Holly Wittenberg

Consultant - Strategy & Transformation @Awesome Problem

FounderRecruiterHRStartup FounderHealthTechAssociateInvestor & VCPartnerC-level ExecutiveConsultingCOOBusiness Analyst

Holly Wittenberg is an experienced management consutlant and entrepreneur with over two decades of leadership in healthcare policy, consulting, business development, and nonprofit governance. She currently serves as a consultant through her firm, Awesome Problem, where she partners with healthcare organizations and mission-driven nonprofits on strategic initiatives ranging from stakeholder engagement and performance improvement to zero-based budgeting and digital transformation. A former Vice President at Avalere Health and a consultant to the Alliance of Community Health Plans (ACHP), Holly has led multi-million-dollar portfolios and advised executive teams on growth, impact, and operational efficiency. She has also worked as a management consultant at PwC and held senior leadership roles at the Advisory Board Company. Holly is passionate about community impact, serving on the boards of Woodley House and Workplace Fairness. Her work has spanned the healthcare, education, and energy sectors, and she brings deep expertise in network building, strategic planning, and revenue development. She holds a master’s degree in International Management from Thunderbird and a bachelor’s in Economics from the University of Chicago. Fluent in Spanish and proficient in multiple languages, Holly is a dynamic public speaker and dedicated advocate for health equity and organizational resilience.

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Work Background

Director of Business Development

Palmetto SolutionsDirector of Business Development

Dec. 2024Washington DC-Baltimore AreaProviding data archiving, EHR performance, data management, and BI solutions for hospitals, post-acute care, and rehabilitation facilities. Focus on building strong customer relationships and exceeding customer expectations in the areas of Healthcare IT, Data Analytics, and Revenue Cycle Management.

Managing Partner

Diversity WorksManaging Partner

Oct. 2020 - Oct. 2024Washington DC-Baltimore Area

Fractional Executive

Awesome Problem, LLCFractional Executive

Apr. 2018Washington D.C. Metro AreaAs the sole proprietor of Awesome Problem, I leverage over 25 years of experience in helping companies set and achieve their goals. My consulting and recruiting firm is dedicated to transforming challenges into strategic solutions. At Awesome Problem, I view every challenge as an opportunity and am committed to helping organizations navigate the complexities of today’s business environment. I draw on a network of subject matter experts to deliver tailored strategies that drive effectiveness and growth, ensuring that we meet the unique needs of each client.

Vice President, Provider Solutions

Avalere HealthVice President, Provider Solutions

Jun. 2010 - Mar. 2018Washington D.C. Metro Area

Manager

PricewaterhouseCoopersManager

Jan. 2008 - May. 2010Healthcare operations consulting

Senior Director

Advisory Board CompanySenior Director

Jun. 2003 - Jul. 2008Academies Division

CEO, CFO, VP of Business Development

Various Positions with Internet StartupsCEO, CFO, VP of Business Development

Jan. 1999 - Dec. 2003Chicago, ILDuring this time, I worked for various internet start-ups, including the Internet Division of the Tribune Company, and two others: eppraisals.com and dating911.com.

Manager

Compaq Computer CorporationManager

Jan. 1994 - Dec. 1999Houston, Texas and Chicago, ILStrategic Planning and Venture Capital Investments

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