A Conversation With Former EIR Sharon Goldstein

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One of XSeed’s recent Executives-in-Residence (EIR) and former portfolio executive, Sharon Goldstein, shared some insights about her career, her time at XSeed as an EIR and new position at ShipHawk.

Tell us a bit about you:

I’ve always been drawn to audacious opportunities with high barriers to entry. My first role out of business school was as part of the team that built the mobile business at RealNetworks, at a time when phones could only support five frames of video per second and apps had to be built into devices. It was a thrill riding the development wave of mobile and building that business from scratch to $11M globally.

Functionally, I’ve taken the “S-curve” approach, following the opportunities that I found the most interesting and high-impact, regardless of my functional position. For several years in the middle of my career, I had my own business, advising mobile startups with their go-to-market strategies, customer acquisition efforts and helping them build their revenue machine. This broad functional career has been invaluable, as it gave me a wide purview into how key decisions affect every part of the business, and prepared me for C-level positions.

My last five years have been in the ecommerce space. I was fortunate enough to become the Director of Corporate Development and Strategy at Shutterfly just as the industry was consolidating, and oversaw the acquisition of TinyPrints. After Shutterfly, I built out the non-advertising revenue businesses at Photobucket, and, most recently, I was Chief Marketing Office of social commerce startup Pixlee.

Why did you join XSeed as an EIR?

XSeed was an investor in my last company, Pixlee. Rob Siegel was the lead partner on the deal and I met him during the interview process. From the start, I was impressed by the whole team’s structured approach to problem solving, Rob’s willingness to roll up his sleeves and his no-nonsense style. When I decided it was time to take a different path, the XSeed team proposed the EIR role. I was impressed by the way in which XSeed’s supported early stage, often first-time founders, building a community around them, accelerating their learning curves, and making the connections necessary to help build a bench of talent to accelerate growth. The opportunity to work with this team again sealed the deal for me.

What was the EIR experience like?

EIR roles vary widely across firms. At XSeed, EIRs are full members of the team, with the option to participate in off-sites, thesis development, pitches, and due diligence of the organization. Rather than simply observe, this EIR structure allowed me to take an active role and have a meaningful impact.

What did you learn in your year?

Because the fund invests across different sectors at the seed stage, I had the opportunity to see a diverse set of opportunities from security and DevOps to marketing technology and consumer products. I honed my pattern recognition skills both on people and businesses. The experience also showed me first-hand the complexities of getting funded from the investor’s perspective. Stage, skills, idea, and timing all have to come together. In early stage investments, your bet is on the jockey (the entrepreneur), and less so on the track. Even with a great idea, if it’s not the right team, it is a real challenge to move forward.

It was also a great opportunity to take a step back and get a bird’s-eye view of tech as a whole. Ultimately, I found that I wanted to stay in the retail enablement space. There’s incredible disruption happening there — in advertising, merchandising, payment and delivery — and we’re just at the beginning of these changes.

Did you do any special projects?

This past summer, the issue of gender bias within the industry was a very hot topic. No matter how you looked at it, the representation of women in the venture and tech communities is still depressingly low. At the request of the partners, I led a full analysis on the issue — of the industry, our investments and our pipeline to see how we fared on investing in female entrepreneurs. We also had some sessions in-house to talk about unconscious bias. It’s a complicated topic that starts with the number of women starting tech companies, the segments they choose to focus on, as well as the legacy of the funding process. The good news is there’s significant interest in changing the venture industry; now we need to work to overcome unconscious bias. From the XSeed perspective, the fund is doing a good job of attracting and funding female founders and executives, but they want to continue to improve and do better. They recognize that there’s untapped opportunity here.

What are you doing now?

During my tenure as EIR I advised several companies within and outside the XSeed portfolio. One such company was ShipHawk, which I ultimately joined after advising the company for six months.

I met ShipHawk through my involvement in Haulery, a retail delivery conference I co-produced, and was immediately impressed by the team and their approach. The founders of ShipHawk, Jeremy Bodenhamer and Aaron Freeman, had started by solving the biggest pain points for the most difficult customers: logistics automation for the freight industry. With the changes happening in the ecommerce world – innovation in the delivery experience, Amazon using fulfillment to lock in customers, and consumers buying ever more diverse items via ecommerce – retailers need help. ShipHawk is shifting shipping from an overlooked back office function to the front and center of the retail business, bringing retailers options, automation and data they haven’t had access to in the past. The potential is enormous, and at a certain point, I realized that I was comparing every other opportunity that presented itself to joining ShipHawk. So, I decided to take the plunge and join full time.

While ShipHawk is not an XSeed portfolio company, the XSeed team was very supportive of the decision. I expect to continue to collaborate with XSeed opportunistically and hope to have the opportunity to work with the team again more formally in the future.