JOB TITLE: Regional Deputy Director of Development

DEPARTMENT: Fund Development

REPORTS TO: CEO

FLSA STATUS: Full-time, Salaried, Exempt

OUR MISSION & VISION:

Big Brothers Big Sisters of Orange County & Inland Empire (BBBSOC/IE) ignites the biggest possible futures for youth through the power of mentorship. Guided by our mission and vision, we believe every connection creates opportunity and every investment in young people strengthens our community.

WHO YOU ARE:

You’re a people person. You are more than capable of cultivating productive relationships, both externally as well as internally. You’ll work closely with Fortune 500 CEOs, philanthropists, influencers, and other diverse personalities. This doesn’t intimidate you but excites you. You thrive on building and developing these relationships with intelligence, maturity, and professionalism. You lead a team with humility and strategy and believe that “all boats rise together.”

You’re a hunter. You enjoy the thrill of uncovering new revenue streams and finding supporters who have never been exposed to the organization’s mission before. You enjoy modeling this behavior to your team and cultivating a culture of winning.

You have a remarkable track record. You have a history of leading successful teams with measurable results that have impacted the bottom line. Your years of applicable experience have cultivated your wisdom and nuanced creativity for this position.

You’re a strategic thinker. You have the strategic prowess and social intelligence required to help build scalable models that leverage Big Brothers Big Sisters brand, assets, relationships, and opportunities to meet aggressive growth goals. You know how to work with a team and set each individual up for success.

You’re an inventor, an innovator. Big Brothers Big Sisters is committed to constantly inventing new ways to connect people with the direct impact of their gifts. You thrive in a creative, inventive, fast-paced environment with people who are passionate about their work and mission. You are an agent of change.

You’re a closer. You’re comfortable asking for money and are not afraid to say or hear “no”. You possess a keen ability to sell ideas and close deals. You operate with poise, dignity, and reliability in both your personal and professional worlds. You have the ability and desire to model this behavior to your team.

You understand the value of our investors. YYou make everyone feel special. You’re able to get anyone excited about what we do and make their experience with us unique. You’re inviting, discerning and thoughtful. You believe in customer support and demand that of your team as well.

JOB SUMMARY

You will report directly to the CEO and will play a critical role in advancing the agency’s mission in the Inland region by spearheading strategic efforts to secure and sustain financial resources. You will be tasked with developing and implementing comprehensive fundraising strategies to support the agency’s overall growth. You will lead all aspects of fundraising including donor acquisition, cultivation & stewardship, brokering key partnerships, and executing special events in the Inland Empire. To be successful in this role, you will lead and motivate an Associate Director of Development and communicate the organization’s impact externally. You will also be required to build strong relationships with the regional board, donors, stakeholders, and identify opportunities for donor engagement and revenue generation. You will demonstrate a proven track record in fundraising, strong leadership skills, excellent communication abilities, and a passion for the organization’s mission.

RESPONSIBILITIES

❑ Developing Fundraising Strategy & Vision
• Create, implement, communicate, and support comprehensive fundraising strategies that guide regional development initiatives towards achieving current fundraising goals and long term, sustainable growth.

❑ Leadership
• Inspire and motivate the regional development team to perform at their best through guidance, mentorship, professional development and fostering a positive and collaborative work environment.
• Lead and help build a strong Regional Board to support fundraising efforts to grow the program in the region.
• Establish a development infrastructure that can support fundraising goals.
• Stay informed about current trends and best practices, in fundraising and philanthropy through ongoing professional development and networking opportunities.

❑ Goal Setting & Accountability
• The Regional Deputy Director of Development is given should set and deliver ambitious yet achievable fundraising goals for the Regional IE Development team and will hold team members accountable to reach set goals.
• They should establish key performance indicators and regularly track progress towards goals, providing feedback and support to ensure team members are meeting objectives.

❑ Collaboration & Communication
• Consistent collaboration with other departments and teams within the IE office and agency regional and HQ office to leverage resources, share insights, and achieve common goals.
• The Regional Deputy Director of Development will communicate regularly with the CEO and larger development Team, senior leadership, colleagues, and Board of Directors to provide updates on fundraising and development initiatives, solicit input and align efforts throughout the organization as it pertains to the inland region.

❑ Donor Stewardship & Major Gifts
• Re-engage lapsed donors, maintain strong relationships with current donors and provide personalized acknowledgment, recognition, and stewardship to cultivate ongoing support and loyalty among existing donors.
• Maintain relationships with major donors, individuals, foundations, and corporations to secure significant financial contributions.

❑ Special Events & Campaigns
• Lead the Fund Development team in planning and executing major fundraising events to engage donors, raise awareness, and generate revenue.
• Partner with Marketing and Development on annual campaigns.

❑ Strategic Partnerships
• Identify and cultivate diverse partnerships, including corporations and community alliances, to drive revenue and volunteer recruitment.
• Negotiate agreements and secure financial support/sponsorships for programs, events, and initiatives.

❑ Annual Fundraising Campaigns
• Execute annual fundraising campaigns, including direct mail, email appeals, online giving, and special events, to solicit donations from individual donors and supporters.

❑ Planned Giving Programs
• Execute and promote planned giving programs, such as bequests, charitable trusts, and gift annuities, to secure long-term financial commitments from donors.

❑ Board Engagement
• Lead the Board of Directors, fundraising committees, and volunteers to engage them in fundraising efforts, leverage their networks, and secure their financial support.

❑ Financial Reporting and Analysis
• Prepare regular reports and analysis on fundraising activities, revenue projections, and donor trends to monitor progress, evaluate performance, and inform strategic decision-making.

❑ Database Management
• Oversee and maintain the donor databases and fundraising software systems to track donor interactions, manage donor relationships, and analyze fundraising performance.

❑ Ethical and Legal Compliance
• Ensure compliance with relevant laws, regulations, and ethical standards governing fundraising activities, including donor privacy, gift acceptance policies, and financial transparency.

QUALIFICATIONS

• Bachelor’s degree required.
• Minimum 4 years of experience in fundraising, development, or management roles with proven success in securing major gifts.
• Demonstrated success in leading and motivating development teams.
• Strong leadership, communication, and interpersonal skills.
• Proven ability to design and execute innovative fundraising strategies.
• Highly organized with strong project management and multi-tasking abilities.
• Proficient in Google Suite, MS Office, Excel, and fundraising software (Salesforce preferred).

WORK ENVIRONMENT

• Routine office environment.
• Frequent independent travel required.
• Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.
• Frequent sitting, walking, and bending. Must be able to move or carry up to 40lbs.

The above statements are intended to describe the general nature and level of work being performed by individuals assigned to this position. They are not intended to be an exhaustive list of all duties, responsibilities, and required skills. Job Description may be subject to change to meet the needs of the organization. Your employment with BBBSOC/IE will be “at will,” meaning that either you or BBBSOC/IE may end your employment at any time and for any reason, with or without cause.

JOB TITLE: Alternative Education Mentor Specialist

DEPARTMENT: Operations

REPORTS TO: Director of Program Innovation & Data

FLSA STATUS: Full-Time, Non-Exempt, Hourly

MISSION: Creating and supporting mentoring relationships that ignite the power and promise of the next generation.

VISION: Through mentorship, all youth achieve their full potential. 

JOB SUMMARY

In partnership with the Orange County Department of Education (OCDE) – ACCESS (Alternative, Community, Correctional, Education Schools & Services), the Alternative Education Mentor Specialist provides mentoring and support to youth who may be credit-deficient, at risk of not graduating, or experiencing personal and academic challenges. This role provides onsite small-group sessions and individualized engagement to strengthen student attendance, boost academic achievement, and promote collaborative skills that support productive citizenship. The Specialist is responsible for enrolling students, facilitating group sessions, and offering individualized guidance as students transition through alternative and continuation school settings, while collaborating with school and district leaders to support long-term student success.

JOB RESPONSIBILITIES

Recruitment & Enrollment
• Present program benefits to school staff and students through engaging presentations and one-on-one conversations.
• Guide students into the program by clearly explaining expectations and helping them understand the level of commitment required.
•  Conduct a thorough enrollment process to gather information about each student’s background, home environment, academic performance, and social networks.
• Collaborate with students to set personal goals for their mentoring experience and use these to shape Youth Outcome Development Plans (YODPs).
• Communicate regularly with school staff and BBBS leadership to share important updates and insights.
• Develop and maintain detailed student profiles in MatchForce to track progress, ensure continuity of support, and inform ongoing mentoring strategies.

Group & Individualized Case Management
• Design and lead group activities that introduce students to mentoring, encourage peer connection, and build teamwork skills.
• Facilitate small-group mentoring sessions that create space for shared dialogue, problem-solving, and skill development.
• Manage a cohort of students, providing consistent one-to-one support focused on setting goals, monitoring progress, and offering tailored support through Youth Outcome Development Plans (YODPs).
• Apply best practices in engagement by adapting activities and communication to accommodate diverse learning styles, cultural backgrounds, and motivational needs.
• Deliver educational materials, presentations, or other approved content developed collaboratively by BBBS and OCDE to enhance student learning and strengthen the mentoring experience.

Student Support & Engagement
• Build trust and belonging with students who may be credit-deficient, justice-involved, or experiencing instability at home through trauma-informed and restorative practices that promote consistency and resilience.
• Conduct goal-oriented check-ins aligned with students’ YODP goals, helping them build self-regulation, confidence, and positive decision-making skills while recognizing and reinforcing progress toward re-engagement and graduation.
• Promote a safe and supportive learning environment by modeling non-violent communication, guiding de-escalation, and teaching conflict resolution.
• Collaborate with teaching staff, probation officers, counselors, and families to address barriers to engagement and support transitions between alternative and traditional education settings.
• Connect students and families with school and community resources that address basic needs and promote long-term stability—especially for highly mobile, housing-insecure, or foster youth.

School & District Collaboration
• Serve as a liaison between BBBS, OCDE, and continuation schools to ensure program visibility and alignment with school priorities.
• Engage principals, teachers, counselors and OCDE representatives in regular meetings to share program impact, highlight student progress, and build stronger collaboration.
• Maintain a regular presence within the school buildings to support students directly & foster stronger relationships with school staff.
• Prepare and deliver presentations for academic administrators that showcase student outcomes, program successes, and alignment with district goals.
• Prepare reports highlighting student growth, mentoring outcomes, and key program performance indicators.

Monitoring, Evaluation & Learning
• Keep accurate records of mentoring sessions, student progress, and outcomes in compliance with BBBS and OCDE standards.
• Use tracking tools to measure student growth in engagement, social-emotional development, and academic progress.
• Collect and analyze data to inform a white paper highlighting program outcomes, insights, and impact.
• Administer surveys and feedback tools to gather input from students, mentors, and school staff for continuous program improvement.
• Any other duties as assigned.

JOB QUALIFICATIONS

Minimum Qualifications
• Bachelor’s degree in Education, Social Work, Psychology, Human Services, or related field (or equivalent combination of education and experience).
• Minimum 2 years of professional experience working with youth, preferably in alternative education, continuation schools, juvenile justice, reentry education programs, mentoring, or social service
• Strong interpersonal and communication skills, with the ability to facilitate group sessions and conduct individualized case management.
• Organized, detail-oriented, and able to manage multiple priorities in a dynamic school-based environment.
• Ability to work independently while also contributing to a collaborative team environment.
• Proficiency in Google Suite, MS Office, and case management/data entry systems (Salesforce/MatchForce experience a plus).
• Bilingual (English/Spanish) is highly preferred.

Preferred Qualifications
• Training in non-violent crisis intervention, conflict de-escalation, or restorative engagement practices.
• Experience working with youth in continuation schools, alternative education settings, or juvenile justice systems.
• Familiarity with trauma-informed care, restorative practices, and/or motivational interviewing.
• Candidates with lived experience in alternative education or justice-involved pathways are strongly encouraged to apply.

PHYSICAL REQUIREMENTS

• Prolonged periods of sitting at a desk and working on a computer, as well as occasional standing and walking.
• Must be able to communicate effectively, both verbally and in writing.
• Occasional bending, stooping, reaching, and lifting up to 25 pounds (such as program materials, supplies, or office equipment).
• Ability to travel to various sites, events, and meetings as required by the role.
• May occasionally work in outdoor environments and be exposed to varying weather conditions.
• Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions of the position.

WORK ENVIRONMENT

• Routine office environment.
• Frequent independent travel required.
• Reasonable accommodations may be made to enable individuals with disabilities to perform essential functions.
• Frequent sitting, walking, and bending. Must be able to move or carry up to 40lbs.

The above statements are intended to describe the general nature and level of work being performed by individuals assigned to this position. They are not intended to be an exhaustive list of all duties, responsibilities, and required skills. Job Description may be subject to change to meet the needs of the organization. Your employment with BBBSOC/IE will be “at will,” meaning that either you or BBBSOC/IE may end your employment at any time and for any reason, with or without cause.