Sept. 14, 2022

Exploring Product Momentum With Erik Dawson of LeafLink

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How does momentum factor into product management? In this episode of Product Chats, Erik Dawson, Senior Director of Product Management at LeafLink, answers that question. We dive into how product teams can build internal momentum to support product growth, as well as external momentum, which helps customers move through the customer journey.


Time Stamped Show Notes

Getting into product [01:19]

Building products for enterprise vs startups [02:59]

How to structure product teams [06:58]

Building customer experience focused products [08:44]

Product momentum [11:24]

Getting quick wins and setting OKRs [13:41]

Product strategy and the three Cs [14:37]

Leading gracefully at a product led organization [16:41]

Measurement and attribution [18:52]

Advice for aspiring product leaders [23:14]



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Kayla: Thanks for tuning into Product Chats. On today's episode, I talk with Erik Dawson, who is the Senior Director of Product at LeafLink and we talk about product momentum and leading gracefully in a product led org. So hope you enjoy the show and don't forget to leave us a review.

Kayla: Hey Erik, thanks so much for coming on.

Erik: Hey, Kayla, glad to be here. Let's get into it. This is gonna be fun.

Kayla: Yeah, let's get into it. So as we get into it, tell us a bit about yourself.

Erik: Yeah. So I am currently a Senior Director of Product leading our marketplace team at LeafLink which is a B2B wholesale platform to enable commercial cannabis transactions.

Erik: So we work with cannabis buyers and sellers to enable their whole plate, their wholesale commerce, and to kind of order management. Along with transportation, logistics, and payments experiences. I got into that, into the cannabis industry and into LeafLink just over six months ago in August of 2021. And prior to that, I worked in product leading really customer experience focused product teams in at American Express, and also in different like FinTech, startups and companies around New York City.

Kayla: Awesome. And so let's back up, right? Let's back up to how you got into product and what that looks like.

Erik: Yeah. So I got into product actually a bit by accident. A lot. I feel like that's a common refrain around product managers, right?

Erik: Because you know, product is one of those functional areas that has evolved very quickly and people just suddenly find themselves doing product. For me it was, my story is I actually started my career in marketing and brand strategy. And I wanted to become a brand manager, which I think is, you know, a product manager, but in a different form. It's a product manager, but in more of a CPG type of experience.

Erik: So I actually went back to get my MBA focused in brand management and ended up taking some strategic technology curriculum. I said, oh my gosh, like, this is where I want to be. So I was able to serendipitously kind of learn from and experience kind of the technology side of product management and make a quick pivot when I was getting my MBA and combine my business marketing brand curriculum with technology product management. And from there, I ended up becoming a product manager at American Express, where I was working in our internal incubator group building new products and features and services for underbanked customers.

Erik: So it was a really interesting way for me to kind of pivot into product and then get into a large company that was investing in technology in different ways. So that's how I ended up in product.

Kayla: Awesome. And so I know like LeafLink is a bit smaller than American Express .

Erik: Yeah.

Kayla: Can you tell us a bit about like the difference in building product at a place like Amex and then building a product at LeafLink?

Erik: Yeah. You know, I think there's a few differences that come to mind. One is at a big company like Amex versus a smaller company and a startup like LeafLink. There's just different risk tolerance. At Amex there's a lot more consideration or I guess, demand to prove out like your, how your product ideas are going to move the needle at scale already.

Erik: You know, a big company has embedded users, probably a larger user base, whereas a startup is, you know, trying to capture that user base and grow that user base, generally speaking. And so at a Amex, there's a ton more like scrutiny over ensuring that your product initiatives and what you're building are going to be improving the customer's experience, improving the business metrics with extremely high confidence.

Erik: Whereas at a startup or a smaller company, like LeafLink, there's a little bit more risk tolerance to experiment and, you know, acknowledging that we are adapting best practices or we have high confidence that a product feature or initiative is going to make positive impact, but we don't know the scale or we don't know necessarily how it's going to impact all users.

Erik: So there's more appetite for experimentation. There's more appetite to move quickly and test things and learn. Right. You know, like these kind of standard things that you hear and you hear about in terms of working at startups and the nature of being truly agile moving quickly, you know, accelerating time to learning and time to value so that you can demonstrate whether something works or not.

Erik: Whereas at a big larger company, you know, there's more scrutiny to prove out that something will work rather than doing an experiment to prove it out. Though, when I was at American Express, you know, just to give some context there, like I was very excited and happy that Amex was also a company that embraced experimentation.

Erik: Right. So I was really trying to though Amex was a very big company. It was learning from startup practice and learning from agile practice and implementing those things. So it was a balance, right, of the scrutiny around experimentation and risk and learning quickly.

Erik: I think something to add, a company, a smaller company is just the scope of ownership and autonomy where you generally are touching more things, right? So that means you can do more, but you also need to think about how you are prioritizing and where you're placing your bets across multiple domains or across multiple areas or user types. At a company like American Express you probably have a smaller slice of the pie so you're able to go very deep very quickly and you have autonomy over like a sliver of your product domain, so you can move the needle in your area.

Erik: Whereas at a startup, you're probably going to be touching more parts of the product, which requires you to have a really great sense of prioritization, really , great sense of like where you need to focus.

Erik: Whereas at a big company, like that's probably already predetermined based on like, just where you sit in the company, those challenges are universal as a product person. You always have to focus and prioritize and make trade offs. But I think at a, a startup that's even more pronounced because there's so much opportunity and so much that you have to do to deliver customer value and also to, you know, just keep the startup moving forward.

Kayla: So with that opportunity, right. Obviously there's different ways of structuring teams and how have you seen it work really well? Like at Amex? I, it seems like it's kind of already set in that way, but like you mentioned, right at a smaller company, you kind of get to choose your own journey in a way. So like, how do you recommend kind of, I know there's not a one size fits all, but what's your best way of structuring product teams?

Erik: Yeah. I like to structure teams where one, teams are set up, so they have autonomy and they have the ability to make decisions and build and deliver and get things done together without too much outside, need for outside, like influence or support. So teams need to have product, data, engineering, design together to have that autonomy.

Erik: That's like a common pod structure, right? Teams also need to be able to have focus in terms of what they are going to be working on in a specific type slice of the company. So I mentioned at American Express you've got teams who are working on very specific areas of the product. It might be one feature or a small collection of features or a specific customer segment.

Erik: I believe in that model as well. At a startup, you wanna have that to the extent that it's possible. So at LeafLink , for example, we do have teams who are focused on specific feature sets within the product and within domains across our business line. They are responsible for, I would say, a wider swath of the product than what I saw teams were responsible for at American Express, but the principle's the same. They need to have the ability to focus on a specific feature set or customer base or like asset on the product so that they have autonomy to move the metrics forward in that specific area.

Kayla: So with that, I kind of wanna talk about, right, building out product and something you mentioned was customer experience focused and being customer experience focused. Let's touch a little bit about that.

Erik: Yeah. Yeah. You know, I mentioned, I do think about myself as a customer experience oriented product leader. And what does that mean right? With digital products and with software today. Experience is so important, whether you're working in B2C or a B2B type business at the end of the day, you need to have experiences that customers are able to interact with, they're able to self-service and they're able to get to value immediately, right. You know, the value you're giving to a customer is only as strong as like the weakest link in the experience. And so digital experiences need to hang together. They need to be self-service. They need to be automated to the extent possible.

Erik: They need to guide the user to the next action they need to take. In complex product ecosystems this is extraordinarily important because you can just imagine like products you've interacted, where you hit a wall or you hit a stopping point. You're like, well, what do I need to do now to complete my action that I was trying to do.

Erik: What do I need to do now to check out and to place an order? What do I need to do now to connect with a customer service representative or to give feedback on my experience? So experiences need to hang together. They need to drive the user to the value that they're getting. They need to do it hyper-efficiently, and in complex eco ecosystems. I'm thinking about B2B ecosystems, particularly. It is crucial to think about that end to end experience that the customer's getting. And then, you know, as companies grow, we're adding on more products, we're adding on more, features, more value propositions, more channels through which the customer can either enter the product or engage with the product like a servicing channel or communications channels, right.

Erik: Or, you know, managing their experience after they've accomplished their original task. Like if you are, you know, shopping on a website, well, what if you have to make a return, you have to come back, you have to log in, you have to access that return form. You need to probably interact with customer service, or maybe not.

Erik: Hopefully not. Anyway, you get the point. Customer experiences are so critical to the success of the user on your platform and your product and, they're omnichannel, they're complex, they need to be self-service and ideally automated to make sure that the customer's getting value and they're getting value as quickly as possible.

Kayla: So on that customer experience, right. We're talking about how to serve your customers, but I wanna kind of pivot a little bit and talk more about that internal piece and product momentum. So let's dive a bit into that.

Erik: Yeah. I think there's a few pieces of, you know, you use the word momentum and it's a, such a strong, like word conveys so much.

Erik: Like I think about the momentum both internally among a product team to be able to build an experience and to demonstrate value and, you know, teams need to get quick wins. They need to think about MVPs. They need to measure and attribute success to the customer experience and to the products they're building.

Erik: And all of that creates momentum internally on teams as they're building out experiences, right? That requires a great discipline to prioritize and, you know, make sure that as a product person you're deciding, what do you need to build first? How do you build on that success and how do you create momentum internally so you can continue to build out your product and your features? And then there's the momentum on the customer side, right? You need to, your customer experiences need to enable the customer, a new customer to be acquired, to be onboarded, to engage with your core value proposition, to discover additional value propositions, to then gain value and say, this is my preferred product for whatever it is that I'm trying to do, and then become a loyal customer.

Erik: Right. We're talking essentially about the funnel or a product led growth flywheel in which you're acquiring users, bringing them through the flywheel and then they become product evangelists. And, you know, you're bringing more customers on the platform that way.

Erik: So I think about it in those two terms, both internal momentum, product teams needing to have a clear vision and quick wins to create momentum, demonstrate success, and grow, and then externally for the user momentum looks like coming onto the platform, easily engaging with the product, having success, wanting to come back and then becoming an evangelist. And that's how you drive growth.

Kayla: So I think off of that, something you mentioned was like quick wins, right, versus building out like the perfect product and waiting and hoping.

Kayla: So let's talk a little about that, how you give your team the space to have those quick wins and also to experiment so that they're not afraid to kind of build out new features when like at Amex you said it's like pretty certain, whereas at LeafLink, it's not as certain that it's gonna be as big of a win.

Erik: Yeah. You know, it comes back. I think it, it starts with rather, it starts with setting really good objectives and goals, OKRs. You know, we talk about OKRs, objectives and key results in product organizations. And that's really important at a company like LeafLink, where we set our north star objectives.

Erik: And that allows teams to, that allows freedom among teams to say, how are you going to help achieve the objective? So if you have a growth objective, let's say, teams are able to say, how am I going to drive growth in my specific product? And then I like to orient our teams to thinking about product strategy in terms of three Cs.

Erik: I like it to call it the three Cs, the company. What is the value proposition we're offering? The customer, what does the customer need, their pain points and their orientation to their product, to the product. And then finally the competition, which is really just means the industry. What's the dynamics happening in, in the industry?

Erik: What are your competitors doing? What are your customers' alternatives? And if our objective is around growth, and we think about what do we offer? What does the customer need? What's their context in the industry, or, you know, their alternatives. And then on the product, what do we need to build or deliver in order to satisfy the customer and then achieve those growth objectives?

Erik: There's so many things we could do based on where the company is and based on what the the customer needs. So teams are empowered to consider all that information, decide where they need to focus, and then provide rationale for, you know, what they're going to do, what wins they want to test, how they're going to work with their partners to attribute success.

Erik: Uh, we need to get design into the conversation and do ideation and, you know, divergent discovery and then convergent, like brainstorm. Engineering is crucial to the conversations about what can we do quickly? What's feasible? How are we going to solve problems based on what research we've done? So, you know, I like to give the teams a lot of freedom to answer those questions as a team, and then come back with a propo, a set of answers and ideas, and then we rank order and prioritize them.

Erik: You know, there's different prioritization methodologies to use in product, but you've gotta get quick wins. They gotta be rooted in research and really good strategy and oriented to objectives. And then if you've got that set, then teams self-organize and they can establish quick wins and really have some success together.

Kayla: So with that, right, you mentioned a little bit about collaboration. I think this ties into like how to gracefully lead at a product led org. So let's talk a bit about that.

Erik: Yeah. Yeah. You know, gracefully leading, it's a challenge, right? Especially in a product led organization where you've got really hungry teams driving, you know, wanting to drive growth and do the right thing for the customer.

Erik: Um, and tons of stakeholders like marketing or operations or business development who are interacting with you and trying to, you know, coordinate to help drive their agenda forward as well. So I think leading gracefully at, in this type of environment means being very clear about your strategies and your objectives, consistently seeking and gaining alignment on a regular basis. Especially in an organization, like an early stage company, a startup where things are changing rapidly, alignment is important. Communication is important. I engage with my stakeholders and my partners on a weekly basis in different forums to just share information, give them updates and make sure that I'm asking for information from them. So knowledge sharing is a big part of that. And at LeafLink, we have one of our, one of my favorite company values is we say it straight.

Erik: And that's important for leading gracefully too. You know, you need, we need to be transparent with each other in an org, in product led organizations. And we need to say it straight and saying it straight means that we are objective, we're focused on the outcomes and the strategies, we're focused on customers.

Erik: And we are not afraid to be opinionated and to really kind of and to champion, what we believe and make it make things happen. So continuous alignment, collaboration, transparency, and communication, strong vision oriented in clear objectives and results that we can measure. Over time and then really allowing teams to organize together and get things done.

Kayla: So on that piece of measurement, right, you said measurement over time. How are you actually like hands on looking at this measurement, are you doing user interviews? Are you using specific tools to track the customer journey? Like what does that look like?

Erik: Oh yeah. Yeah. I mean, measurement and attribution is key, you know. Without data, you've just got a lot of, you know, anecdotal information or qualitative information, which is critical because data without context is just numbers, but you need data with context equals insight, and that's so important. So the measurement that underlies that, we have a very strong data team at Leaflink , we partner very closely.

Erik: So we've got a combination of self-service tools powered by a data team that really helps us with business intelligence, platform intelligence, analytics, data science, and data engineering. They're awesome to work with. Some tools we use is we have business and product metrics, dashboards in Tableau. I've also used Looker in past organizations.

Erik: We use Full Story to get to access like customer interactions on the platform. We use Segment to measure customer interactions on the platform and, you know, various other tools and data sources to, you know, measure net promoter score, to measure business attribution, making sure that we can link and label a customer action with an outcome.

Erik: So, you know, the ways we measure are myriad. Tools are critical, a team is critical, and a really good understanding about what to measure and how you're defining that is important. And then, you know, all of those need to converge into a really well thought out kind of data warehouse so that we can access the data centrally and connect data from disparate sources.

Erik: So the data's critical to power the measurement, to inform how we think about objectives and whether or not we're achieving our goals.

Kayla: So I think you bring up like a great point, right? Like you can have data and data's there, but it's like, is it actually tying back to these objectives that then tie back to like your company goals and always making sure that there's this context versus you could have just all this data.

Kayla: And also this gets into piece of bias, right? You could have this data and be like, oh, I wanna build this out because I have this data on it, but are you actually taking a step back and saying, hey, is this what's best for the customer? Is it just because I believe this thing and I have this data that I feel aligns with what I want.

Erik: Yeah. Yeah, absolutely. You know, we've all seen how data can be manipulated and how data can be shaped by bias. So, you know, we have, when we're looking at data, we really have many voices in the room to be able to ask questions, to kick the tires on the data. We need to combine the data with, like I said, you know, context around what was the customer doing?

Erik: What else was happening in the business at this time? What was happening in the industry? You know, if we think about LeafLink and the cannabis industry, for example, we're a nascent industry. So a lot of our business data, we're looking at seasonal trends or data and change over time. Well, in an emerging industry, like there's not a whole, there's not a major data set over time that you can look at and say, oh, this is how like the industry performs because it's new.

Erik: So we're learning as we go. You know, many people and voices in the room, making sure that we're asking the right questions and interpreting data correctly, that we're being objective about it. And then looking at change in data over time and in relation to each other, right. A data point and a moment in time could be interesting, but a data point in relation to others over time is more compelling because it shows you change, impact, and the Delta over time. So it's really interesting to just like dive into the data, have really smart people who can help you with that. And, you know, it's a lot of fun.

Kayla: So on that subject, right, we've talked about product momentum and leading gracefully in a product. So I wanna know what's one piece of advice that you would give to an aspiring product leader.

Erik: Oh man, keep moving. Keep going. I think, you know, product is, product's a really challenging function. It's a really fun and really rewarding function. And there's so much to do. And I find that one of the big challenges is potentially getting bogged down in like the opportunity or what should I do next?

Erik: Or am I doing the right thing? My advice is, you know, if you have really strong, like objective, strategy, and you are consistently seeking deep understanding of the customer and of the business, then keep going. Don't stagnate. Like in your product backlog, on your roadmap, you know, plant a flag and go. Deliver great work, learn from it and just keep going.

Erik: If you keep going, then you're going to make improvement and continuous improvement to your product. You're also gonna grow as a product leader every day over time. You know, product management is a marathon. It is not a sprint. And even though, you know, we love to talk about agility and velocity and iterating and doing, getting quick wins, like that, those are all like in the moment. And over time, product success is achieved by keeping moving, staying the course, learning, making some like strategic and important pivots at times, but just keep pressing forward.

Kayla: So on the subject of keep pressing forward, what roles are you hiring for?

Erik: Yeah. Yeah, we've got a, you know, LeafLink is growing and we are hiring and you can check out LeafLink's open roles at .

Erik: On the product side, we are hiring for design roles. We are hiring for product management roles in our different marketplace, logistics and payments domains. We are also hiring for technical product roles on our integrations team. So we are hiring across functions and across domains. And like I said, you can check out careers at .

Kayla: So on that note, where can people find you and connect with you?

Erik: Yeah, the best way is really to connect to on LeafLink, on LinkedIn. It's, it's all combining. Yeah. The best place to connect with me is on LinkedIn. I'm very active on LinkedIn. I love learning from others on LinkedIn and you can check me out on LinkedIn at Erik Dawson, E R I K D A W S O N.

Kayla: Awesome. Well, thanks for coming on today.

Erik: Thanks for having me, Kayla. This was a lot of fun. Thanks.

Kayla: Thanks again to Eric for joining us on today's episode of Product Chats. For more product management resources, head to, and we'll see you next time.