Chief Strategy Officer (3464)

YOUTH GUIDANCE•Chicago, IL

1d•$190,000 - $240,000•Hybrid

About The Position

The Chief Strategy Officer (CSO) serves as a senior leader responsible for defining and advancing the organization’s long term strategy, growth, and economic sustainability. This role leads enterprise wide strategic planning and plays a critical role in translating vision into clear priorities, investments, and decisions that strengthen organizational performance and impact. The CSO will help guide the organization through its next phase of growth by strengthening its position as a national organization, supporting a shift toward a nimbler and technology enabled operating model, and driving the evolution of its economic model to increase earned revenue and scalability. Working closely with the CEO, Board, and executive team, the CSO will identify opportunities for growth across philanthropy, educational organizations, public sector partners, and other strategic markets; shape go to market strategies; and ensure strong alignment across programmatic, operational, and financial priorities. In addition to leading enterprise strategy, the CSO is responsible for identifying and securing new pathways for organizational growth by bringing external relationships, market insights, and funding opportunities that are not currently accessible through existing organizational structures. The role serves as the organization's lead strategist for growth capital, innovative revenue generation, and expansion opportunities.

Requirements

Master’s Degree required
10 years nonprofit management experience with a superior record of achievement in complex, mission driven organizations
Experience working with or within education systems, particularly school districts, strongly preferred
Experience scaling an organization
Five years’ experience serving on an Executive Management Team
Experience managing a diverse, high performing and mission-driven team
Demonstrated success securing transformational funding opportunities and strategic investments through venture philanthropy, strategic partnerships, major institutional funders, or innovative financing structures.
Proven track record building new revenue streams and business models that increase organizational scale, sustainability, and impact.
Experience establishing and managing executive-level relationships with national foundations, philanthropic investors, impact investors, corporate partners, educational organizations, and public-sector leaders.
Experience leading growth initiatives across multiple markets, regions, or states.
Strategic approach to advancement of mission, with a keen eye for ensuring alignment of external activities with Youth Guidance’s mission and growth plan.
Strong executive presence and communication skills, with the ability to represent the organization and influence diverse stakeholders.
Proven ability to attract, structure and manage transformational growth investments through venture philanthropy, strategic partnerships, major institutional funding, and innovation financing approaches.
Sales & Partnerships development
Go-to-Market strategy design and execution
Economic model development and financial strategy
Product innovation and scaling
Organizational culture building in complex, multi-site or national organizations
Possess commitment to equity, cultural competence and respect for differences
Entrepreneurial business development and revenue generation expertise in nonprofit, social enterprise, or mission-driven environments.
Ability to evaluate and structure revenue opportunities using market analysis, investment frameworks, and impact metrics.
Strong network within education, social impact, corporate, philanthropy, and investor communities.
Experience translating organizational impact into compelling investment and partnership opportunities.
Communication: Uses effective written and oral communication with internal staff, teams, and community served; demonstrates empathy and listening
Client orientation: Recognizes needs of diverse stakeholders and approaches relationships with a service orientation, to ultimately maximize the impact
Equity mindset: Understands and is committed to goals of equity, consistently brings an equity mindset to the organization’s work and workplace
Growth mindset: Views growth as important for personal and professional development; seeks out opportunities to expand skills, even if the change is required, demonstrates curiosity and eagerness to learn
Ownership and quality of work: Effectively manages own work, and work of the team to ensure delivery of high-quality work
Supervisory skills: Effectively manages and develops others
Mission drive: Demonstrates commitment to the missing of the organization as a whole and alignment with organization values
Continuous improvement-minded: Takes initiative to identify and execute strategies and processes to continuously improve one’s leadership to strengthen organization’s overall impact.
Develops and motivates others: Motivates others and supports their development through strong coaching and mentoring.
Effectively stewards self and others through both small and large scale change.
External representation and relationship building: Represents the organization among external stakeholders, and builds strong, trusting relationships with stakeholders
Leads with vision: Has an inspiring vision for the future of the organization, beyond the status quo, and communicates it effectively; leads with courage and willingness to take risks in service of impact
Manages with data: Understands data; analyzes data and identifies insights and implications
Strategic thinking and resource management: Considers the future of the organization proactively and responsively; weighs diverse inputs to inform strategies; identifies innovative opportunities when relevant; makes and communicates decisions that effectively balance tradeoffs between financial sustainability and impact
Team building: Builds strong relationships with teams and colleagues; fosters effective teams and collaborative interactions

Nice To Haves

Experience working with or within education systems, particularly school districts, strongly preferred

Responsibilities

Serve as a primary steward of the organization’s enterprise wide strategy, partnering with the CEO and executive leadership to define priorities, sequencing, and success measures.
Lead multi year and annual strategic planning processes that are actionable, mission aligned, and grounded in external realities.
Drive disciplined decision making regarding strategic investments, market opportunities, and organizational priorities, ensuring clarity around where the organization should lead, partner, scale, or not pursue opportunities.
Continuously assess strategic assumptions, performance, and external trends to recommend strategic shifts as needed.
Serve as a trusted advisor to the CEO and Board, providing clear, data informed perspectives on strategy, growth, and key organizational trade offs.
Lead the organization's growth strategy by identifying, evaluating, and prioritizing opportunities to expand impact, strengthen sustainability, enhance offerings, and develop strategic partnerships or new areas of work.
Ensure growth initiatives are supported by realistic operational capacity, financial assumptions, and success measures.
Drive organizational revenue growth through new business models, venture philanthropy investments, national strategic partnerships, fee for service opportunities, and innovative investment structures that complement the organization’s fundraising strategy.
Identify and develop strategic partnerships that expand organizational capabilities, markets, and long term impact.
Develop and execute go to market strategies that support scalable growth and mission impact.
Lead, develop, and provide strategic direction to team members and functions responsible for business development, partnerships, and growth initiatives
Develop and execute enterprise wide business development strategies that diversify and expand organizational revenue beyond traditional philanthropy.
Identify, cultivate, and secure new sources of growth capital, including venture philanthropy, social impact investment, public private partnerships, and other innovative funding models.
Build relationships with education leaders, national funders, philanthropic investors, intermediaries, and mission aligned capital providers to accelerate organizational growth and sustainability.
Lead the identification and design of transformational funding opportunities that support geographic expansion, product innovation, technology investments, and scalable program delivery.
Partner closely with the External Affairs team to align organizational growth initiatives with fundraising priorities while focusing specifically on new and emerging revenue opportunities outside of the organization's established fundraising portfolio.
Develop investment cases, growth propositions, and strategic partnership frameworks that demonstrate organizational impact, scalability, and return on investment.
Maintain a pipeline of strategic growth opportunities with measurable revenue, market expansion, and impact targets.
Advance national program portfolio decisions based on clear trade offs between cost, impact, scalability, and long term sustainability.
Support disciplined portfolio decision making, regarding the launch, scaling, redesign, or discontinuation of programs through strategic and economic analysis.
Partner with program leadership to ensure the sustainability and evolution of national portfolio programs through redesigned delivery models and alignment with the organization's broader economic strategy.
Establish clarity around centralized versus locally driven decisions, balancing consistency with flexibility.
Lead efforts to streamline operations and support a more nimble, agile organization, including adoption of systems and delivery models.
Lead the design and evolution of the organization’s economic model to ensure sustainability of core programs (e.g., BAM and WOW), balancing cost efficiency with revenue generation.
Drive tighter integration between programmatic strategy and financial planning, ensuring program decisions are grounded in clear economic models, cost structures, and long term sustainability.