Lessons from the Enterprise

Suzanne: Why does an entrepreneur give up a business that he built from the ground up to go and be inside of a company? It’s a large company. It’s eighteen hundred you said.

Chris: Yeah. It’s very big.

Suzanne: Not to say that you’re a cog in the wheel, but that’s a big machine.

Chris: I’m very much a cog in the big wheel.

Suzanne: Right. What’s the appeal there?

Chris: The big appeal for me was to learn from the CEO. Adam is about thirty feet away from my desk, and he’s obviously built a company way larger than I ever did. I figured in the interim of figuring out what I’m going to do next, this would be a really good place to learn from somebody who’s done it on a grand scale.

Suzanne: How would you describe your personal mix of skill sets?

Chris: That’s a great question. I think I’m much stronger on the vision side and understanding where the market has opportunity and dynamics, more so than I am on the writing user stories and managing the process side of things. Then my second biggest strength I think is leading the teams. Part of what I think I’ve done at Cornerstone fairly well so far and what I’ve done in the past with my company was really find great talent and bring those people up. Produce those people if you will. Really energize teams. My two strengths are definitely on the management side of the people, and then the vision side of the product. Then the third piece of that is the visual design side. I’m a pretty strong designer. I don’t think I’m the best designer, but I can get the point across and get us to the next place.

Suzanne: This is one of the things that I think is so interesting and then also challenging about product management is you’re in the pressure cooker between technology, business, and design. You could be any mix of those skill sets and then what’s the right mix? Especially if you’re somebody that’s learning to go into this or wanting to go. What’s the right thing? What would you say, where would you put your money on for bolstering skills?

Chris: I think for bolstering skills, you should spend the time on the things you’re not naturally good at. If you go into a GA or any extracurricular learning scenario or opportunity, that’s where I would spend my time. I do think though that there’s a nice blend of strengths in product management that can benefit each other. There are people on my team who are great on the business analyst side of things. There are people on my team who are really, really strong at managing agile process. Those are things that I’m not great at, but I can lean on those people for support, and likewise, they can lean on me for product vision and understanding what we’re capable of actually accomplishing.

Suzanne: What’s the construct of your team in terms of total people? How do you fit into that constellation?

Chris: I believe that we’re thirty-five product managers at Cornerstone now. I run one of the products called “extended enterprise,” which is an offshoot of our big core product, which is our learning management system. Beyond that my team has three PMs specifically, and then an overarching lead PM that manages that product. Then I am this satellite to them. We each have our own pod of anywhere from five to ten engineers. Engineers and QA I should say. Then we have a satellite design department and front end department that support all of the different pods within Cornerstone. We’re an interesting mix. We don’t have design and UX in front end on the dev pods at all, which is challenging sometimes.

Suzanne: Is it challenging because you’re all fighting each other out for the attention of that shared pool of UX resources?

Chris: I wouldn’t say fighting is the term, but there’s definitely a need for more resources, as there always seems to be. I think what that’s done more so than create any fighting for the resources is create not necessarily the best case scenarios in how we build the user experience. Because those guys are so short-handed, we’re making decisions as PMs on front end scenarios that could probably be better served somewhere else, if that makes sense.

Suzanne: Right. It absolutely makes sense, and then at the same time, a lot of PMs really want to own more of the UX. This is another pattern that I see where you’re so integrated. You’re integrated with the customer view, you’re integrated with the vision, that sometimes it can seem like the long way around have to drop the work off …

Chris: Then go back-

Suzanne: Primitively speaking at the desk of a UX designer and say, “Do something great.”

Chris: Sure. I think, however, that being said, understanding your strengths and weaknesses can allow for product managers to own the process but pull the right talent in. I think that’s where we should be really good, is leveraging the different skills sets that the team brings to the table. Not trying to be all of them at once. I think that product management in general is an interesting place to be because you’re what every team’s satellite’s around, but you’re not anyone’s direct boss. Everyone reports to you, but you have to know influence them to want to do what you want to do and where you want to take things. Then each of those people go back to their own existing management structures and leadership teams, and hopefully those are cohesive enough and collaborative enough and communicative enough that the message you’ve created gets produced correctly. That’s not always the case either.

Suzanne: I had somebody else on the project describe it as being the product manager is like being a mini CEO without any of the power.

Chris: That’s so true.

Suzanne: We joke, but this is one of the things that comes up in class all the time is that presenting to stakeholders component.

Chris: Absolutely.

Suzanne: You’re a translator. You’re talking to developers and developers see the world through a very specific set of lenses.

Chris: That’s very true.

Suzanne: Then you have to-

Chris: It depends on which side of dev we’re talking about. Front or back, right?

Suzanne: Right.

Chris: We’re in the middle there, if you like it-

Suzanne: Absolutely. No that’s an extra important insight. A front end developer, they’re a little closer to the design side of thinking typically, but a back end programmer …

Chris: It’s very logic-based.

Suzanne: Yeah, and then they’re going, “You know how much great programming is here? Who cares if the input field is off.” You’re like, “Everybody.” That’s pretty much all that everyone cares about.

Chris: The people who can’t use the software that you built.

Suzanne: Yeah. You’re responsible to the business side, the marketing team, the C-level executives.

Chris: The sales team.

Suzanne: You’re responsible … Yeah. Sales.

Chris: The product marketing team, the general marketing team, the sales team, the client executives team. We have the customer support, or customer success managers team. We have the engineering team and the front end team. The UX team. We have, yeah, we are the API layer between all of those teams, if you want to call it that.

Suzanne: I’m not asking you to out anyone at Cornerstone, but in your experience, which department is the most demanding on a PM?

Chris: It depends on what time of year I think.

Suzanne: Okay.

Chris: We have an interesting quarterly release cycle. We’re not a continuous development shop. With that every three months come these interesting cycles. When we’re releasing new products, the release communications people want all your attention because they need to know what to say and how to say it. That also becomes a product marketing conversation. The minute that’s done, it’s a sales conversation, and then those people need your time. Then from day to day scenario, I spend most of my time with my team. It just depends when and how what we’re doing is in existence that people suck my time up. We just had a big national conference we call Convergence, and that experience was very much all clients wanting my time. For three days, I was in session after session after session with different big corporate clients that we have that want to talk about road map, want to hear about what features are coming down the pipe, want to know where I’m thinking I’m going in terms of vision, but also very much want to tell you exactly what they want and how it should work. They want a lot of air time for that, which is good. For a product manager, those are the people that you’re building these things for and your job is to find the patterns and the vision in all of that feedback, but it can be daunting at the same time.

Suzanne: Yeah. Is it different when your customer is an enterprise level customer themselves, versus a business to consumer, and how is that different?

Chris: I think it’s a much slower pace, first of all, and the expectations are much greater. Sales cycles are typically much longer. The level of critical path, I’ll call it, is severe, and big corporations that have compliance-driven scenarios that have hundreds of thousands of employees, infrastructure is super important when you sell something to a LinkedIn, who’s one of our big clients. They’ve got obviously thousands and thousands and thousands of users that this thing has to work for. When you’re in the B to C space, I think there’s a little more flexibility in terms of MVPing products and releasing them and iterating quickly, but in short verse, we’re really seeing things in big chunks that have to go through tremendous user acceptance testing. That have to go through incredible load balance testing that we have to make sure are incredibly secure for the pharma companies of the world. It’s a different game for sure, enterprise versus B to C. I wouldn’t say one is better than the other. I like B to C better personally, but I’m in B to B.

Suzanne: You’re here to learn.

Chris: Yeah.

Suzanne: Are you familiar with Startup Vitamins?

Chris: Yes.

Suzanne: Yes. They have that one “Fuck it, ship it.”

Chris: Yeah.

Suzanne: Sounds like that’s not a mantra you guys use at Cornerstone.

Chris: Exactly. It will never happen at Cornerstone.

Suzanne: What’s the Cornerstone equivalent?

Chris: If it does, it creates a massive problem. The Cornerstone equivalent is “descope, descope, descope.”

Suzanne: Man.

Chris: Make sure it works, even if it’s less large than you wanted it to be.

Suzanne: Right. No bugs at any cost.

Chris: Yeah.

Suzanne: PwrdBy, just to go back to your entrepreneurial past, versus your interpreneurial present. In your entrepreneurial past, PwrdBy really built products for businesses. Business would come-

Chris: We got to that point. When we started, we really intended to be a B to C … Originally started as a consumer photo hosting platform before mobile was mobile. When that started working, we saw because it was a photo storage site, we saw camera phones starting to happen. I remember I had a Palm tree that had a stylus that pulled out of the back. I think it was a half a megapixel camera that almost was worthless, but we were in that environment and saw that coming. We originally built then the next layer of Picture Healing at the time was a photo sharing app, but it shared from your phone to our storage site. Then we were getting pictures of things like sandwiches, and we didn’t understand what was going on at first. Why are you keeping a picture of your sandwich?

Suzanne: You guys were at the bleeding edge of the amateur foodie photography world?

Chris: Yeah, it was interesting. Then we decided, “You know what? Let’s scrap this web-based shoe box if you will, where people keep keepsakes, and become about the moment.” That’s really what we were seeing in the photos that we were collecting from the mobile devices was … It was more about what was happening right now and wanting to share that moment, but there was no way to share it yet, other than push it to a site like ours and then grad it from a site like ours, and put in MySpace or Facebook at the time. We built a photo sharing app, and that was doing fairly well until Instagram just crushed us. After that, we had to come to the table and figure out what are we good at? What are we bad at? What do we know, what don’t we know? The whole point of the business has always been to support non-profits through technology. At that point, the model was based on this point system. The more you use the platform, the more our ad revenue went to your favorite organization.

When we decided to come back to the table and figure out do we kill the photo sharing thing, because Instagram’s totally won? What do we do next? Next really became a platform for non-profits to build mobile applications easily. We’re this do-it-yourself mobile app builder. The problem that we identified was that non-profits all wanted to go mobile, but didn’t know how to go there or have the budget to go there. We created what you would consider a mobile platform nowadays for non-profits back then. That started working fairly well. We had decent traction with that, and then we met Habitat for Humanity. Ended up building a platform for Habitat that was a customer version of the platform, and that was really our foray into the B to B instead of B to C perspective. Habitat has seventeen hundred affiliates and they wanted one mobile application that serviced all seventeen hundred affiliates, and at first we didn’t think we could do that. We realized we had already built the underlying technology to pull that off based on the user’s location.

We accepted the contract, moved into that space, and built basically this CMS back end with the mobile app on the front end that allowed each of the seventeen hundred to manage their content, if you will. Their volunteer opportunities, donation requests, et cetera. Based on the user’s location that had the application, we changed the content dynamically for the local affiliate. Once we did that, it opened the doors for us to work with these big chapter-based organizations. The project that PwrdBy is currently working on is for Children’s Miracle Network, and that’s a big mobile application for a hundred and seventy children’s hospitals in North America. Really to manage their corporate fundraising partnerships within their territories. Again, we’re using that location-based mobile concept, but re-purposed for the way that they do business.

Suzanne: Wow.

Chris: It morphed into that. It was never intended to be that, but pivot, pivot, pivot.

Suzanne: Exactly. How do you think it’s different or how was it different for you product managing from the vantage of a third party consultant? When a company like Habitat or whoever comes to you and says, “Build something, and we’re not technology “… You’re managing a product for somebody else for a term, and that’s its own beast.

Chris: Totally. Yeah, and you’re probably well aware of that experience.

Suzanne: It’s certainly part of my, but … Yeah, maybe I’m just looking for solace.

Chris: Yeah.

Suzanne: Tell me something good, please.

Chris: I think at the end of the day, that’s all about setting proper expectations, and we made the mistake of not doing that well a few times. That bit us in the butt later, but I think building that relationship and helping them understand the process that you’re going to take them through is really paramount to making a successful product at that point. Then creating terms that are equitable on both sides for managing that going forward. Not something where you’re going to gouge somebody for the upfront cost and just consume, consume, consume, trying to make the money and run away. With those big enterprise deals, it’s about a lasting long-term relationship I felt like, and really making it something that we could partner with them on, because we’re an extension of their business ultimately. They weren’t an extension of ours, right? It’s almost as if we were this outsource office for them, the way that we ended up going through that.

Suzanne: I guess my question to you, and this is opinion, people talk a lot about should I in-source development, should I outsource development? That’s a separate beast in conversation that I don’t want to touch, but I’m curious what you think, having now been on both sides, would you advise a company to allow a third party like PwrdBy be the product manager, be that out of house extension of product manager? Do you think it’s a role that every company with product should internalize?

Chris: I think the answer is both. I think it’s two-sided and really dependent on the company’s strengths. Children’s Miracle Network, for example, incredibly strong company. They have an awesome in-house innovations team. They have their own in-house web development team. They do a really good job on the products that they build, but they didn’t have the mobile expertise, and we did. We were an extension of their team by having that thing they didn’t have, and that’s where the relationship really worked well, because they had the head of product, and we had a head of product. It was easy to have those conversations. When it’s really hard, when you’re outsourcing things, is when you think you know what you want, and you ask someone else to do it, but you have no way of communicating that the right way or an effective way. You generally get something close to that back from those outsourced companies, but it’s not a very fun process sometimes. If there aren’t the right people on both sides, I guess is where I’m going.

We at PwrdBy did both at the same time also. We had an in-house team and we had always some outsourced people. We’d pull people in for certain projects. We’d pull certain teams in for certain projects, but we had our core unit as well. Sometimes when we didn’t project manage well, it was our own mistake on why outsourcing was going sideways, because a lot of times when you outsource people, just take the box that you give them and they don’t think creatively or care necessarily about the outcome, because they did what you asked and they should get paid for that.

Suzanne: Right. Yeah, or didn’t ask the right questions upfront.

Chris: Yeah, exactly.

Suzanne: We talked offline before about product management being this black box of mystery for a lot of people. What is that even? What do you think is the most misunderstood aspect of … Do your friends even now what you do?

Chris: No. I think they have a semblance of an idea of what I do, and I’ve actually more recently been asked the question, because before, I was the CEO of my own company. That was an easier thing to grasp. Now they’re like, “I know you work for some big enterprise software thing. What do you do? Are you writing code?” I’m like, “No. Not exactly.” I think the misunderstanding is that there is just this giant room of people or young kids eating pizza, writing code in the dark thing. Nobody’s supervising them and everyone’s playing table tennis or pool, which does happen. Don’t get me wrong, there’s a lot of pizza at Cornerstone and a lot of table tennis, including trophies.

Suzanne: Right, I was going to say, you just took me through what appeared to be a carnival-

Chris: I just took you through a wine mixer.

Suzanne: On a Tuesday afternoon. Yes, okay.

Chris: It does happen, but there is definitely a lot of pressure and a lot of demand on time, and we’re dealing with Fortune plus companies. At the end of the day, if this stuff doesn’t work that we’re making, it’s really expensive and problematic, and legally problematic for both sides of the equation. I don’t if that answered the question or not.

Suzanne: Absolutely. What’s the hardest lesson you’ve learned on the job since being here at Cornerstone?

Chris: I’m still figuring out I guess the politics of corporate life. I’m very fast I think. I like making things work and making decisions, and moving quickly. It doesn’t work like that here, or any big company. I worked briefly for Mass Mutual as the marketing director when I was much younger in between touring life and starting my own company, and I remember that there, but I forgot about that when I came back to this life. I’m still figuring out how to shut up at the right time I guess. I don’t know if I want to learn to do that. I may just decide I’m not that guy.

Suzanne: Right. Yeah, it’s definitely a lot of chains of command. How many layers of decision-making do you typically have to go through? I’m sure it varies depending on the decision.

Chris: Yeah. It does, for sure. Just from a high level product leadership perspective. I’m a senior product manager, so I think there’s one layer below me, and one or so above me before our head of product, but I just learned we have a title called “product manager manager.” I don’t know who that is, but there’s somebody who’s a product manager manager.

Suzanne: You’ve never met them.

Chris: Maybe I’ve met them and I just don’t know that’s their title, but we were sitting in a presentation about org charts, and it was on the org chart, and I laughed, and then was like, “Is that a real title?” Someone’s like, “Yeah, we have that at Cornerstone.” I went, “God.” There’s maybe layers that I’m unaware of still.

Suzanne: Right.

Chris: I’ve been here for six months.

Suzanne: It’s definitely been … It’s a choice, right? I have students asking me all the time, “How do I get a job? What’s your advice?” I always give them the answer they hate to hear, which is “It depends. No two situations are the same.”

Chris: Totally.

Suzanne: One of the things I like to say is remember that you’re auditioning opportunities as much as they’re auditioning you, and I think having a sense of “Am I the kind of guy that likes to have to go seventeen layers deep to get a yes, or am I the kind of guy who’s used to just bulldozing?”

Chris: Making the decisions.

Suzanne: Yeah. You’re a bulldozer.

Chris: Yes, I am.

Suzanne: A bulldozer learning to prune with scissors in a large organization.

Chris: Very much so.

Suzanne: Right. Choose your environments wisely, prospective product managers everywhere.

Chris: Yeah. I think one of … I guess I shouldn’t say that. Never mind, we’ll keep going.

Suzanne: All right. What about books, podcasts, influencers?

Chris: My god, I’m not ready for this.

Suzanne: Yeah. Give us two or three that you think should be on everybody’s reading list.

Chris: Sure. Product-specific, a book I’m reading and just about done with that I actually really, really enjoy is Peter Thiel’s book, “Zero to One.”

Suzanne: Okay.

Chris: Which is a play on technology. You didn’t catch on to that. A book I just finished on management, or managing creative companies is the book from the CEO of Pixar, Ed Catmull, called “Creativity Inc.” I’m a nerd for a ton of blogs, but the one that comes up right away is called “Futurism.” It’s more about the confluence of biotech and artificial intelligence, and how a lot of those things are coming together. I read the typical tech crunch stuff as well. I have a number of … I have an email address specifically set aside for news articles from Tapiphany and Wired, and all these other sources that I just … When I have a minute or I have … Before you came out, about ten minutes before the interview, and I’m like, “I don’t have enough time to start another project.” I read something when I have those moments.

Podcasts, gosh. “Freakonomics” is one that I love, that totally isn’t related to the job necessarily, but I feel like at the end of the day, part of product is not just understanding the technology. It’s also understanding the people that you’re communicating to at the end of the day. Having those different perspectives of where things are going and what’s happening outside of what you spend your day to day workload on is super important to having enough of a future vision of where to take things.

Suzanne: Such a beautiful answer. We tapped into the book nerd in you and all of this delicate … That was nice. Thank you. This is not in the right order of things, but I wanted to ask you … The other thing that comes up for me a lot is realizing that I spend a lot of time teaching concepts that, man, I wish somebody had taught me.

Chris: Yeah.

Suzanne: You know. I say this is a luxury. Even the cornerstones, pun intended-

Chris: Nice.

Suzanne: The Lean Startup, right? This is a book and a movement that’s only a handful of years old, and yet, it is so completely …

Chris: Taken over…

Suzanne: Yeah, so completely changed the landscape of things. I guess my question is how many of the frameworks and the tools, lean model canvas personas, all of these customer … Steve Blank four-step customer framework. How many of these tools have you adopted, or do you adopt versus, yeah, we know they’re out there, but man, we’re just winging it as best as everyone?

Chris: In my former company, we used quite a bit of all of those things, depending on where we needed to be. The current CEO of PwrdBy, who is a good friend of mine, and we worked together for years before he took that seat, was a former Deloitte consultant. We borrowed a lot of … Also, the Lean Six Sigma stuff. At Cornerstone, we don’t do as much of that as I would like. We have a semi-structured process of how we review ideas from our customer success portals and things like that, but I’m really pushing on design sprints here, which is something I value tremendously. Google Ventures, IDEO, have really paved the way for communicating that well. We used to just call them discovery sessions before all that, and they’ve made a formal five-day process out of what we were doing. Not because we were doing it obviously. They also discovered that.

The other thing that I think is more and more interesting are just coming up with our own versions of some of those concepts. With Lean Startup and the whole MVP concept, and pulling that in … We use Agile at Cornerstone I guess I should say. We’re finally in Agile Shop. Not all of our dev teams, but some of our dev teams. Mine is thankfully. No more waterfall and giant hundred and thirty thousand-page specs. Really how do we adapt those to our existing processes less than how do we follow those books, one of those frameworks, by the code? For example, the whole design sprint concept of five days at Cornerstone is highly unlikely to get that many people in the same room for that amount of time, but we’ve adopted a three-day process that we’re going to take out to Texas hopefully in the next couple weeks and do with a handful of really big clients over a course of a couple days. That won’t prove the same prototyping MVP outcome that that book is talking about, but it will give us clear insights and actionable initiatives that we can take to refine the product to better suit the customers that we have that are using it.

Suzanne: They say about Agile, “The Agile that’s right for you is the right Agile.” That’s the beauty of it.

Chris: “Agile.”

Suzanne: Yeah, exactly. Imagine we’re sitting here, and this is typically my luxury, but I’m projecting it on to you. You’ve got a room full of people, they’re looking to you for advice. “How do I get into this industry?” The conundrum. “How do I get experience when I have none?” What would you say to a prospective product manager?

Chris: I would say a handful of things. One, I would definitely take a Udemy or a Coursera, or Cornerstone has a new platform called CyberU course online to just be introduced to the concept. If that’s something that’s interesting to you, then find a GA, for example, that you can go to and do an immersive course. It’s not right for everybody, but like you said, there are such different colors of people that do this from different perspectives. If that’s exciting to you and you’ve gone through that stuff, then it’s find side projects. Even while you’re doing that stuff, find side projects. If you’ve got a friend who’s probably got a startup, just go volunteer to help out and get into leads. You probably have a friend in a startup if you live in Santa Monica or downtown, or San Francisco, or wherever, right. Doing it is everything. I don’t think you’re going to go get a product management job by just going to GA or just taking a course on [inaudible 00:34:57], and applying with a resume that has no relevance to technology.

I would also say that I’ve seen people track out from project management because then you get some experience in the Agile workflows, understanding the development life cycles, that stuff. Ultimately I think it’s all about educating yourself and finding projects that you can use as a learning platform, if that makes sense.

Suzanne: For sure it does. Last question.

Chris: Whoa.

Suzanne: I know, we’re done already. Do you have a personal mantra or a quote, something I can put on a mug and sip out of, and say, “This is Chris’s ultimate POV distilled down to a sentiment”?

Chris: God. There’s a handful I guess, or there’s two. My girlfriend just got me a mug that says “Got singularity,” because I will bore you to tears with my opinions on where that’s going. One of my mantras is “humanity is perception,” and that’s tattooed down my spine, and my whole thing with that is that at the end of the day, it doesn’t matter what reality is to you. That reality is something completely different to the person next to you. If you can accept that, then you can move on hopefully in a collaborative way. What’s real to you is different than what’s real to me, and hopefully we can find a middle ground.

Suzanne: Right, absolutely. I’ve a variation on that. It’s “whether you think you are or whether you think you’re not, you’re right.”

Chris: Yeah, that’s good.

Suzanne: It’s true, right? We have made up our minds, and so have our consumers about our products too.

Chris: That’s very true, and that’s very hard to change.

Suzanne: Yeah. One of my favorite all time books about it, “Positioning,” Jack Trout. Did you ever read that?

Chris: I haven’t read it, but my girlfriend is currently reading it.

Suzanne: Really?

Chris: Yeah.

Suzanne: This is an old book. I think it was ’71 it came out.

Chris: Wow. Red and white cover.

Suzanne: Red and white cover, yeah. If you are the book nerd you purport to be, he writes with such conviction, and even though it’s a lot of old school marketing and brand, I think the concept that’s the most powerful is people are going to make up their minds. If you can help them make it up the way you want them to, that’s the best thing you can do as a brand, because once they decide otherwise, it’s there too.

Chris: That’s very true.

Suzanne: Yeah.

Chris: Yeah.

Suzanne: Cool. Check it out, and thank you so much for being part of the project.

Chris: Thank you.

Suzanne: We’re richer for having had your opinions here today.