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Strategy Director-Education Grantmaking

Ascendium Education Group
tuition reimbursement
United States, Wisconsin, Madison
38 Buttonwood Court (Show on map)
Jul 18, 2026
Description

Are you an accomplished leader with experience driving change across state education, workforce, or economic development systems? Have you built partnerships across sectors, connected data to improve decision-making, and helped translate complex challenges into coordinated action? Ascendium is hiring a Strategy Director to provide leadership and oversight of one of Ascendium's three core grantmaking strategies. Each of three directors leads a specific body of grantmaking, overseeing $40-70 million in active grants while supporting and supervising a team of three to four grantmakers in developing a pipeline of approximately $30-50 million in new funding annually.

The three strategy directors work closely with a Director for Learning and Impact and a Director of External Engagement and Partnerships in managing the philanthropy's overarching grantmaking. They sit on the philanthropy's leadership team and are responsible for shepherding high quality, strategy-aligned projects through the internal review process and developing materials that effectively communicate this alignment.

For this position, we're looking for a strategy director to lead a body of work focused on connecting and aligning systems to ensure all learning counts and that learners do not experience dead ends as they move between settings and sectors to pursue postsecondary education and workforce training. This body of work is referred to as the Connect and Align Systems strategy, and addresses problems across systems - often at the state level - such as K-12 to higher education, higher education to workforce, and corrections to workforce.

Ascendium's grantmaking priorities in the Connect and Align Systems strategy include improving alignment between postsecondary systems to support credit mobility (e.g., community college transfer), between public workforce and postsecondary systems to ensure credentials are in demand and provide an economic return, and among the state-level systems involved in the delivery of postsecondary education in prisons. The ideal candidate will have expertise in one or more of these areas of state/system-level policy and practice.

The planned salary for this position is approximately $155,000 with potential for higher compensation commensurate with experience. In addition, this position may be eligible for a bonus based on performance and achievement of key results.

This position requires residence in or relocation to Madison, Wisconsin, where Ascendium is headquartered. Madison-based employees have a hybrid schedule, working three days per week in the office and two days remotely, which provides the opportunity for valuable in-person collaboration. While preference will be given to candidates based in Madison, a remote hire may be considered if no qualified Madison-based candidates can be identified. This role also requires up to 25% travel to conferences, convenings, and other events.


Job Responsibilities

On a day-to-day basis, you may do the following.



  • Develop and oversee a grantmaking strategy and team in pursuing Ascendium's philanthropic objectives related to connecting and aligning postsecondary education and workforce training systems to better serve learners from low-income backgrounds
  • Lead a grantmaking team in designing, implementing, and routinely improving a multi-year funding strategy focused on improving system alignment to minimize credit loss, strengthening measurement of and accountability for learner outcomes, and realigning public resources with evidence-based models and reforms.
  • Maintain expertise in state and system policy, administrative practices, and other key leverage points for systemic change within postsecondary education and workforce training ecosystems.
  • Develop and oversee annual grantmaking budgets and workplans and lead semi-annual strategy reviews in partnership with the Learning and Impact team and other colleagues within the Education Philanthropy division.
  • Oversee a high-volume pipeline of new grant concepts and proposals, providing support to grantmakers to ensure the efficient development and execution of strategy-aligned grants. In limited instances, strategy directors may also directly hold grants or oversee grantmaking initiatives.
  • Prepare reports and other materials to communicate strategy progress and learning to Ascendium's board of directors, in partnership with the Vice President - Education Grantmaking, Senior Learning and Impact Officers, and the Director of Learning and Impact.
  • Provide internal and external expertise and thought leadership on topics related to the grantmaking strategy, maintain a network of partners and experts in related field(s), and represent Ascendium's philanthropy in strategic field engagements. Strategy directors attend eight to 10 conferences or other offsite meetings annually, with travel typically concentrated in spring and fall months.
  • Develop relationships with other national and regional funders working in postsecondary education and workforce training to exchange information, share lessons, and leverage each other's efforts.
  • Manage, develop, and support a team and contribute to cross-team organizational development and improvement
  • Provide day-to-day management of a team of program officers ranging from early to advanced career professionals.
  • Oversee the recruitment, vetting, and onboarding processes for new team members when the opportunity arises for new hires, in partnership with Ascendium's Human Resources team and the Vice President - Education Grantmaking.
  • Provide regular performance feedback, coaching, and support, including identifying and supporting direct reports' professional development in alignment with their roles and strategy objectives.
  • Contribute to whole-division learning and professional development. Strategy directors have opportunities to serve in cross-cutting leadership roles within the team, including serving on the Justice, Equity, Diversity, and Inclusion Committee and in other forums and capacities.
  • Serve as a member of the Education Philanthropy leadership team supporting development of annual cross-team objectives, development and accountability for annual administrative budgets, conducting periodic policy review, and practicing shared accountability.
  • Cross-Unit Collaboration
  • Collaborate with the Director of Learning and Impact and the Learning and Impact team to draw insights, identify priority learning needs, support program officer team collaboration, and elevate learning across strategies.
  • Collaborate with the Director of Grants Management and the Grants Management team to ensure efficient workflow, address concerns that emerge from financial due diligence reviews, and ensure that any grant administration issues are resolved in a timely manner.
  • Work closely with Communications and External and Strategic Engagement teams to facilitate coordination and amplification of related issues, priorities, and audiences.


Knowledge and Skill Requirements

A highly qualified candidate will possess the following.



  • A commitment to advancing upward mobility through postsecondary learning.
  • Knowledge equivalent to a master's degree, with training in social science, education, public policy, or a related field.
  • At least 7-10 years of experience working in postsecondary education or workforce training systems adequate to have acquired deep familiarity with the landscape of key agencies, stakeholders, and constituents of those systems.
  • Strategy development and execution leadership experience, along with budget development, management, and reporting experience.
  • Excellent organizational and execution skills to support high quality and efficient movement of proposals through a rigorous internal review process.
  • Strong collaboration, oral and written communication, and leadership skills. At least two years demonstrated experience effectively leading and managing a team of skilled professionals; and practiced at effective "horizontal" collaboration working with peer managers across different departments.
  • Demonstrated experience working in partnership with leaders across sectors and systems, and on-the-ground understanding of state and federal policies and funding streams - especially related to public workforce training, credit mobility/transfer, prison education, data systems, and/or cross-sector workforce development. Experience working in a state postsecondary or adjacent system or other state agency within postsecondary education or workforce training is preferred.
  • A strong understanding of the different levers that drive systemic change, especially at the state level, plus an understanding of how to effectively engage policy- and decision-makers (including from institutional/system audiences).
  • Effective interpersonal skills exemplified by initiative, courtesy, diplomacy, a positive attitude, and a high bar of professional ethics and integrity.
  • Ability to work under pressure to meet critical deadlines yet remain flexible and gracious in responding to changing requirements.
  • Experience working at or in partnership with philanthropic organizations is preferred, but prior philanthropic experience is not required. Selected candidates without grantmaking experience will be provided opportunities and expected to participate in training related to philanthropic practice and legal considerations related to public charity tax status.


Other Information

Ascendium offers an outstanding benefits package designed to provide employees and their families with a high degree of security. These benefits include, but are not limited to:



  • Student loan repayment assistance and tuition reimbursement.
  • Paid volunteer time off.
  • Ongoing training and professional development opportunities.
  • Retirement savings plan with employer match.


Ascendium provides equal employment opportunity to all individuals regardless of their race, color, religion, sex, age, national origin, creed, disability, veteran status, or any other characteristic protected by state or federal law.

H-1B sponsorship (initiation or transfer) is not available for this position.

If you would like assistance with the application process, please email Ascendium Human Resources. We invite all applicants to complete the Voluntary Affirmative Action questions when submitting application materials. The questions are found at the end of the online application process. To learn more about our commitment to Equal Employment Opportunity, please visit the Ascendium Careers webpage.

Ascendium requires criminal, employment, and education background investigations before hiring.

Equal Opportunity Employer

This employer is required to notify all applicants of their rights pursuant to federal employment laws.
For further information, please review the Know Your Rights notice from the Department of Labor.
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