Shyp, Marketing, and failing fast and often

Last night, I had the chance to attend General Assembly SF’s Changemakers event which showcased Lauren Sherman, Head of Marketing at Shyp. The Changemakers Series interviews professionals under the age of 30 who have done and are doing cool shit, and Lauren certainly fits the mold. A veteran of startups such as Taskrabbit, ZipCar and now Shyp, Lauren answered questions from  Ben Muessig from the San Francisco Chronicle about Shyp, her career, marketing, and tech in general. She also took some Q&A from the audience.

General Assembly

What I most appreciated was her honesty and candid nature, especially around talking about failures and missteps along the way. Recently, at her address to the Kellogg MBA graduation, Gina Rommetty said something that I have been thinking alot about in that comfort and growth do not always come hand in hand. Lauren illustrates this perfectly, as she’s taken on meaty and challenging roles pretty much her entire career, and despite her failures (or what she considers failures) she’s in a pretty awesome spot.

Below are some of my notes from the event. And of course, if you need to ship something, don’t have the materials, but do have $5, check out Shyp!

Lauren Sherman Head of Marketing Shyp

Lauren Sherman
Head of Marketing


On Shyp

  • Shyp solves a problem that many of us didn’t know we had until we learned about Shyp
  • Our Founder is so laser focused on solving this problem. He was an eBay powerseller that almost had to shut down because it was so difficult to manage shipping.
  • Lauren’s role right now is to build a world class-marketing team. She’s using the structure of an agency as a model to build her team, which is a little bit different than what others do, but she’s confident that it’s what is best for Shyp.
  • Early versions of Shyp included a Google Form, and the Founders using Lyft/Uber to deliver packages
  • Most business is in the Consumer segment, but there are opportunities down the road for B2B
  • We’ve got seen several different uses cases for Shyp and it continues to grow. We’re in 5 markets today, and we’ll look to expand
  • Not revenue positive – any money we make we’re plowing back into the business


On Managing and Leading

  • It’s a challenge, I make mistakes, but I learn and move on
  • I took the role because Kevin told me that he didn’t know a ton about marketing but that he trusted me unconditionally to run marketing and to help him learn. He also promised he would support me through successes and failures. I try to do the same for people on my team.
  • I want them to try things, fail, learn, and move forward. The only way they can do that is if I truly demonstrate my support for what they are doing
  • One of the biggest challenges right now is focus. There are so many opportunities we can chase – it’s truly exciting! We need to be laser focused on the 1,2, or 3 that will make the highest most impactful progress right now, and wait for the rest to do later
  • There’s some areas of marketing that I don’t know, so I surround myself with people who are really good at those things.


Failure and Fear

  • In a startup culture you have to move fast. I move fast, and thus, I fail often. That’s okay, because I can learn quickly.
  • I’ve failed and missed the mark on a lot of things, in my career and at Shyp, but I’m still here so I guess it’s worked out okay
  • You need to determine for yourself what you’re comfortable with. If you’re someone who wants a steady job with steady tasks, a startup probably isn’t the best place for you.
  • I’ve always loved throwing myself into something, having a handful of different roles, failing but learning etc, so I’m totally okay with this environment.
  • I’m working on a redesign right now, and I’m definitely somewhat afraid of what the design bloggers are going to say when they see it. That’s okay – that’s natural, but it shouldn’t prevent you or paralyze you from taking action. Test and learn, and then move on.


Some Workplace Hacks

  • I’ll often email people I think are really interesting or have done something cool to talk shop and learn from them
  • I keep track of the people that I’ve worked with who I really liked or respected. Many of the folks on my team are people I used to work with.
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