Rural Democracy Initiative - Deputy Director (Remote)

Posted by
Clover Search Works
Seattle, WA
Published 12 days ago

The Heartland Fund, part of the Rural Democracy Initiative, is seeking an experienced leader with strong management and team-building skills to serve as our Deputy Director. This is a senior leadership position in a rapidly growing new funding collaborative dedicated to rural civic engagement. Priorities for this position are management of a high-performing staff team and engaged advisory and steering committees, honing and implementation of our strategy and work plans, working in close partnership with rural-focused funders and leaders across the country, and communicating program accomplishments and trends to our funders and grantees.

The successful candidate will be a strategic thinker and excellent communicator with significant staff and project management experience. They must have a thoughtful approach to relationship management, strong racial equity analysis and share our vision of connecting leaders and building civic and political infrastructure in rural areas.

About the Organization

The Heartland Fund, part of the Rural Democracy Initiative, is a funding collaborative that connects rural leaders with funders to build powerful, permanent civic infrastructure in small towns, small cities and rural areas. We challenge the stereotype of the conservative white rural voter, and instead center racial justice and partner with groups working in rural communities of color, and modeling groundbreaking anti-racist organizing in majority-white communities.

Our coalition of rural innovators and aligned funders is working in 20 states across diverse regions, including Alaska and Montana in the Northwest, Wisconsin, Michigan, Minnesota, and Pennsylvania in the Midwest and Northeast, Arizona in the Southwest, and North Carolina, and Georgia in the Southeast. We support rural people working to transform rural America – and therefore the entire country – for decades to come.

Why Heartland / RDI

Small town, small city and rural voters maintain disproportionate power to shape national politics. The progressive movement was built on a strong coalition of rural farmers and urban laborers. But in recent decades, progressive leadership and funding infrastructure has largely withdrawn from non-metro areas.

At the same time, regressive interests have invested heavily in rural voters. They’ve built organizing, policy, and communications machines to spread disinformation and ignite fears among rural electorates, promoting their own political agendas to deepen urban-rural divides.

Progressives are winning again in small towns and rural communities.

In 2018 and 2020 it has become clear that with focused organizing progressives can win in rural communities: even though rural areas voted overwhelmingly for Trump, rural Democratic gains in the 2018 midterms and 2020 presidential election were actually larger than the gains made in urban and in many suburban areas, and were decisive in the battleground states.

With small, grassroots investments in strategic rural engagement, a motivated coalition comprised largely of rural women, people of color, and younger voters fueled an historic progressive bounce-back in small cities, towns and rural areas.

The Heartland / RDI approach

The Heartland Fund is a 501c3 grantmaking and power building organization that, alongside the 501c4 Rural Victory Fund, invests in civic infrastructure in small towns and rural communities.

Building power in these communities is essential to establishing an enduring progressive,

multi-racial national majority, and to implementing the policies required for rural and small city communities to have vibrant, thriving futures.

 The Position

The Deputy Director will work closely with the Executive Director as part of a small senior management team. Their particular role will be to support the growth, satisfaction, and effectiveness of a close-knit, powerful and mission-driven all-remote staff, and a diverse group of consultants, advisors and steering committee members. Reporting to the Executive Director, the Deputy Director will supervise the team, represent the organization in important external settings, and oversee operations and financial systems.

Heartland Fund / RDI takes pride in building an organizational culture rooted in learning, collaboration, equity, and a deep commitment to our mission. We center racial justice and. anti-racism throughout all of our work. All staff are expected to provide leadership and vision to advance our mission, vision, and core strategies.

Primary responsibilities include:

Organizational Leadership: Partner with the Executive Director in developing strategy that allows Heartland / RDI to achieve its ambitious mission, guided by core organizational values and commitment to racial equity.

  • Support and implement yearly plans, and guide ongoing strategy planning. Engage staff, key stakeholders and advisory and steering committees in strategy and plan development
  • Support the Executive Director in managing advisory committee and steering committees, fostering strong relationships and a high level of engagement
  • In partnership with the Executive Director and staff, support the operationalization of racial equity vision and commitments across the organization
  • Represent Heartland / RDI externally to further relationships with a variety of funders, decision makers, grantees, stakeholders and in community spaces

People and Culture Management: Create and maintain a high-performing learning culture, grounded in racial equity values, that fosters excellent employee morale, teamwork and collaboration

  • Run engaging and productive staff and team meetings and retreats
  • Supervise, manage and coach the team to set strategic goals, meet fundraising and communications plans and support individual growth
  • Develop and lead results-based individual and organizational performance evaluations that incorporate the strategic plan, work plans and grant commitments
  • Lead staff recruitment and onboarding
  •  Provide strategic leadership in layering racial equity values into developing employee recruitment, onboarding, management and succession planning processes

Operations Management: Create and maintain dynamic systems that facilitate efficient and joyful organizational operations for our growing, hard working staff and consultant team.

  • Oversee the Grants and Operations Manager in their role ensuring that all operational and administrative functions run smoothly including: remote work platforms, IT systems, safety and security, contracts and vendors, and legal separation between entities
  • Select and manage relationships with external consultants, brokers and administrators for operational functions
  • Develop critical organization-wide systems, policies and processes ensuring staff, information, and technology work effectively across departments

Financial Oversight: Partner with Executive Director to oversee Heartland and Rural Victory Fund annual operating and grant making budgets totaling $20-$25 million.

  • In partnership with the Executive Director, oversee financial and business planning activities including budgeting and financial reporting
  • Working with fiscal sponsor, prepare and present financial reports and cash flow positions to management and steering committees
  • Produce financial models, scenario planning and cash flow projections to ensure proper funds available to meet operational and programmatic needs


The Heartland Fund / RDI is seeking an experienced leader who is excited to work in an entrepreneurial, fast paced, and creative environment. The person should exhibit a high degree of professionalism, initiative, and independence while also being collaborative and team focused. Specifically, the successful candidate will be able to demonstrate:


  • 4+ years of organizational leadership in a non-profit, campaign and/or foundation setting with working knowledge and experience in organizational development, change management and/or workforce planning
  • Demonstrated understanding of civic engagement, advocacy and/or political strategy
  • Experience with 501c3 and 501c4 nonprofit legal frameworks
  • Strong commitment to racial justice and fluency with anti-racist practices
  • Excellent storytelling skills, with an ability to clearly communicate an organization’s mission and impact both verbally and in writing
  • Demonstrated experience coaching and mentoring staff
  • Personal or professional connection to and passion for our rural mission
  • Strong relationship management skills with diverse constituencies


  • Aptitude for fundraising and an ability to build relationships and present with confidence to funding partners
  • Experience in the philanthropic sector and with grant making
  • Previous experience working with and reporting to a Board of Directors
  • Lived experience in rural America

For More Information

Questions regarding this opportunity are welcomed and can be directed to

The Heartland Fund, part of the Rural Democracy Initiative, is seeking an experienced leader with strong management and team-building skills to serve as our Deputy Director. This is a senior leadership position in a rapidly growing new…

Details at a Glance

  • Time Commitment
    Full Time Schedule
  • Application Deadline
    January 21, 2022
USD $110,000 - USD $125,000
/ year


This is a permanent, full time staff position. The organization is virtual, and the Deputy Director will be a remote position. As COVID allows, the position will require occasional travel across the United States. Expected compensation will be based on skills and experience, with an approximate salary range of $110,000 - $125,000 per year. Our comprehensive benefits package includes employer-paid health, dental, and vision insurance, 6% employer match on 401k contributions, pre-tax transportation benefits, and paid holidays, vacation, sick, and volunteer time off.

To center the safety and well-being of its employees, Windward Fund requires that any employee who is required to conduct in-person activities for their job must be fully vaccinated against COVID-19 within four weeks of their start date. This position may require candidates to be fully vaccinated against COVID-19. Accommodations may be sought and approved in accordance with the law by contacting human resources at

The person holding this position may also work part-time for a coordinated project, Rural Victory Fund, in the Sixteen Thirty Fund, a 501(c)(4) organization, under a resource sharing agreement between the Windward Fund and Sixteen Thirty Fund. The responsibilities under that position will be overseen by Sixteen Thirty Fund.

This is a permanent, full time staff position. The organization is virtual, and the Deputy Director will be a remote position. As COVID allows, the position will require occasional…


Work may be performed anywhere in United States
Associated Location
5901 46th Avenue Southwest, Seattle, WA 98136, United States

How to Apply

Priority deadline January 21, 2022. Applications will be reviewed and considered on a rolling basis with interviews anticipated to start mid-January. The desired start date is March 15, 2022.

 The Heartland Fund is a project of Windward Fund, a 501(c)(3) public charity that incubates new and innovative public-interest projects and grant-making programs. Windward Fund is an equal opportunity employer. People of color, LGBTQ people, and women are strongly encouraged to apply. We believe that a diverse workforce and inclusive workplace culture enhances our ability to fulfill our mission. Employment and promotional opportunities are based upon individual capabilities and qualifications without regard to race, color, religion, gender identity or expression, pregnancy, sexual orientation, age, national origin, marital status, citizenship, disability, veteran status or any other protected characteristic as established under law.

Priority deadline January 21, 2022. Applications will be reviewed and considered on a rolling basis with interviews anticipated to start mid-January. The desired start date is…

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