Ep 257: Justin Welsh is the former SVP Sales @ PatientPop, the startup that offers the first all-in-one practice growth platform that’s HIPAA-compliant and is proven to grow your practice. During his 5 years at PatientPop, Justin grew sales from $0 to $56m alongside the full build-out of the sales team. Before PatientPop, Justin was one of the first 10 employees at ZocDoc, where he spent 4 years in different roles including Director of Strategic Sales.

Pssst 🗣 Loving our podcast content? Listen to the start of the episode for a promo code to our upcoming events!

In Today’s Episode We Discuss:

* How Justin made his way into the world of Sales and came to be one of the industry’s leading scale up Sales leaders with PatientPop and ZocDoc.
* How did Justin experience burnout? What were the first indications and signals for him that he was suffering from it? How did it manifest itself in how he carried himself and his behavior? How did Justin communicate the situation to his bosses? What does Justin advise others in communicating burnout to their superiors?
* As a manager observing their team, what are signs that an individual is burning out? What is the right way to approach them to discuss the situation? What options do managers have available to them when faced with a burned out employee? How does micro-management fit into the signals that suggest clear burnout of the individual?
* Justin has said before that “culture must precede performance.” What did he mean by this? What actions and communications must they adopt to ensure that this feeling of culture over performance is accepted by the team? With that in mind, how does Justin think about KPI and goal-setting? What can leaders do to create an environment of safety for their team? Where do many leaders go wrong here?
* Having seen multiple scaling culture, where do SaaS organisations tend to break down both in terms of culture and process? What are those inflection points? What can be done to actively mitigate these 2 significant points of failure?


Ep. 258: Companies that have access to more accurate financial data have the ability to develop seamless exchanges of information, providing consumers with improved ways to manage their finances. But how do companies gain secure access to that data in the first place? Enter the platform company. Hear from Plaid co-founder and CEO, Zach Perret and CNBC’s Ari Levy as he walks through his lessons learned building Plaid and how it found itself at the center of the fintech ecosystem.

SaaStr’s Founder’s Favorites Series features one of SaaStr Annual’s best of the best sessions that you might have missed.

This podcast is an excerpt of Zach and Ari’s session at SaaStr Annual 2019.


If you would like to find out more about the show and the guests presented, you can follow us on Twitter here:

Jason Lemkin
Justin Welsh
Zach Perret

Below, we’ve shared the full transcript of Harry’s interview with Justin Welsh.

Harry Stebbings: We are back for another week in the world of SaaStr with me, Harry Stebbings and I always love to hear what you think in terms of amazing guests to have on the show. You can let me know on Instagram @HStebbings1996 with two Bs, and I respond to all messages there personally. But to the show today, and we have a special episode. Why? We always talk about metrics and targets and KPIs, but as we know, there’s real people building these businesses and behind these numbers. And today we touched on some more personal elements of scaling SaaS companies.

Harry Stebbings: And so with that, I’m thrilled to welcome Justin Welsh, former SVP of Sales at PatientPop, the startup that offers the first all in one practice growth platform that’s HIPAA compliant and has proven to grow your practice. During his five years at PatientPop, Justin grew sales from zero to $56 million, alongside the full build out of the sales team. Before PatientPop, Justin was one of the first 10 employees at ZocDoc, where he spent four years in different roles, including director of strategic sales. I do also want to say a huge thank you to Luke Kervin, founder at PatientPop for the fantastic intro to Justin today. Mojitos on me for that and I really do appreciate it.

Harry Stebbings: However, you’ve had quite enough of my dulcet British accent and so now I’m very excited to hand over to Justin Welsh, former SVP at PatientPop.

Harry Stebbings: Justin, it is such a pleasure to have you on the show today. I’ve heard so many great things and so thank you so much for joining me.

Justin Welsh: Harry, thanks so much for having me. I appreciate it.

Harry Stebbings: Not at all. As you can tell, I’m very excited for this one, but I do want to kick off today with a little bit about you. How did you make your way into the world of SaaS and then come to be SVP of Sales at PatientPop until recently?

Justin Welsh: Yeah. I graduated school in 2003 and my dad had been in sales for 41 years. And so when I looked at our nice house and two cars, I thought, sales was the role for me. And I jumped in in 2003, and to be very honest, for the first six years of my career, I sort of had this very meandering career where I moved from small town to small town. I was in pharmaceutical sales. I went into med device sales, but I really, candidly, wasn’t very good. I was average to below average. I was pretty immature. I didn’t take it very seriously and I sort of got my break in 2009. I had my resume on Monster and I got a call from Cyrus Misumi who was the founder and CEO over at ZocDoc in New York, and I was living in Allentown, PA and he said, “Hey, we have an open sales role.” ZocDoc was just nine people deep.

Justin Welsh: And I took the bus from Allentown to New York and interviewed for the role and I landed at ZocDoc as the second sales hire and the 10th employee and that’s really how I broke into SaaS. I spent five years there at ZocDoc in multiple roles, from individual contributor, I moved up really rapidly into local management and then regional management. Ended up managing five states and then my last year there, spent time reporting directly to Cyrus working on some special projects.

Justin Welsh: And after my tenure there, which was about, again, five years, that’s where Luke and Travis, the co-founders of PatientPop, began reaching out to me about what they were doing there. They needed a VP of sales, they had one person and my name came up frequently when they were interviewing folks at ZocDoc and in January of 2015, I accepted the role of VP of sales there of one person and I went there five years, grew the team from one to 140 people and went from zero to just south of 60 million in recurring revenue when I left a couple of weeks ago.

Harry Stebbings: What an incredible journey. I do want to go slightly off schedule already there and just unpack a couple of elements because it’s too interesting. You said about your father there being in sales for 41 years, incredible career in history. Did you have any major learnings from seeing your father in that sales role from an early age? Were there any big takeaways from him that you’ve learned along the way?

Justin Welsh: Totally. I think when people think about salespeople, there’s this stigma around salespeople of slick or dishonest or whatever. I think there’s something to be said, salespeople are trusted around the same level as politicians, and my dad, he always earned his living and spent his time at his company being extremely honest, transparent and candid. And I think if you were to ask people around me about how I am in my daily role, honesty, transparency, being very candid, are traits that he really passed down to me. And I think that’s the opposite of what some people think of when they think of sales or sales leadership. I was really happy to get that from him. That stuck with me my entire career so far.

Harry Stebbings: No, I think it absolutely is and what a learning to have. I guess my next question would be just in terms of, you mentioned that your career maybe slightly meandering before the entrance with ZocDoc, because that’s the meandering to then becoming a regional leader and then actual kind of set, what changed to make that mediocre to sub-mediocre to then star performer in the team?

Justin Welsh: Great question. I think it was an intersection of really three or four things that all happened at once. I think the first one was a lucky one, which was, I was just ready to be mature. I was 28 years old, I matured a little bit later than some other folks and was ready to take my career seriously. At the same time as that, I met this incredibly smart group of people at ZocDoc that just blew my mind. They were so intelligent. They were so smart that that really rubbed off on me. There was the product and the service, which I just completely believed in. Was the first entrance into online doctor’s appointments. I thought this was an incredible software product. And so that happened. And then the fourth one was I ended up moving to New York and I started feeding off that energy of the city. It was the city, the product, the people, and just the stage in my life. I call it the intersection of those four things that happened at once, that it was almost overnight the way that my life and my career changed.

Harry Stebbings: I love the intersections there and totally see that. But I do want to dive into the show today and as we said before, I’m super excited for this one because it’s a topic that I’m very passionate about and I don’t think honestly we discuss it enough on the show and that’s the topic of burnout. Before we dive into the nitty gritty and discuss maybe process and solutions, can you talk to me a little bit about your experience with burnout and maybe how it manifested itself?

Justin Welsh: Yeah. It happened really slowly and it had this sort of compound effect where I spent those five years at ZocDoc in this culture of hard work and grinding it out, which by the way, I loved, and then really transitioned directly into my first executive role at PatientPop. And the first sort of three to four years there, it felt excellent.

Justin Welsh: But as I started to sort of come towards the end of my career there, it’s bigger revenue targets, being handed additional teams and responsibilities that I was just maybe less familiar with, more work to be done cross-functionally with more people and suddenly found myself attending way more meetings and then I couldn’t find the time I needed to do the necessary things to really prepare the business for the future. That naturally meant getting up at 5:00 AM and finding time there and then finding additional time at 8:00 PM and that internally leads to more of an unhappy personal life. And when that happens, what do you do to cope with the stress and frustration of that? Maybe you have one too many glasses of wine at night and then you wake up feeling crappy the next morning and then it just keeps going and it’s sort of very circular in motion.

Justin Welsh: But it was really slow in the way that it crept up. And as I entered the last part of my career PatientPop, it just became really clear that I was exhausted. And so I think one thing as I look back is, I wish I could have seen that compounding happen in real time and done a better job of recognizing it until it, it just sort of snuck up on me.

Harry Stebbings: I guess my question is, having had that experience, what would you do next time, maybe slightly differently along the process? In terms of how you think about it and how you approach it?

Justin Welsh: Yeah, I think I would be more candid with my CEO. I started talking about it maybe a little bit too late and I think I could have been a bit more proactive because the co-founders at PatientPop were hugely supportive and so I could have been more proactive. And I think I probably could’ve done a better job of delegating. As a first time executive, I like to have my hands in everything and I was really proud of what we were doing. But I’m also somebody who likes to get into the details every once in a while. And I probably could’ve done a better job delegating and staying high level, it probably would have slowed the compounding growth of that burnout. Those are two things I really would have done differently.

Harry Stebbings: I often like to look at where responsibility lies and taking account of that. In terms of the ‘we’re all killing it’ BS that we have so much of it in this industry, my question to you is, really, who do you think maybe, and blame is the wrong word, but who do you think maybe should take some level of ownership for this burnout culture? Is it kind of the VCs that put the pressure on? Is it the CEOs that put the metrics and the KPIs in place? Is it the contributors themselves actually for not realizing soon enough? Where do you think accountability may rest?

Justin Welsh: Yeah, I’d love to think that there’s one person or group to blame or paint with sort of this brush across a group of folks. But I think it’s really a combination of things and I think sure, there’s pressure from VCs to grow, but that’s a good thing. I also think that a lot of founders are young and often it’s their first experience or executives like myself, their first experience in executive roles. You’re sort of all learning together and you’re all working really, really hard together, but it’s likely that a lot of the things that could make the job or the processes easier are being missed because it’s people’s first go round.

Justin Welsh: It’s not really a blame game, it’s more just not knowing how to navigate building this hyper-growth company and suddenly it just, like I mentioned before, it sort of compounds and I think it gets added onto by some of the stuff that you mentioned, like this BS that you see online. I’ll read quotes like, I’ll sleep when I’m dead, and things like that. Which to me is silly stuff. Even pioneers, of this mentality. Take a look at someone like Gary V, who by the way, I love, but two to three years ago, his sort of talk track was all hustle and grind. And it’s interesting that recently he’s moved his talk track to empathy, and away from this hustle, grind mentality. And I think that’s a good sign. I think that means, you know, people are getting tired of hearing this type of stuff. What VC wants to truly invest in a founder who is quote unquote, hustling 24/7. They want someone well rested.

Harry Stebbings: Now listen, I couldn’t agree more. I once said, I’ll sleep when I’m dead to a mentor of mine and he said, “That’s wonderful Harry, you’ll die so much sooner.” That’s very kind of you, mentor. But I do want to ask, though, in terms of management overview, as you said, you kind of manage multiple people in the sales team. If you were to look back now, what to you are the clear signs that maybe now you know with the benefit of hindsight, are kind of indicative signals of burnout that founders and managers should look out for in their team?

Justin Welsh: Yeah, I think when you see that, there’s a couple of different things. For me, I guess I always consider myself as someone who likes to know what’s going on. For me, it was pulling back. I observed this thing in myself where I started to pay a little bit less attention to be a bit more absent, to work from home a bit more, to miss a few company events and so on. That’s just sort of wasn’t my normal style. That was something that I noticed in and of myself.

Justin Welsh: But another clear indicator to me of burnout is when people start getting, I guess what I’d call more Chutzpah, for lack of a better word. They say and ask for things they normally wouldn’t. They make demands. They back you into a corner. To me, that just shows that they’re pushing their chips in and they don’t really care what happens.

Harry Stebbings: Yeah, no, I do agree with you in terms of these kind of ask and requests. I guess if we take it to the flip side there, if that’s the manager’s overview of it, if you ask the individual who’s actually feeling this kind of intense pressure and burnout, what would you advise them to do? What’s the right course of action once one’s realized that actually this is quite a precarious situation?

Justin Welsh: Yeah. Well, as I mentioned earlier, my whole career has really been built on honesty and transparency. If someone were to come to me and ask me what I advised, I would say to speak with their boss. I sat down with my co-founders and I spoke to them about this at length and we had an incredible relationship and they weren’t just willing but truly interested in helping. Ultimately as the conversations progressed because I was open to it, I was able to communicate effectively and leave my last business in this incredible spot and have this wonderfully amicable separation that I think a lot of people don’t get. To me, honesty and transparency is always the best path. I would recommend they start with their boss and they work on a solution to alleviate what’s burning them out. I think you have to be open about it.

Harry Stebbings: I agree in terms of identifying that solution. In terms of the drivers of potential burnout, often the driver itself is just ruthless expectation on performance. Both of the team and the individual, that we put on ourselves and others. But I guess my question to you is, when we chatted before, you said to me culture must precede performance. What did you mean by this culture preceding performance?

Justin Welsh: Yeah. I guess what I mean by that is you can sort of manufacturer short term performance without strong culture. You can whip people hard enough, you can threaten people’s jobs, you can pace the floor, you can do a bunch of different stuff. But in order to truly maximize long term performance, in my opinion, you have to have an incredible culture. And to be clear, like when I talk about culture, I often encourage founders and sales leaders to not confuse that for amenities.

Justin Welsh: I’m not talking booze and ping pong and dogs, none of that stuff. I’m talking about the values that you’ve instilled in your team and the behavior that is a result of those values. I think that has to be in place for long term performance. Whereas on the opposite, you can always manufacture that short term performance. That’s sort of what I mean by it.

Harry Stebbings: No listen, I totally agree and especially in terms of not being the amenities. I guess my question then unfair off schedule, but as a sales manager itself, often the requirements in terms of quarterly targets and numbers that are expected to hit for the team and the individuals within the team, my question to you is, how do you think about setting targets with that culture preceding performance and wanting to hit your targets, but also not wanting to place undue stress and pressure on, I’m sure an already pressurized and tired team? How do you think about that balance when it comes to KPI and quarter goal setting?

Justin Welsh: Yeah. I think a lot of it is around expectations. So to me, what I’ve found over the course of my career is yeah, you have to have the right targets. You have to have targets that are relatively attainable and but decent portion of your team is hitting those targets. But to me it’s all about expectations. It’s about starting with expectations of KPIs in the interview process. It’s about continuing the expectation of those KPIs through the training program. It’s about getting sign off on those upon graduation, and it’s about really reinforcing those on a regular basis. To me, by doing that, you sort of take away the gray area, which to me often leads to a bad culture. When people say, “Oh, I didn’t know I was supposed to do 50 of these. I thought I was supposed to do 40.” Or, “I wasn’t aware that I needed to sell eight units in my first three months. I thought it was five units.”.

Justin Welsh: I think that that’s where a lot of times I see a poor culture because there’s miscommunication. I think it’s establishing your KPIs, being very consistent about how you set those expectations and then reinforcing those on a regular cadence. To me, that’s a good balance of culture and performance that I think you need in a fast growing startup.

Harry Stebbings: No, I really like that balance. I guess my next question is, we both agree in terms of the importance of transparency and vulnerability. From the sales rep, a BDR level, how do you think about fostering a culture of actual real vulnerability, care, and transparency? And often as we’ve said before, a more kind of chest thumping elements of the industry.

Justin Welsh: Yeah, I think what you have to do is you have to make it really safe. I think that the culture gets set from the top and if from the top it’s a chest thumping mentality if it’s hustle, grind 24/7, if it’s always be working, always be closing, you’re going to build a team like that. And to me yes, your team needs to work hard, don’t get me wrong, I’m a fan of hard work. But you have to create a space in your environment, in your culture where people know that it’s safe to come to you and talk to you about their mental mindset. Where they’re at personally, where they’re at mentally, where they’re at with their performance.

Justin Welsh: And I think you do that through being open and honest as a leader, I think you do it through creating a leadership team of transparency, vulnerability, being open, being honest, having office hours where you make people aware that there’s two hours every week where they can come in and sit down in your office and talk to you about what’s going on without feeling the need to thump their chest or play a character that they think is the right character to play. To me, it starts at the top and it makes its way through to bottom.

Harry Stebbings: Totally agree in terms of starting at the top. I guess my next question is in terms of from starting at the top, often it starts very well in terms of the culture building and while the team is small, it’s a highly efficient and there’s often good culture. As it scales, often things start to break down. Having seen multiple scaling sales cultures from the inside, and outside even as an advisor, I guess, where do you see the process in culture really start to break down?

Justin Welsh: Yeah, there are really two areas where I see it break down most commonly. I think the first is when a company doesn’t establish some sort of the fundamental elements of a strong culture in the beginning. Examples to me, would be things like really crisp career pathing, appropriate compensation plans, providing ample opportunities for learning and development, a recognition program. A lot of that stuff may not matter when you’re 50 employees deep, but go from 50 and suddenly you’re at 500, and if you didn’t establish this stuff really early, it can get very messy. And when it gets messy and you’re playing from behind and you’re trying to catch up, people get really upset. And so I think laying that foundation early is really important.

Justin Welsh: And I think the second place that I might see it most often is when companies are going through a hiring burst and they’re putting tremendous emphasis on filling these individual contributor roles, whether it’s SDRs or AEs, but they’re not being mindful enough of management ratios. Like I mentioned, behavior and culture comes from your team, but it’s often driven by the strong leaders. And I’m a real firm believer in tight management ratios. I like to keep one to eight and if suddenly if you’re hiring really fast and you go from one to eight to one to 12 or one to 15, I’ve seen that cause a lot of issues in terms of culture.

Harry Stebbings: Can I ask, and this is a super interesting one that I haven’t discussed before, in terms of the management ratios, how does a change in terms of getting worse, the more the ratio expands itself? How does one to eight change when it’s actually suddenly one to 15?

Justin Welsh: Yeah, great question. Culture to me, a huge part of it, one of the biggest slices is learning and development. And so I think the place where it changes is people just get less of that. I know when I was at ZocDoc, as an individual contributor, early in my career, my boss Ryan Stam spent a tremendous amount of time with me. And I think that was a huge part of the reason why I had such a great career there and why I started to treat my career differently. And as you sort of scale your teams and you don’t scale your management, you’ve got people floating in the wind, you’ve got people meandering the way that I did early in my career without being able to have that learning and development and that spreads. That’s the stuff that ends up on Glassdoor. That’s the stuff that people talk about if they’re not getting enough of. That’s sort of why I think it’s so important.

Harry Stebbings: The final one, before the quick fir, you mentioned there kind of the management ratio itself. I guess that makes me think of straight away to actual mentorship outside of the workplace. Do you think mentorship outside of the workplace and having that independent but also knowledgeable air on your industry, it can help when it comes to the burnout culture, the vulnerability, the transparency? Do you think that that actually is a very valuable element? Or does it have to come from internal in terms of company itself?

Justin Welsh: No, I think it’s great for it to come externally. I think as I look back in my career, one thing that I’m disappointed in myself for not having done was getting an executive coach. I think that having an executive coach, somebody outside of my organization to bounce ideas off of, to work through some of the burnout, to talk through inheriting new departments or things that I hadn’t done before would have been extremely valuable.

Justin Welsh: And, I spend a lot of my time today mentoring younger sales leaders and in actually saying, “Here are all the mistakes that I made that you want to avoid.” And I think that gives them a tremendous sort of leg up. I’m a huge fan of external mentorship and motivation for sure.

Harry Stebbings: Thrilled to hear that. I think my career would be very different if I didn’t have some of the mentors that I do so thrilled to hear you agree with me there. I do want to move though Justin into my favorite elements of any episode, which is the 60 second SaaStr. I say a short statement and then you hit me with your immediate thoughts. Are you ready?

Justin Welsh: I am, yeah.

Harry Stebbings: Okay. What do you know now about the process which you wish you’d known at the beginning of your time at really, and you can choose either with ZocDoc or PatientPop.

Justin Welsh: Yeah, I would say delegating effectively is your best friend.

Harry Stebbings: Got It. No, I totally agree. It’s a tough one. I struggle with it immensely. How to create a sense of urgency in a sales process.

Justin Welsh: I use a methodology called PASTOR, which stands for a lot of things, but the P and the A are the most important. Create pain, amplify that pain, and then tie that to an opportunity cost.

Harry Stebbings: Love it. Anything with an opportunity cost’s got my thumbs up. Sales leader you most respect and admire and why?

Justin Welsh: Yeah. I really enjoy what the gang over at Outreach is doing. It’s Mark Costello, leading sales and Max Altschuler leading marketing. They got a great product. They use it to maximize their own revenue and they’ve created this really incredible thought leadership community.

Harry Stebbings: Couldn’t agree more. I think Max is amazing and I loved working with him on the show. Okay, discounting, is it always bad? And what leads your thinking here?

Justin Welsh: I don’t think it’s always bad. I think if you’re an SMB SaaS like I’ve been and you don’t have a dual sided marketplace that requires price integrity, I think that you can use it to drive some results. If you want to do it at the end of month or quarter or a year. But I think that if I could do it over again, I probably would have chosen to stay consistent with my pricing and and not allowed discounting. I think that’s something I would change.

Harry Stebbings: And then final one, if you could change one thing about the world of SaaS today, what would it be and why?

Justin Welsh: I would like to see diversity and inclusion continue to become more important. And I think the reason why is because the more diverse the community, the more we all learn. And I think that’s a good thing.

Harry Stebbings: I couldn’t agree with you more there. But Justin as I said, I was so passionate when you sent through the suggestions and so love the open and kind of free flowing discussion. Thank you so much for joining me today and it really has been such a pleasure.

Justin Welsh: Harry, thanks so much for having me on. I appreciate it.

Harry Stebbings: Such a fantastic guest and I so appreciate Justin being so open there about his experiences. And if you’d like to see more from Justin, you can find him on Twitter @JustinSaaS. Likewise, it’d be great to welcome you behind the scenes here. You can do that on Instagram, @HStebbings1996, with two Bs.

Harry Stebbings: And as always, I so appreciate all your support. It really does mean so much to me and I can’t wait to bring a brilliant episode next week.


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