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PODCAST 90: Key Mistakes Companies Make while Building their Skills or Revenues w/ Justin Welsh

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This week on the Sales Hacker podcast, we speak with Justin Welsh, Founder at The Official Justin.

Justin is the former SVP of sales at PatientPop and a current advisor to it, as well as a tremendous number of SMB SaaS companies. When he left PatientPop, he helped grow it to over 60 million in recurring revenue. They’ve raised over $75 million in funding and he’s putting out a lot of amazing content on LinkedIn, including a Sunday newsletter, called the Weekly Content Rundown.

If you missed episode 89, check it out here: 89: Using Customer Data Platform to Scale Your Org w/ Pat O’Brien

What You’ll Learn

  • Lessons Justin learned from a career in startups
  • Top mistakes companies make (hint: it’s hiring)
  • Data isn’t the whole answer — you need anecdotal feedback, too
  • How to manage downwards and upwards
  • Creating a culture of winning means investing in employees

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Show Agenda and Timestamps

  1. Show Introduction [00:07]
  2. About Justin Welsh & The Official Justin [1:50]
  3. Lessons Learned from Startups [9:45]
  4. Mistakes Companies Make [17:42]
  5. Data Isn’t The Whole Answer [22:23]
  6. Managing Downwards & Managing Upwards [24:26]
  7. Getting Wildly Creative [29:37]
  8. A Culture of Winning [33:20]
  9. Sam’s Corner [42:52]

Show Introduction [00:07]

Sam Jacobs: Welcome to the Sales Hacker Podcast! This is the last episode of 2019. Tonight, if my math is correct, is New Year’s Eve, so I hope you’re doing something fun and safe. Today on the show, we’ve got Justin Welsh. Justin helped build the sales team in ZocDoc. He then went on to help build PatientPop to over 60 million in recurring revenue and now he’s consulting to SMB businesses. The conversation’s fantastic. It’s all about how to build a great culture, how to think about incentivizing a team, how to help pull out a quota if you’re going to miss the number, and some creative things you can do to get there.

Now before we get there, we want to thank our sponsors.The first one is a company that everybody’s heard about — DocuSign. Every sales org feels the pressure to close deals faster. Take control with the DocuSign agreement cloud, a suite of tools that automates sales contracts and quote, all right in your CRM. Create custom contracts in a click, sign them digitally, and automatically pull data back into your opportunities. See why more than half a million businesses use DocuSign with a free trial and discount exclusively for Sales Hacker listeners at go.docusign.com/saleshacker.

Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Now, without further ado, let’s listen to this interview with Justin Welsh.

About Justin Welsh & The Official Justin [1:50]

Sam Jacobs: We are incredibly excited today to have a friend and rising star amongst thought leadership in the world of high growth companies. It’s Justin Welsh, the former SVP of sales at PatientPop and a current advisor to it, as well as a tremendous number of SMB SaaS companies. When he left PatientPop, he helped grow it to over 60 million in recurring revenue. They’ve raised over $75 million in funding and he’s putting out a lot of amazing content on LinkedIn, including a Sunday newsletter, called the Weekly Content Rundown.

Justin Welsh: The real goal was just to aggregate as much valuable content that I can find on LinkedIn each week and release it to the community on LinkedIn so they don’t really have to search for all the good content. It’s just right there on my newsletter.

Sam Jacobs: Give us a little bit about your origin story. How’d you get here? Tell us a little bit about your career and what you’re up to now.

Justin Welsh: I have a, maybe not an extremely unique story, but potentially different than some of the other folks that you’ve interviewed. I came out of school in 2003 and really for the first six years of my career, I was pretty much what you would label a complete failure. I worked at three different companies in the pharmaceutical and medical device space. I got fired from all three of those companies and across six years, I never achieved a quota a single time. So by the time I was 28 years old, I had never been successful and I had never even really tasted success.

I got reached out to by a company called ZocDoc in New York City. Back then they were just nine people in a thousand square foot office in Chinatown and they were selling me on coming to New York City and becoming one of their first salespeople. And I did, I took a bus from Allentown PA to New York and moved in and made very little money. But for some reason, like when I joined ZocDoc, it was like how I described this really perfect intersection, like super smart people, a product I absolutely loved and could stand behind, and then this environment of New York City, the energy, the hustle. I think all those things combined with my own perfectly timed maturity where I went out my first day and made a sale.

Sam Jacobs: What was the spark? I think a lot of people probably feel that way, that they don’t have the passion. What was it about you personally that had shifted that you could find your calling?

Justin Welsh: I was so proud to represent something that I thought was transformational. When you couple that with these really incredibly smart and hardworking people in this really energetic city. I finally saw the opportunity to be successful for the first time in my life. Went out day one with Ryan Stam, my boss, and made a sale, and I think that was the switch. That was the confidence that I needed.

Lessons Learned from Startups [9:45]

Sam Jacobs: So what are the things that you learned that help take a company from risky and unformed to a big business. What are the lessons as a leader that you internalized?

Justin Welsh: The first one that stands out to me in is everything breaks all of the time, every hour, every day, every week, every month. Stuff in really high growth startups are breaking. And when you’re building your team, whether it’s your leadership team or your sales team or your marketing team, you have to make sure that you’re bringing people into your environment that appreciate that and can get through that. And to me it takes a really special person to thrive in an environment when things are breaking. When we were interviewing and building our team, we wanted to see people who had come out on the other side as a really positive, curious, executionary type of person. When I’m looking for people like that, one indicator is they’re investing in themselves always.

Sam Jacobs: You mentioned working hard, and there’s this debate about expectations to the customer service team. Is hard work just what it takes? Where do you come out on that spectrum of what it takes to build a great company?

Justin Welsh: When you’re forcing people to work hard, in my opinion, you don’t have a culture of hard work. When you empower your employees to own the growth of the business at all costs and to invest their time wisely in growing the business and you make that a fundamental piece of your culture. Employees work hard without feeling threatened. They work hard without being commanded. If I go back to either PatientPop or ZocDoc, there was no belittling or berating. A lot of people stuck around at the office, especially at ZocDoc, because they wanted to get stuff done. Belittling is the opposite of the way that you encourage people to be accountable and to work hard.

Mistakes Companies Make [17:42]

Sam Jacobs: You get so many different business models. You experienced so many different founders and companies and go to market motions. Just curious, what are some of the key learnings that you’ve had as you’ve developed your consulting business? What are the big mistakes that you see companies make time and time again when it comes to trying to build their skill or their revenue?

Justin Welsh: The first and the number one mistake that I see people make is when they go to start building their sales team, the first few hires they make, they are not 100% sold that this person is a top 5 to 10% performer. And when you start building your sales team, the very first sales hires are so crucial.

And then number two is following advice that they believe will always be true, even though it doesn’t apply to their current situation. Let me give you an example of that. Aaron Ross is obviously very famous for predictable revenue, and I think he’s one of the best thinkers in sales. With that being said, sales specialization is not always right for your business. So, I walk into an early stage company, they’re selling a $2000 ACV product. And I say, “Hey, how are we going to market with this? Tell me about it.” “Well we’ve got, marketing, we’ve got outbound SDRs, we’ve got people waiting on demonstrations.” And it’s like, “Hey, whoa, whoa, whoa, this thing is $2000.” Let’s reevaluate how you’re going to go to market with the folks that you have. And so I see so many people just following advice without thinking whether this advice is actually applicable to my business.

Data Isn’t The Whole Answer [22:23]

Sam Jacobs: You’ve talked about how data is not always the answer and that people over rely potentially on data. Walk us through your thinking there.

Justin Welsh: I love data and the fact that I can get my hands on as much data as I could at PatientPop was super helpful to me growing the business. But while I think it’s extraordinarily important, it can be misinterpreted. It can also be misconstrued in a lot of different ways. That’s because often you’re depending on data that just isn’t that good to begin with. You’re reliant on your sales team entering things in Salesforce, you’re relying on making sure that you’re actually looking at the data and interpreting the right way. So I always tried to use both quantitative and qualitative analysis when I was a VP of sales. I look for patterns, I look for roadblocks, I look for things that I can isolate and say, “We definitely have a problem.”

But then I’m out on the floor. I’m talking to my sales people, I’m talking to my leaders, I’m talking to marketing because I want to hear the anecdotal feedback as well. One mistake that I see sales leaders making is not getting a well-rounded picture of both the data analysis and the anecdotal feedback from their team in order to come to a good conclusion. So I always emphasize with my customers today: “Don’t just sit in a room and scan your data, get out and talk to your team because there’s a lot more to uncover.”

Managing Downwards & Managing Upwards [24:26]

Sam Jacobs: When you’re a VP of sales, first you have to manage downwards and then second you have to manage upwards. And I think managing upwards comes naturally to some folks, but not to everybody. What are the key lessons and what are the key skills that you needed to develop as a leader to help these organizations grow and to be responsible for a team of 50 or 100 people? And how do you think about the difference between managing upward and telling a story to the CEO and the board that is compelling and meaningful and resonant at the same time that you’re also getting your hands dirty with your managers and helping grow the team?

Justin Welsh: Managing downwards is about two things. It’s about consistent communication, so, making sure that you’re talking to your managers, your directors, your other VPs. And when I’ve worked for folks that were VPs of sales when I was an individual contributor or a manager or a director, one thing happened all the time, which was those one-on-ones got canceled, things got moved and suddenly it’s been 30, 40, 50 days and you haven’t talked to your VP of sales. To me that was always problematic.

And then the second thing that I focus on when I’m managing downwards is, how can I be the roadblock remover for my team? When you’re talking to managers or directors, they don’t have as much experience working cross functionally as you might as a VP. There are things that keep them from succeeding and often it’s in the form of a roadblock from product or marketing or CS, and they don’t have the expertise or the experience in going and talking to the person and removing that roadblock. So outside of consistency, the second thing that I focus on is how can I remove roadblocks from my team so that they can go and do the jobs that I’ve hired them to do. So those were the two key points that I look at when managing downwards.

On the flip side going upwards, to me it’s about a proactive expectation. Luke, my former boss and the CEO of PatientPop, basically had a mantra: “Don’t surprise me.” Instead, “Open up a line of communication and proactively, let me know what’s going well and going poorly all the time. And if something’s going poorly, I want you to have a gap plan. I want you to have a plan B, I want to understand how you’re going to de-risk this.” For me it was constantly being very proactive in looking 90 and 180 days out and informing my boss of what was going well and poorly so that we never walked into a one-on-one or a board meeting and he was hearing something for the first time.

Getting Wildly Creative [29:37]

Sam Jacobs: You mentioned getting wildly creative. What are some of the most creative things you did over the last 10 years to close the gap between the number that you needed to hit and what the pipeline would indicate?

Justin Welsh: We’ve done some things that I don’t want the audience to take away as always good recommendations, but I can recall times where it’s like, “Hey, we have some partners.” We would get out to our sales team and say, “Hey, each of you find three deals in your pipeline, right?” I had 140 reps, that’s 420 deals. You get three opportunities where we’ll eliminate the implementation fee. From an SMB SaaS perspective, when you hold onto your customers for a long time, we were willing to roll the dice on those things in order to hit our bookings targets.

Sam Jacobs: Did you ever ask for forgiveness, not permission?

Justin Welsh: One thing that I really enjoyed at PatientPop was autonomy. Luke, our CEO, and then Jason Gardner, our CFO, really trusted me to make good decisions. Typically was really good about working cross functionally to make decisions. We’d just get agreement as a team and then we’d execute on it. For us, we’re a growth company, and we wanted to make sure that we got our product into the hands of as many doctors as possible, because it was an awesome product and it works really well and they stick around.

A Culture of Winning [33:20]

Sam Jacobs: You’ve talked about how a culture of winning is one of the things that you really believe strongly. What does that mean to you and how do you do that?

Justin Welsh: A lot of things into building a culture of winners. It comes down to setting expectations during the interview process, which I think a lot of companies don’t do. Step number two was showing your team that you care. For me and my leadership team, we truly and personally celebrated wins. We were proud when people succeeded.

One thing that I think is really important is giving people some money every month or every quarter and saying, “Hey, what do you want to get better at? We think that better people make better employees. So here’s 500 bucks, go grab a course, go buy a book, go take this workshop.” Those were things we were always doing at both ZocDoc and PatientPop. I know that’s a long winded way of saying invest in your employees. But to me it was just the most important and most crucial.

Sam’s Corner [42:52]

Sam Jacobs: Hey, folks. Sam’s Corner. A couple things to take away from Justin’s conversation. The first of them is he called himself a failure for six years. It took a while for something to click for him to find his passion, and one of those ways was being around inspiring and smart people. Think about that when you’re “looking for your passion” — look around you at the people you’re surrounding yourself with and figure out if those people are inspiring you at work. Also, figure out if you believe in the product you’re selling. Justin was a huge believer in ZocDoc and PatientPop and that helps.

The other thing that he talked about is awareness that when you’re in a high growth business, everything breaks all the time. Everything is flawed, everything is imperfect. This is true anytime you’re seeking to change. When you join a startup, the startup is trying to change things. To change things, you have to go in and do things differently.

A huge thanks to Justin. Follow him on LinkedIn or head over to his company website, theofficialjustin.com, or to his thought leadership website, thelinkedinplaybook.com.

What We Learned

  • Lessons Justin learned from a career in startups
  • Top mistakes companies make (hint: it’s hiring)
  • Data isn’t the whole answer — you need anecdotal feedback, too
  • How to manage downwards and upwards
  • Creating a culture of winning means investing in employees

Don’t miss episode 91 (next week’s episode)

I hope you enjoyed the show. Before we go, let’s thank our sponsors.The first is DocuSign. Execute contracts and get to revenue faster with DocuSign, used by employees in 90% of the Fortune 500 businesses. Learn more at go.docusign.com/saleshacker. Our second sponsor is Outreach, the leading sales engagement platform

If you want to reach out to me with feedback, you can reach me on LinkedIn. If you haven’t rated the show, please give us five stars on the iTunes rating system so that we can remain in business and continue to bring you this show.

As always, thanks so much for listening, I’ll talk to you next time.

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