Brittany Skoda — All Raise’s Enterprise SaaS #WomanCrushWednesday
In May, we will focus on Enterprise SaaS and the brilliant investors and operators who bring their expertise to the industry. Our third feature this month is Brittany Skoda, Vice President of Investment at the newly launched Workday Ventures. All Raise’s ‘Woman Crush Wednesdays’ (#WCW) is a series where we highlight genius women who are funding or founding tech companies. Please come back to the All Raise Medium blog every Wednesday to find a new profile of an awe-inspiring female VC or founder.
Brittany Skoda, Vice President of Investments at Workday Ventures, knows what it takes to achieve excellence in highly competitive spaces. Originally from Cleveland, Ohio, she became a nationally ranked junior golfer and went on to compete at the Division 1 level at Georgetown. Skoda was then a Technology Investment Banker at Goldman Sachs (GS) for nearly a decade. While at Goldman Sachs, she worked with some of the largest and most exciting companies, like Amazon, Atlassian, Dropbox, Google, Tesla, Tableau and Zendesk on almost every type of transaction ranging from private placements, IPOs, M&A and investments.
Driven by a love for enterprise companies and a desire for a new challenge, Skoda took her experience and expertise to the world of enterprise venture as a lead investor for Workday Ventures. Workday Ventures is the strategic capital arm of Workday and focuses on accelerating the growth of emerging enterprise software companies that enhance Workday’s products and customer experience. Workday Ventures portfolio includes Automation Anywhere, Beamery, Guild Education, Landit, ScoutRFP, and Workato.
Being at the ground level, Skoda is responsible for leading new investments and working with portfolio companies post-investment to unleash their potential. She credits Workday’s leadership for prompting her to move into investing and pushing her to expand her boundaries and leverage her skills differently. Skoda told us about her transition to Workday, learnings in her career thus far, and advice for women younger in their journeys.
What prompted the shift from Goldman Sachs to Workday Ventures?
Goldman was an incredible place to start my career. It provided a platform to peer inside and work with many of the most interesting companies on important transactions and strategic decisions they faced. In banking, you can scale to relatively senior levels relatively quickly, which means you are in the mix of many important conversations earlier in a career journey than most other careers provide. I was able to learn and add value on different types of deals/products like IPOs, M&A, debt & equity transactions, and raid defenses working with companies during exciting and challenging times.
After nearly a decade, I was ready for a new challenge and when Workday called to join as part of the leadership team to build out Workday Ventures, I couldn’t resist. What could be better than joining one of the most iconic enterprise companies of our time, at the ground level of a new business venture, with the opportunity to peer inside the organization and invest while being exposed to broader strategy and operations?
How does technology investment banking look different than tech investing?
I have always enjoyed meeting with entrepreneurs and learning more about their businesses. In many ways, the move to Workday is the same ecosystem I’ve been operating in for a number of years at GS, having worked with many enterprise companies. But this was just a different seat. Both roles require hustle and creativity. Now instead of being an advisor and laying out decisions, I am the one making principal decisions. I love being able to put my thoughts to work funding great teams and ideas at the earlier stage, and companies ready to break into their next level at the later stage. Workday Ventures is stage agnostic, so I have had the opportunity to see seed stage companies through the growth phase. At Workday, there is also a deep bench of very talented product and technical minds to bounce ideas off of, learn and benefit from.
What excites you about enterprise?
Innovation in and around enterprise is ever present. This is true across the entire technology stack — applications to infrastructure. It’s hard to imagine that Workday was just getting started 14 years ago. Before us, other leading SaaS companies of today like Salesforce were treading new territory with a SaaS model. Today it is a household concept with multiple SaaS companies valued over $1B.
New platforms and technology continue to introduce themselves like blockchain and microservices, and people are brilliant, leading to ever-changing business models and modalities of work. There is constant change to keep up with and learn about. Machine learning, for example, has the opportunity to redefine how we engage and learn from software in an extraordinary way. Businesses face interesting decisions in engaging new technologies. I just love being at the center of it all.
You’ve spent time as a D1 golfer, investment banker and now venture investor. How do you navigate fields that are usually dominated by men?
I don’t think about it too much. In some ways, I never knew any differently. I grew up with three very athletic brothers, spent endless hours at the golf course practicing and playing with primarily men, and then saw those same environments carry through at the start of my career. This is not to say there is not tremendous room for improvement; there is. But I truly do believe we will get to the most equal position possible when there is engagement on both sides of the table on the issue. Bringing more women into venture requires men to be on board and active in solving the problem. All Raise has been an amazing organization to be deeply involved with over the last year, as it has provided the network to create a fabric of women investors and friends to lean on for advice, deal sharing, etc. It is also so inspiring to work alongside so many talented women involved in driving change.
Your life experiences to date require you to be calm under pressure. How did you develop this skill?
Golf taught me this requirement early. As a competitive golfer, you wouldn’t get far if you overreacted to any one shot. It’s a game that’s played over several hours and, often times, it’s still possible to score well with bad shots. So each shot has to be approached with a clean slate and a can-do attitude. Learning to go shot by shot has been a skill that has been transferable to the business world. It turns out nearly every deal I have ever worked on has an issue at some point. I learned you can either get flustered or work to get underneath it.
What is a common misperception about you?
I am often underestimated. It seems to come with being 5 feet tall and maybe a penchant for dressing in colored and fun clothing. What people often miss in the external package, is what has been built through many unique experiences. Things like having grown up with three brothers, playing nationally ranked junior golf / Division 1 college golf, working on Wall Street for nearly a decade, and now chartering new territory at Workday Ventures. I used to be self-conscious about the things people underestimated, but now I just own it and will let the other side decide when to be surprised.
What advice do you have for women early in their career?
Don’t be constrained by convention. People often have mental models of what it takes to be successful and the attributes required. If I think back over my experiences to date I had heard at different times: you will never be a good golfer. You won’t be able to get to Wall Street. You won’t succeed in finance. None of these statements have turned out to be true. Decide what you want, get after it, drown out the voices, and show the world what they don’t understand about you. A dream and significant hustle can overcome a lot!
