Ann Goggins Gregory

Chief Operating Officer
“An admired author once wrote that ‘the home is the wellspring of personhood.’ I whole-heartedly agree and am grateful to be part of an organization that creates the kind of communities where people can become fully who they were meant to be.”

Ann was promoted to Chief Operating Officer of MidPen Housing in April 2024. With a grouping that includes Property Management, Resident Services, and Data Analytics, Ann also has an explicit focus on strategic planning and supporting large-scale initiatives across the organization.

Ann first joined MidPen in August 2019 as head of MidPen Services, a MidPen affiliate that provides onsite services to empower 20,000+ residents to advance in key areas of their lives. She oversaw all aspects of the company including strategic direction, staff development, resource management, program delivery, and producing and measuring impactful outcomes for residents. She and her talented team enhanced MidPen’s permanent supportive housing strategy, formed and launched our first-ever $10mm innovation fund, set new standards of impact in economic mobility for working-age residents, and in deep partnership with Property Management, demonstrated remarkable adaptability and responsiveness in supporting residents during the extended COVID era.

Prior to MidPen, Ann served as a senior advisor to Habitat for Humanity International, strengthening the organization’s support model to over 1,300 US affiliates. Earlier, she was Habitat Greater San Francisco’s first Chief Operating Officer where she oversaw all operations and spearheaded the organization’s strategic direction. Her oversight included homeowner development, neighborhood revitalization, and volunteer engagement, as well as impact measurement and organizational learning initiatives. Before Habitat, Ann was a Senior Director at the Bridgespan Group. She’s authored several articles on leadership development, knowledge sharing, and systems and infrastructure, which have appeared in publications such as the Harvard Business Review and the Stanford Social Innovation Review.

When she’s not hard at work, Ann likes to get outside and enjoy the great outdoors with her family.

Fun Fact

Ann’s hometown of Oconomowoc, Wisconsin, often appears on lists of words with the most repeating vowels. Its residents take the honor seriously: the local baseball team is even called the Five O’s.