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Michael MassadVice President

Elsewhere Operating Advisor Spotlight: Shelley Perry

For this month’s OA Spotlight, we talked to Shelley Perry who has spent her career in product, C-Suite, and board roles at scaling SaaS startups. Elsewhere Operating Advisors (OAs) are seasoned executives who have scaled and exited numerous startups. As board members, functional advisors, or executive hires, they use their collective expertise to help Elsewhere portfolio companies navigate the next phase of growth.

Shelley most recently served as executive chair of Elsewhere portfolio company Airbrake, which was acquired by LogicMonitor earlier this year. Below, we discuss her perspective on the “art of the possible,” interactive content platforms like Clubhouse, and the key to founder-investor alignment. Read on for our conversation, edited for clarity and length.

What have been your most surprising learnings of the last year?

I think back to when Mark Hurd was running Hewlett Packard; he could move the organization by a singular focus. Some people thought it was very restrictive, but with a one-way highway focus, you can move a massive company.

To me, the most amazing thing was to see the art of the possible when things can move that fast: how governments can move, how the acceleration of digitization can move, how schools can go remote. The art of the possible was there and it was only us holding us back. When you see that experiment it should unleash so much innovation.

I never wanted to work in healthcare or education because they moved so slow. Now you see how fast they can move if they put their mind to it.

What sectors are poised to grow in 2021?

The things that are going to spike are the things that embrace this hybrid approach of not 100% virtual and not 100% in person. There's so much pent up demand for human interaction and collaboration and travel. For example, instead of these models like big conferences, you’ll see more unique experiences. I think all offices are going to be reconfigured; people are going to go in for more meetings and collaboration.

Some of the things like Clubhouse that people used as they were bored and stuck at home are going to evolve. Clubhouse reminds me of the party lines in the 80s, then it went to video, and now it’s back to the conference calls.

But anything that gets content out—whether it’s Substack or Clubhouse—is not going to go away. We talk about product-led growth, but I think it’s more about content-led growth. I think content is really the new acquisition and retention channel. Things like Clubhouse are great for people who don't like to write—like me.

Those platforms allow you to get thought leadership out in a way that is authentic and interactive. I think that interaction is not going to stop. I can listen to podcasts and live video while I’m on my exercise bike. Things like Chorus are popular because leaders will listen in on calls when they're doing something else. It's the same with Clubhouse, because you can be engaged in the conversation and be out. There’s a demand for that kind of interaction.

What was a time in your career where you saw misalignment between a startup and their investor base?

I see misalignment all the time, but it's not on purpose. What I see more often is investors assume that operators understand the terms they're using, or the reason they're giving certain advice.

Operators don’t want to feel like they're not in the know, and they won't ask questions. And so the misalignment comes from these different perspectives, and each group hearing the same conversation in a different way. Both sides make assumptions. And even when they're using the same terms, they interpret them differently. That's where I see the misalignment mostly.

It’s important to set context. It’s about being comfortable enough—especially in a growth-stage company—to just ask for clarification, or to have a network where you can quickly get that clarification. There are just some really key things to understand as operators. For example, as investors we talk about the concept of secondaries all the time. But it's not something that just rolls off the tongue for operators. In the same respect, investors don't want to sit in on customer calls all the time. It’s about understanding and recognizing those key things and not taking for granted on either side that there's an understanding.

Board meetings aren’t governance meetings: The investors for growth-stage companies are there to help you grow. So write down a term when you hear it. And if it's impactful in the conversation, but you're not comfortable enough to ask what it means, rethink your investors. But, also ask someone you trust and know if a word gets used over and over again that you're not fully understanding, don't assume. Because it could mean you're wasting a lot of time, and in growth stage companies time is key.

Also, sometimes operators don't want to share bad news with the investors, when in fact, sometimes it's not bad news, it's just news. And when both sides have the information, they can make different decisions. Each side has levers. So communicate bad news, or even upside news, in a way that allows each side to use the maximum amount of levers.

What was the most defining moment of your career?

As a total introvert tech geek, I realized the key to networking is giving—and that networking is critical. When you let people know what you're wanting to do, and you ask for it, they're going to help you. It’s not about an obligation to pay it back, but it’s more about how they want to help and you want to help. When I reframed this understanding of how networking really works, it changed the trajectory of my career.

What is your advice for founders who are building and scaling a business?

For me the theme is: Begin with the end in mind. People often say “just go and build a good business. Don't worry about anything, just build a good business and make your customers happy.”

While I believe that you should make your customers happy and you should build a good business, I think that it's impossible to make everyone happy. Understand the constraints you have and the stakeholders that you have in their entirety. The fastest path to anything as a straight line. When you don't waver on what that end is—that end can be a funding event, it could be debt equity, it could be an acquisition, it could be a major exit.

This goes back to what I said of the impact around COVID. There was a straight line. Everyone had to go home; everyone needed to be protected. It happened so fast.

The more you waver and don't have that end in mind or that next major goal in mind, the harder it is. That’s how most startups fail. The ones that don’t fail have good timing, but also have a maniacal focus.

So as you start to scale, don't lose that.


Cover Photo by Stefan Cosma on Unsplash

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About the Author

Michael Massad

Michael is a software investor at Elsewhere Partners where he co-leads all sourcing and diligence efforts in the IT infrastructure and cybersecurity sectors. Michael strives to connect capital and operational expertise with growing software companies across industries that are located outside of traditional VC hubs.