Strategic Advisor to the CEO

About Oakland Promise:

Oakland Promise is available to young learners (from newborns to college students) and their families who reside in Oakland. OP offers every child financial resources, educational programming, mentorship, and a supportive community to help them and their families, to seek out and thrive in higher education and the career of their choosing. The mission of the Oakland Promise is to engage the Oakland community to advance equity and economic mobility through cradle to college and career achievement. The Oakland Promise includes four programs: Early Learning, K-12, and College & Career. Our program strategies touch the lives of children and families in early childhood (ages 0-5), elementary, middle and high school; and culminate in multi-year scholarships and support for students in college.

About the programs:

The Early Learning program supports children’s early healthy development and school-readiness by setting up College Savings Accounts (CSAs) for babies, offering financial coaching and early learning resources to parents and caregivers, and building a supportive community for the whole family. Early Learning supports parents’ early expectations for their child’s educational success.

Oakland Promise K-12 helps K through 12th graders in Oakland think of themselves as college-and career-bound individuals. We provide scholarships, as well as technical support and incentives to families who open a family-owned college savings account. Additionally, we provide program support to build a college- and career-going identity within students, which includes college visits, family and student workshops, scholarship celebrations, and more. K-12 serves both middle and high school students in Oakland’s district and charter schools! Our vision is to support all students in accessing a clear and solid path to post-secondary educational experiences that lead to a variety of career options - 2-year, 4-year, and vocational or technical programs. Our goal is to offer integrated programming to students and families that targets the elimination of structural and cultural barriers to intergenerational social mobility.

College & Career supports college and CTE students with scholarships and persistence support and equips students with social and emotional support through mentoring, peer advising, counseling, retreats, and scholarship distribution. Oakland Promise designs holistic educational programming to create a culture of career and college preparedness in students, families, and educators, so we can dramatically increase the number of college graduates from Oakland public schools.

About the Role

Oakland Promise seeks a Strategic Advisor to the CEO, a senior partner who ensures the CEO operates with clarity, focus, and strategic discipline. This role is dedicated to helping the CEO translate vision into actionable plans, organize the “messy middle,” and ensure effective execution across leadership, planning, decision-making, and Board engagement.

This position is not a Chief Strategy Officer and does not oversee programs, strategy, or a department. Instead, it supports the CEO’s leadership by building structure, preparation, discipline, and follow-through around her priorities and around the Executive Team’s work.

The Strategic Advisor must excel at bringing order to complexity, sequencing ideas into plans, coordinating across functions, and designing systems that improve alignment and execution. This role requires exceptional judgment, writing ability, organizational discipline, and analytical problem-solving — an engineering-style mindset is welcome.

This is a senior support role for the CEO, not a C-suite progression role.

Duties & Responsibilities

Strategic Partnership with the CEO

• Serve as the CEO’s primary advisor on priorities, preparation, communication, and operational alignment.
• Bring structure and clarity to complex or ambiguous issues, ensuring CEO-directed initiatives move forward effectively.
• Manage the CEO’s inbox, meeting briefs, preparation documents, follow-up, and decision pipeline.
• Filter and triage requests, protecting the CEO’s time and strengthening boundaries around priorities.
• Manage the CEO’s leadership rhythm: weekly priorities, Executive Team meetings, All-Staff, quarterly reviews, and annual planning.

Organizational Planning, OKRs, & Performance Systems

• Lead the Annual Planning Cycle, coordinating priorities, departmental alignment, cross-functional integration, and organizational goal-setting.
• Co-develop organizational OKRs and KPIs with the CEO and build systems to track progress.
• Surface risks, bottlenecks, and misalignment early; create structured plans, frameworks, and sequences to turn ideas into action.
• Provide disciplined project management on cross-functional CEO-directed initiatives.
• Build and manage systems that support strategy (clarity, alignment, visibility), without directing organizational strategy or programs.

Board Management & Governance

• Manage Board operations, including logistics, agendas, materials, communications, documentation, and follow-up.
• Prepare the CEO and Board Chair for meetings with clear briefings and background.
• Maintain an organized archive of Board documents, decisions, and governance materials.
• Support Board engagement, recruitment, and onboarding.

Communication & External Engagement

• Draft CEO communications including internal messages, staff updates, crisis communications, and organizational announcements.
• Prepare CEO briefings, talking points, presentations, and reports for internal and external audiences.
• Represent the CEO’s office with funders, partners, public officials, and community stakeholders.
• Ensure the CEO is fully briefed for external meetings with context, goals, and supporting documents.

Executive Operations & Special Projects

• Build systems that improve decision-making, information flow, and organizational alignment.
• Lead senior-level special projects at the CEO’s discretion.
• Coordinate contractors or fractional support roles (e.g., project consultant or EA).
• Handle confidential matters with professionalism and discretion.

Required Qualifications

• 5+ years in senior project management, executive operations, strategic advisory, management consulting, or Chief-of-Staff–type roles.
• Exceptional ability to structure complexity — turning ideas into systems, processes, and actionable plans.
• Strong analytical and problem-solving skills; able to bring order and logic to ambiguous situations.
• Excellent writing skills for internal and external executive-level audiences.
• Proven ability to support a senior leader on priorities, operations, and decision-making.
• Highly organized with strong follow-through and attention to detail.
• Strong relational intelligence; able to build trust and influence without authority.
• High discretion and comfort handling sensitive information.
• Comfort operating in a fast-paced, dynamic environment.
• Commitment to equity and Oakland Promise’s mission.

Preferred Qualifications

• Structured, solution-oriented thinking — ability to break down complex issues, identify root causes, and design clear, sequenced solutions (engineering-style orientation welcome).
• Exceptional integrator able to translate high-level strategy into operational frameworks and coordinated execution.
• Experience designing or managing organizational workflows, strategic planning processes, dashboards, OKRs, or performance systems.
• Strong synthesis and communication skills — able to convert complex information into concise briefs, decks, and recommendations.
• Action-oriented with disciplined execution; able to move work forward proactively and keep stakeholders aligned.
• Backgrounds in engineering, consulting, operations, or similarly structured fields are welcome but not required.
• Knowledge of and connections to Oakland communities.

Compensation and Benefits

• Full-time, exempt role
• Salary range: $120,000–$150,000, based on experience
• Competitive benefits package including medical, dental, and vision
• 401(k) with employer match
• Generous paid vacation, sick leave, and holidays
• Currently hybrid work environment (in-person + remote)
• Opportunities for professional growth and engagement with community leaders
• Occasional evening and weekend hours required

Application Process

To apply:

Send a single PDF (NOT a Microsoft Word document) of a resume and thoughtful cover letter with “Strategic Advisor to the CEO”– [Your Name]” in the subject line. Please use your last name and first initial (ex: Doe_J) as the filename of your PDF containing your resume and cover letter.

Failure to follow these instructions may delay the review of your application. Applications will be reviewed immediately and candidates with the best fit will be contacted for interviews. Unfortunately, the volume of applications will prevent us from responding to all applications received.

Oakland Promise is a place-based organization located in Oakland, California. Oakland Promise requires that employees work in person at various engagements. Currently, Oakland Promise staff are working in a hybrid model, with some work being done remotely and some work being done in the office or at specific locations in or around Oakland. It is a requirement that all staff reside within commuting distance to the main office, located at 484 9th Street, Oakland, CA 94607. Please note that at any time, a full in-person work plan may be required, and it is of utmost importance that all staff are able to meet this requirement.

Oakland Promise is proud to be an equal opportunity employer. Oakland Promise is committed to providing a work environment free of harassment, discrimination, retaliation, and disrespectful or other unprofessional conduct based on sex (including pregnancy, childbirth, breastfeeding or related medical conditions), sex stereotype, race, religion (including religious dress and grooming practices), color, gender (including gender identity, gender expression, and transgender), national origin (including language use restrictions and possession of a driver's license issued under Vehicle Code section 12801.9), ancestry, physical or mental disability, medical condition, genetic information, marital status, registered domestic partner status, age, sexual orientation, military, and veteran status or any other basis protected by federal, state or local law or ordinance or regulation. It also prohibits discrimination, harassment, disrespectful or unprofessional conduct based on the perception that anyone has any of those characteristics, or is associated with a person who has or is perceived as having any of those characteristics.

• Competitive benefits package including medical, dental, and vision
• 401(k) with employer match
• Generous paid vacation, sick leave, and holidays
• Currently hybrid work environment (in-person + remote)

English