The Rick Neuman Hypothesis: Great Teams Are Built With Clear Communication and Focus

Rick Neuman is an eCommerce, Retail Technology, and Product veteran having worked across Canada, the US, and Internationally for retailers like Canadian Tire, Sears, and Walmart. Joined Flipp a year ago to help families make life more affordable, and now leads the product strategy and technology development for this Canadian start-up.

In this episode of the Product Science Podcast, we cover Rick’s journey through product in Canada’s retail markets going from Sears to Walmart to Flipp. We also cover strategies on how to re-platform, the value of constantly listening to a customer’s pains, and how to empower teams and build trust in the shared product vision.

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Questions We Explore in This Episode

“As a chief product officer, you have to hire really talented people, empower them to truly own a piece of the overall strategy and make it clear how that piece connects to the others.”

How did Rick get into Tech & Product? Was product a well defined role in 2005? How important is a data driven strategy in a retail market? What was email marketing like in the 2000’s? What was the state of the Sears ecommerce platform when Rick came onboard?

How do you decide when you have to re-platform? What strategies and factors should be considered when re-platforming? How do you build a platform that meets both the customer’s & business’s needs at the same time? What was it like transitioning to support mobile in the early 2010’s? What benefits did Walmart experience after their re-platforming to support mobile?

What was it like to work at Walmart? What drew Rick to Walmart in particular? What was Walmart’s philosophy for empowering teams? What insights can be gleamed from being hands on with a company’s processes? How can product get closer to a customer and understanding the customer journey?

What is it like to work at Flipp? What in Rick’s career made him want to switch to Flipp? How was working for Flipp different from Walmart? How was Rick able to network his way into a role at Flipp?

How did Covid affect the retail industry? How did Flipp weather the pandemic? What are the 3 ways to make money in retail? How has the pandemic changed retail shopping? How has the pandemic affected customer loyalty with brands?

How do you bring innovations to market? How do you get insights into the needs of your customers, especially in retail? How can market innovations benefit merchants & brands alike? How are a brand’s needs different from a merchant’s when considering your go to market strategy?

What is consumer insight? What value does having a dedicated consumer insights group bring? How does customer research help keep you connected to a customer and their needs? What behavioral and shopping patterns can consumer insights reveal? Can consumer insights be used to test new product features?

How important is “focus” in product? How does focus differ between small startups and larger companies? What allowances do larger companies have that small startups can’t take risks on? What happens when small startups try to be multiple things at once? How does focus help you gain product market fit? Can focus help make a company more agile or does it lead to tunnel vision?

What makes a good relationship between product, engineering, and design? At what stage in problem solving should product start to include engineering? How can product better convey vision to engineers? How do you build trust between groups? How do you prevent friction between groups? When can problem solving be iterated on?

How do you launch a product without all of the promised features? How do you decide which features support your goal and which ones create obstacles? Are there benefits to pushing back a feature launch? How do you convey to stake holders that a feature needs to be pushed back? How can Agile help keep focus on core goals?

What advice does Rick have for advancing your career in product? What are Rick Neuman’s 4 key product principles on how to best manage your time? How do you keep listening to a customer’s needs? How do you expand a product vision from what it is into what it could become? How quickly and frequently should deliverables be shipped? How much time should be dedicated to building relationships & trust? How much coaching is involved in being a product leader?

Quotes from this episode

“As a chief product officer, you have to hire really talented people, empower them to truly own a piece of the overall strategy and make it clear how that piece connects to the others.” Click To Tweet ”There are really four pieces to product management that I stress over and over again– listening, vision, delivery and trust.” Click To Tweet ”Don't be afraid to ask for what you think is necessary for your product to be successful.” Click To Tweet


Holly: This week on The Product Science podcast, I’m excited to share a conversation with Rick Neuman. Rick is the Chief Product and Technology Officer at Flipp. He’s an eCommerce retail technology and product veteran who’s worked across Canada, the US and internationally for retailers like Canadian Tire, Sears and Walmart. He joined for Flipp a year ago to help families make life more affordable, and now leads the product strategy and technology development for this Canadian startup. Welcome, Rick.

Rick: Thanks so much. It’s great to be here.

Holly: I always like to hear a little bit about people’s backgrounds to start, so tell us a little bit about you. How did you get into tech and product?

Rick: How did I get into tech and product? I think like so many others, it was a bit of a surprise for me get into product as when I got into product I didn’t actually know what it was. I’ll tell you the story. I was at Canadian Tire, which is a large Canadian retailer. For those of you who didn’t grow up in Canada, you might not be familiar with buying hockey sticks and skates and auto parts all in the same spot. But I was working for Canadian Tire on their eCommerce team and I was responsible for their email marketing program. I considered myself a digital marketer. I got called up by a competitor, by Sears Canada to say, “Hey, do you want to come do our email program?” I met with the team and it was interesting, but at the end of the day, I said, “You know what? It’s not the right time for me. I don’t think I’m going to learn anymore doing that email program for a different retailer than what I’m doing. I just crossed a million subscribers. It’s a really exciting time.”

Rick: This was back in 2005 when that was a large number and at least in Canada. So I told them no. Then they came back to me and said, “Well, we’ve got this other job we’re thinking about, but we don’t know what it is and you don’t know what it is. But based off of the stories that you’ve told us around how you’re bringing data into automating email and trying to get more personalized, we should figure this out together.” I became the first product manager at Sears Canada, helping them kind of rebuild their eCommerce platform and think about how to kind of dynamically shape the experience in eCommerce. I got to hire up my first three product managers and start the team and learned along with an organization, what it looks a like as both Sears and myself had been reading about this as a discipline, but not really seeing it in action back in the early 2000s. It was fun to define it.

Holly: Yeah, that sounds awesome. I’d love to hear more about that. I mean, the company must have been pretty big, Sears Canada.

Rick: Yeah. I mean, Sears Canada was at one point one of the larger retailers in Canada. I mean it no longer exists, so that’s part of the story as well. But certainly of the large retailers, Canadian Tire is one of the largest retailers in Canada. Sears was at the time. Then I moved on to Walmart. I had an opportunity to work at some of the larger retail operations in product, which was really exciting.

Holly: Were you always sort of on the eCommerce touching email marketing sort of things? Did it become a much bigger picture? What did that look like?

Rick: It certainly became much bigger, especially when you’re defining product eCommerce retailer. I mean, the very first thing I did was revamp the checkout flow for to improve conversion and kind of work on the funnel. Then from there, we re-platformed. At the time, Sears was on the Amazon eCommerce platform and it didn’t make a whole lot of sense as Amazon was moving away from that direction and Sears was obviously powering a competitor. It was an opportunity for us to step back and rebuild from the start, which led to kind of end to end eCommerce exposure.

Holly: That’s really interesting because I think a lot of our listeners have gone through or are going through re-platforming. Tell me more about what that story was like. Early on, how did the re-platform decision even get made? Were you there for that or did it get passed to you?

Rick: I was there for that and then we did a similar re-platform when I moved to Walmart. If you want to talk re-platforming, I can definitely talk to you about a couple of different stories on the eCommerce front there. At Sears, it was a fairly straightforward decision. Again, we were on a platform that was delivered by Amazon. The features and the ability to customize and really kind of optimize the experience wasn’t there. We were on a different kind of black box system and it really left us wanting in terms of our ability to drive strategy.

Rick: We knew that we had to move to something else, and then the question was, what is that going to be? At the time, things like Shopify and some of the more advanced black boxes that actually give you more capability weren’t available and so we really had to step back and think about what are our needs, what are we trying to be and how are we going to continue to grow this eCommerce platform? Which was the growing piece of the business. It was exciting to be a part of a double digit growth entity back at that time.

Holly: Then tell me more about the re-platforming process itself. I mean, I know one of the big debates that I often see in re-platforming is, do you do lift and shift or do you sort of start with something new where you’re figuring out what the needs are from the people you have today instead of what you’ve built before? Tell us a bit more about what the approach was there.

Rick: Yeah. The approach was very much, I would say, like traditional product management. Understanding the needs of our customers first as a retailer. We were definitely looking at the customers who we had as well as the customers that we wanted to acquire, but it wasn’t as much of a brand shift in terms of a re-platform. It was more of a capability reset and then the ability to grow further from there. Understanding the customer needs of how do you want to shop for a variety of different categories. Sears at the time was very well known for major appliances and fashion and homewares, so you have a variety of categories you’re trying to cater to. Looking at those different customer segments of what journey are they on? What category are they trying to buy?

Rick: How do we cater to them best? It was definitely a chance to step back and rethink that, but then also think about where is our business going. What is the proportion of eCommerce that’s going to be happening? What do we assume their needs are going to be from a content perspective and then from a delivery and fulfillment perspective? How do we bring together an experience that’s going to be relevant to them as we continue to progress from there? Those were some of the major decision points that we had to make and reflecting on what the customer needs were. Then there were a ton of technology choices that had to be made inside that as well.

Holly: Yeah. Were there any things coming out of the customer conversations and reflecting on the customer needs that ended up being surprising to the team?

Rick: On the Sears front, I wouldn’t say so. But when we were doing this at Walmart a number of years later, that’s where I think more of the customer shifts came into play when it came to re-platforming. At the time, this was 2012, the major shift that was truly happening was the transition to mobile and the need to be far more mobile enabled and mobile ready. I think we were the first major retailer to have a fully responsive website that will transition across a number of break points in order to cater to a more mobile environment. That was some of the surprises that came out of the customer journey that led to technology and experience choices that really resonated. It helped us grow triple digits for a number of years after that point of the re-platform as kind of turned into what is now one of the largest eCommerce sites in Canada.

Holly: That’s awesome. What was it like working at Walmart Canada?

Rick: Working for Walmart was awesome. A ton of autonomy, because you had relatively small teams with lots of ambition and lots of capabilities in order to drive change. The people there were incredibly welcoming and looking for change and always looking for new ideas. I think the biggest thing is that you could bring a big impact to the people around you. To the customer base, you could actively make a bigger impact than you can in a lot of other places. My motivation for going there was very much … I mean, at the time I was doing my MBA, and my wife and I just had our second child and I was living this extremely busy lifestyle and so we needed to use another grocery competitor for online grocery.

Rick: But at the time, it was the only player in town, but it was incredibly expensive. The web experience was not what I was looking for. The delivery fulfillment was excellent, but I was paying 40% more than I needed to and I didn’t have that when you have two kids at home. It was purely out of necessity and I was super excited to bring online grocery as a concept to people like me who needed it but couldn’t necessarily afford the alternatives. That was one of the motivations. Having that kind of impact, being able to bring Walmart prices but to your door on a commodity that you definitely need the help with, it was inspiring. Those were some of the reasons why I absolutely loved it there.

Holly: No, that sounds amazing. Tell us more about the culture. You mentioned the teams were empowered. What made it work like that?

Rick: I think when you’re working for a everyday low cost operator, when you’re trying to keep your cost down so you can keep your prices down, you look at every facet and that means that you also look at the people side of things and try and make sure that you have a low cost base. So you stretch your team members. If you hire passionate people who are looking to be stretched, it can work incredibly well. At least in the eCommerce team, I felt like we built a really passionate team, but we didn’t have, let’s say, the same type of scope or scale that I’ve seen at larger organizations in the US or those with a different cost structure.

Rick: We all had to pitch in and do things that were way beyond our job description. The moment after Black Friday orders started to ease off the peak, I drove to the warehouse and I was picking orders and I loved it. It got you super ingrained in the entirety of the process. I think that’s healthy. It’s one of the reasons that I feel like you learn so much more in those high pressure environments where you’re pitching in all different cases because you’ve tried so many different things.

Holly: That’s really interesting. It’s interesting to hear that you actually drove to the warehouse and started picking orders. What are some of the other things that you’ve done to get a sense of the process or the customer experience?

Rick: I mean as a product manager, if you are not actively on the phone in your call center as another way to get close to the customer, you are missing a massive opportunity. Our call center was in Montreal and we would go to the call center and spend a day on calls regularly so that we really understood what our customers were going through. That was one other way that you can get closer to your customer. Not only on the order picking side, but on the what’s going wrong and how can you help them side and get a sense of their pain and frustration. Which then motivates you to go and make the whole system better. I’m really proud of where we’ve got it to and where it’s continued to get to in the years since I’ve been at Walmart Canada. After that, I moved down to the international side of Walmart and now I’ve spent a year at Flipp, which is equally exciting in terms of the things we’ve done there.

Holly: Yeah. Tell us more about that. What made you switch to Flipp?

Rick: Yeah. I’ve been working with Flipp for about a decade. I had worked with them at Sears. I had even done a little bit of work with them back at Canadian Tire, and then I had integrated with them at Walmart as well. If you’re not familiar with Flipp, it’s a platform that allows effectively your savings and deals as a retailer to reach an audience. Flipp’s whole purpose is to make life more affordable for families. We do that by taking all of the savings and deals that a retailer has to share and making them available inside that retailer’s web presence, on their site or on their app. But then aggregating that and providing a platform back to shoppers so that they can really better choose where they’re going to go put their hard earned money that week based on what’s on sale, what coupons are available and where they can meet the needs of their family best.

Holly: Okay, awesome. You’ve been working with them for a decade or so through these different companies and then something made you decide to go join them. How did that happen?

Rick: Yeah. I had been in the US for about two years working on Walmart International doing technology strategy and product management on the merchandising desk for international. Which was really exciting. I got to work with teams in China and Japan and Mexico, helping them think through their technology strategy. Hiring CIOs in different markets and really making the international technology landscape come together in a way that we had done in Canada. That was a lot of fun, but I realized that I was learning skills and I was further away from the customer than I’ve ever been before. The skills I was learning would only be applicable to Walmart. It was, how do you get 50 different people to agree on a product direction and then continue to agree over a number of weeks as you kind of built out that product and rolled it internationally? That was not going to be applicable.

Rick: It had been a little bit too long since I had done a UX deep dive with a customer. A little bit too long since I had truly grappled with a problem in the way that I love to, and I wanted to try something smaller. My family had also given me license to not live in Canada for only a number of years, and I was getting closer to the end of that license. I got a call from a head hunter who was looking for a CTO at Flipp and knowing Flipp, instead of returning the call to the head hunter, I called the CEO and said, “Hey, Wehuns, what are you absolutely looking for in a CTO? Because you know that I’m not especially technical. I don’t have a technology background. I am a computer geek by upbringing, but that is about as far as my technical skills extend, but I’ve been a CTO at Walmart. I’ve been a technology leader for a number of years now and my passion is product. Is that what you’re looking for and am I a fit?”

Rick: He got really excited. We had a number of calls over a number of months and it met all of my needs. I was looking for something smaller with an incredibly bright team. The people at Flipp are super passionate and some of the brightest people I’ve had the opportunity to work with in an area where I felt like we could make a big impact. My Walmart days of save money live better, translates really well to help families save money so they can live more affordably. It was a very, very nice transition. Getting to work in a tech startup has been something I’ve really been looking forward to as the pace of change and the extreme ownership are something that I never had in a Walmart or a Sears or even a Canadian Tire. It really checked all the boxes. I’ve been here for a year now. I literally crossed my year about a week ago and it’s been an awesome journey. It’s such a great team.

Holly: That’s awesome. Tell me more about the team at Flipp. How many people work there? Is it growing a lot? What does that look like?

Rick: Sure. We are a 400 person team based out of Toronto, Canada. It’s grown significantly. I think this past year with COVID was an interesting one. It’s a kind of tale of two stories pre, during and now a little bit post. I know that we’re not fully beyond, but certainly the retail environment is very different now than it was in those early days of March, April when you couldn’t find anything on a shelf and panic buying was at its peak. The growth this year has been phenomenal. It’s been our best year from a profitability perspective. We’re serving more merchants than we’ve ever served before. We are growing our content on the app. Our user base is growing. The frequency has grown. I don’t know if you’re familiar with the retail triangle. Has anyone ever talked to you about the retail triangle?

Holly: No. Tell else about the retail triangle.

Rick: All right. The three ways to make money in retail, and you can really only tug on any of these at a given time. You can get more customers, who come more often, or buy more when they come. That’s the retail triangle. Very, very basic. It’s exciting to see that over the last year at Flipp, we’ve gotten more customers who have come more frequently and have consumed more content when they’ve come. Which helps them then make a transaction with the merchant of their choice that week. It’s been a good year in a very tough year. The plans that we have for this coming year are really exciting. We’ve got lots of really cool product innovations that I’m so excited to bring to market.

Holly: Wonderful. So tell us a bit about how you bring innovations to market. What does that process look like?

Rick: Yeah. I think number one, it’s the insight and research into what are the needs of your customer. From a Flipp perspective, when I began, we really had two customers. We had shoppers and merchants. We’re trying our best to create a match. Helping shoppers choose where to go shop by bringing the merchants best foot forward and trying to create a match so that the shopper feels excited to go there and get the best deals possible, and the merchant then wins by building baskets, building traffic, and bringing in new customers that they might not have gotten otherwise. We’ve since expanded that a little bit to include brands because we realized that brands are equally incented to have the shopper ultimately choose them. The way that we did that is kind of the process that I wanted to talk about. If you ask what’s our innovation process, it’s starting with stepping back and then looking strategically at what our customers are looking for. In this case, our shoppers were looking for the best access and understanding of what savings and deals were available in the market.

Rick: As much as the retailer was trying to put their best foot forward with flyers and coupons and online deals and the things that we’re all trying to aggregate, the brands were equally interested in telling their savings and deal story. By being able to bring that voice in, we’re giving something more to the shopper and helping them choose even better by learning about new product innovation, new product launches, temporary discounts, or coupons that were available, that the brand wanted to push forward in order to give them the best opportunity to save money. Identifying that as an insight of what our shoppers were looking for, allowed us to then look at, okay, so what are the brands’ needs? What’s different in the way that we go to market that wouldn’t serve a brand? Then how do we evolve our platform to better incorporate a brand new customer set into it? We did that work over the summer and it’s been hugely successful in the back half of the year.

Holly: Cool. Let’s dive a little deeper into how did you identify that there was a need in the market that there was this unmet opportunity for the direct connection between the brands.

Rick: In the case of this particular example, the mechanism that we were looking at was really, we call it content comprehensiveness. We want to have all of the savings and deals. We want you to know as a shopper, that if you come to Flipp, you can find all of the deals that are available so you can make the most informed choice. There are some gaps in the content that we had and it’s always good to understand where you’re strong. We’re really strong in flyer content. We’re really strong in coupons. But also where you’re not as strong and where you can continue to serve your customer better. When it came to product innovation, new product launches and the voice of the brands, we recognized that that’s something our shoppers were interested in and we didn’t have the content.

Rick: It was an opportunity for us then to go and look at what would it take. What would it mean for us to be able to support brand messaging alongside retailer messaging to help that shopper choose? We started with some really lightweight innovation testing, a couple of placements here and there to gauge early adoption and how brands would feel and how shoppers would react. From there, we saw really positive results, and so we continued to iterate against it and continued to look at how we serve those different customer constituents.

Holly: Tell me a bit about the actual interaction with customers during research. I’ve seen companies of different stages and sizes can often do this very differently. Sometimes you’ve got a scrappier product research operation and sometimes you’ve got a whole consumer insights group and all these things. What does it look like at Flipp?

Rick: Yeah. We do have a consumer insights group, and I’m very thankful for that. I think sometimes it’s difficult to see your way to justifying having that type of dedicated focus on your customer research, but it’s absolutely pivotal to making the right decisions. Not only identifying new product opportunities, but then evaluating how you want to bring that product to market and how it’s being kind of consumed and then responded to by your customer. We use our product insights team extensively to understand the needs of the customer and what the gaps are, what the opportunities are. I would strongly advocate, if you are able to, to dedicate the focus there and maintain a direct connect to your customer base.

Holly: Yeah. One of the things that I’ve learned in my time especially since I went into consulting after being in startups, is that retail in particular often has really robust consumer insights. But I know that some of our listeners are coming from other industries where they’re not in retail and maybe they haven’t seen what consumer insights looks like in a retail organization. Can you tell us a little bit more about what kind of things come out of there that you guys are able to use?

Rick: Sure. I mean, part of it is looking at macro trends of what’s happening with shoppers in general. Kind of looking at third party research and aggregating that together to pull out insights on what is on the mind of the shopper. How are their buying behaviors changing? What are their shopping patterns? Some of the insights we’ve gotten that have been really helpful over COVID are things like, the average amount of trips that people are making is declining. It’s declining for a couple of different reasons, but primarily it’s because shopping is no longer as enjoyable as it once was for a lot of different reasons I’m sure you’re very familiar with and can resonate with. You want to do it less frequently because it doesn’t feel safe. Baskets then are growing as more consumption is happening in the home.

Rick: As baskets grow naturally and frequency declines, the value of each basket is so much more. We use that insight then in the way that we work with our retailers to kind of show them how important it is to win every single week as customers are kind of changing behavior in that way. Then the other thing that we’ve seen through more direct interaction with our customers is that loyalty is way down from where it was previously as more people change behavior. The reason loyalty is changing is not only behavioral shifts in terms of the frequency, but behavioral shifts in terms of how you shop. A lot more online shopping has really led to, “Okay, well maybe I don’t need to go to the same store that I always drove to because it’s five minutes from my home. Maybe I’ll open up and try something different because really the barrier is only a couple of characters versus 20 extra minutes of a drive. I’m willing to take that if the discount are better.”

Rick: Loyalty also dropped over COVID and kind of reset itself. Now you’ve got the need to go win and loyalty being no longer the moat that you thought you had in the past, and it really changed the game for a lot of grocers at the very least. Insights like that are really important then in how we work with our retailers to help them win, because it shows that we’re really in touch with how customers are thinking and behaving. That’s more of the pure insight side. Then we look at feature launches and how those are going to react with the customer base. We do a lot of listening sessions and interactive sessions with early features to get a sense of, will these things help you? How will you react if we put something like this at scale in this experience? To get a sense of, should we build A or B or something completely different? Because there’s so many ideas. You can only do so many of them and so many of them well, especially.

Holly: Yeah. What you’re touching on there is the importance of focus. Have you found a difference in how important that is at the different companies you’ve been at? Has that changed between the startup and the large eCommerce giants?

Rick: It’s interesting. Working in the startup has helped me appreciate the value of focus a whole lot more. I once had a one-on-one with Doug McMillan, he’s the CEO of Walmart. He described Walmart as an and company. It needs to do this and this and this and this because it’s gotten to a certain size. I really appreciate that perspective, but it also means that there is, at times, a lack of focus because there are a lot of ands that can be added to that list. I don’t begrudge it. In many ways it was inspiring and they’ve done incredibly well by continuing to kind of push the pace of innovation. At Flipp, as a smaller company, we don’t have the luxury of being in an and company.

Rick: We’re 400 people strong and if we don’t have focus, we can very easily do a little bit of this and a little bit of this and a little bit of this and do none of them very well. That focus has actually been really empowering to do a few things much better. At least, in the context of Flipp, the results have really proven out. By doing a few things better, we’ve seen incredible traction over the last year. The hard part is getting those things right. Sometimes if you’re taking fewer bets and a few of them don’t go the way you want, and if you don’t recognize that quickly, you can dig yourself a hole pretty fast. It’s not just what you do, it’s how you react to how things are working.

Holly: Have you had any experiences like that where you’ve learned that the hard way?

Rick: Definitely, both at Walmart and at Flipp. On the Walmart front, I think we actually went too far in building out a product, launching it, only to realize at that point that it wasn’t going the way that we wanted to, and then shelving it. In this case, it was Gift Registry, the Wedding and Baby Registry at Walmart. Which isn’t necessarily top of mind for those types of actions. Although I’d say we built a compelling product, but in the end, we didn’t have a team to go and operate it. If it didn’t exist at the store level, and if it didn’t exist with a team that was actively getting out there when people were making those decisions, no amount of technology was going to have it succeed. I think that was one where focus would’ve really helped us to identify earlier that this was not going to fly or that we had to approach it differently and change tact, and we didn’t fast enough.

Rick: Then at Flipp, there was a recent example. We were looking at a data services product to help retailers tell better stories off of our platform on the wider internet. The reaction was, the very large retailers have access to that kind of data and weren’t as eager to work with us as they could do a lot of it themselves. Then the smaller merchants weren’t really ready to tell that kind of dynamic and interesting story. It really opened up a rather narrow niche in the middle. Thankfully, I think we identified that really fast and we pivoted that product to focus on brands instead who really could use that kind of data to tell better stories for themselves off platform as well. It’s about how quickly you react.

Holly: How did you figure it out more quickly in the more recent case?

Rick: As a smaller team with focus, if something’s not working quickly and you can identify why it’s not working, you can’t justify continuing down that road. You have to pivot.

Holly: Yeah, absolutely. Tell me about working with engineers. We’ve talked a lot about high level product stuff and strategy, but what are some of your experiences with partnership with engineering or leading engineering? What do you think makes a good relationship between product and engineering?

Rick: What makes a good relationship between product and engineering? I mean, the normal things that make good relationships, communication, trust, respect. I’d say those are the ones that definitely come to mind. The wonderful thing about engineering is how it thinks about problems completely differently. If brought in early enough, can absolutely reshape your thinking on what’s easy, what’s hard, what’s possible even, and take a completely different approach to how you go and solve a problem. As long as your product team respects that that’s the kind of contribution you’re looking for and then trusts an engineer when they say, “This is hard for these reasons. Maybe we start here and it can give us a faster path to understand value.” I think you can get really, really far. But you also then need your engineering team to trust the product group and believe in the vision of where you’re going. I completely don’t buy into the philosophy of the engineers, just tell me what to build. I think you do need to help them understand the why as much as you’re informing the rest of the organization and your product team itself.

Holly: Yeah, absolutely. What about the other member of the triad, the designers?

Rick: The designers, a very, very similar story. Trust, communication, respect, it all plays into to how you balance the relationship and the dynamic. Everybody’s got a role to play, so let them play the role.

Holly: Do you have any lessons you’ve learned along the way about how to build trust between groups like these?

Rick: Lessons learned along the way on how to build trust. That’s a great question. I think honestly, it’s about building relationships. Getting people to know each other and know the different motivations, and also get a little bit more empathy for how the other functions work and what type of work they do. I mean, it comes back to some of the basic agile principles, but allowing the team to go through that storming and norming phase is what ultimately will build that trust. The more you can keep those teams dedicated and embedded and participatory with each other, the more that trust naturally builds up over time. Then honestly, I hate to say it, but a former boss of mine always stressed that when you bury people in work and focus them on the task at hand, a lot of the other things that build mistrust go away when you are really, really kind of laser focused on a mission. Nothing builds trust faster than a joint mission that one has to deliver against and something that seems monumentally hard and challenging.

Holly: Interesting. So you like to go for the big, hairy audacious goals?

Rick: Yeah. I’m trying as hard as possible to create as much stretch in the team. We look for, how do we create enough psychological safety that people aren’t worried about making a mistake. While creating the focus and the energy towards how do we stretch and how do we truly dream about what’s possible. I had a former boss of mine who when I was joined up at Walmart came and said, “Rick, we’re going to completely re-platform We’re going to do it six months and no retailer has ever done something like that before. Here are the keys. Here’s everything you need. Now just go do it. Put your head down and get it done.” It was incredibly inspiring. Hard, but we got it done.

Rick: From there, we iterated. Did we do every last feature that we said we were going to from the start? No, of course not. It’s an agile process and some things got cut off at the end, but did we do what was important for our customer? Absolutely. Did we see the results? Absolutely. Being kind of buried in that kind of work was incredibly inspiring. I look for opportunities to give the team a chance to step back and say, “Whoa, that’s really hard. I don’t think we can do it.” With enough safety to say, “Well, what’s the worst that happens if we don’t?”

Holly: Yeah. That sounds great. I’m really intrigued by the re-platforming timeline you just shared. What was it like getting through that?

Rick: Tiring, challenging.

Holly: Yeah. Were there many battles about the things that wouldn’t make it in? Or how did you get the chance to launch without all of the features that you had maybe at one point said you wanted? Because I know that’s a challenge that a lot of product people face.

Rick: Yeah, absolutely. I think it’s about communication and focus. We’ve talked about this already, even in the short time we’ve been talking, but being able to communicate clearly and regularly with leadership and with the wider team and then having a focus on what’s really important and what is mission critical, you can’t fail it. That and what is going to be part of your roadmap regardless and what you’re going to build up. The example I would use is, at Walmart, the feature that was really disappointing that I was disappointed that we didn’t have for day one and our leadership team was as well, was the ability to build a list on

Rick: It wasn’t a very well adopted feature on the previous platform, but there were people who used it. We knew that if we tried to maintain that feature and transition everything, et cetera, we’re not going to meet the timelines on quality on your basic function of finding a product, adding it to your basket and buying it and having it delivered in a timely fashion with great customer service. That was core. You have to understand where the line is and where you need to then make some adjustments in order to deliver your core with quality. We decided that was not on the right side of the line, so we should move it out. In all honesty, four months afterwards, that feature was alive and well and getting adoption than it had previously. But by moving it, it protected the launch. It protected the core of what we were trying to do. It was the right decision.

Holly: Yeah. It sounds like true agile, really shipping the thing that helps the customer get the core thing done. That’s what matters the most. Then if it’s outside of the core thing, then maybe it doesn’t have to be part of the first version.

Rick: Yep. In normal agile process, you’re using your story points and your forward projections on how you’re working to know where that line even is. That’s just another form of communication that’s necessary.

Holly: Yeah, absolutely. Are there any other sort of learnings that you’ve had along the way that you feel like we haven’t had a chance to talk about?

Rick: Any other learnings along the way? I mean, the role of product is constantly dynamic and changing, but one of the things that I found super useful in thinking through how to build the team and how to then train the team and keep people on the same page is helping product managers know how to divide their time and manage their time. I constantly come back to some principles on that that I think are important and that have resonated with my team. I’ll share them and maybe they’ll have somebody that’s out there. But there’s really four pieces to product management that I stress over and over again. The first is listening. Listening to your customer, listening to your company strategy, and then kind of constantly pulling yourself back into a listening mode. Because has what you heard one day is not going to be the same three months later.

Rick: The second is vision and having a really long term vision and knowing where the product is going, and being able to communicate that, articulate that, get a leadership team on board an investment team on board, and then ultimately your execution team on board. The third is delivery and being really, really good at shipping and shipping frequently, even if you’re uncomfortable. But just getting things out in front of customers as quickly as you possibly can. That’s having a great team that’s delivering frequently. Having an agile process, whatever that is, that you believe in and can run to see how things are going to be delivered. That’s all part of the delivery piece.

Rick: Then the last is trust. If you’re not spending a significant amount of your time as a product manager on having your customers trust that your product meets their needs, having your delivery team trust that you’re working on the right things and then having your leadership and investment team trust that you’re delivering against the vision that you sold originally, you’re never going to get the permission to keep the cycle going. Those are the four pieces of product management that have really helped me shape how different people spend their time. Then I get the most out of a product team that perhaps others can take advantage of as well.

Holly: Yeah, that’s fantastic. It aligns really well with what we at H2R Product Science called the product science principles. There’s three of them, but one of them is continuous discovery and delivery. I feel like you’re covering that well with listening and delivery, and the others are very similar. We’ve come to some similar conclusions in terms of what’s really important in having a core functioning product organization. That’s awesome. What are some ways that you’ve gone about helping product managers develop those skills?

Rick: Yeah. It’s actually kind of interesting when different product managers come from different backgrounds, they are often strong at one or two and then weak at one or two. So identifying that is really helpful. I’ve seen a lot of product managers come out of engineering or scrum or part of the delivery track. So they’re often very good at the delivery front and in many cases good at trust because they really understand what and where they can bring things forward, but have less skill on the listening and the vision front. Then in those cases, I can work with them to say, “All right, how are you getting market insights? I don’t want you just listening to me and then go writing a backlog. I want you pushing back on where things are going with real insight. The only way to do that is to get out there and listen to your customer. What’s your path? How are you doing that? Let me help you.”

Rick: Then conversely, what is the vision that you’re pushing for and how bold is it and how aggressive are you trying to get to? How can you sell me on what amazing looks like, and then the steps we’re going to take in order to get to amazing? In many cases, that’s just storytelling and synthesizing. But then also packaging that not just in a, here’s where we’re going, but the confidence that you’ve actually broken it down and know how to get there. Then I can work with them on how to better tell that story, how to do more analysis in order to show what it’s going to take in order to get there and what the risks are. Kind of drafting up the actual strategy documentation that helps you put it on paper to get everyone kind of on the same page.

Rick: I can then help them with that. in other cases, I’ve hired people right out of MBA who are incredibly hungry and have gone through the strategic process. Are really, really good at synthesizing data and setting a vision, and they’ve never worked an agile day in their life and they don’t know how to write a story. They don’t know how to respect the needs of an engineer in terms of prioritizing different things first. You’ve instead got to lean in and teach them the agile fundamentals and how to work with engineers and what expectations to set and just what does it mean to ship frequently and get over the fear of shipping. Using the framework helps me then understand the needs of a product manager and how to help them become more complete.

Holly: Yeah, that makes a lot of sense. How do you see the role of product leaders and coaching overlapping? How much coaching is there involved in being a product leader in your view?

Rick: As a chief product officer, you kind of have a couple of primary roles that you’ve got to do. One is, you have to hire really talented people that you believe can do all four of those things, and empower them to truly own a piece of the overall strategy and make it clear how that piece connects to the others. That’s kind of job number one, is the strategy and then the structure of how you’re going to enable things. Then giving people enough autonomy to really own something that’s meaningful that’s going to matter. From there, you’ve got to give them enough context on the macro vision of your company so that the work that they do connects, and they can make choices independently and really drive things on their own. To me, that’s coaching. That’s increasing context on the customer problem and the way that you see it kind of coming to bear across all the different products that you have.

Rick: At Flipp, we have three primary product areas and inside each we have a number of products that helps us deliver against that. We’ve got a shopper set of products, so Flipp app, Flipp web. All the different feature is inside of Flipp app, help to do that. You can browse flyers, you can clip coupons, you can add things to your list. Those are all the elements that bring together our shopper platform. We’ve got a merchant platform that helps merchants showcase their savings and deals on their own website. We call it Hosted because it’s hosted on the retailers’ property instead of Flipp property. We’re constantly innovating and growing that product set. Now we’re building out a new product set that looks at how do we allow the authoring and publication of totally new stories based off of what’s in your eCommerce feed, et cetera.

Rick: We’re building out those products. But you have to have a really clear understanding of how these different pieces connect together to create a whole, for the organization and then give a product leader the chance to go and own it. I’ve got a product manager who’s leading that Hosted product and I’m constantly pushing her on what’s the vision? Where is this going? How do we help those merchants tell even better stories in their own property? Today, it takes the form of an IFrame with their print content behind it and their coupon content coming in. We just re-platformed it and she’s doing a lovely job, but in the future, what could it be and how could it then shape our broader strategy? Super excited about the progress the team has made on that, and we’ve seen a number of merchants kind of move over to our latest Hosted platform and see great results from it.

Rick: I think there’s just tons of room to go there. But if I didn’t understand the role between that product and then the app and the different features and functions that fit between it, it would be really hard for me to inspire her to own something and then coach her on the context and everything else. I think that to me is the most important part. Then you can go and coach up on the fundamentals of product, how to write a story, and those things that I think are a lot easier to teach.

Holly: Context is so important and helpful for everyone throughout the organization. The higher up you go, the more that’s part of your job.

Rick: Right. Exactly.

Holly: If you could share one piece of advice with someone who’s maybe mid-career and looking to grow into a product leader position, what would you tell them?

Rick: I would tell them to embrace those four things we talked about, listen, vision, deliver, trust, and look at your product. If you’ve been given a chance to be in product management, I already think you’re one of the most fortunate people in the world. If you’re truly owning a product, I want you to especially lean into that vision side of things and look at what your product could be and think about the adjacencies and how far you can push it. Don’t be afraid to ask for what you think is necessary for your product to be successful. I see far too many product managers who have their agile team and have their vision, and it’s going to take six years to go get there. If you really, really believed in it, you would go to whoever your leadership team or your investment team is and ask for more or ask for what’s necessary in order to achieve your vision.

Rick: I mean, if you don’t ask for what you actually think you need, you’re never going to get it. If you pull your punches even before you ask, you’re never going to get it. If you pull your punches before you explore what’s possible, you’re never going to truly achieve what is the potential of your product. If you’re really solving a problem that exists out there and you’re super passionate about it, you should be going and asking everybody for help. I see too many product managers just getting into the head space of, I was asked to deliver this and I’ve got my resources, so let me just go write some stories and see where we get. That to me, isn’t product management.

Holly: Yeah. Well said. Where can people find you if they want to follow you?

Rick: Best place to find me is on LinkedIn. I think that’s the place where I am the most responsive. There’s various social media presences that exist across the web, but most of them are in various states of disrepair as you’ve got to focus your time and energy as well. I feel like social media just continues to pump out new options and you can’t keep up with all of them. LinkedIn is the best place to find me. But you can also find me on the Flipp app. Go download that because that’s where the fruits of my labor are being put every single day. I certainly hope that if you have opinions about it, you’d be willing to share them with me.

Holly: Wonderful. Well, thank you so much for your time today, Rick. This has been fantastic.

Rick: Yeah, it’s my pleasure. Thanks so much. This has been fun.