Open Positions - Five Keys Charter School - San Francisco, Los Angeles, East Bay, Solano — Five Keys Schools and Programs

Director of Development and Communications (DD&C)

    • Job Tracking ID: 512638-680954
    • Job Location: San Francisco, CA
    • Job Level: Management
    • Level of Education: BA/BS
    • Job Type: Full-Time/Regular
    • Date Updated: July 03, 2019
    • Years of Experience: 5 - 7 Years
    • Starting Date: ASAP
    • Salary: Commensurate with experience
    • Site/Location: San Francisco
    • Work Schedule: Full-Time, Monday – Friday
    • Reports to: Executive Director
    • Retirement: Optional 403(b)
    • Other Ino: San Francisco
Invite a friend
facebook LinkedIn Twitter Email

Job Description:


Five Keys’ mission is to further social justice and restorative justice by countering poverty, inequity, and trauma with accessible high quality programs that offer meaningful opportunities for individuals, families, and communities.


Five Keys’ vision is that all people have access to the resources they need to lead positive, productive, and self-determined lives. Five Keys’ commitment to the pursuit of equity is expressed through collaborative partnerships and innovative approaches across 3 AREAS OF IMPACT: Access to Education, Workforce Development, and promoting Vibrant Communities.


Five Keys was founded in 2003 by the San Francisco Sheriff’s Department as the first accredited high school in the nation to provide diploma programs for adults languishing in county jails. The "five keys" expressed through the school’s curriculum are: Education, Employment, Family, Community, and Recovery.

Today Five Keys has more than 500 dedicated employees serving 25,000 individuals each year (4,000 on a typical day) in seven counties, including San Francisco, Alameda, Solano, San Mateo, Santa Clara, San Bernardino, and Los Angeles counties, with expansion into Marin and Sonoma Counties on the horizon. Beginning in 2008, Five Keys extended its schools and programs into underserved neighborhoods, where students returned after their release from jail. Central to Five Keys’ model is the development of collaborative partnerships with workforce, criminal justice, and social service agencies; community-based organizations, and postsecondary institutions. Five Keys now operates more than 80 community learning centers, in addition to high schools and programs inside 20 county jails. Approximately one third of Five Keys’ program participants are currently or formerly incarcerated. In addition to high school and college access pathways, Five Keys provides reentry case management; cognitive behavioral interventions, parenting classes, life skills programs, job readiness and education assessments, workforce training, and job placement services. Five Keys offers CTE training and certification programs in more than 20 vocational skills, from construction to dog grooming, and horticulture to welding. In Los Angeles and San Francisco, Five Keys operates career centers inside county jails and creates linkages to community-based workforce networks. In recent years, Five Keys has been called upon to manage transitional housing shelters and provide transitional employment opportunities for formerly incarcerated individuals and people currently or formerly experiencing homelessness. Five Keys’ expansive work touches the lives of thousands of people who are "Ready to Learn. Ready to Work. Ready Together."


The Director of Development and Communications (DD&C) is a new role at Five Keys, charged with expanding fundraising beyond the organization’s current reliance on government funding, to sustain new program areas that have grown well beyond Five Keys’ publicly funded high schools. 

The DD&C will report to the executive director and serve on the leadership roundtable, along with senior program directors and school superintendents responsible for advancing the organization’s broader interests and strategic plan.  

A successful candidate must be an energetic, forward thinking, and creative individual with superior written and verbal communication skills. The role requires high ethical standards, while working with confidential information and complex issues that require considerable discretion, judgment, tact, and diplomacy. 

The DD&C will formulate new approaches to fundraising that reflect Five Keys’ culture of innovation and are compatible with its long-standing governance structure. This new hire will focus on developing relationships with funders and individual donors by (1) building a portfolio support; (2) instituting Five Keys’ first donor program; (3) leading Five Keys’ first fundraising campaigns and events; (4) overseeing a portfolio of 19 current contracts and grants; and (5) solidifying infrastructure, systems, and processes to support engagement and stewardship.

As such, the selected candidate will have exceptional aptitude to quickly learn programmatic content and convey that information in clear and compelling communications with senior program officers at foundations and corporations.


Five Keys welcomes candidates from other fields who bring transferrable skills and experience with a high-degree of alignment to the requirements of this role. Five Keys recognizes the value of nontraditional education and unconventional life paths that lead to meaningful accomplishments. Comparable, equivalent, and supplemental experience that is relevant to the duties of this position will be considered when evaluating candidates’ qualifications. 

Required Proficiencies in Development 

  • Experience identifying prospects and developing donor-centered strategies;

  • A verifiable track record of securing grants, contracts, and / or gifts;

  • Demonstrated expertise in creating compelling and competitive funding proposals, includingthe ability to understand and develop complex budget models;

  • Orchestrating partnerships for collaborative funding opportunities; 

  • Ability to effectively manage expectations of funders and donors and fulfill stewardship, reporting, and recognition obligations;

  • Proficient in devising message strategies, managing audience segmentation, and planning campaign timelines across multiple communication channels;

  • Strong professional writing, editing and oral communication skills with an ability to work closely with program staff to develop technically accurate, compelling and creative content for case statements, concept papers, logic models, presentations, briefing documents, LOIs, MOUs, letters of support, and stewardship materials.

Required Proficiencies in Leadership

  • Ability to think strategically and communicate ideas successfully across multiple departments and levels of the organization, and with geographically-dispersed colleagues, with a positive, collegial, and collaborative outlook;

  • Progressive leadership experience directing development and marketing activities;

  • Self-directed and proactive, holding oneself to the highest standards in meeting responsibilities; Demonstrated ability to manage multiple projects with strong attention to detail, balancing strategic and operational needs; 

  • Excellent project and process management skills, including anticipation of potential risks and opportunity costs; 

  • Use of a strengths-based approach to management that motivates and inspires others with ongoing guidance and coaching; Effective presenter, active listener, open to new ideas;

  • Demonstrated ability to build skills of staff and volunteers, providing guidance to ensure high performance across the team.

Experience and Skills:


Institutional Funding  

  • The DD&C will oversee the acquisition, compliance, and renewal of government grants and contracts that currently make up the majority of Five Keys’ grant revenues;

  • Set fundraising targets in collaboration with the executive director; provide stewardship of existing grants; determine opportunities for renewed and/or additional support; identify and cultivate new relationships to secure new funding through partnerships with foundations and corporations; and prepare proposals in partnership with teams of program and grants staff;

  • Nurture and develop relationships with funders; Attend speaking engagements to build visibility and opportunities that place Five Keys at the center of key conversations with researchers and funders in the fields of education equity, workforce development, criminal justice reforms and reentry, and housing;

  • Arrange visits to program sites that deepen relationships with the grant making community; 

  • Develop strategy, objectives, timetables, and action plans for fundable programs; 

  • Ensure that due dates are always met, drafting proposals, budgets, invoices, and compliance reports, as deemed necessary to support the grants and program design teams. 

Individual Donors 

  • The DD&C will build the organization’s first individual donor program;

  • Inspire a culture of giving that is compatible with the ethos and spirit of the organization;

  • Consult with key leaders and staff to expand the pool of volunteers. Identify, qualify, and cultivate prospects with a continuum of mission-driven activities, leading to solicitation; Prepare briefings for the ED prior to visits with prospective donors, and debriefings after;

  • Draft gift receipt policies for board approval; Develop a meaningful recognition plan;

  • Prepare for Five Keys’ first Annual Fund, potentially to be launched through special events;

  • Work with senior leaders to identify projects for targeted campaigns, under the Annual Fund, or as stand-alone strategies; integrate these donors into the broader base of support.


  • The DD&C will design and execute an annual development and communications plan, proactively identifying funding targets and strategies with timelines, resource allocations; and campaign communication calendars, prior to each fiscal year; 

  • Oversee a team of writers to update website content, reorganize navigation; and generate useful content; Work with a graphic design vendor to ensure visuals are congruent with messaging; and oversee social media policies; social media messaging strategies; and coordination of donor communications through multiple channels; 

  • Prepare (or delegate) production of communication pieces and PPT presentations for senior leadership, as requested for speaking engagements and conferences;

  • Train staff across departments to effectively communicate about the organization


  • Provide oversight for the launch of Five Keys’ CRM for fund tracking, gift and pledge processing, campaign communications, and moves management strategies; and direct collection of relevant donor and volunteer information;

  • Oversee staff in the creation of assets (photos, stories, template content, data points, research, etc.) and cataloguing into Five Keys’ asset management libraries (in Smartsheets);

  • Work across departments to integrate disparate data and communications systems and ensure staff are properly trained and scheduled to maintain data integrity.

  • Oversee development of daily, weekly, and monthly reports to track the status of fundraising activities, proposal pipelines, awards granted, and compliance requirements;

Events Management 

  • The DD&C will work with Five Keys’ leadership to launch the organization’s first major fundraising events (in Northern and Southern CA);

  • Work with leadership to identify and invite honorary (celebrity) chairs; 

  • Oversee event calendar, production of printed and online invites, committee membership, table captains, ticketing, seating assignments, ambassador matching, and follow-up strategy;

  • Monitor event budgets to ensure full offset of production costs; 

  • Prepare leaders’ speeches to pace the “factual-emotional” balance to achieve maximum fundraising results;

  • Prepare multi-year pledge card strategies and other motivating asks during the events;

  • Ensure proper acknowledgements so thank you’s are made to all parties appropriately (time, place, and messenger) and repeatedly, throughout event preparations and in follow-up. 


  • 3+ years of demonstrated progressively responsible nonprofit development and grant writing experience, as well as communications and marketing; or 5+ years senior non-profit executive experience overseeing development, grant writing and contract procurement.

  • Bachelor’s Degree or equivalent. 

  • High proficiency with MS Office Suite; familiarity with donor relationship management databases; aptitude for learning new software systems.


  • This position originates in either Northern CA (San Francisco Bay Area) or Southern CA (Los Angeles County) and requires extensive travel between the two regions. Travel can be expected to dozens of program sites, including county jails, and to private and public meeting spaces outside of Five Keys’ offices or program sites. 

  • Regular hours are Monday through Friday, 8 a.m. to 4 p.m., with extended hours, as needed. 

  • This job requires frequent and prolonged standing, walking, sitting, reaching with hands and arms, and the ability to lift and bend, as necessary. The role is not expected to perform heavy lifting regularly, but does carry the expectation of lifting and transporting materials which weigh approximately 20-25 pounds, such as boxes of paper, event supplies, and presentation materials. The work involves a moderate noise level, frequent talking and hearing conversations, and requires the ability to follow oral directions in emergency situations.


After carefully reviewing the requirements above, qualified individuals are invited to apply. Include a well-crafted cover letter, resume or CV, salary requirement (or range), how you learned about this position,  professional references, and sample work product samples.

Five Keys Schools and Programs is an affirmative action /equal opportunity employer.

We seek diversity within our staff that reflects the diversity of the communities we serve.

Applicants’ qualifications are considered without regard to race, color, religion, sex, national origin, age, disability, veteran status, genetic information, sexual orientation, gender identity or expression, or any other basis prohibited by law.

Five Keys complies with the Americans with Disabilities Act (ADA), as amended by the ADA Amendments Act, and all applicable California State or local laws. Applicants with disabilities may be entitled to reasonable accommodations to assist in completing this application to the extent required by applicable law, without imposing undue hardships on Five Keys. Please inform Five Keys if you need assistance completing any forms or participating in the application process. Consistent with those requirements, Five Keys will reasonably accommodate qualified individuals with a disability if such accommodation would allow the individual to satisfactorily perform the essential functions of the job, unless doing so would create an undue hardship.

Position is open until filled. 



• Medical with employee premium contributions
• Employer paid Dental
• Employer paid Vision
• Employer paid Life Insurance
• Employer paid AD&D, Short and Long-term Disability
• HRA Benefit
• Pre-Tax Flexible Spending Accounts
• Pre-Tax Transit and Parking Accounts
• State Teachers Retirement (STRS) with Employer Matching for eligible employees
• 403 (b) retirement plan with Employer Matching for non-STRS positions
• Free Employee Assistance Program
• Generous Paid Time Off
• Gym membership reimbursement up to $100 for employees

Five Keys Charter School is an Equal Opportunity Employer and supports diversity in the workplace.