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Meet Ashley Raggio, COO at Joint Venture

Chief Operating Officer, Joint Venture Silicon Valley

By Robin Doran | Published: August 2023

Ashley Raggio, Chief Operating Officer at Joint Venture, is a visionary leader committed to transforming her community and to inspiring her young family to carry on a tradition of service and compassion. With unwavering dedication and a profound understanding of the inequities in Silicon Valley, Ashley has for years taken on roles that bring about positive change.

Ashley envisions a future where every member of her community thrives and is appreciated, and she energetically works to turn that vision into reality. As an empath, she says that her compassion is worn on her sleeve, a trait she inherited from her mother.

Born and raised in Redwood City and San Mateo County, Ashley is the mother of three teenage boys: 15-year-old Joey and 14-year-old twins Matthew and Ryan. Bam. Three baby boys arrived in less than two years.

One glance at her CV and her commitment to public service leaps off the page, from her early work with students with learning disabilities to her current role at Joint Venture.

Ashley volunteering with two of her sons

Ashley feels blessed to have been raised with options and honors what she refers to as privileged origins, yet she understands that when one is given much, one “builds a longer table, not a higher fence”.

Her mother served as a dynamic role model for volunteerism. From a young age Ashley recalls licking envelopes for fundraising appeals and went along with her mom on regular service endeavors. “We went to Samaritan House in San Mateo every other Thursday night to volunteer,” says Ashley. “We would help cook and serve up food to those in need.”

Ashley’s parents were also California natives. Her father, a tech executive, grew up in Millbrae and her mother, the former proprietor of an antiques shop in Burlingame, spent her formative years in Pasadena. Ashley helped at her mother’s shop after school. Her father instilled a strong work ethic and the notion of giving your best. “I am pretty darned driven and organized,” laughs Ashley.

Ashley graduated from the University of Oregon with a BS in marketing, fully intending to go into business.

But on her first day on the job after graduation as an account coordinator with a publisher, she found herself in a cubicle poring over ad copy. She bolted. “I was like, I am outta here!” she remembers. Soon she found a gig at Webvan, a startup where she recruited professional talent and hired distribution center workers who genuinely needed jobs. It was a better fit. “I wanted to work with people,” she says.

When Webvan folded, she became a trainer with Lindamood-Bell Learning Processes, a center for students with learning and developmental disabilities. There she taught math, reading, and comprehension, which inspired her to return to graduate school at San José State for an MA in education administration so she could work with students outside of the traditional classroom.

Her “aha moment” came while working as a student success coordinator at the Center for Service Learning at San José State. “I helped students reflect on their service experience and to connect it to their learning, especially to civic participation,” she says. “And that’s where I got hooked!”.

She followed that inspiration to additional community service-oriented roles as a program coordinator with Silicon Valley FACES and as a consultant for Susannah Sallin, who recruits talent for nonprofits.

She took a few years out of the workforce to raise her young sons even as she contemplated ways to encourage her own children to work to better the community. She discovered Doing Good Together, a nonprofit that connects parents with community service and provides resources on how to raise kids that give back. She volunteered before starting a Silicon Valley chapter. She conducted parent workshops and service fairs designed to teach parents how to develop essential skills. “Because nobody teaches you how to do that with kids,” she says emphatically.

Asked how she pulls off volunteerism with her own kids, Ashley says that empathy is a muscle and if you don't use it, you lose it. “You have to keep doing it with them and they won’t love it but it will eventually stick,” she says. One suggestion: keeping kits filled with essentials such as socks and snacks in the car for unhoused people, which she or her kids find themselves giving out often.

Ashley met her husband, James, her senior year in high school. The crush was instant, but they didn’t get together until college.

“Ashley is an extraordinary convener and is able to synthesize multi-layered issues while navigating complex systems.”

James had graduated from college and Ashley had one more year left when they began dating. “We've been together ever since.” James Raggio is Senior Vice President of the Commercial Real Estate Group at Comerica Bank.

Ashley has a love for “figuring things out,” as she calls it. Earlier in her career she completed a three-day intensive study session on personal bias. “We were placed in uncomfortable positions, talking about lived experience and doing exercises that expose unconscious bias ⎯ I was never the same after that,” she says. “If I'm honest, I am a white woman with a ton of privilege. I need to do something with that knowledge and awareness.”

In 2019 Ashley landed at Joint Venture where she took on leadership roles for both the Silicon Valley Talent Partnership and the Lighthouse initiatives. She also plays an ongoing role in regional efforts such as the REAL Coalition, the Equity Forward advisory group and is a new member on the board of Project Safety Net.

In the fall of 2022 Ashley stepped into the role of COO where she is responsible for strategic planning and organizational operations.

When she took on the new role, she was not at all certain that internal operations was something she would excel at but admits to “loving a good spreadsheet and a structured to-do list.”

“Ashley is an extraordinary convener and is able to synthesize multi-layered issues while navigating complex systems,” says Kelly Kline, Joint Venture board member and Associate Vice President of Local Government Affairs at Stanford University. “She has been invaluable throughout the pandemic — skillfully bringing different sectors together to help reimagine workforce services for our region’s most vulnerable populations.”

“Ashley is perfect for her role as COO of Joint Venture,” says Susannah Sallin, with whom Ashley worked as a sourcing and research consultant. “She is grounded, authentic, super-organized, and knows everyone!”

Ashley with her family

At Joint Venture, Ashley is also tasked with driving the organizational aspects of strategic planning. Joint Venture’s current leaders envision an organization doubling down on its unique ability to convene the region and for building out an Institute with the nation’s deepest expertise on metropolitan issues.

Ashley is delighted to facilitate the development of the plan and to operationalize this vision across all functions of the organization in collaboration with staff, board members and our valued partners.

Nearly two years ago Ashley was diagnosed with chronic vestibular migraines, a condition that has upended her penchant for early morning exercise and other physical activities. She is managing the symptoms and fatigue with medication and vestibular rehab therapy. Sensitive to light and sound, she gets frustrated that she can’t handle nights out or loud environments.

Her husband and kids have stepped up significantly to help with family chores. But there’s still time for fun. Ashley and her family are often found enjoying the kids' sports. Ashley loves to immerse herself in reading, music, and film when she has the chance. If the boys are away, she likes to get out a cookbook and put on some music to make something not particularly kid friendly.

Meanwhile, her passionate focus is on Joint Venture Silicon Valley, where “…nobody is putting the pieces together about how challenges impact our region as a whole better than we do,” she says. “We provide the region-specific data and analysis and we can share it with the community and its leaders to create change. I want more people to see that.”

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