • Maintain a donor database, including data entry, gift processing, acknowledgment generation, and reporting.

Board Development and Strategic Leadership:

  • Collaborate with the Executive Director to provide leadership and strategic direction to the board of directors, focusing on their development and leveraging their expertise as a valuable resource.
  • Monitor fundraising environments that may influence philanthropic and corporate giving and communicate these factors to board members effectively.


  • Bachelor’s degree (BA/BS) in a related field is required.
  • A solid 5-7 years of relevant work experience in Development/Fundraising.
  • Exceptional oral and written communication skills.
  • Proven experience in managing various facets of fundraising events and campaigns.
  • Excellent time management, follow-through, and unwavering attention to detail.
  • Ability to stay organized, self-motivated, and effectively juggle multiple responsibilities.
  • A collaborative team player who thrives within a close-knit team 
  • Comfortable serving as the organization’s principal ambassador to external stakeholders.
  • Demonstrated excellence in project management, with a unique ability to think both strategically and operationally, and a track record of successful implementation and delivery.

Work Environment

Dare2tri is a rapidly expanding nonprofit with a hybrid work model that includes both office-based and work-from-home arrangements. Candidates are required to reside in the Chicagoland area.


Please send a resume and cover letter to Keri Serota (keri@dare2tri.org) with “Development Director” in the subject line. Applications received will be evaluated on a rolling basis, so early submission is recommended. Please understand that Dare2tri will be unable to notify all applicants of their submission but will contact those applicants shortlisted for interview.

Dare2tri is committed to a culture of diversity, equity, inclusion, and access, and is an Equal Opportunity Employer. People of color, people with disabilities, LGBTQ+ individuals and all others are encouraged to apply.

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