Ashley Cravens of Uncork Capital
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In the world of VC operations, Ashley Cravens is a known entity. She is a powerhouse of productivity wrapped in a charismatic personality with an infectious laugh you never forget. A consummate professional whom others look up to and aspire to be, she is, unquestionably, the complete package. For Ashley, 2020 marked over a decade in VC. This past November, she celebrated 10 years at Uncork Capital, where she currently serves as Director of Operations and Head of Platform.
Back in 2010, Ashley joined Jeff Clavier as the only employee of the fund, which was called SoftTech VC at the time. A creative problem solver, Ashley had the autonomy to build many of the firm’s systems from the bottom up, and build she did. She led the charge on everything, from deciding which portfolio tracking mechanisms to use to what company events should look and feel like. Though she was originally hired as an executive assistant, the breadth and depth of her role quickly expanded to support the fund’s operations. As the firm grew and brought on new partners, they expanded the operations team with Ashley at the helm, allowing her the opportunity to spend more time working with Uncork’s founders.
“Ever since she joined me 10 years ago, Ashley has always figured out how to make it happen for me, the team, and our founders.”
– Jeff Clavier, Managing Partner, Uncork Capital
Ashley currently divides her responsibilities into two main categories: platform support and managing operations and communications. As head of platform, she is the linchpin connecting Uncork’s portfolio companies, helping them find the services they need and providing both educational and networking opportunities. As director of operations, Ashley manages a team that includes an executive assistant as well as an operations and communications manager.
“Like every great entrepreneur, Ashley shows up with the energy, passion, and drive to tackle challenges big and small.”
– Stephanie Palmeri, Partner, Uncork Capital
Ashley’s path into the financial world seemed set in the stars. While in school, she spent her summers working for one of her father’s best friends, a broker who needed help with day-to-day office organization. During her first day on the job, the broker offered an important lesson:
“I walked into the room without a notepad, and she told me never go anywhere without something to write on and a way to organize your thoughts.”
That advice stuck with Ashley. “Now my favorite sign is the checkmark,” she says, referring to the state of her to-do list. “I know how to get things done quickly and efficiently.” After college, she continued working for the broker, managing client relationships and accounts. Ashley eventually became a registered stockbroker and worked under several brokers as a registered associate. She soon realized the path wasn’t for her and decided to try her hand as an executive assistant and marketing director at an investment advisory firm.
While at a social event in San Francisco several years later, Ashley connected with a friend who worked in VC. That friend mentioned knowing someone who was looking for an assistant and put Ashley in touch with Jeff Clavier. They met soon after, and he offered Ashley a job on the spot. The rest is Uncork history.
“I didn’t know VC, but I had a strong financial background on the investment side,” Ashley says. “So while there was a bit of a learning curve, I had experience a lot of folks going into an assistant or ops role in this industry probably didn’t have.”
A normal day for Ashley includes an impressive range of responsibilities. She helps track investments, cash on hand and keeps important fund and portfolio data up-to-date. All the while, Ashley works to ensure Uncork’s Partners have the best research tools and the information they need to make critical decisions quickly.
“Ashley knows the portfolio inside out, she knows the partnership inside out, she knows the broader community inside out, and she knows the underlying business inside out. She's like a one-woman knowledge bank of everything Uncork.”
– Andy McLoughlin, Partner, Uncork Capital
Ashley excels at building and nurturing meaningful human connections. She cares deeply about helping founders succeed, providing them with key and well-timed introductions to the experts, consultants, and service providers they need to move their businesses forward.
“Ashley has been personally invaluable to me. She has helped me hire people for my EA and head of finance/ops roles. The advice and guidance she gave me helped me hire superstars.”
– Vlada Bortnik, CEO and co-founder, Marco Polo
While juggling a long list of daily tasks, Ashley also takes the lead on projects with longer arcs. She’s integral in creating and facilitating 15 to 20 events per year designed to support founders. These events range from master classes on how to create a sales team and navigate the COVID-19 pandemic to portfolio summits and networking events. A survey of founders in August revealed how highly Uncork’s portfolio companies value these events. As a result, she has spearheaded a project to house this valuable information in one easily accessible place.
“Ashley is one of those people who is super organized and on top of everything—there are literally hundreds of companies she is working with, and she knows who everyone is and how everyone is doing.”
– Jim Warner, CTO, Upwave
Passionate about both people and standing up for what is right, Ashley leads the firm’s efforts to create a diversity, equity, and inclusion (DEI) process. “We’ve been making a conscious effort to work with underrepresented founders and investors. This includes having active conversations with our founders about the importance of DEI within their organizations, providing them access to expert resources on best practices, making ourselves available to underrepresented founders and GPs as a support resource, inviting underrepresented investors in our investments/funds, and establishing KPIs that allow us to measure our progress and keep our firm accountable,” she says. Last quarter, she sent a diversity questionnaire to past and current founders/CEOs to establish a baseline from which the firm can measure progress. She also hopes to launch a diversity, equity, and inclusion handbook in the first quarter of 2021.
One of Ashley’s greatest strengths is her ability to pinpoint exactly what needs to get done to move projects forward. The key is not identifying when something is perfect, she says, but rather knowing when a project is strong enough to succeed. “That’s the line ops managers need to focus on,” she says. “You could sit on something that’s close to launch for months, but it means nothing unless it’s pushed out into the universe.”
The passion Ashley brings to her work has helped make Uncork one of the top venture capital funds in the world. The firm’s ethos of working as one holistic team and treating each person with respect is a key factor in their success, and a mindset Jeff and Ashley embody and instilled early on. “I consider my team a family, and I look to all of them as mentors,” she says. As Ashley continues to help lift Uncork to new heights, we in the VC ops community continue to be in awe of her.
Outside the office, you can find Ashley spending time with her two daughters, making art, hiking, and traveling the world.
“Being a mom has really shaped my thought process. You have to be able to get things done in the way that makes the most sense or risk falling into a circle of never-ending madness!”
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Let’s Talk Ops (LTO) is a community of first-class operators powering some of the most successful venture capital firms in the world from behind the scenes. We provide connective tissue, mentorship, and tactical support to help members execute at top form across the many verticals they manage inside their funds. LTO also provides high-powered professional development to assist members with career navigation and to ensure the best talent stays. In that vein, we’ve launched our LTO Member Spotlights, aimed to elevate the visibility of VC operator contributions to the venture ecosystem at large.