My challenge to Sheryl Sandberg: if you’re offered a window seat on a puddle jumper, just get on.

Let me preface this post by saying that I am a massive Sheryl Sandberg fan; in addition to being downright brilliant, she has brought to light a refreshing and inspiring perspective around the state of women in business as well as unique frameworks for how to think about professional development in general. For the past two years, I have maintained that if I could have dinner with any person in the Silicon Valley, it would be her. (Sheryl, if you’re reading this, I’m perpetually available and I enjoy sushi.)

That said, I want to expand upon Sheryl’s “if you’re offered a seat on a rocket ship” speech given at this year’s Harvard Business School Class Day, which (rightfully) went pretty viral in the industry.  Specifically, I would like to encourage people (especially junior talent) to also consider the window seat on the slower and less commodious puddle jumper, a post from which they can see it all.  There is no doubt that there is amazing work experience to be gained from working alongside folks at the likes of Google, Facebook, etc., but the view from those seats will inevitably be somewhat provincial.  And while that level of specialization may work for some people, it doesn’t work for me, and I suspect it would also fail to resonate with many other aspiring founders/startup operators.

A few months ago, I was invited to interview for a position managing subscription activation for AmazonLocal. (I had been offered a job with Amazon in business school but was put off by the narrow scope of it and turned it down, but apparently they kept my name on file.) I was intrigued enough about what I heard that I proceeded with the phone screen, at which point I was once again immediately put off by the narrow scope of the role there. The conversation went something like this:

  • CLY: So can you tell me if there have been any data or decisions around what is going to work best for subscriber activation, or would I pretty much have carte blanche to figure that out, i.e. test some email tactics versus other website tactics, etc.?
  • Recruiter: Email would not be part of your job. Someone else does that. And someone else manages the website, so you would not be dealing with that either.

Um, WHAT does that even mean? Obviously I am not a master IA nor do I fancy spending my days obsessively monitoring deliverability rates, but as someone with P&L responsibilities, I damn well want to be able to leverage whatever channels needed as the analytics deem necessary. And as someone who aspires to run a company (God willing), I crave heavy exposure to all parts of business operations. Obviously the senior leaders at Amazon think about the business comprehensively (and they do it quite well – that company’s story is nothing short of amazing), but I found it perplexing/disturbing that the company was not trying to cultivate that same wide lens at other levels in the company, especially in a division lauded as its own “startup!” I don’t want to learn about Python in some stupid 25-minute “lunch and learn” with bad sandwiches, I want to live and breathe Django woes alongside my development team – and the best place to do that is at a startup. And hey, much to my chagrin, the vast majority of startups are not going to be rocket ships.

When I joined TheLadders in 2006, it was candidly because there weren’t really many other startups in NYC at the time, and I was not ready to relocate out west. I lucked out. Though the company may be facing some new challenges today, it enjoyed tremendous growth during my three-year stint there ($5MM in revenue to $65MM with only $7MM raised – pretty cool) and I was incredibly fortunate to work alongside amazing colleagues and mentors. I learned more there than I will ever learn in any other job – ever – and I was too immature/ignorant to even realize it at the time. I worked in “marketing,” but I use that word loosely because marketing was the revenue bread and butter at that time. Our small team oversaw everything from user acquisition to email activation to website conversion to subscription analytics to balance sheet management (have to watch that deferred revenue from the longer-term subscriptions!). We were also instrumental in helping to market various new products, many of which still exist today and many others of which were never even launched. TheLadders was a true meritocracy and if you could carry your weight, you could take on endless responsibility. My manager there has been my biggest mentor to date; she looped me on literally everything and never isolated me from a single conversation or decision. She described our relationship as a partnership rather than something hierarchical. When I was 26 years old, Marc Cenedella took me on a 2:2 BD meeting with Janet Robinson and Martin Nisenholtz at The New York Times. Enough said.

Last night I had dinner with a good friend of mine (also an aspiring founder) who works for one of the Silicon Valley juggernauts. He’s at a juncture where he’s ready to move on to a new role within the company – either product or sales-oriented – and he was picking my brain about it. At one point, he said to me, “I guess my concern is that I am never possibly going to be one of the best product people that [Company X] has,” which prompted quite the diatribe from my end. As I told him and as I’ll tell my loyal (maybe? one day?) readership now, this an utterly flawed framework for assessing the decision. My friend is quite candidly off the charts smart, but he will never be the best product person in the land nor will he be the best sales leader, nor should he aspire to be. Instead, he should take the job that’s going to let him learn the most with regards to how to one day run his business. (Along those lines, the answer to his question is undeniably sales. Holy SH*T do I wish I had paid more attention to the sales curricula in b-school, but I did get schooled sufficiently in the subject during my time at Savored.) There are thousands of analytics and marketing people out there far stronger than me, but I’ve built marketability based on my ability to think like a general manager, to consider decisions cross-functionally and to craft compelling and digestible stories with numbers. Flying puddle jumpers (and soft-crashing a few of them along the way) helped me get there. I’d have far fewer (valuable) war wounds with the security of a bigger craft.

Last point here because I’ve been known to ramble endlessly: rocket ships are loud; you can’t hear anything that’s going on around you without special equipment. On puddle jumpers, you can’t help but overhear the conversations around you, and this is an amazing thing. I always tell my directs to eavesdrop a-plenty, ask questions, and interact with people outside of their comfort zones. In this light, even at a company of 15 people, the opportunity for learning is immense. I regularly talk about startup time as “dog years” in that every day feels 7x longer than normal life, but you also learn 7x as much; a large driver of that reality is the ability to work intimately with a smaller group and learn through ongoing and real-time dialogue (i.e. not a weekly “download” from your manager). I had to exaggerate my understanding of an HTTP POST for legitimately 6 months at TheLadders to hold my own with developers, but I sure wow’ed the dev time at Savored with my ability to spec one out five years later. Discomfort that challenges you ultimately breeds confidence which then, likely aboard a new plane, earns you some pretty nice street credit.

So if I were a betting woman, I’d think about trading my Dippin’ Dots for stale peanuts (if you’re lucky) and reconsider the window seat. Yes, go forth to a crooked floor-bearing, mice-infested, eavesdropping-friendly office (for more on how to make sure your office is not NASA-approved, read more from Mike DeLuca, my former colleague at Savored, on some best practices).

And hey, if you change your mind, consider this definition of puddle jumpers: “These shuttle planes usually run connecting flights to … a hub location. From this hub, passengers are able to board a connecting flight that will take them to another major airport as the next leg of their journey.” In other words, if the window seat doesn’t cut it for you in the way that it has for me, there’s always the next journey; I think the fact that Amazon ultimately decided to reach back out to me despite my decision to go early-stage for a while is living proof of that.


About cassyoung

A startup junkie through and through, Cassie has been immersed in the New York tech scene for almost a decade and is presently VP Client Analytics & Optimization at Sailthru, where she works with top brands in commerce and publishing to improve the relevance of their marketing and increase their customer lifetime values. Before joining Sailthru, Cassie spent a year at Gerson Lehrman Group working on new business line development by way of the minimum viable product/growth hacking approach. Prior to GLG, she was vice president of marketing for (acquired by Groupon in 2012) and she previously held a variety of marketing roles at, primarily within the company’s consumer subscription business. Cassie began her career as an analyst on the TMT coverage team at Citigroup Investment Bank, but quickly realized the error of her ways! She fondly recalls her banking colleagues insinuating that she'd legitimately lost her mind when she walked out of the bank in a boom year to pursue the startup dream, and is incredibly excited about the growth that the NYC tech scene has enjoyed in the years since. Cassie holds a bachelors degree from Duke University and an MBA from the Tuck School at Dartmouth. In her free time, she is a Master Teacher with Skillshare and loves talking shop, dive bars and all things Duke. For more information, please visit her LinkedIn page at
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