PODCAST 54: How to Pick Your Next Company to Build a Great Career w/Nick Worswick from WeWork

This week on the Sales Hacker podcast, we speak with Nick Worswick, Global Head of Growth for WeWork. Nick walks us through one of the more impressive track records in start-up land. He discusses how to scale a multi-billion dollar SaaS company, as well as the key elements to navigating a successful career.

If you missed episode 53, check it out here: PODCAST 53: The Secrets to Moving Your Company Upmarket w/David Katz, Intercom

What You’ll Learn

  • Why training is so important
  • How to hack your hiring process to drive scale
  • The importance of due diligence in company selection
  • Building an onboarding process to quickly identify top talent

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Show Agenda and Timestamps

  1. Show Introduction [00:09]
  2. About Nick Worsick: An Introduction [00:31]
  3. The Value of Making Mistakes [12:03]
  4. Bridging the Age Gap [16:50]
  5. Pick a Boss Who Will Join You in the Foxhole [20:11]
  6. Take the Time to Research Your Next Move [31:25]
  7. Don’t Be Afraid to Re-Train [35:33]
  8. Get Good at Asking Tough Questions [40:05]
  9. Inspirations [42:39]
  10. Sam’s Corner [44:10]

Show Introduction

Sam Jacobs: Hey everybody. It’s Sam Jacobs, founder of The Revenue Collective. Welcome to the Sales Hacker Podcast. We’re going to talk to Nick Worswick, who runs growth for WeWork, which is a $2.5 billion ARR business. Nick has had an incredible career where each of the companies that he’s worked at over the last 20 years has had some kind of major event.

Before we get to that interview, we want to thank our sponsors. The first is Showpad. Showpad is the leading sales enablement platform for the modern seller. Showpad’s all-in-one platform empowers sales and marketing teams to engage buyers through industry leading training and coaching software and innovative content and engagement solutions. Using the most comprehensive data on successful sales interactions, Showpad fuels AI to discover, replicate, and automate what works for top performers.

Our second sponsor is Outreach.io. They are the leading sales engagement platform. Outreach supports sales reps by enabling them to humanize communication at scale and by automating the manual work.

About Nick Worswick: An Introduction

Today we’re very, very excited to have both a very important person and a good friend. Nick Worswick is currently the global head of sales and marketing at a company we’ve all heard of, WeWork. He spent eight and a half years at IntraLinks and helped them IPO in 2010. He ran global sales and service for Bullhorn, which was acquired by Vista Equity Partners in 2012. He then ran the corporate division for GrubHub, which IPO-ed in 2014. And now he is essentially the head of revenue for WeWork. He is well known as somebody who is an exceptional leader, exceptional executive, and also a good person. Nick, welcome to the show.

Nick Worswick: Thanks so much, Sam. I’m pleased to be here.

Sam Jacobs: Well, we’re pleased to have you. First, tell us your official title.

Nick Worswick: I’m officially the head of sales and marketing globally at WeWork.

Sam Jacobs: Tell us a little bit about the company.

Nick Worswick: We actually just reported to our public investors last night. We exited last year on a $2.5 billion run rate, which was 100% growth year over year from 2017. The company, for its first nine years of existence, has grown 100% year over year, every year, almost exactly 100% year over year. So we’re going to obviously try to do that again this year. Little bit harder on a bigger base.

Sam Jacobs: And you’ve been building companies for how long?

Nick Worswick: I got my career started in finance, and I learned that I didn’t really want to be in finance. I got an introduction to the guy ran Priceline, joined that business. That’s how I got my introduction during internet 1.0 into the startup space.

At Priceline, I joined this really interesting group of people that was focused on new market development. Priceline at the time was very well known for its airline ticket business, and we were trying to extend that platform into other verticals, so I was part of a very small group of people. I would call it sort of class new market development. I got good at figuring out how to create something that the market world embrace after quick iteration with early adopters.

Sam Jacobs: From there you went to IntraLinks?

Nick Worswick: Yes. That was also sort of a new market development role. You have to cast your mind back to 2000. Back then, SaaS didn’t exist. Our job was to convince bankers and the like that putting documents into the cloud was a safe, reliable, and expeditious way to get everyone involved in a sensitive financial transaction access to documents. We hired a group of people who went out and evangelized this market. From 2000 to 2009, the company grew 40% to 60% year over year. We had an IPO in 2010. My career trajectory was from this new market role into a sales management role, with increasing responsibility, mainly because we were trying lots of things that hadn’t been tried before. Frankly, I made every mistake in the book.

The Value of Making Mistakes

Sam Jacobs: Did you have mistakes that helped you learn those lessons?

Nick Worswick: Yeah. The way that you learn and the way that you get better is you have to experience those mistakes. You can cut down on mistakes by reading, by talking to colleagues, but again, predating all of this in 2000, we were forced to figure a lot of these things out because this was the beginning of sales 2.0 when you’re really figuring out what customer-centric selling looked like.

During that period of time, hiring that first group of salespeople, I had a 50% success rate. Not only did half of them fail, at the end of that it probably took us collectively nine months to recognize that it wasn’t working. And I think part of your job as a sales leader is to compress that time as much as possible.

Bridging the Age Gap

Sam Jacobs: Did management come naturally to you? What do you think are the top one or two mistakes first time managers make?

Nick Worswick: When I was placed into management for the first time, I was in my late 20s. A couple people on the team that I inherited were in their early 40s. That is probably the most difficult position to be in, in a first time management role. It was incredibly helpful to be able to say, “Look, you’ve forgotten more in the last 20 years about selling that I’ve ever learned, because I’m new in this job. But I can be helpful in how you craft your story. I can be helpful in go to market. I have some interesting ideas around how we can prospect within this particular market because I’ve spent some time talking to the first 25, 35, 45 customers.” So I had some instant credibility there.

There are conditions on the field of play that you inherit that aren’t of your making. You have to play to your strengths, and you have to be very candid. You have to be transparent about what your strengths are and radically transparent about your weaknesses. I remember lots of conversations where I was like, “That was a really cool meeting. I learned so much from you about how you approach that customer’s problem because you’ve been doing this for 20 years.”

I looked at it as a shared learning experience. And that’s the way I treat my team today. We’re on this crazy journey together. We’re going to learn a lot along the way. I don’t pretend to have all the answers. Salespeople tend to be very smart, what they want from you is transparency. They want honesty. And they want you to provide them air cover. If you were to distill down into three nuggets, those are the three things.

You need to figure out a way to bring wins to people. Typically, that’s through lots of listening to your team. I make very few decisions in my first 30-45 days. Your job is to take counsel from people who know more than you do. And then slowly, through lots of good questioning and interactions, start to formulate opinions. Your job is to be radically transparent so that you demystify for people whatever it is that they’re vibrating about, and create trust and transparency around what you’re going to be doing for the team.

RELATED ARTICLE: How Sales Managers Should Build Their Career Path

Pick a Boss Who Will Join You in the Foxhole

Sam Jacobs: You were at IntraLinks for a long time. How did you know it was time to go? How did you figure out that Bullhorn was the place that you wanted to go?

Nick Worswick: When everything becomes a wash, rinse, and repeat cycle. I was ready to try something new. And I had this sort of demon on my shoulder asking me whether I was good or lucky.

I got a call from a recruiter. And I met the CEO, Art Papas, a phenomenal CEO. And we had this like-minded view of the world. It looked a lot like IntraLinks five years prior, figuring out how to take that next step. Do we build an inside team? Do we hire enterprise salespeople? Should we go upmarket? I met a CEO that I think I could be in the foxhole with for a couple years. There are all these problems that I’ve solved in a prior life. Could I do it again? So that was the genesis of the decision.

It’s very important that your interests are aligned with the interests of the CEO. And obviously, the CEO’s interests are aligned with the investors. Art and I were in lockstep. We did three or four things really well at that company. We decided to invest in an enterprise sales team because we had done that at IntraLinks. I thought that there was a market for this product upmarket, so we invested in that one. We invested in international expansion. And now I think half of their business or more is coming from companies outside of the US. And the last thing was we had this idea that you could create a robust business development function to get partners into the company to help you sell. And in the space that we were in, that worked out well.

On the investor side of the table, and on the go to market side of the table, we were very much in lockstep. And when you agree with your CEO on those two things, it creates magic.

Take the Time to Research Your Next Move

Sam Jacobs: Your track record demonstrates your ability to select the right company. What are your strategies for company selection? And how do you ensure that you’re positioning yourself?

Nick Worswick: I have lots of people call me for career advice, and I love those conversations. I love talking to people about opportunity assessment. I tell people, “Think about it as if you were an investor. Your risk is indexed to a single entity. You want to have an impact. You want to build a great team. You want to have staying power.”

You have to find a company that you think has real potential. Dig under the covers. If it’s hard to figure out how that company’s going to have a big opportunity, they’re either not playing in a big market, they’re still figuring it out, whatever it is. Some people are indexed to that, and that’s fine. But if you want that longer run, find something that has a real shot at success in a big market.

The team is incredibly important. You have to connect with the team. You have to connect with the CEO. You have to connect with the rest of the exec team. It’s imperative. I go really deep with people. I have dinner with them. I connect with people that worked with them. Ensure that you really want to be in that foxhole with those people.

Your pattern recognition has to be relevant. Your experience in everything in and around the sales apparatus has to be super relevant. You can obviously learn, but you want to make sure that the value you’re adding is going to be additive on day 45, not on month eight or nine, because that will end in tears.

RELATED ARTICLE: Risk vs. Reward: 3 Secrets That Will Change the Way You Think About Your Career in Sales Forever

Don’t Be Afraid to Re-Train

Sam Jacobs: If you want to be relevant at the 20-50 or 50-100 stage, but you haven’t done it before, how would you suggest people develop that competency?

Nick Worswick: Assuming you’re a high growth person and you want to be in those environments, go get that experience. Go be a regional person at a company that is growing really quickly. Go be a director of regional sales for an awesome company that will slot you into the Northeast role, where you’re going to inherit a team of five, and grow to a team of 20. Then you’ve got your experience. Build your muscle memory around that. And then go fight for the big job.

Get Good at Asking Tough Questions

Sam Jacobs: In the past, you’ve mentioned a question that you ask VCs to help due diligence. I think it’s about TAM.

Nick Worswick: TAM is wildly important. When you meet with the investors, you should ask, how big is the TAM? And they’ll give you the CEO’s pitch deck view. The second question is, is that the existing TAM, or are you also including the next product development cycle where you’re going after this next market segment that you haven’t yet approached? Be very specific about current and future TAM because sometimes those things get co-mingled in the conversation.

And I always ask them to walk me through their investment thesis. Why’d you get excited about both the company and the team? VCs tend to revert back to why they got excited about the space and the company. You want them to really dig into the team. And be specific. If you met with a marketing person, and the marketing person was a little bit off, or you’ve heard that the marketing person isn’t awesome, ask the VC. Ninety-nine percent of the time they’ll say, “Why are you asking?” And then you can get into an interesting dialogue. The worst they can do when you ask these probing questions is say, “Not comfortable sharing.” And that happens one in 100 times.

Treat it like it’s the most important sales conversation you’re ever going to have. It’s your life. You’re going to spend eight, 10, 12, 14 hours a day in this place. Train yourself to ask the questions. Role play it. Sit in front of the mirror. Sit with your wife or your husband. Sit with your significant other. Get really good at asking them.


Sam Jacobs: When you think about either people or books that have really inspired you, give us some names.

Nick Worswick: There’s a book called Five Dysfunctions of a Team. Art Papas had us read that book. And I make every one of my leaders that report directly to me read it. It’s proliferated its way through the rest of the org at this point. And then the other one is this book called Who by Geoff Smart. It’s about demystifying how you hire people.

Sam’s Corner

Sam Jacobs: Hey everybody. This is Sam’s Corner. We were honored and excited to have Nick Worswick on the show. Nick is an incredible executive. His track record is unparalleled. And he’s also a mentor and has given me a lot of advice over the years.

Things We Learned:

  1. Why training is so important
  2. How to hack your hiring process to drive scale
  3. The importance of due diligence in company selection
  4. Building an onboarding process to quickly identify top talent

Don’t Miss Episode 55

If you want to check out the show notes, see upcoming guests, or play more episodes from our lineup of sales leaders, visit gtmnow.com/podcast-subscribe. You can also find the Sales Hacker podcast on iTunes or Stitcher. If you enjoyed this episode, please share it on LinkedIn, Twitter, or elsewhere.

If you want to reach out to me, you can find me on LinkedIn. If you have any interest or curiosity in learning more about the show, please reach out.

Thanks so much to our sponsors. The first is Showpad. Showpad is the leading sales enablement platform for the modern seller. As well as Outreach.io. Outreach is the leading sales engagement platform. I’ll talk to you next time.

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