Product Management Image
This weeks episode we’re talking to Jennifer Limotte. Jennifer is an Entrepreneur and Technology and Product Leader who has successfully innovated, built and scaled, products and teams for start-ups and enterprises in the  B2B & B2C space across a number of verticals, Omnichannel Retail, CPG, healthcare, manufacturing and supply chain management. Along with owning her own businesses, Jennifer has consulted for some of the largest companies on the market. 

Jennifer’s Top 5 Leadership Tips:

Below is a summary of the Top 5 Leadership tips shared during the interview this week. Take a listen to the episode to learn more about the thoughts behind these tips –

  1. Always Be Learning
  2. Listen Carefully
  3. Culture Fit Is Key
  4. Building Products Is About The Journey
  5. Tech Is Not A Supplement For Good Business Strategy

We hope you enjoy the episode. You can find even more Full Stack Leader episodes here:


Show Transcript

Jennifer Limotte Session

Ryan: Hello and welcome to this week’s episode of the full stack leader podcast. This week, I’m excited to have my friend and colleague Jennifer who I’ve worked with. Dionne CPO level on a number of projects. She’s an expert in e-commerce and she’s got an exciting new thing that she’s about to begin and announced soon. We’re excited to have you here this week. Jennifer. Welcome. 

Jennifer: Hey Ryan. So great to be here and be able to talk about commerce and retail and my career and leadership. So thanks for having me. 

Ryan: Yeah. Amazing. Maybe you can tell us a little bit about how you got into this for the industry and, and how your career path has led you to this time.

Jennifer: Certainly. I started my career at EDS and at the time I was really looking at two career paths.

My educational background was in accounting and information systems and I had the choice to kind of go the pure accounting route or technology. It was the end of the first.com boom. And it was an exciting time and tech and I was one of the few females at the time and had a great opportunity to go work for EDS. 

And, it was an exciting time there was Y2K happening and everybody was worried about the massive legacy system shut down. and so it was really a great time to be a female in tech and learning. But I yearned for it. More challenges. And, I had the opportunity to go work for a startup very early on one of my cohorts and the engineering program at EDS reached out to me because he is working for a startup that was later acquired by CMGI.

It was about that time that I dipped my toe in more emergent tech and definitely more emergent. Delivery practices. Talan was one of the early shops, doing precursors to agile and scrum. And so we’re extreme programming. We were looking at working with a lot of startups at the time.

And then there were companies like Barnes and noble.com that were really starting to dip their toe in the e-commerce market. And we were really entrenched in those companies and delivering that first generation of, of.com systems.

And so it was really at that time that I went to work for my first startup and we were really helping all the early startups and people looking to go into the early.com and build their first commerce sites direct to consumer build this site. So we had customers like in capital and delivered their first capability around e-commerce and modern consumer banking.

We had Barnes and noble.com that we were working with to roll out their early, e-commerce and buy online, systems. And then we were working with, a company called exchange path, which was a very early competitor to PayPal.

Jennifer: Following that, and the.com crash was really the first time. I jumped into more of the product side. So we had been working with these customers delivering in this very kind of agile, extreme programming way. And I really found that my passion lied at the intersection of the consumer experience, the business and the technology.

 And so I had the opportunity to go work for a startup that was in the supplier relationship management space, back then to be in product. You needed to be much more technical in nature. And so this was really a heavy data-driven product and the supplier relationship management space, they were trying to roll a product to market.

And the big gap there is they had 10 customers and over $9 billion of GEs direct material supply chain flowing through their system, but they actually hadn’t built a product. They branch their code base about 10 times. So this is kind of a very early lesson in B2B and my task parallel code. Yeah, exactly.

Parallel code, a lot of branching. And so my task was really to come in and look at that and help them develop a product that could scale and roll out to the rest of their customers. So I spent it. The next couple of months, working with customers and digging and reading code to figure out what had been built and then really developing this very complex system that dealt with, EDI, believe it or not.

So you can imagine that large manufacturers were dealing with something called rip and read EDI. So that meant the guys like Boeing and Caterpillar and John Deere and others were receiving printed faxes and other things that they needed their supply chains to deliver. They would rip it off and have these expedited meetings.

That’s why they called it rip and read EDI. And we were really at the forefront of consolidating all that information. And you can imagine as the supply chains were changing, there were things like the planning that was happening. You know what it was. It was a very exciting time. I know it doesn’t sound super sexy, but it was because we were doing things like just in time delivery and just in time manufacturing.

And we were working with some of the early guys like Toyota on what they called at the time, milk runs, meaning we knew what the supply chains needed. We knew what the new manufacturing process needed. And so we were taking the product and staging it in distribution centers. The vendors themselves were holding this product and our binner managed inventory kind of way.

And then it was, really arriving on their manufacturing lines and floors to be able to produce that product just in time. 

Ryan: Wow. And it really highlights how much the evolution of this entire process has taken place over the course of. 

Jennifer: Yeah, I think that’s exactly right. I think it’s really interesting because the supply chain now with AI is going through its oh, metamorphosis.

And then when you start to look at other industries, just like retail, it was only recently that we really started to move into this drop ship paradigm or this idea that vendors hold the inventory. Ultimately it’s kind of much more complex because you’re dealing with a finished product. A lot of these ideas came from those late nineties, early two thousands and came from manufacturing, right?

Just like lean business models and lean UX. All that really came from the efficiencies that were gained by those companies. Really trying to think about how they delivered products to market in a more effective way. 

Ryan: Yeah. I mean, even the entire combine system coming out of Toyota as a whole, right. So that there’s an entire project management methodology built out of supply chain methodology.  And that always makes me, 

Jennifer: yeah. And I really, I think that’s why I gravitated towards it. And I think, it was a very tangible learning point for me in terms of, as these new, you know, agile and technology and methodologies, can come to market. And we started to use them. I had a very early entry point to that, right?

Not only extreme programming and really, this idea of partner programming and teams working together to build broader products. But also, you know, things like weekly builds and iterative development and getting real time feedback from your customer, all along the way. In some cases, some of that is, is just making end to industry or has, and the past five years.

But, for me, that’s something I experienced in the early two thousands and experienced it not only in the technology way, but in an analogous way and manufacturing. So I think that was this really instrumental point in my career where not only was I really learning what it meant to build products and products that scale and can make money.

I ate the branch code. We often learn from, from other people’s mistakes and from our own as well, but we learn more from seeing things done wrong sometimes than we do seeing it done. Right. But then I had this very early exposure to these technologies and methodologies around just in time and efficiency and it’s really all these experiences that start to culminate and.

You know how I think about retail and how I think about technology and how I think about product 

Ryan: and how did that evolve after you kind of came out of those early legacy startup, technology companies, what happened after that for you? 

Jennifer: Yeah. So from there I went to work for another startup.

 It was really one of the investors that at the time, Connecticut innovations that connected me with Dr. Alex Schuessler and he had a startup coming out of NYU. It was in the original equipment manufacturing space, and really what it was an early marketplace. To drive network effects between the heavy equipment rental companies.

So think of the time of the nation’s rent and the United rentals, right? Like when you drive down the street and you see somebody with that lift equipment or the tractors and other things, and then the OEM manufacturers themselves, and it was really focused around equipment lifecycle management.

 And we had a lot of technologies that, kinda mimicked, early IOT. So the whole concept was as this company, Piece of equipment rolled off the manufacturing line. It had this very intricate series of pieces and parts that pulled it together. And, honestly , it was a very complex data structure.

So you might have John Deere who’s assembling and the motors are coming from Honda. And the widget is coming from some small mom and pop, but to take care of that piece of equipment, you have to know all those things. You have to know things like which parts are up for her safety and warranty recall, based on the mileage, how long do those parts work based on the usage?

And so there was a really interesting problem happening at the time where as you start to, to look at that complex kind of manufacturing chain and the piece of equipment and its afterlife, and the aftermarket, how do you even care and feed for that? And so really we were instrumental in that.

So we accumulated all that information. So we went to Honda and we got their motor information. And, we went to a small mom and pop and got their widgets. And so we knew everything about every piece of equipment in their fleet down to, you know, what bolt was on its tire. We knew its entire rental history and where it was in the market.

And when the equipment came in and checked in from being rented. We knew everything that needed to happen to that piece of equipment. We also managed that equipment when it was in the field. So if it was in the field and it had a safety recall, then we were really stepping into that gap and helping both the manufacturer and the rental company and saying, Hey, this piece of equipment is safe and we need to trade it out.

Ryan: So how much, how much R and D does it take to create something like that? Because it really is a pretty wide array of variables that exist within it. Did you guys spend a lot of time just iterating or did you have a lot of perspective going. 

Jennifer: Yeah. We worked with this very, Ronnie Peters was his name and he was really great at design.

 He came out of Apple, and you know, I was very fortunate to work with someone, that talent kind of at that point in my career, very early in my career. And we really went in and spent a lot of time doing customer discovery. 

We put ourselves in the shops and we figured out what was going on.

And we went into the manufacturer, but we also leveraged a lot of Dr. Schuessler’s knowledge at the time, he had spent about two years consulting in that space, and knew a lot about it. And one of the big challenges these rental companies faced was equipment utilization and tool time. And so that sounds really buzzwordy.

 But if you think of these mechanics as the rock star of that industry, and you think about the economics of that equipment, one of the really interesting things is once you buy that equipment, which has a decent cost and its life, it’s actually longer, than its depreciation life.

And so once it’s sitting on your lot, then if it’s not being rented out, then you’re losing thousands of days for each piece of equipment. Right. And so really for us, our initial objective was really to. Increase the equipment’s utilization. And we use that as an early KPI and benchmark around really optimizing the process.

There was a little bit of iteration and kind of learning around that. For example, we learned things like, oh gosh, we had the background screen is white. And once we went into the rooms where they’re repairing the equipment and you have shopped lights, the white doesn’t play right.

You’re glaring the mechanics in the eyes. But we also learned some really interesting things about the fact that, at the time, all of this information about a piece of equipment was rolling out in a manual way. And so what that really meant to the manufacturers is they were getting all these missed orders in this spot.

And every year the rental company and the OEM would come to the table and there would be these very contentious kinds of negotiations around the price of equipment and what things look like. And there were really big pain points on both sides of that market. And so the fascinating thing is once we got in and started to understand how this information flowed, we started to see that, you know, if Honda changes its numbers, or if this tractor starts to use a different motor than the material might not reach the rental company until six to nine months out.

Right. And so you can imagine over that timeline, not only the misfires on the parts, but equipment was sitting on the lot that could be redeployed because maybe there was a broken right. And so the P was really around making the information available. And then providing the ability to quickly order the part and then the money at the time was made off the transaction, on each and every deal.

And you can imagine today, where there was a wealth of information, this was 2003 to five. And so you can imagine the type of information they’re sitting on in terms of data and how effective certain parts are and how those parts have worked over time from kind of motors to wheels, to all these things.

So that was a super exciting time. And, I still consider Dr. Schuessler a great mentor of mine. I learned so much from him. He was one of the very early behavioral economists. Which, you at the time they didn’t even, it was very concise in economics and they weren’t really considering kind of consumer behavior that could be somewhat erratic and how that kind of played into all of that.

 So that was probably one of my favorite product jobs to this day. I was one of their early key hires and then grew out their product and went to the market team and took them from about zero to 7 million in ARR. so 

Ryan: Wow, it’s amazing. 

Jennifer: So then from there I actually launched my own direct to consumer company.

I think the premise for me has always been a learning mentality and I always loved consumer behavior and wanted to dip my toe in the water there. So that was really my first shift, as a product person in terms of direct to consumer. Prior to that, as an engineer, we had definitely developed these early direct to consumer sites and, it w.

Before the time of really heavy UX. I mean, we certainly had UI designers and that sort of thing, but we weren’t thinking about consumer behavior. So this 

Ryan: was a lot like pre-built commerce engines that exist now. And we kind of take it for granted because we have them in our capabilities, or like at our fingertips.

But back then, I think you were probably in, at that early stage, direct to the consumer. Really inventing a lot of things, I assume. 

Jennifer: Yeah. A hundred percent. I mean that all, you know, the information as a service, the platforms as a service, the accelerators as a service, none of that really existed.

We were building everything from the ground up and, and in some ways, you know, sometimes it was easier and sometimes it was certainly slower, right? I mean, anytime you start to put all this third-party software together, sometimes it doesn’t mesh and there’s learnings there, but I think there was value in having to build things from scratch and the type of background that gives you and the type of technologists that creates right.

So at that time I started my own company called milk and cookies. It was really honestly a side hustle. My husband and I had always dreamed about having a little coffee shop in the west village. And we originally just said, Hey, we’re gonna launch this cookie shop. It was the cupcake craze of New York and Magnolia bakery and all those things.


Ryan: You know, very similar to the fracturing and industry, but totally different, 

Jennifer: completely unparalleled. I mean, talking about jumping off a cliff, I’m going to make some cookies. How about that? 

Ryan: And aunt’s still instilled very much, have to be user centric and get feedback and, you know, make adjustments.

Jennifer: It was a lesson and it was a really great lesson. So I had gone from EDS where, you know, funding isn’t a question to Talan during the kind of first.com where people were throwing money at you, to these two very cash-strapped startups where you have these very lean teams trying to do exceptional things.

And then talk about bootstrapped and no cash tray starting your own direct to consumer business. So we launched this little big shop in the west village. It was a very early lesson, ironic lesson, at the time. I don’t know if you ever remember daily candy. Do you remember them? I do remember.

Ryan: Yeah. The email newsletter. 

Jennifer: Yeah, they were great. And so we started this little cookie shop because of that, at the time. You know, in the west village, there are plenty of Italian bakeries and then there were cupcakes and, but nobody was really doing simple Americana. So we developed this concept called milk and cookies, a bakery, super unique.

And it was really focused around Americana, fresh organic ingredients. And, you know, hearkening back to you just in time and manufacturing the food business. It can be very challenging in terms of margins. And so I was really trying to think of a way to prevent the wastage. And so we came up with this idea that people could come in and kind of construct their own cookies.

And so they could come in and choose from a number of base doses. None of these doses could be made in advance. They could be frozen, they could be kept fresh. And then you can choose from over a hundred different ingredients. And because cookies could be baked in near real time, eight to 10 minutes, maybe even shorter and a commercial oven, we were allowing people to kind of call in orders.

So we had the website that my husband and I built, and they kept placing their orders online. And then we were doing delivery kind of in those early days. 

Ryan: How would you receive those orders if they were replaced online? 

Jennifer: They were just going into a database. And then we had the orders that we could kind of pull up on our POS systems and it was integrated.

 The beauty was my husband and I were both technologists. Right. And that’s it, it was hard. The POS as systems were super limited, there was no square, there’s some challenges even with those types of tech. But yeah, so as a technologist, we were, we were well-suited to do some of this.

And so we were able to kind of put our own systems and processes in place that helped drive some efficiency, around that and allowed us to kind of give consumers what they want. And so here we are in the west village doing delivery and Christmas rolls around. And at the time, I had gotten connected to some folks over at the hotel.

And they wanted to make gift baskets. So here I am, Christmas time, 500 square feet in the west village and w hotels who want to order 10,000 gift baskets for me. Can you imagine 

Ryan: A classic leadership moment right here? 

Jennifer: This is a classic leadership and entrepreneur moment. So I was not in my head and said absolutely.

 Ironically I was pregnant at the time with my daughter. And so that had a set of challenges of its own. And then. I signed the contract and then I proceeded to figure out how it was going to deliver 10,000 gift baskets out of 500 square feet in the west village. 

Ryan: And know this particular version of it for you was in this kind of baking.

But it is a very true scenario that happens so often it’s like we automatically hit scale. Like we’re kind of building towards it thinking it’s going to come, things come and then scale. And, I imagine that was a great lesson in how to work with 

Jennifer: that. There are a couple of great lessons there.

One is, PRS. Great. And your friend, and I think in the world of social media, we’ve kind of drifted away from that a little bit, but you know, the consumer in general, trust that. And, as the cost of, this is an aside, but as the cost of digital advertising has gone up and all these things kind of return to nostalgia, I think the second thing is my experience in scale was really around process and technology.

 And I’ll tell you, process and technology are a heck of a lot easier to scale than a physical business. Right? And then the third thing is, Going back to the PR point, daily candy did a very early release for us. They stopped by, we were very fortunate. They wrote an article on us and at lunchtime, the day it was released over 600 people showed up at the bakery and were wrapped around the corner.

Ryan: Did you have any idea that you would have that kind of response? 

Jennifer: I had zero idea and, obviously it was overwhelming, launching this thing and remember, this was just a passion project. This was, Hey, I had been in technology. I’ve been working really hard. I started this as a passion project on the side, but it really kind of hastened my exit from technology because now we had this company.

You know, it has grown ahead of its own. Right. And, these are obviously first world problems. It was an exciting time, but it was also extremely overwhelming. So here I am pregnant, very sick, right before Christmas driving upstate to find a co-packer to help me create 10,000 gift baskets and under 30 days.

And that was certainly a learning curve for me, even thinking about how you scale recipes to be able to create any cookies? And 

Ryan: then packaging fulfillment, things like that. Yeah. 

Jennifer: , a hundred percent. And so then, so then we really leveraged, well, I think there was kind of an aha moment.

So we were, we had a lot of great press. I was on the today show and good morning America and Roker on the road. And, you know, it was certainly an exciting and fun time. and then I, you know, then you anchor around, well, now it’s the holidays and it’s a little bit dead. I should tell you, we kind of made it through the holidays.

 With the subway strike. Do you remember when that happened? And the kind of the subways were shut down and all of that and in New York, maybe not because you were out in LA, but, uh, you know, even simple things like doing delivery, my delivery guys couldn’t get on the subway. And there were a few bumps and bruises, but all the things we kind of experienced as entrepreneurs.

And it was really at that point, we hit the post holiday lull. My husband and I went to LA and kind of took a two or three week break. And I came back and started to think about, well, certainly that time’s coming up. As each of these spikes in press hits, as a food business, it’s very exciting.

And you got these big blips on your radar, but then, you’re in New York and it’s highly, highly competitive, and very few businesses make it through the first, you know, first year or two. And so you start to, 

Ryan: especially in that city where there’s so much competition, 

Jennifer: a hundred percent and you start to think about, well, gosh, how am I going to scale this and keep this alive?

And then it was really at that point that we started to look at a kind of two different lines of business. One was wholesale. So we had a partnership with, With w hotels and we were doing Mandy cookies and their locations across the us. I, we started to work with some other corporations and we were doing a delivery for them.

Like the J crew would call in orders to us and AIG. And so we had a line of business going there and then we started to do a ton and, and parties and entertainment and, you know, weddings and that sort of thing. So that’s really how we were able to scale that business. 

Ryan: We’re in, where did that lead you? So you come out of that and how do you come back to tech itself? 

Jennifer: Yeah, so it, you know, certainly it was a fun time, but at the time, you know, funding a food business, It was not something like now there’s all this excitement or there was, you know, there is around CPG and retail and fashion brands and all those things.

But getting that type of funding back then was really hard. And again, this was just supposed to be a passion project. So, we got through the holidays, it was about two years in and we had really scaled the business and built out this line of business. But ultimately, I miss my day job.

I miss launching products and I miss technology. And so, we were fortuitous at the time. My husband had an opportunity to go to San Francisco and work for a startup. And at the same time, we were approached by a restaurant family in New York who owned a number of businesses. And they offered us a bit of a sweetheart deal and we stepped out, and we took off to San Francisco.

Ryan: New chapter.

 And so what, when you come back around to this kind of evolutionary period in the time that you had exited the kind of formal tech industry, although it sounds like you were on the ground learning a bunch of things, what did you come back with? 

Jennifer: Yeah, so we were in San Francisco at the time and, you know, again, I had gone from kind of large, big high-tech to, fast paced.com tech and the startup world, product in the startup world, launching my own business.

And at the time I had my daughter and I felt like I needed some flexibility and my husband was also working for a tech company at the time. And I really decided to then start to dip my toe in the water with consulting. And so that was really my first foray into large companies and industry. So I had always been on the outside looking in, and it was really at that time that I started to consult with a healthcare company.

And that in itself had learnings for me that I think has really helped, evolve my career and evolve my thinking and that sort of thing. 

Ryan: Yeah, absolutely. 

Jennifer: So at that point, I was working for a healthcare company in San Francisco, and you know, they. I think this was kind of my first lesson and in culture fit because my personality certainly was entrepreneur and it fits startups, , a belt, like a glove.

And here I was kind of with this wealth of experience, jumping into a company. And, you know, I, it was a stark contrast, it was a stark contrast in how they thought about the product and, frankly , they weren’t right. It was, when you started to look at these companies, it was that whole project versus product culture.

 Here, I used to like developing strategies and launching software, and now, you know, I’m helping a company in healthcare and they’re doing basic things like. Gosh, how do we launch software that supports our B2B clients and onboards them and, simple things I took for granted like integrations and API APIs and all these things that I had been working on or small agile teams or, teams and agile methodologies really 

Ryan: slowed right down.

Jennifer: It slowed to a screeching halt. 

Ryan: I think this is an interesting point too, because the area that you’re talking about project versus product and the way that maybe legacy enterprise companies look at it versus startups, it was. Where the space was left disrupted by the startups and people like you who are getting in there and going, oh, okay.

How can we fill this hole in a, some kind of a, a business that deals in manufacturing or parts and things like that all the way to, really like people that aren’t thinking about their customers on the user experience level, quite yet at this phase and startup after startup, when after that.

Jennifer: I am a hundred percent, and really the startup culture is around results and it and taking risks and having outcomes. And when you start to get into these larger companies, you start to see that, rightfully , by wall street and others they’re held to a different measure, right? I mean, even if you look at what happened with Amazon versus what happened with traditional retailers, right?

Retail retailers are expected to make returns quarter over quarter. Amazon very early on was given a lot of grief. Right. And frankly, they’re not really a retail company, they’re a tech company and they’re both, so they have this great opportunity, but how do these companies really think about technology and what’s the risks their executives can take and, you know, more important.

Ryan: Yeah. And like really on that same topic is really as who’s already entrenched in the business. And I think that you bring up bookstores, it’s a great example of what Amazon really early was most of the kind of traditional brick and mortar bookstores had to take a defensive position to protect their foot traffic.

 It was the most important thing. And Amazon was able to come in a much more unique, totally unique way to, to, really gather customers in the digitals, which people didn’t value at the time. And they were just simply making sure that those pieces were taken care of. 

Jennifer: Yeah, a hundred percent and you know, I studied a lot of history in school and I think that, that really plays into how I think about the world and how I would think about strategies and other things.

But you know, those who fail to study history are doomed to repeat it. And, I’ll tell you I was consulting well, as part of the work I was doing with some of the largest retailers in the US in 2010 to 12, and one of the fascinating things is they didn’t view Amazon as their competitor at the time.

Right? I mean, they really didn’t 

Ryan: That’s that, that is within the last decade, I think really everyone, the scope of what Amazon is doing. And then some of those really powerful tool sets that they had developed on the technology side or on the fulfillment side. They, once they kicked in, if everyone became.

Jennifer: A thousand percent. And that’s really been fascinating for me. So when I jumped in consulting, I really started in healthcare. So I’ve worked in a number of industries. I did some work in finance with some large credit card companies, but really my passion was anchoring and having my own retail business was really on the retail side.

And so I really started to focus there , and obviously, you know, that’s how you and I met. You know, retail is very exciting. But when you think about focusing on this Amazon thing a little more on what happened when you think about these traditional retailers, they were in a position of power and.

You know, this is really important. When thinking about innovation and thinking about innovation placed it for things like a startup’s job is to innovate, right? But once you reach a certain capacity as a brand, then the old adage was really to protect the brand. And so you start to suppress innovation to protect the market.

And then really what we’ve seen with this drastic shift in consumer expectations and startups kind of leading the market and shifting and changing the customer expectation is everybody else was forced to come along for the ride. And so that was really leaning to these large kinds of fortune 500 retailers being in the space where, you know, they launched e-commerce as an incubator and innovation idea, but it was a little bit like separation of church and state, right.

Where the brick and mortar didn’t talk to e-commerce. And so how do you really even think about that unified commerce experience? And I know I was at the time working, with an executive over at Macy’s Mike Tobin. And you know, I think he was a really early strategic leader in kind of bricks versus clicks and thinking about stores as a fulfillment center.

And we got to work on some super exciting projects, putting digital in store and, you know, there were a number of challenges when you think that these companies aren’t a tech first company, first of all, like how they approach product teams. So there was a big shift from. Taking these traditional BA some project teams and then trying to hire and shift them to a product team.

And then there were struggles with, comm versus stores and there were struggles with even data infrastructure and the scale of data. Right. 

Ryan: So, yeah, and I think, I think that actually is highlighting like some of the kind of key elements that made Amazon so cool is that they solved a lot of the foundational commerce elements that had to be solved.

And they thought about it from a technology and a unification point of view, but a lot of the fragmentation happening, even with really large retailers, over the last decade, meant that a lot of the basic tool sets to create commerce or to create fulfillment. They didn’t mature until pretty recently.

Jennifer: Yeah. And I still think some of them are muttering. And again, a lot of that innovation is coming from startups and pushing it. But I think there’s one other really important aspect, that, you know, as a tech leader and as a product leader at it comes top of mind, and that is Amazon didn’t have to deal with legacy technology.

 It was very easy to say, I’m going to launch this. And I don’t mean easy. I don’t mean that flipping 

Ryan: Amazon’s easy. Yeah. I hear you. They weren’t refactoring an entire system. , in order to create a technology that could support it, it was new. They were creating a new system. 

Jennifer: They were creating a new system and a new company and they were building it from scratch and they were highly funded and they were given the graciousness of not being obligated to wall street and quarter over quarter.

Right. Yeah. And early on, I mean, obviously that has shifted now, but they’re also a tech company and that was a very smart strategy. Right. And so I think with a lot of these retailers, , as they started to morph, they were Laden down with this legacy technology. And how do you get that data out of your legacy systems and, frankly, A lot of them just didn’t have the infrastructure or the teams that had built something from the ground up.

. A lot of that lived in startups. So how do you take teams who have managed pieces of technology and shift them to this innovation space and kind of creating new business models and creating new tech stocks and that sort of thing. So, yeah. 

Ryan: And educating, , business owners who may not even care about tech at that time too.

So you have to educate them, have them understand this future wave is coming and they either have to think. Level of disrupt or they’re not going to be able to keep up, but they don’t know that at the time, this is, this has just become clear in the last decade, but maybe in the last five to seven years for a lot of these companies, 

Jennifer: A hundred percent and that, and so I was really kind of at the forefront of that and , it wasn’t glamorous, it was almost like a startup again. But, I consulted with this innovation team that was kind of set in the core and we were doing things like buy online and pick up in store and how do we enable associates?

 But it goes back to the crux and this is where I really leaned on my technology background. There were things like, how do you get networks in store to work when you’ve got two Tones running into them? And you’ve got people walking into them with mobile devices, right? How do you make APIs and services work?

They’re networked and orchestrating store procedures on the mainframe to build MVP. And how do you start shifting out of that? And so really I cut my teeth in that world and then worked with a lot of startups in the space that we’re trying to approach these retailers. And I think that’s where my experience really came in because I had a ton of experience in the B2B space and really thinking about how you approach manufacturers.

so the other thing I was really focused on is helping startups and really helping startups. I realize how their technology could apply to these large retailers and help them approach the market.

 And this is where I talk a lot about the great divide between innovation and industry. So, you know, I really started my product career there and trying to sell into these large manufacturers and really trying to get them to understand how this technology could apply to them and help them. And here I had come full circle, right?

 I had gone from high-tech technology to B2B, to launching my own direct to consumer, to really helping these retailers in their modern kind of unified commerce strategies. And now I start working with startups and how they approach these retailers and think about the go to market. And this, for me, it was, you know, a moment.

It was a moment to realize that there really was such a huge gap like that gap between innovation and technology and the industry really had become exponential. And so one of the things I saw a lot is tech companies showing up and selling their TAC. But it was a bit like the telephone game or a translation game, right.

So they’re showing up and they’re talking about API APIs and speeds and all these things. And, you know, it was like one speaking English and one speaking French. And I really started to step into that void. And, I would say with things like AI and machine learning, um, and other things, that gap just keeps growing and growing.

So the ability for industry to absorb those innovations, I think, keeps getting worse. 

Ryan: Yeah. And I think this is one of the interesting parts about your career and why I want to talk to you is that leadership, it comes in lots of different forms, but one of the forms is actually leading the pur leading the evolution of an entire industry and being there in, in the very early stages and watching it evolve over the course of time, but like being able to guide people and open things up for a big audience.

It’s one of the things I’ve appreciated about the work you’ve done. 

Jennifer: Yeah. A hundred percent. And honestly, that’s been a learning curve, so one of the big things is like, how do you lead innovation teams when they’re in a structure that half is traditionally waterfall, half learning agile or they’re behaving and fragile mandates.

Ryan: Yeah. And it doesn’t facilitate innovation. 

Jennifer: It certainly doesn’t facilitate innovation and it certainly highlights a culture fit and, you know, really hiring the types of teams that can disrupt becomes very challenging, right. And not space because, people that want to innovate are really at the startups and they’re changing things, but people that need to disrupt need that skill and they have to have cycles and they have to have experienced it.

You know, they can’t just dip their toe in the water, or they can’t just develop features. Like we’re talking about building something from the ground up, discovering business models, figuring things out and you know, you and I have talked a lot about this, but this is where it’s not just the, what, it’s the how.

Right. And it’s the type of leadership you bring to the game that really shows up here. So , a lot of my job, I love to deliver products. I love innovation and I love pleasing the consumer, but, I’ve really developed and honed my skills over the past 10 to 12 years in helping people that don’t understand technology, understand that.

And coaching people and bringing them along for the ride and using all these experiences from my early career. And, how do you do agile? And, certainly, there were some frustration and friction points for me, where I had to learn really viable skills in terms of listening because you know, I, as a tendency can be when you’re an entrepreneur and an innovator.

She liked to deliver goals and results. But the reality is, you have to follow the lead in these organizations and you can’t come in like a bull in a China shop and kind of disrupt them. You have to take them along for the ride. And there’s some patients that develop from that. But I think it’s also, you know, really valuable as a leader and really valuable as an entrepreneur to have that experience.

 And I was going to say, and then I think that’s kind of led me full circle to where I am today, which is really an amplification of that. I know you and I have talked about this new venture I’m working on and really. What we’re really focused on is, in this day and age of the Amazon world, how do we help these small and medium businesses compete?

And so when you really think about the dynamic shift in digital, kind of going back to my milk and cookie days, right. Where I was able to build my own tech by most small and medium business owners. Can’t and certainly there’s platforms out there, but, I think you’ve worked on them.

I’ve worked on them. They’re not the easiest in the world, especially when you don’t understand these things. And it’s really been interesting for me. So how do I take those opportunities and try to start to support this class of businesses. That really is where my heart is and where.

 I don’t know if you know this, but small and medium businesses produce almost 50% of our GDP and they represent about 99% of businesses in America. 

Ryan: Yeah. 

Jennifer: Yeah. And they’re, you know, they’re really out dancing. So when you think about search, Amazon and Google own the top of the funnel, and then when you think about social, it’s really, I mean, certainly it’s emerging over time, but that Facebook has gobbling up all these, these social platforms.

So they really own that. When you think about the kind of CPG brands and others and, and these local makers getting their products in stores like Walmarts and the targets of the world, as well as the large CPG brands really own that. So in this new world of the digital age, where, you know, really only about 25% of these small and medium businesses have effective, common strategies and kind of modern web three auto moving into four Dido, probably less, how do you start to help them compete?

 And we’re gonna be launching soon with this new capability around that, and really kind of helping up-level those brands with everything that I’ve learned from owning my own small business to TAC, to, you know, what I experienced in big retail. 

Ryan: Is going to come back in a big layer.

Jennifer: It’s definitely going to come back in a big way. And it definitely provides the right level of empathy to be able to kind of work with these businesses. And, you know, some of these local businesses are super powerful and they’re doing great business, but they’re starting to see dwindling cells and COVID certainly hurt them.

But, they’re small and mighty and, they really are open to change and a different way, , the enemy is outside the door and they’re looking for change and they’re looking for help. And so that’s really kind of the next stepping off point in my career, coming back full circle.

So that was a lot 

Ryan: That’s amazing. No, that’s amazing. And I really do see how it all comes back around and kind of. Circular motion, but like at the same time, these themes are running through your career, they’re running through your life. And it really is great to see how your leadership through a lot of these industry changes over the course of the last 20 years has led you to a spot where guess what you get to disrupt again and have some impact in that world.

And that’s amazing. 

Break One 

Ryan: It was amazing to hear about Jennifer’s journey through the world of digital commerce. She has the very unique perspective of being a part of this bridging and platform development since the very early days. One of the key leadership take-homes I gathered from her was the importance of experiencing the challenges you’re crafting software for firsthand her journey from technology to brick and mortar, and back to technology offered her the unique capability of putting yourself in the end user’s shoes. This small nuance is not only helpful when thinking about the engineering of a solution. But invaluable to helping create a true evolutionary step in the challenges of that particular segment.

Jennifer: Yeah, absolutely. So, we’re excited. So I’ll keep you posted, 

keep us 

Ryan: posted in the meantime, let’s jump into your top five tips. 

This was a really great lead into those. I’d love to hear a little bit more about what you think leaders should have and how leaders might be able to guide through some of the stuff that we’ve been talking about.

Absolutely. If you’re up for it, let’s go to number one. 

Tip One (Always Be Learning)

Jennifer: Okay. Number one is always learning. And that means a few things to me, one, just with this entrepreneurial mindset, I mean, as an entrepreneur, you’re always learning, you’re always refining your business models. You’re always thinking about things in a different way, but I think it’s kind of core to a technology and product career. It sounds very cliched, but we’ve talked a lot about my career and how it intertwines and the differences between startups versus big companies and the learning curve.

So I think it’s important to kind of keep fresh, keep up with technology and really, educate yourself, seek those experts. If it’s something new, be honest with yourself and understand where you’re strong and where you’re weak. Because I think that’s going to be instrumental to where we go next, right?

With a rapid pace of change and the rapid pace of the consumer. If you’re not growing and learning, then you’re standing still and you’ll get left behind. 

Ryan: Yep. That makes sense. All right. Thank you. How about number two 

Tip Two (Listen Carefully)

Jennifer: at number two is to listen carefully and not just listen to words, but listen to actions.

And, I alluded to a little bit of this in my story, as I went from a startup and I jumped into industry and, I came in a little bit like a raging bull and kind of had to tame myself and I wanted to move fast and I wanted to innovate and I wanted things to happen and all that.

And you know, it was really interesting to me how, you know, sometimes people didn’t tell me no, they told me yes. Yeah. But they took no action. Right. And it was really interesting, the dichotomy between startups and enterprises. And so that’s where, I’ve had to really hone my spidey senses around that.

And you know, when people say yes or the slow, no from investors, you see a lot. So it’s like, keep your eyes open, listen, carefully, watch people’s actions. And frankly, that goes to teams too, right? As we start to move or have been moving for some time in this global world, cultures are different and that sort of thing.

 And then I think finally, when it comes to leading product and tech teams, it’s really critical to listen to them and let them know that you’re there for them. And you’re a sounding board because you know, whether they’re innovating in a large company or. They’re out changing an industry. It’s frustrating.

And sometimes people just want to be heard and you know, sometimes that’s perceived as some level of weakness, but as a leader, you have to be empathic and you have to be there and you have to have your team’s back. And you know, when, when they feel like you have their back, then they’ll go above and beyond for you.

Ryan: That’s completely true. I’ve experienced the same thing over the course of time. Amazing. Okay. How about number three? Tip number three. 

Tip Three (Culture Fit Is Key)

Jennifer: So number three is a little cliched, right? So we all say hire really strong teams and empower them and give them objectives. And you know, all those, 

Ryan: all the foundations, 

Jennifer: the biggest six and the foundations, but you know, this is where I want to loop back to kind of culture fit is key.

Right. So, as I thought about hiring these teams in a startup. What I might be looking for in a startup is very different from what I might be hiring into an industry company or a not-for-profit. And it’s really around understanding the tolerance for change. And so you could have the smartest team in the world, and I certainly have teams on Rolodex that I could pick up the phone and call.

 But there’s also a component that says for everybody’s mental health, there’s got, there’s kind of gotta be a good fit there but the second is really, giving them ground cover and making them focus. And, you know, I want to pause there for a minute and. Give a little more insight there.

Okay. So one of the things I think in the startup culture, we all understand innovation and agile and design sprints, and all those things. We take all those things for granted, right. But I talked a little bit about moving into industry and then, you know, even some of my experience working with a small and medium businesses and we take the things like, sometimes technology is just delayed or sometimes things come up and you have to pivot and it’s a learning curve and nothing’s perfect, but I think people’s tolerance for that looks very different.

And so it’s not just about hiring the right team and getting the fit right. It’s really about as a leader. It’s your job to kind of clear the way and be the educator and shield them so that teams can focus. And, you’ve worked with technology teams for a long time. And one of the things I’ve really learned about technology teams.

 Being a technologist myself, we like to focus, right? And there’s, there’s if you’re yanking them from one exercise to another, and I think you’ve probably seen us where people are like, what we’re doing Kanban, but what does that really mean? Like leave this on the side. I know you only finished 10% now we’re over here today and now we’re over here tomorrow and it really creates this culture where people can’t deliver and they can’t deliver outcomes.

 And that’s where I see these teams breakdown. So strong teams set them up for success and showed them so they can focus and be cognizant if you’re in the learning mode of what it means to build these product and technology teams, educate yourself and make sure you’re being aware of what you’re doing to these teams.

Cause you can really kind of demoralize them if they’re not given the right support. 

Ryan: That’s I think it’s a, the concept of shielding for attention, like allowing the attention to to exist and to thrive is actually what leads to innovation as an interesting concept, because it’s often overlooked as a leader where you kind of like, oh, I’m going to be the one to come up with it, or 

Ryan: I’m going to be the one that, but like actually just facilitating that shielding for the attention and, and your whole team is allowed to create and have something beautiful arise from it.

Jennifer: Absolutely. And, I would say above anything else that’s the most critical, especially, especially when you’re in enterprises, but I’ve certainly seen it in startups too, where teams get paralyzed and can’t deliver. Yup. Yup. 

Ryan: Right. How about number four? 

Tip Four (Building Products Is About The Journey

Jennifer: Uh, so building products and strategy is not about a project or a process.

It’s the journey. Right? And so I think I talked about this a lot. I mean, again, going back to start ups, we know what product teams look like, but when you jump into these large innovation teams, we often launch projects over products and products have a life cycle. As they’re born, they grow.

 Sometimes they don’t make it, and then sometimes they go through their full life cycle and they have to be sunset. And so really thinking about, building products, starting from the strategy and not thinking about it as a one-time delivery and understanding that it’s an iterative process, you’re listening to the market and this is where people get really uncomfortable with agile.

Right. And so I think you and I have both seen it, you see it in larger companies better, or, it’s more amplified in larger companies where it’s okay, you need to lay out a strategy. Okay. I’d laid out a strategy. I think it’s a really good assumption, but the market might tell me five other things.

And then somebody wants you to estimate it and somebody wants you to design it and they want to know how much it’s going to cost and how much it’s going to return. And then, you know, the team gets paralyzed and paralysis analysis. It really is about stating your hypothesis. Tested in the minimum viable way.

Is it a questionnaire to your customers? Is it a landing page? I mean, this goes back to Zappos and, and 

Jennifer: Really early testing. Exactly, exactly. Those methodologies. And then I think the other thing is this accuracy versus kind of precision mindset, like when teams get formed, they don’t know that and discovering every single detail that’s going to come out and our product launch, you know, you’re probably not going to get some, all, you can certainly hire experienced teams, but assuming that you’re going to be both accurate and precise following these methodologies, you know, ultimately agile ends up being cheaper and better because it’s an evolution and you can make decisions in real time.

And that’s a really important piece. Yeah. 

Ryan: I know we deal with this on a constant basis. But the idea that you’re talking about a product being a lifecycle and having an actual life, right there is an organic quality to all of it. And the second you remove that organic quality, it does limit where it can go.

Sometimes it works. Sometimes the imagination is able to get it on paper, you build that exact thing and it happens. And then I think the biggest point is like a lot of the magic actually happens as you’re getting into it and discovery and ha and engaging with that organic process. 

Jennifer: And some of the magic happens.

Post-launch right.

A hundred percent. And so really thinking about teams and engaging teams and thinking about these products more as funding gates and these larger companies, right? Not thinking about funding them as a project and then launching it and leaving. But as funding gates, just like a startup and feeding it into a pipeline, and letting the team achieve the outcomes and results.

Ryan: Amazing. Awesome. Okay. And the last one, tip number five. What do you got 

Tip Five (Tech Is Not A Supplement For Business Strategy)

Jennifer: tip number five is that tech is not the answer to new business strategy. You know, I’m sure. Um, and I think, you and I had had a consulting gig where this very much, um, Came up, um, and was at the forefront. But, you know, I often see this, especially consulting and CPG and retail.

 I met with a company a couple of weeks ago and you know, it really does require taking a step back and saying, as a company, what are my growth goals and how can I achieve that and really thinking about it from a top down approach. And so I often have a number of conversations that start with, oh, Hey, there’s this really cool geospatial intelligence?

And I’m like, yes, geospatial intelligence is amazing. What business problem is it going to solve? Or kind of at a more rudimentary level meeting with CBG and retail brands that say, Hey, I’m going to double my revenue by launching a new web and mobile stack. And it’s okay. But Do you need to launch a new stack yet?

Or can you be discovered along the way and then validate that? Right. Like 

Ryan: My favorite version of this right now is AI. We need to get AI and be okay. That’s a big, big topic. Like w what do you want to do with it? 

Jennifer: Yeah. It’s my favorite too. And that was kind of a way I was alluding to geospatial intelligence and other things.

I need to get myself some AI. Yeah. Well, what business? I mean, AI can solve a lot of problems, right? It can solve your supply chain. It can solve recommendations, it can solve all these things. So what do you really think you need to automate and optimize, and then what’s the outcome going to be, or what’s your hypothesis around that outcome?

So, I think we struggle in the Amazon world and everybody thinks. Tech has the answer and tech is simply an enabler and it’s an amazing thing. And it allows us to accomplish amazing things, but you first have to start with, how am I changing my business and what does that look like? And just delivering some tech doesn’t solve that problem.

Ryan: All right. Well, those are some amazing tips. I really loved the last one, especially, it really hit home for me. , I appreciate you really running through such an incredible, very career in, in, and also like, Really bringing back like that. I really appreciate how you brought back that, that very kind of small business brick and mortar piece, that was in the midst of your career in part of your passion and actually seeing how technology can help, help evolve some of that and disrupt some of what’s existing.

 I’m excited to. Hear about your new venture and what’s going to happen with that. And we really appreciate 

Jennifer: Having you here. Yes. I certainly appreciate the time and we really launched and can get some traction. I’d love to come back and talk to you about that. 

Ryan: That’d be amazing. All right. Thank you, Jennifer.

I appreciate it. 

Jennifer: Thank you for your time. Talk to you later. 

Ryan: As Jennifer points out, leadership is often about taking a step back and refocusing everyone on the actual goals of the business. It’s especially important to recognize that this applies to yourself as much as it is. How much you, as a leader, dive into the challenges you’re trying to solve will be directly relational to your ability to guide teams effectively through the murky waters that arise as you’re trying to solve them.