Episode 149: Fueling Small Business Growth with Kelsey Ruger, Chief Product and Technology Officer at Hello Alice

In this episode of Product Thinking, Kelsey Ruger, Chief Product and Technology Officer at Hello Alice, joins Melissa Perri to discuss the importance of supporting small businesses. They dive into the triad of tech, UX, and business strategy; key insights for mastering product management in startups; and how to empower small businesses for entrepreneurial success.

You’ll hear them talk about:

• [13:29] - Understanding the intersection of user experience, technology, and business strategy is key for career advancement, especially in leadership roles such as Chief Product or Technology Officer. Understanding a company's business model enhances a designer's ability to personalize user experience and contributes to the broader business goals. For example, identifying the distinct strategies of companies like Apple and Walmart, where Apple focuses on selling experience rather than commodities, can significantly improve a designer's effectiveness.

• [16:00] - Small businesses form the backbone of many economies, employing a significant portion of the workforce. Hello Alice is a multifaceted toolkit designed to support small businesses, offering a mix of financial support and educational resources to thrive in competitive markets. The platform assesses a business's health, guiding them in growth strategies and funding opportunities, including loans, grants, and credit.

• [22:10] - Startups should align the hiring of their first product manager and leader with their scaling phase. It's essential to bring in a product manager early, ideally alongside a UX professional, to focus on UX and execution and free up founders to concentrate on critical early-stage tasks like fundraising and sales. A product leader's success in a startup hinges on quickly identifying whether the founder is visionary or operational-driven. This helps shape the product roadmap and guides effective collaboration.

• [33:20] - Building a highly effective product management team starts by designing a well-thought-out job description that clearly outlines the role's specific needs. This becomes the foundation for a tailored interview process, which should begin with assessing basic product management skills, followed by scenario-based questions to evaluate a candidate's fit for the specific demands of the role. This approach ensures that the team has the right mix of skills and experiences directly aligned with the job's requirements.

Melissa Perri - 00:00:36: Hello, and welcome to another episode of the Product Thinking Podcast. Today, we're thrilled to have Kelsey Ruger with us, who is a Chief Product & Technology Officer at Hello Alice. And he's gonna talk to us today about his career journey and how his combined experience in software, UX, and product helps him be a great Chief Product Officer. Kelsey's dynamic journey in product and technology leadership spans from fostering over a million small businesses in the US with innovative toolkits to spearheading user research initiatives at renowned firms like Truist and P97 Networks. As a futurist and design thinker, he has consistently pushed the boundaries on how we envision product ecosystems. His tenure as an adjunct professor at the University of Houston is a testament to his commitment to nurturing the next generation of problem solvers. And as a recognized 40 under 40 by the Houston Business Journal, his accolades reflect his deep dedication to his craft. Before we talk to Kelsey though, it's time for our Dear Melissa segment. So in this segment of the show, I answer all of your product management questions. So if you have a question for me, go to dearmelissa.com and let me know what you would like me to answer on a future episode. Let's dive into this week's question.

Dear Melissa, I imagine there's no golden ratio of product engineering and UX. There may be different ratios for different products or desired outcomes. However, do you have a sense of ranges where you've seen the best generated outcomes? Or is there a way that you would recommend thinking through this? I found moving and learning fast is only possible when we have the right team in place to focus on the important areas of discovery and an imbalanced team can create barriers to progress and morale.

Well, that's certainly true. When you don't have the right size team, it can definitely cause a lot of different issues. So we want to make sure that we get that right in product development for sure. So when I think about structuring teams for product development, there's a couple of different factors that you need to look at. One, are we in discovery or are we in delivery? For things like a new product, you want to keep the team small. You usually are going to have a product person, a UX person, an engineering lead involved in it. And then as you start to build or you're testing, you might have one or two developers involved if you're building out code. The smaller that team is, the more you can actually iterate. So when I was leading teams that were doing a lot of experimentation, we actually had two engineers, me and I was a hybrid product and UX person. That allowed us to get really tight on what we were doing, iterate very quickly, and we weren't building gigantic feature sets. So it allowed us to get things out the door very quickly and just test the waters and see what was actually working.

Once you have a defined product vision and you've done those tests, that's where you have to expand the team. And this is where we would look at bringing in more people in a balanced way to actually execute. So if you don't have a product vision and you don't have product market fit, you want to keep teams smaller so that you can iterate quickly. The more you actually add people, the slower you will go. That is true for all companies. That is true for all product teams. So if you have 10 engineers, one product person, one UX person, you better have a really solid product vision and a lot of work to actually be done. I would never go over 10 engineers per one product person. Ideally, you want about six engineers per product person. Now, you can do 10 if you have a giant backlog, a really developed division, and you've got to build a lot of stuff up front. Sometimes you can do 10, start to split that work and get that first thing out there. I've seen that work, and that's totally fine. But I really wouldn't go over that amount of people. UX Designer is usually one UX designer to one product manager.

That's the ratio that we see work. With engineers, again, it really goes for what stage of the product you're in. Now, if you are working with an engineering team, let's say of six product managers, and they're working on things and you need to go into discovery mode to figure out what's next, you're probably going to be working with that engineering lead, your UX Designer, and yourself as a product manager. And then you're going to pull the engineers in once they're finishing the stuff that's already in progress and once you're defining what that product vision is going to be and that you're actually building it. So it definitely flexes. Depending on what you're working on and what the context is. If you're doing backend stuff, of course, you're not going to have a UX Designer. If you're doing like API things or other stuff like that, you're not going to have a UX Designer. You may need data people on your team, depending on what you're doing with data. Sometimes we see data engineers pair with product managers or with product teams to help get the right information back out and help inform the team on what to do. Some teams are structured like that, or you might have a data person that's aligned to a couple different products. So that's a good thing.

That really just depends on what kind of instrumentation you have in the company and what's going to work for you. So no, there's no hard and fast rule for what works. It's really about how fast you need to go, how much work needs to get done, and what stage you're in. And then the context of the product, whether UX is really important for it or if it's a backend thing. That's how I would think about structuring teams, but it's definitely flexing around that product lifecycle. So I hope that helps. And just as a reminder, if you have any questions for me, go to dearmelissa.com and let me know. I also want to bring up that Denise and I recently published a new book on product operations. And if you are interested in doing product operations, you can head over to productoperations.com and get a copy of that book.

Product operations is really the enablement function in product management. And we are excited to bring a book to the world to show people how valuable this can be. It can help you really tie your strategy back to the actions of the teams. It helps inform the teams with the right data that they need to actually get things done. And it helps communicate across the organization what the product management team is doing. So if you are interested in product operations, head to productoperations.com and buy our book. Now we're going to dive into talking to Kelsey. Ever wish for total alignment with executives? The end to those never-ending debates? Results that make everyone sit up and take notice? Amplifying influence across your organization? The secret? It's not just about managing. It's about facilitating. Level up your ability to facilitate clear, powerful conversations with stakeholders through Voltage Control's Facilitation Certification Program. Learn more and get $500 off at voltagecontrol.com slash product. We'll be putting that link in the show notes for you as well. Welcome, Kelsey. It's great to have you here.

Kelsey Ruger - 00:07:01: Thanks for having me.

Melissa Perri - 00:07:02: So you've had a really interesting career path. You have been a software engineer, a UX Designer, and now you're the chief product officer of Hello Alice. Can you tell us a little bit about how you got in technology, starting off as a developer, and maybe even how you made that transition from developer now to UX Designer?

Kelsey Ruger - 00:07:23: So there's a really interesting story about how I actually first got into technology. And this was back in the 80s. And I think you probably hear similar stories from lots of people who were early childhood computer geeks like me. And so the story as it goes is my aunt used to have a IBM computer that she kept in her office and she'd let me use it because pretty much I knew more about it. And so one day I got this idea that I was going to go through every single command in the user manual. You know, you get through the user manual. And then I got to FDISC and I erased her computer and didn't tell her until she came in and tried to do work on it. And she calls me frantic. She's like, you better get over here and get my computer back. And at 10 years old, I figured out how to do it.

Melissa Perri - 00:08:14: Wow.

Kelsey Ruger - 00:08:15: Got the operating system reinstalled. Got all of her software back. And that was sort of the catalyst for me getting into technology the way it is today. And I always tell people I never set out to be a software engineer or a designer. I just liked building things. And so those skill sets really came to me early. So I spent my high school years going to a what's called the magnet school here in Texas that was focused on computer science and graphic design. And so that's where I started to really learn about graphics. And it was sort of. Always a thing for me. And as you move through college and into the work world at that time, really, if you're going to go make a career out of it, it was going to be technology because what we knew as UX today didn't exist as it does today. So you might have had that skill set. But if you're going into technology, you're going to be an engineer or a database administrator or something like that. And that's how I sort of started down that path.

Melissa Perri - 00:09:13: I also went to a technology magnet school. I don't meet many people who actually did that in high school. So that's really, really fun that you went there too.

Kelsey Ruger - 00:09:21: Was it here in Texas?

Melissa Perri - 00:09:22: No, it was in New Jersey. It was called High Technology High School.

Kelsey Ruger - 00:09:26: Oh, wow.

Melissa Perri - 00:09:26: Which is the lamest name for a school. Also, our mascot was an atom.

Kelsey Ruger - 00:09:31: Oh, we had a regular mascot.

Melissa Perri - 00:09:33: You had a good mascot. You probably had like a much, much better. Did you have sports teams?

Kelsey Ruger - 00:09:38: We did have sports. It was a regular school with the magnet program added onto it, which was really weird. The magnet kids rarely ever mixed with the other kids unless we were taking like honors classes and then it would be both sets of kids. But most of the classes we took, it was all magnet school kids. And then we played sports if we wanted to.

Melissa Perri - 00:09:57: That's cool. We did not have a sports team because we were only, there was like 65 people in each grade in our high school. It was public, but we all came from all over. And you had to go back to your home high school if you wanted to play sports. So I think they thought us nerds couldn't. Sports or something, but everybody I knew played a sport and always went home for it. So didn't get the full real like high school experience, but it paid off because we learned about technology, but it sounds like you did. You still got that like normal high school experience.

Kelsey Ruger - 00:10:26:The normal high school experience. I still keep in touch with pretty much a good chunk of people from high school, too.

Melissa Perri - 00:10:33: That's cool. We have, yeah, we spread out. One of the girls I went to school with, she is now the head of development at Google Chrome. So yeah, Adrienne. So she's on Twitter, always talking about really cool stuff. It's fun to see people from high school pop up all over the place, doing really cool things, especially in technology.

Kelsey Ruger - 00:10:51: That is cool.

Melissa Perri - 00:10:52: Yeah, I like that. I was like, it keeps us together. At least we're all on Twitter. So you went to this magnet school, kind of got you interested in technology, and you became a developer straight out of that. How did you transition into user experience design?

Kelsey Ruger - 00:11:06: So the backstory on the design portion, I actually started in high school. And in high school, we had the ability to do both things. But when I got into college, I spent some time working as a graphic designer slash production artist for the University of Houston newspaper. But you really quickly learned back then, you're like, okay, there's probably not a lot of jobs in this area. And so once I graduated from college, I went to work for a consulting company and then quickly transitioned into my first startup. When I got to that startup, there wasn't really a whole lot of people there that understood how to tie the technology to the design. And so I think you hear this story a lot. It fell into my lap because I was the one who knew how to do it. And over time, what ended up happening is I would do both or I would have the option to choose one path or the other. Depending on which company I was working for. But in the late 90s, early 2000s, it was, Kelsey, you know how to do graphic design or you understand how to do that portion of the works. We're going to give that to you. But back then, it was really like, give me a button. It wasn't really as much the UX work that we understand and do today.

Melissa Perri - 00:12:19: So where did you see it start to evolve more into what we think about UX today?

Kelsey Ruger - 00:12:24: You mean personally or as an industry?

Melissa Perri - 00:12:26: Personally.

Kelsey Ruger - 00:12:27: So probably for me, the catalyst that really moved me into that direction is when I went to work at Prodigy and we had full teams. It was the first time I ever saw a company that had a team of UX people, that had engineers. We even had an accessibility team. So a lot of that started to coalesce for me then where it was, oh, there is, you should really think about the flow and you really should think about people with disabilities and how they use the software as well. And so really right around that time is when I started to see that there's really three legs to this. How desirable is the software from a UX perspective? How feasible is it from a technology perspective? And is it viable from a business perspective? And you start to see those lenses and actually even to this day, I tell product managers and designers, if you really want to understand how to move around the company, you have to have all three lenses. You can't just be in your discipline and that's all you really understand.

Melissa Perri - 00:13:29: It's so true. So you have the technology lens, which is like very feasible. Are users going to actually use it as a UX lens, right? The desirability of it, understand their problems. How do you start to learn as well, like that viable piece from a business perspective? Because to me, that's one of those things where a lot of people who come up through technology don't understand kind of the business impact on the products that they take. And to me too, I see that hold people back, right? From getting into the C-suite, from becoming the chief product officer or chief user experience designer or a CTO. What did you do to kind of cultivate that knowledge?

Kelsey Ruger - 00:14:04: So for me, I think a lot of it was because I always worked at startups and they always offered a quick path for me to learn those things. Early on, I worked at a couple of startups where I was actually able to be exposed to, here's how we make money. And I always tell designers, if you understand the company's business model, and then you understand how they apply that business model, you're going to be able to do a lot of things. To give you a couple of examples. So if you look at Target and Walmart, they're essentially the same thing, but they have very different business models and how they approach running their businesses. And I think as a designer, when you're really trying to understand who is the user and how does this user interact with our business, understanding the business model and how the company actually derives value from that customer is really key to being able to accelerate your career. In the business side of the world.

Melissa Perri - 00:15:00: Okay. So in startups too, I think that's like so important if you're not paying attention to the viable piece as well, like you'll go out of business, right? Pretty quickly. Like it's got to be able to make money or sustain or hit some kind of goal. Otherwise you have no cash, you will run out. So trial by fire.

Kelsey Ruger - 00:15:16: Right. Another way to sort of look at it, that's probably a more stark difference is the way Apple sells their products and the way Walmart sells their products. They both sell products. Apple is not selling on commodity, right? Like they're definitely selling an experience. And as a designer, if you understand why they do it and why they approach it that way versus why Walmart does it or why they approach it that way, it actually will make you better at your job too, because you can build better experiences for that particular model.

Melissa Perri - 00:15:46: Okay, so deeply understanding the business model, what they're really doubling down on, why it works for them, how they actually perceive the value coming through it. So that's what you get your product managers to look at.

Kelsey Ruger - 00:15:59: Right.

Melissa Perri - 00:16:00: So you were in user experience design. You've got this robust knowledge too of how that works. And now you're the chief product officer of Hello Alice. Can you tell us a little bit about what Hello Alice does? What kind of drew you to that company?

Kelsey Ruger - 00:16:15: So Hello Alice really is, I call it a toolkit for small businesses that want to grow a healthy business. And so we have several different things that we help businesses with, whether it's really understanding how to grow it. We have a tool called the Health Score. Like it will give you an assessment of where you stand as a business and what types of things you should be doing. But even starting in 2020, when the pandemic started, businesses wanted to know, how do I fund my company? And so we spend a lot of time with grants and loans and credit to help them once they know what they need to be doing to build a healthy company, find the funding to do that. And we have a simplest series of tools and educational material to help them get there. And I was drawn here because I've always been around entrepreneurs, even starting as a young kid. My grandfather, back then, I didn't know what was called an entrepreneur. My grandfather owned a business where he helped people build houses and we would go work with him. We didn't know what it was. It wasn't until you get older and you realize, okay, I've always been around this. And then my godfather also introduced me to several other types of businesses. So it was always something that I was passionate about is helping businesses grow, largely because I could see very early on that, at least in our country, small businesses make up the majority of the employers. And so most of us don't realize it, but the vast majority of our country works for small businesses. We hear the flashy startup stories and we hear the big brands, but most of us do end up working for small businesses or medium-sized businesses.

Melissa Perri - 00:17:52: I'm so happy you brought that up too. I'm like so passionate about this because I feel like we lose that story about small businesses a lot. And it's true. You hear about Google, you hear about Facebook and you hear how they started a startup and they grew as a tech business. But I moved from New York City down here to South Carolina too. Most people I know work for some kind of mom and pop shop around the corner, whether it's a roofing company or a construction company or plumbing or my neighbor does kitchen cabinets. He did my cabinets. That's really, I think, a big part of what America is built off of. So this passion for this drew you to Hello Alice. And how does Hello Alice help these types of companies succeed? What's the way and the value that they provide to them?

Kelsey Ruger - 00:18:32: So there's a couple of big buckets, right? Probably the biggest one that people know us for is funding. And either through our grants programs or through other types of funding, helping them get the money they need to either establish, grow, stay in existence. The other part is educational. And so I think for me, especially when I interact with our small businesses, it's relaying knowledge that I've gained working for larger businesses that translates directly to what they may be going. If you think about the structure of most small businesses, it's one, two or three people, right? Like it's not like they have a full team of product managers or even a project manager to help them manage things in the business. And so a lot of our work is also educating them on things that to us may seem second nature or obvious, but to a person who is, you know, struggling to make it through and grow their business, they don't have all that knowledge in house. And so that's one of the things we're really passionate about. Passing that knowledge on to those small businesses.

Melissa Perri - 00:19:34: What are those types of things that they're usually have questions about?

Kelsey Ruger - 00:19:37: If you can think of it, they've asked me. So in the last year, I have gotten asked whether I should start a corp, whether I should start an LLC. I've gotten asked, how do I do strategic planning every year? In fact, we do a workshop for that every year. We do revenue growth. We do budgeting. So it's a lot of different things that we do. And the good thing is almost everything that we teach is things that we do ourselves. I actually said this to the team once. It's like, we should probably not teach things that we don't do. We should mimic some things that we do. So like when we talk about goal setting, it's nearly identical to what we do internally.

Melissa Perri - 00:20:16: That's really neat. It's like applying a lot of the stuff that we do in product management back to small businesses. Very cool. So when you came into Hello Alice, what did the company look like and how did you figure out where to start? With startups, there's usually 8,000 different directions you could take when you come in as a leader. What was your process for really diagnosing what you should start with and how you should help?

Kelsey Ruger - 00:20:41: So this concept I'm going to introduce is something that I actually use now every time I hire a new person, and it is establishing what is north and what is true north. If you are a Boy Scouts or anyone that's spent time outside, you know that north and true north are slightly different. And so you come into a company and you come in with these ideas about, like, here's what I was told we need to do. And then you come in and you assess the lay of the land and decide what the slight pivot that we might need to do. And so what I was told when I started here, we were between 20 and 25 people. There were four engineers and they all did everything. So they were front end and back end. They did their own QA. And the only PM we had got hired two days before I started. And so we quickly figured out we had to put infrastructure in place to make a product team run in addition to building all the stuff we need to go build. And so we sort of in parallel put in pieces to manage the product process. So, you know, our scrum process and how that works. We put in a backlog that we could go and look and say, okay, here's what we're going to be doing for the next year. And we started adding to the team. Right. And so I think it's probably not that different than a lot of startups that you go into that are, you know, sort of making that transition is everyone's scrappy. And you get to a point where if you're really going to scale, you've got to put some additional structure in place.

Melissa Perri - 00:22:10: So I think it's interesting. There's always this topic going around about for startups, when should you hire your first product manager? And then also, when should you bring in your product leader? For Hello Alice, what do you think was the crux to say like, well, apparently two days before you got there, they hired their first product manager. But what was the push and what was happening in the company where they said, we really need some kind of leadership to come in?

Kelsey Ruger - 00:22:31: I think really the scale, right? Like if you're starting to scale and you need someone who is looking at it on a day-to-day basis and really sort of assessing what's priority, how do I make sure that each engineer and each designer and each, if you have writers or whoever's on your scrum team, they know what to go do. I think that's really the catalyst. If I were just making a run, not necessarily Hello Alice or any other company, I tell people all the time, hire your UX person and your product manager first. And the reason I say that is I think people wait too long to bring in UX. And to start really thinking through what is the user going to be doing? A product manager thinks about things differently than a founder or even a head, right? So they're thinking from an execution standpoint, like how do we take a batch of work and get it done? And the sooner you have someone who that's their job, it actually frees you up as a leader to go do the other things that you need to be doing at an early stage, like raising money or selling so that you're not focused on like, what are the things that we have to do in a tax? Every day.

Melissa Perri - 00:23:40: You've also worked in a lot of startups and I'm sure with a lot of founders as well. What do you think is the key to success coming in as a product leader to a startup where you have to work with those founders? Sometimes this can be a huge point of tension for product leaders and I hear about it all the time. What have you found to be successful?

Kelsey Ruger - 00:23:58: You know, I actually, a good friend of mine a couple of years ago introduced me to this book called Rocket Fuel. Up until then, you're not worked with lots of founders and been in positions where there's that push and pull for the different areas of what needs to happen. But what it helped me realize is typically in a company, your founder is going to be one of two things. They're either going to be a visionary or going to be operational. You got to figure that out really quickly so that you can determine from a product perspective how to operate in that world. So if you're dealing with a visionary founder, your mode of operation is going to be completely different. Completely different if that founder is operational, right? And so I think figuring that out and then determining whether the company is what I would call experience driven, sales driven, or tech driven, because that's really from a product perspective going to help you form your roadmap and understand what themes are going to be necessary and where you're going to have to spend more time. So in a tech driven company, you may not have to be as deep as you would be in a sales driven company. And I think probably even what you see happen at Hello Alice is for us, I think what happened with my role is the chief product and the chief technology roles, they have so much overlap in a lot of companies today that we just combined it because I was doing both things anyway. And so understanding how to fit those two roles into the company is really key when you're coming into a company.

Melissa Perri - 00:25:30: That's an interesting one too. I also structured roles where we'll combine product technology and UX under one person, but there is some backlash out there about should we have the same person running product technology, UX, all those different ones. What have you seen be the pros and cons for consolidating it under one person?

Kelsey Ruger - 00:25:48: I was going to ask you a question. What's the backlash you hear?

Melissa Perri - 00:25:51: Oh, well, I'll tell you what I hear. So I guess they think that one person could have too much power, right? It's like somebody who's really overseeing all of those things is kind of calling the shots and people believe there should be a healthy tension between product and technology. So I get that piece. Almost always I see UX fall under product. It's been rare that it kind of gets bumped out unless it's a smaller company and then it almost always gets consolidated under your chief product officer one day. With the technology versus the product being consolidated, I think some people believe that product people just don't have as good technical expertise as like a chief technology officer. But I'm curious what you've seen from your experience, you know, running this. Why does it work for you? Like what makes it work for Hello Alice?

Kelsey Ruger - 00:26:40: If you're a chief, you gotta let your people do their job, right? And our head of technology and our head of product, they work together every single day. They get along really well. And that's because they have to, right? Like they both have the same up chain. And I think what you see in a lot of companies is there's too much tension between product and technology where nothing gets done.

Melissa Perri - 00:27:04: Yes.

Kelsey Ruger - 00:267:04: Or the two groups are not listening to each other because there's no incentive for them to do it because they all know they report up to different chains. And when I arrived at Hello Alice, I really took a step back and said, what are we trying to accomplish? Are we trying to build technology? Are we trying to build a product? You're trying to do both. And so you've got to make sure that those teams are comfortable working together. And there's plenty of tension, believe me. But they are working toward the same goal. And I think maybe that's what I saw is in a lot of companies, those two groups end up not working toward the same goal.

Melissa Perri - 00:27:39: I have also seen that. I have structured, like when I've helped people hire chief product officers or structure their teams before, we've had really good success having a CPTO, you know, run the whole thing. And in cases where I find it really works out well, one, there isn't a strong product or technology leader. Let's start with that, right? Like there just isn't one there already. So now we have a choice of like, do we hire two people or do we hire one person? And then I usually do, I almost always work with like scale up organizations that are kind of like probably about 150 people up in personnel. And we do it as well when it feels like there's a technology leading the product decisions or when it feels like there is no product vision and the technologists are not on board with like following a technology, let's say a product vision, right? Like we could tell if we keep it separate, everybody's going to be going in 18 different directions and you don't have time to do that in an organization. So I've done it. And actually like four or five organizations where we brought somebody in for like the scale up mode and we brought in a CPTO, somebody who had a great technology background like you do and a product background and understood UX and they were able to hire either a director at smaller stages, right? Of product UX and development to kind of be functional leaders over that. But they were able to manage it, do the vision, the strategy pieces, kind of train up their teams and still run all those different pieces. And then we've also seen a great time as well when I did this in one company, it was a healthcare company. We had this technology leader who was not quite CTO level. He was probably a strong VP is what we would say. And he was not capable of being a CTO or getting trained to be a CTO immediately.

So we brought in a CPTO who kind of took him under her wing and she said, my goal is to make you my peer one day, right? And I would love to be able to raise you up and have you be the CTO when we get bigger because I'm not going to be able to oversee this all forever. And I don't really want to, but I've run technology. I've run product before. Like I can help you become an executive, right? And that's what I want to see. And that worked out fabulously. And five years later, six years later, he is now a CTO and he knows what he's doing and he's really good at it and he's thriving. And I've seen that work out super well too for like a chance for development, but it also saved the company because they weren't going into 18 different directions because they didn't have all these leaders fighting with each other. So I'm pretty passionate about this, but I'm not going to be able to do that. I think it still upsets some people about having all of this report into just one person. And maybe it's because they think that person almost always will be more, I see product people get upset about it because I think they think all the people that it would be consolidated under. And I guess I do see this outside of the companies I've helped with. Sometimes it's just a technology person, like a CTO, but they don't understand product. And I think that's what the fear is.

Kelsey Ruger - 00:30:30: Yeah, and that's a reasonable concern. I think in those cases, you just have to know your company. The other piece that I didn't mention this earlier that's really, really important to me is we all talk about Agile and we all talk about Scrum. For us, it's a real thing. When we were setting up our product teams, there's engineering, QA, there's a designer. In some cases, there is copywriting. In other cases, there may be a data team member. Once that team is established, there is no more engineering said this or the designer said this. That is a team. And as a team, you guys are responsible for the delivery of whatever flows through there along with the product manager. And that has worked wonders because now everybody understands that you're not going to be able to go back to the head of engineering or the head of product and say such and such. Because if it bubbles up to me, I'm just going to put both people together and say, go figure it out.

Melissa Perri - 00:31:28: Yeah, that's a really good point. So you've got these cross-functional teams, then everybody's working together collaboratively. How do you think about structuring the organization? Like, do you have any functional leads yet? Is that something you're looking at in the future?

Kelsey Ruger - 00:31:41: We do. We have under our engineering team, data, QA, engineering, DevOps, under product. So our product team today is going to function more as a PMO. So we have our product managers. And we, earlier this year, we made attempts in the past, but earlier this year, the entire company is on Scrum now. And so we also have PMs that work with other teams that are also working in the two-week cadence. And the whole company's on the same schedule. So if I say, what's in Sprint 95, for example, I can look at it across the company and see what everyone's working on. And everyone has functional leads, but the functional leads are not responsible for work delivery. The PMs are.

Melissa Perri - 00:32:25: Yeah, that makes sense. So it's the PMs and the teams that are the ones who are responsible for it. Okay. And for your product managers, you mentioned there was absolutely no product managers when you walked in, except I guess the person who got hired two days before you. How do you think about growing that team?

Kelsey Ruger - 00:32:42: Well, for us, it was, we, we grew as we needed more people. And so when the workload or the number of features started to get to a point where we knew one person couldn't manage it, we added more. And so as we added, you know, our loan product, our credit card product, our, and additional features, we had to add additional people to help manage those with a director over everything.

Melissa Perri - 00:33:06: And then your product managers, did you hire them externally? Did you promote them internally?

Kelsey Ruger - 00:33:11: We had them externally. I had to think to see if we promoted anyone internally. We didn't promote anyone, but it's always a possibility. I've had that question recently.

Melissa Perri - 00:33:21: So when you were going out and kind of looking for this team, you were mentioning to me before we jumped on here, they got kind of various different types of backgrounds too. What were you looking for? Were you looking for a mix of different experiences to come together? Were you looking to balance out anything? Or were you looking for people who've done product management before? Like how did you come up with the right framework?

Kelsey Ruger - 00:33:42: Well, the way we approach it is we write the job description first. And we really pay attention to what we're saying in the job description. And then we build our interview process around that. And so in the case of a feature that may be more user-facing, I probably will lean towards someone who has worked with UX a lot or someone who's worked in that type of environment because it's going to come up as a part of their work. If it's a data-driven component, you may want someone who comes from a more technical background or specifically understands things like data science, machine learning, and all those types of things because that will be more of their day-to-day. And so we start with a job description and then we look at what is the area they're going to be in and then we build our interview process around that.

Melissa Perri - 00:34:32: Okay. And then that helps you actually figure out what types of skill sets you need. So do you kind of do a core, this is a basic product management skills and here's where I would want people to spike depending on the feature or is it just custom for, for everybody?

Kelsey Ruger - 00:34:46: No, to kind of break down our interview process, the first interview is skills. And that's typically managed by a PM or multiple PMs. And they're asking the key questions. How do you run Scrum? How do you manage projects? How are you working with stakeholders? Then we do more scenario-based interviewing at the next level. We really do focus on what do we need them to do? Can we validate that they can do that as we're moving them through the interview process?

Melissa Perri - 00:35:16: Got it. So with your team now, how are you thinking about, you know, the next phase of Hello Alice and what are your kind of like growth ambitions? How are you thinking about the team going forward? Startups are always moving incredibly fast. How do you balance like kind of growing this team, managing all these people, right? And then also looking at the strategy of where this company is going?

Kelsey Ruger - 00:35:37: So there's, it's twofold, right? So I'll look at our roadmap and what we've said we're going to build. And then we've really gotten to a point where now we can actually say, what should we be building given market or innovation or technology advances? So for example, we've started to look a lot more at AI and how AI is going to drive the platform long into the future. I think a lot of people, when ChatGPT came along, everyone jumped on the bandwagon.

Melissa Perri - 00:36:06 Oh yeah.

Kelsey Ruger - 00:36:06: We were kind of like, that could plug in, but let's take a step back and make sure we're doing this right. So for example, we wrote an AI policy before we even started thinking about building anything AI, because we wanted to really think through like, how does this fit into the roadmap? And then when we get to budget season, it lets us say, okay, if we think in the next 12 months, we're going to go build something that needs this. I know the budget for a PM that fills that role. In enough time. To do requirements and get everything working.

Melissa Perri - 00:36:39: Great. And when you are looking at the budget and trying to get buy-in to go get a PM, I feel like this is a struggle for a lot of leaders, right? I want to hire people. I want to go ask for budget to hire this person. We could be doing so much more with it. How do you put together that business case to go ask your investors or talk to your CEO and say, we need more money to do these things?

Kelsey Ruger - 00:37:02: We do have a framework that we look at based on things we think are coming or things we think we need. But a lot of it's driven by the budget. For example, if I know a stakeholder is asking me to go build something and we don't have the bandwidth or the person or the expertise, in one way or the other, we have to fill those gaps. So it may be a consultant. It may be a new hire. It may be a contractor. But if we know we need that, I try to get it into the budget early by pulling all those things together. And so we try to build business cases for those things early on and then flesh them out over time so that when we get to the point where we need the hire, we've got all of the justification there.

Melissa Perri - 00:37:44: Yeah, that makes sense. So when you think about the future for at Hello Alice and also for your role as a chief product officer and technology officer, what are you excited about? What's next?

Kelsey Ruger - 00:37:55: That's a big question for me. I think really being able to grow into more thought leadership around the things that we do or things that we're building, particularly as it as it relates to helping small businesses. So what I tend to focus on with my team is and no one ever everyone always they misunderstand what I say when I say the best policy for any leader is to try to make yourself obsolete in different areas. And so you train your team members to feel things that you're doing so you can go explore and do other things. And I think sometimes in startups, people get so ingrained in what they do day to day. There's a great article that I'll send you, and it talks about giving up your Legos. Right. And sometimes you have to give up your Legos to go get new Legos. And it puts you in a position where you don't have to worry about things like a tree. because people are getting an opportunity to grow. Right. So I think as I look at like where I'm going personally is how can I help the team grow to go open up time and opportunity for me to go do other things. From a Hello Alice standpoint, I think you're only going to continue to see small business be sort of the core of what we do in America. So there's always going to be a place for companies like Hello Alice that's focused on helping small businesses. It's just where do we do it? And I think I see lots of new opportunities from both the technical and social perspective to help those small businesses.

Melissa Perri - 00:39:28: I'm really excited to see where Hello Alice goes and also for you and your career. Thank you so much, Kelsey, for being on the podcast. And we will link to those articles that you mentioned too in the show notes for those people listening. So go to productthinkingpodcast.com to see those links. But where can people also connect with you and learn more about you?

Kelsey Ruger - 00:39:46: The best place to connect with me is on LinkedIn. I do write and publish in other areas. And I'll probably be doing more of that next year. But LinkedIn or Instagram are probably the best places to reach me now.

Melissa Perri - 00:39:59: Great. Well, I hope everybody goes and checks out Kelsey and all of his great knowledge that he has to share with us. And for those of you listening to the Product Thinking Podcast, we really appreciate you being here. If you liked this episode, please like it and subscribe to our podcast so that you never miss an episode. We'll be back next Wednesday with a new episode. And in the meantime, go to productthinkingpodcast.com to see all of our other great guests that we've had on and to learn more about Kelsey. We'll see you next time.

Kelsey Ruger - 00:40:26: Thanks again.