The Best Team Wins Podcast: Clancy Ryan, CRO of Punchkick Interactive

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Talking about flat organizational structure and sales management with Clancy Ryan, CRO of Punchkick Interactive and Director of the Sales Leadership Center at Chicago’s DePaul University.


Adam Robinson: Welcome to The Best Team Wins podcast, where we feature entrepreneurs and business leaders whose exceptional approach to the people side of their business has led to incredible results. My name is Adam Robinson, and for the next 25 minutes, I’ll be your host as we explore how to build your business through better hiring. Today on the program, Clancy Ryan. Clancy Ryan is the Chief Revenue Office of Punchkick Interactive, a company based in Chicago founded in 2006. Clancy’s been there for about a year. They’re a 54 employee business, and completely self-funded, so a bootstrap business on the program today. Clancy is also interestingly the Director of the Sales Leadership Center at Chicago’s DePaul University, which is where I got my MBA. Did you know that DePaul University is the only university in the country that offers an undergraduate major in sales? It’s super interesting to me, especially because they have such a need in the industry, particularly in technology in SaaS and B2B sales, for amazing entry-level sales people, and so DePaul is, in my opinion, filling a real need there. Clancy, we’re excited to have you on The Best Team Wins. Thanks for being here.


Clancy Ryan: Thanks for having me, Adam. It’s my pleasure to be here.


Adam Robinson: We know here that the best learning happens through the sharing of real experiences by fellow entrepreneurs and business leaders, so really excited to tap into your wisdom and considerable experience, and I’m excited to learn a lot from you today. But first, let’s start off on the right foot. As is the tradition here on The Best Team Wins podcast, we always start off on the right foot, which is the best business news or personal news that happened to you in the last week. Clancy, kick us off. What’s your right foot?


Clancy Ryan: Wow. Lots of right feet I should say, instead of just one foot. I’ll do several other feet, because when I look at this, Adam, I always look at my life from three different lenses. First the professional side, then a personal side, and then a charity side, or paying it forward. In looking over the last week, I would say from a professional side, wrapping up on a strong 2016 with year over year growth, and double digit growth that we’re looking here at Punchkick Interactive, and then really getting done and wrapping up by the end of this week our objective and key results, our OKRs for 2017. As you know from putting that in play, it takes a long time to get those rolled out, so I’m excited to wrap those up this week.


Adam Robinson: Yeah. Fantastic.


Clancy Ryan: Then from a personal side, having three younger girls, they’re excited for the holiday season, and my wife and I have all the shopping done. Knowing that they won’t listen to this podcast, it’s safe to say that all of the shopping for them is done so far.


Adam Robinson: That’s damn impressive, I got to tell you.


Clancy Ryan: I can’t take full credit for that. I really have to divert that to my wife. Then last but not least is, there’s a professional side, there’s the personal side, but something I’m very passionate about, and we could talk later on is paying it forward, or the charity side. The fundraising for our nonprofit, which we could talk about later on, called the Sid Feldman Legacy Fund, which as you mentioned is part of DePaul University, and started in 2010. We awarded two scholarships in 2016 and ended a solid fundraising wrapped up about two weeks ago. Then last but not least, I coach a high school basketball team. We won our second game of the season, even though we’re about five games in, at the beginning of last week, end of last week, so excited for that.


Adam Robinson: Congratulations. Thank you for sharing that with us. You have nothing going on, man. That’s a full life, my friend. Let’s jump into Punchkick. First off, tell us a little bit about Punchkick Interactive, and a bit about the work that you’re also doing with DePaul University.


Clancy Ryan: Sure. Two things. First and foremost on Punchkick, Punchkick is really separated in two businesses. We have our service-oriented business. As you alluded to earlier, we’ve been a business for about 10 years, doing mobile web, mobile applications, and websites for large brands, and even small to medium size brands. That’s really what has been the crux of our business here at Punchkick Interactive. Some of the clients you might recognize, and your audience might recognize is Marriott the hotel chain, Harley Davidson, Allstate, Blue Cross Blue Shield, and just wrapping up a project with PetSmart. That’s the service and-


Adam Robinson: Small company, small brands is what you’re telling me.


Clancy Ryan: Yeah, well there are some that we work with. Really if the need’s there, we’re willing to work with them on the service side of it. Then on the product side of the business, really came out about a year and a half ago coming from the service side of the business where some of our clients, like Marriott, like Lifetime Fitness, we solved some of their needs on the service side, but then their other biggest need that we’re solving for was in regards to hiring, and so really kind of moved our way in of applying our service side of the business to the HR vertical and with HR talent acquisition. That’s been our first product called TUX, which is wrapping up its first year this year, and that’s on the HR vertical side. Our second product will launch middle of next year. That’s Punchkick Interactive.


Then as you had mentioned earlier, DePaul University, just like you had said, we’re really servicing a need. After getting done with my masters, I realized that even at the masters or the undergrad level, nobody really teaches you how to sell. You really learn from organizations like yourself at Hireology, Punchkick, you learn on the job, but that doesn’t mean it can’t be taught at the university level. Way back when in early 2003, started a sales class, with the hopes of building a program. Brought the right people there, and have built a very solid sales program there with I think it’s at last count somewhere between 13 to 15 classes, both at the undergrad and the graduate level, and partnered with about 55 different corporate partners at DePaul who are looking to hire those best of the best sales folks that know that they want to be in sales.


Adam Robinson: Yeah, that’s fantastic. It’s an amazing program, and excited to dig into it in a few questions later. The first thing I want to talk about with you is this notion of flat organizations. I know Punchkick is a flat organization, which we’ve talked about on this show with a few different guests. In my observation it means different things to different people. I know you’re very passionate about this topic. What does flat organization mean to you, and what does that look like at Punchkick, so our listeners get a sense for how you’re actually implementing that in your daily management?


Clancy Ryan: Well, now you have my interest piqued, so I will have to listen to those other three podcasts, because I’d be curious to hear what their interpretation is. To answer your question directly, what it means to us at Punchkick, the two founders are really geared and focused on a self management framework, so organizing in the roles of self management. That’s really what the framework here is set up to do with a flat organization. When we think about a flat org we kind of focus on three different areas. First and foremost, the biggest item is buy in. In order to ensure that self management works, in order to ensure that flat works, everyone needs to buy in, and I mean everyone. We could talk about it even later on when talking about recruiting and hiring the best talent, because in the interviewing process, getting a hint for whether or not someone can handle self management is really, really key for us, because if they can’t it’s going to be a tough fit within the organization. First and foremost, buy in, and that’s across everyone. You notice I just didn’t say from the top down, because we don’t speak that way. It’s just that when we look at everyone, everyone has to buy into this.


The second part to it, Adam, is around empowerment. What we mean by that is, every team member feels like they are empowered to make whatever decisions they want. Now, it’s not just total anarchy and total chaos. There is a structure and a process to the way that they are empowered to do things, what we call advice channel. You can make any decision you want to here, but before you do that, seeking the advice from your peers, or more importantly the people that that decision’s going to affect the most. We call those advice channels before doing anything here. That’s the empowerment piece.


Then last but not least, what we always talk about is especially with hiring millennials, what we’ve noticed is folks want to feel like they’re part of something larger. They want a real sense of meaning to the organization that they’re tied to. With everything we do here, so that nobody feels like, “Hey, there’s two folks in a corner office. What are they talking about?” everything is open, from financials, to information about everyone here. That real sense of meaning and being transparent with everything so that people feel like they’re an entire part and they’re part of something larger.


Adam Robinson: Okay. Did Punchkick start off as a flat organization, or was there a transition?


Clancy Ryan: There was definitely a transition that occurred. 2016 was a big move to it where we rolled it out, but it really started in 2015.


Adam Robinson: Share with us that process to the extent that you can. When you moved from a traditional organization structure to flat structure, what were the differences, and what went well, what didn’t go well, and what would you do differently?


Clancy Ryan: Sure. I think we had a really, really large rollout with everyone here, because there are a lot of questions. This whole notion around empowering individuals, and not having to go to one of the founders, or not having to go to someone you think is your “superior” and ask for permission. One of the things we did is made sure that we rolled it out and taught everyone and had people lead different discussion groups around what does an advice channel look like, how do you become part of something larger, how do you ask financial questions? As a technical company you can imagine some of our engineers on the development side, they might not want to know what the numbers are, but why do they want to know what those numbers are, and how does that impact them overall in their job and what they do here? Early on in 2015 we rolled this out, and subsequently we’ve formed different groups amongst the team members here. We’re about 54 employees here, so we have subgroups that meet on a quarterly if not monthly basis to answer any questions around here.


Some of the struggles that, I think to answer the second part of the question, that we had is getting people to untrain from old habits in that, like I said earlier, if they had a question, not to come to someone that in the former was their “boss” or one of the founders, or maybe the CFO, so if they wanted to buy something for the organization, not having to go to the CFO and ask for permission. As long as they presented their case well to those most affected and got the advice channel, you wouldn’t necessarily have to go to the CFO. Untraining people of habits from the typical top-down hierarchy organization that most of us come from and our experience is in, I think that’s been the most difficult part.


Adam Robinson: If you look at the biggest benefit so far, and maybe it’s self-evident, but what’s been the lift? What could you point to as the reason to look at this go, “You know what? I would do this again”?


Clancy Ryan: Yes, so I think for us, the thing that we’ve focused on most, and the biggest lift is getting everyone’s buy in and input, and that sense of they’re part of a lot of the decisions. You can imagine, instead of me just making a decision on my own, when I go and ask opinion from other people, it’s almost flattery to say, “Hey, I expect and value your opinion. Could you give me insight as what direction I should take this?” so that when it does roll out, everyone does have a sense of ownership, especially those that you’ve sought from the advice channel. I think that’s been the biggest lift is that there’s nothing that’s held in secrecy here. Most folks know about what we’re doing.


We have here everyday at 10:00, between 10:00 and 10:30, a huddle, and in that huddle, all this information is shared. We share good news. We share special shout-outs we want to give for people going above and beyond. We talk about things going well in our personal lives. We throw out some questions for people to ponder. I think that’s been the biggest lift is that since that you know out of the 54 individuals, the 53 other individuals that I work with here, I know pretty much a lot of what’s going on in both their personal and their professional lives here at Punchkick because A, they’ve sought advice from a lot of us, and they shared it with us on a daily if not weekly basis.


Adam Robinson: I feel like the values of the company, well they’d have to be congruent with running a flat organizational structure. Can you take us through the core values at Punchkick, and how they’re lived through this implementation?


Clancy Ryan: Sure. A lot of what Punchkick follows here is we had mentioned it earlier in that we keep it simple. Our motto is to keep it simple. We don’t think that a ton of tools and processes are needed for every single thing. Now, on some of our core projects, obviously we do do that. That being said, one of the ways that we do that is we ask for people to be casual about things that don’t matter, things like bureaucracy or hierarchy. With a flat organization, that helps out a lot.


We also with some of the work that we’re doing, because it is exciting work on the mobile web on websites. I mean, it is excellent work that we do for great brands. We ask folks to be fanatic about their work, and think of quality of craft is really what we preach to them. Then especially from the sales side, this is something I’ve always been passionate about is that our clients are a gift to us. It takes a lot of effort to bring in a new client. That is a gift that we will cherish and continue to grow over the course of the years with those clients.


Adam Robinson: Some questions I’ve received in response to some of these discussions on the show about flat organizations is about revenue management. Of course sales is a production job. The scoreboard is very clear, how much did you sell? As a sales leader, how do you develop and motivate a sales team in a flat organization?


Clancy Ryan: Sure. Just because we are flat doesn’t mean, I think the myth out there is that people aren’t held accountable. One of the ways that we do it here at Punchkick is, and this goes back to my previous experience working with Google and working with Apple, is Google is one of the innovators, besides Intel, on OKRs, objective and key results. Just because we are flat does not mean we don’t hold ourselves accountable here. That self management goes all the way down to the individual level. We do have individual OKRs, or objective and key results, that we measure here, but those really boil up to the department level. What I mean by department, even though we’re flat, we still have an outside sales team, we still have a account management team, we still have a marketing team. Those individual OKRs boil up into the department level, and then boil up to the overall organizational level, whether it’s the service or the product side of it. Those really help to move each other to the individual OKRs and aligning and making sure that we’re on the same page.


Adam Robinson: It takes a certain kind of person to, like you said, work into this system, and you have to understand whether or not people can self manage themselves. What is the most important thing you’re doing in the hiring process to make sure you’re hiring the right people?


Clancy Ryan: Sure. For us, again we sell some really exciting stuff here when it comes to technology. The first thing that we look for is does the person have the passion for what they are currently selling. Now, one of the ways that we do this is, after the first interview, we really ask them to pick something that they’re passionate about, it doesn’t have to be one of our products, anything that they’re remotely passionate about, and come in and sell it to us. This is everyone from an account manager that has maybe five years sales experience to an outside sales person that has 10 to 15 years. The amount of insight that we garner from those presentation skills, because number one, that’s what they’re going to be doing in front of the client, but also number two, it really gives us insight as to the passion level that they have, because we don’t dictate what they are going to sell to us. I think that’s the first one is on the passion side.


The second one is grit. Now, grit is a tough one to measure, but based upon previous experience, and previous opportunities, we look for someone that has that grit, someone that has that drive. Now, one of the ways that we do this is we drill down. One of my favorite questions to ask in an interviewing standpoint is, Adam, tell me one of your biggest successes you’ve had in your career? What that gives me the ability to do is determine where they’re focusing their priorities and what they’re determining as success, but then more importantly, based upon that one question, I have about 10 to 15 other questions that I drill in to really understand why they saw that as success. Everything from tangible numbers, from what position and role, to who that affected, how it benefitted them and others. That really helps determine the grit that that person had in order to get that success, and really it shows in the passion and the way that they provide that answer to myself and the others interviewing them.


Adam Robinson: In your experience, it’s possible to assess this particular factor which you’re defining as grit, through structured interviewing. That’s your approach.


Clancy Ryan: Correct. Yes. Yeah, very structured in the fact of our first interview process, we have a series of questions that we ask. Three or four people may interview them on the first interview. One of the things that we do is have whoever the interviewee is fill that out so that you don’t discuss your opinions, because in the typical organization, after you interview someone, what do most people do? They sit around the water cooler and say, “What’d you think of that person?” What we’ve found out, Adam, over experience, as I’m sure you have, is some people tend to dominate and influence the way other people view those candidates, and so by having this form in the first interview, that really takes that part out of it. Then that’s why in the second interview, once they’ve come through the objective and the subjective part of it, that’s when we ask them to come and present something to us that they’re passionate about.


Adam Robinson: One final question on a related topic before we move to the lightening round. Looking back on the considerable experience you have, what’s the biggest people related lesson you’ve learned specific to your time as a sales leader?


Clancy Ryan: In motivating people, or what specifically?


Adam Robinson: First thing that comes to mind. A lesson learned that you could look back and say, “You know what? In all cases I’m going to approach it this way because of this experience I had?”


Clancy Ryan: Sure. I think to me whether it’s from managing sales reps, teaching them at the university level, now having kids, it’s what motivates each individual is going to be totally different from person to person. Most people think in sales it’s pay them a bigger commission, or pay them a bigger salary. At the end of the day, each individual on our team here, each individual at the university level, and my children, they’re all motivated by totally different things. It’s your job to figure out as a leader, what motivates each of them on an individual basis.


Adam Robinson: That’s fantastic advice. All right. Let’s move on to the lightening round here. We’re going to ask you some quick hit questions, just barometer readings on some macro level stuff. Question number one, do you think, based on what you’re seeing right now in the market, that the US economy is going to get better or worse in the business climate over the next 12 months?


Clancy Ryan: From a sales perspective I’m always the optimist, so I will always say “yes’ to that answer, and it’s our job to seek those customers out, but looking at what the markets are doing, it’s hard to bet against what they’re doing right now, which is on the uptick.


Adam Robinson: Okay. I like the optimism. On the staffing side, do you think it’s going to be easier or harder for companies like yours to find the people they need over the next year?


Clancy Ryan: Again, being analytical on this answer, and being in the talent acquisition side of the product side of the business, knowing the stats, unemployment lowest since 2007, participation rate lowest since the 70s, I’m going to answer more difficult.


Adam Robinson: Okay. The what’s on your nightstand question. What book are you reading right now, and would you recommend it to our audience?


Clancy Ryan: I would say that two part answer. The type of sale that we do here is called “The Challenger Sale,” written by Brent Adamson. It’s also what we reinforce at the university, and Matthew Dixon. The second part that I’m reading right now is “The Challenger Customer,” so once you bring in that new opportunity, how do you grow that customer? Yes, I would highly recommend it, both of them.


Adam Robinson: Fantastic. Final question. If you were to come back on this show a year from today and report to us on whether or not you accomplished the most important thing on your plate right now, what is that thing?


Clancy Ryan: Well, since that ties into how we started this off, I’m going to stick to the three areas. From a professional standpoint, I would say double digit service growth in launch of our second product in the HR vertical is number one on the professional side. Personal side, expecting child number four, so a healthy wife and a healthy baby and more attention to the others-


Adam Robinson: Congratulations. All right.


Clancy Ryan: Thank you. Thank you. Decided to do it again. That everyone’s healthy, and giving more attention to those other three kids with the new addition. Then last but not least on the charity, volunteer slash what I call paying it forward side, coaching more basketball teams with my daughters, and growing the nonprofit that we have called the Sid Feldman Legacy Fund, and awarding not just two scholarships, but trying to push for three scholarships next year.


Adam Robinson: That is the final word. You have been learning from Clancy Ryan, Chief Revenue Officer at Punchkick Interactive, and Director of the Sales Leadership Center at DePaul University in Chicago. Clancy, thank you for spending time with us.


Clancy Ryan: Adam, thanks for having me. Great time.


Adam Robinson: All right, that’s a wrap ladies and gentlemen for this episode of The Best Team Wins podcast, where we feature entrepreneurs and business leaders whose exceptional approach to the people side of their business has led to incredible results. I’m Adam Robinson, author of the book “The Best Team Wins,” which you can find online at We’ll see you next week.


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