Welcome to Flux's Mobility Spotlight where we share stories of people who have made successful job transitions and the companies with cultures that encouraged them to do so. Our goal is to highlight these transitions and understand what drove them, experience and working-style overlaps that might not be obvious, and to share advice for others considering a similar move.
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In this episode we're speaking with Kate Doebler who leads Product Operations at Cockroach Labs. Kate shares her journey from starting as a Business Analyst at Deloitte, transitioning to Client Services at a start-up, and then helping establish Business Operations and Production Operations practices as those companies grew. We'll cover skills and experiences that were helpful in her transition, and advice to others wanting to make a similar move. In this discussion we cover:
🏭 Key differences between Business & Product Operations and how they can vary by company
🥰 Using what you like to do and are good at to guide career transitions
🚀 How things outside your job description could be your biggest career opportunities
Nick (Flux): Welcome to Flux's Mobility Spotlight where we are sharing stories of people who've made successful job transitions and the companies with the cultures that have encouraged them to do so. And today I've got Kate with us. I've been excited about this, Kate and I worked together back at FreeWheel, which is now part of Comcast.
Kate is currently at Cockroach Labs, and she's going to talk a little bit about what she's doing there. There's a whole arc here. We're going to talk about from business analysis work at Deloitte. So really doing consulting. Then, ultimately what brought you to FreeWheel where you played a lead solutions engineer role within Max's services team and then similar to Talia who with us a few episodes ago moving into Product, but actually to build out a Business Analyst function as we were scaling, and then you moved into Product and Bus Ops. We can talk about the differences between those roles and similarities, because I think both are newer but a real spectrum of things from being very operational in very different ways. So thanks for joining us.
Kate (Cockroach Labs): Thanks so much for having me.
Nick (Flux): Tell us about your current role, what are you doing at Cockroach? What does that look like?
Kate (Cockroach Labs): Sure. So for those who don't know Cockroach labs provides cockroach DB, which is a distributed SQL database and if you would like to know about all the details of why distributed SQL is the best we have tons of blog posts on that. But I do Product Operations at Cockroach Labs, which means that I help the product designers, product managers, as well as our documentation writers with process as well as data and analytics.
Nick (Flux): That's great. Let's walk backwards because I feel like Product Ops we had a version at FreeWheel which was really this Bus Ops role that was applied to Product. And you'd been doing this as ops before going to the cockroach. So talk a little bit about , what are the similarities, what are the differences? How, how should people think about these two different roles that I think are becoming pretty common in at least software companies?
Kate (Cockroach Labs): Yes, I'm definitely seeing that a lot more software companies are starting to hire operations specialists for their individual departments. The description of the role varies pretty widely by the company. So it's important to understand if you're pursuing one of these roles. What is the description? What are the roles and responsibilities? The description at Cockroach Labs, which really appealed to me personally, is that the role is kind of broken down into three parts. The first is it has some chief of staff responsibilities, which includes supporting my executive with executive level responsibilities, like preparing for board meetings, doing financial forecasting for the company, preparing for those. Really important executive spotlight moments where they need a lot of support and prep.
The second piece is process. So how do you make sure that these very expensive product managers, that you're hiring are really providing the most value possible for your company and making sure that there's no inefficiencies, ideally in that product creation flow. The third piece that I offer is analytics. So there are tons of metrics, especially that product managers want to look at anywhere from how is a customer using this feature has so and so turned it on all these questions they want to ask to create better products. I provide those three services. Now you may see at different companies that the job and contains only one of those services. And I think it's to clarify that and understand it.
Nick (Flux): Would you say is the function you're playing atypical or more typical or this one of these things it's so early that the role is usually different company to company?
Kate (Cockroach Labs): I had a boss who once said that operations can be a little bit like a kitchen, Either it's like a line where someone does the fish, someone does the meat, someone does the vegetable or someone owns the entree from the time it's ordered to the time it goes out the end. I have worked in operations teams that are both where you own the whole life cycle, or you own a slice.
I feel that those are the two main camps, really. So I own all of products, which involves the ideation, the business case development for a new product line or feature line. But there are some cases where it is central and you might be delegated to a project at a time, but your team is responsible for the operations of the entire company. I think those are the two biggest flavors. And then the question after that is the level of detail.
Nick (Flux): That's a great explanation. And I think that's a good way to think about it. And even hearing you describe it, I can think back to things you were doing as we set up the Business Analyst team within Product and just the structure we you're trying to get around roadmap. And managing a lot of software development across 500 engineers that were global and a team of 40 something product managers , there's the coordination, there's the balance of having process and structure and data and using that to inform and guide things, but also trying not to have it slow everything down because it's such a dynamic environment, which is never easy.
Kate (Cockroach Labs): And I think that's the balance that everyone who works in operations is trying to meet right efficiency and monitoring and intelligence, but without the expense of taking it too far,
Nick (Flux): Process for the sake of process . So you're doing this product operations role, and it sounds like you're really the right hand of and tell me at Cockroach the person that runs product also run s engineering or are those separate?
Kate (Cockroach Labs): So we have a CPO who is responsible for product management design, as well as documentation and training. And we have a separate CTO. Who's responsible for engineering.
Nick (Flux): Got it. Okay, cool. So let's walk backwards. let's take this back to the start. So you I think it started as a business analyst out of school at Deloitte doing the big consulting company thing. And you moved into working at a startup. So you stepped into a solutions engineering role, which at freewill , was very focused on how our products were being implemented and applied and used within our largest enterprise customers. So there's definitely some parallels to consulting but share a little bit about just like what brought about the transition from doing the BA work at Deloitte and moving to a startup and doing the solution engineering work, and also functional change and the company changed because obviously that was a very big cultural shift in terms of environments.
Kate (Cockroach Labs): For sure. And I think anyone that you talk to when you're looking at a career transition moment, you're really asking yourself two things. One, what do I like? And two, what am I good at? Those are really the most important pieces and what I was finding at Deloitte. Is that what I liked was I liked being assigned to technical programs. I liked, so look at me badly for this, but I liked my implementation of Hyperion that I did. It was very fun.
I really liked the projects where I worked with more free spirited teams, there's a wide range of companies that I consulted for from very conservative to very free spirit. And I preferred that free spirit environment. The second piece was, what am I? What I found was at Deloitte, I always received stellar reviews from our clients. They said, I'd have Kate back anytime. She's great with client service, she has great bedside manner, she's great at saying no, without saying no, all these kinds of things that you need when dealing with customers. So when I went out into the market to look for a job other than salary requirements that I had, those were the two things I knew I was. I was wanting and I was bringing to the table. And so when I spoke to them hiring manager at FreeWheel at the time, I said, I really want this free spirited environment. And I really want to work on technology because those are the two things that I know that I've figured out. And I told him that at the time I'm great with clients. They will never be upset with me. They will never complained to you. I may not know all the answers, but I'm great with clients. And he said, well, you know, we just launched this big client in Europe and in the UK and we really need someone who's good with clients. I said, Perfect. And so I think it's really important when you're navigating that change to know what you like and what you can bring to the table and offer it to that person.
I don't work with clients anymore. And I work with internal clients . But it is still something that I rely on as a skill that I knew I had figured out right out of undergrad, that it was something that I brought to the table.
Nick (Flux): That's great. What do you think in that transition, going from this analyst's role in a consulting environment to something that was also client facing, but in the scrappy startup environment what were the main skill gaps o r working style adjustments you needed to make to feel like you had transitioned well and were keeping your head above water.
Kate (Cockroach Labs): I think I definitely had a huge on-ramp when it comes to technology. And I think, you know, if you even look at my current role, I still have a huge on-ramp when it comes to technology. And I think being willing to buckle down and learn what I didn't know and being aware of my gaps from a technological perspective were very important to my success. I also think the second piece beyond the hard skill is the soft skill, which is the ability to deal with ambiguity. When you work for a large company, there's generally either a sense that errors are to a certain extent have less of a ripple effect than when you're at a smaller startup where every dollar matters, every account matters. And I think that level of ambiguity was very difficult for me to digest. When I first started working at the company. Honestly to get over that hump was really some excellent coaching from the people that I worked with that helped me get through that.
Nick (Flux): Yeah, let's talk about your transition from Solution engineering. So this is when you and I got to know each other much better and you were in the New York office. I was in San Francisco and I feel like we all spent time in a lot of different offices as the company was growing. We had reached a point and I'm dating myself now because this was a while ago. I think we were around 400 people. It was post acquisition. The company was actually unique in a way where we were just growing even faster once Comcast had bought us and product was just getting to a place where it was really hard to manage all the expectations of a global sales team and a broad product portfolio. And then we had an engineering team that was predominantly in Beijing and there was just so much coordination the product team was having to do in translating sales needs, customer needs and then also working with an engineering organization that wasn't totally lined up. Engineering was functionally aligned to the product and then we were repackaging how the product was actually being sold. And so all this translation was happening in the product team.
And I remember at a certain point of scale where we'd actually brought Adit in to do Business Operations, where it was just like, we need to redo a bunch of process. We were at different size, communication's breaking down like let's rethink this, but then this other problem, we're just not understanding, like, I believe product should always be deeply embedded with customers, but there's just a point where the size of customer working with the complexity of the product, the configuration for that customer gets really hard to know very well unless you're servicing it. And there was like a breakdown where I feel like we weren't building the right things all the time and there's not like a feature level. And it was kind of clear. It's like, you know what stuff isn't being translated right from customers there's this role we need, and that needs to help do that translation. And it feels like sit in the product team. As I remember, I talked to you and some other people, and this is where it was business analyst idea came from. So it was like bringing you back to your roots, but it was establishing the practice and the team, and then actually building the team, which you were then leading in that whole process.
So talk a little bit about that transition. You were starting something from scratch, which happens a lot in startups when you're growing. How did that transition happen? And let's talk a little bit about how that went.
Kate (Cockroach Labs): Sure. So one of the things that I really remember about that transition was as a solutions engineer, it was not part of my job description to do consulting, but someone came to me and they said, Hey, I've got this consulting gig with this client in Europe. And like, I really need you someone to do it. And I think you can do it. And I had a moment there where I could have said. No, this is not part of my job prescription, but I said, okay, you know what? I'll bite the bullet, I'll do it. And I added it. It's my workload. And I worked on that for awhile and I presented my findings to the executor. We have team of which at that time you were a member. And I remember you came back to me about two years later or something like that and said, I remember your presentation and that you gave, and I think that this is the kind of analysis that we need to add to our product team. And I think the lesson for some folks is it might not be in your job description. It might not be something you're technically supposed to do, but if someone offers you the opportunity to step and do something different and gain exposure, you know, think of those as opportunities to really develop your brand, to get to know executives, to help you find that next step.
And I really did use that presentation as a bit of inspiration for how I develop the team. The outcome of that presentation was I had interviewed a bunch of these stakeholders at this client, gathered all this information and synthesized it into some findings about our clients. And so what I tried to do when I was modeling the business analyst team was how do we pre package and support these findings to our product managers in a way that makes their design development and deployment process as easy as possible that they don't need to go to talk to 15 customers. They should still definitely go talk to a few, but that we can help front some of that work. And I think that was really crucial. And I think the second piece was the investment that I put into augmenting that interview data with quantitative analysis, which brought me back to my Deloitte roots. I leveraged those old skills and dusted them off, but I think it helped our department have both an empathy for the customer in the stories and the anecdotes, but also some proof because there's always a couple clients who scream very loudly, but don't represent the general population.
Nick (Flux): Yeah that's a great point. And I just love the story in that too, because I think for a lot of people startups can be very chaotic, particularly when they're growing, but that's also where all the opportunity is. And so being able to seize it and not turn those things down. In the right environment those things will come back around. And you built a great team. It became a feeder also . I feel like by the end of my tenure there running product, we had this great feeder in from services. We had the BA team now that we could staff into that many of those people became product managers, or they were going off into this ops speak, which was becoming this centralized departments. So there's all this great pollination that was happening on top of a pretty critical function we needed. As we had gotten to a certain size where there was just a lot of disconnect happening, which again it happens when you grow and when more organizations show up.
Kate (Cockroach Labs): And I think from a value perspective, that was something that I very much appreciated about my time at FreeWheel. When I started that group in your department, one of the first few questions you asked me, other than what's the value of this team's going to provide is what will the next step for these people be?
That was always a part of the design. And I do think that unfortunately at many companies, especially startups, the design of a new department of a new team have a new role, does not include answering that question. What are the potential other paths? And if I recall, I actually put together a presentation for you as well as some other leaders that said. These are my hypotheses of where these people could move based on their interest and their capability. And that was part of the thought process from the very beginning .
Nick (Flux): That's great. I think that that intention around development it's hard to find. And I think our culture helped spawn a lot of that and getting people to think that way, because they also is you're able to uncover those opportunities yourselves and grow you have that kind of empathy when you become a manager to want to make sure that these things that happened for you are instilled in the structure you're now creating for others, which I think you did an amazing job with.
Kate (Cockroach Labs): I think that from a company's perspective, personally, maybe this is wrong, but is that really motivated people who want to do good work, want to know what's next? Yes. And I think so, if you want to have the best team on the ground, when you're interviewing them, you should be able to say to them, we have at least some ideas of what you would do in two, in four years here. No interview candidate wants to say. I have no idea what happens after this.
Nick (Flux): Yeah, one hundred percent so now let's talk about your shift into operational roles. You moved from then running and like building and then running this business analyst team within product, into a product operations role. And then that then became Bus Ops and then back into Product Ops again. Let's talk about your transition from the running a team like that and then moving into the operations function.
Kate (Cockroach Labs): Sure. I think anyone who has worked in a technology organization can empathize with my story. The business analyst team was coming up with all these amazing findings and the findings were saying, Oh, we should fix this. Or we should focus on that customer segment or, Oh, there's all this you know, revenue living in this pocket over here. And every time I went to Product, they would say we don't have any development time left. And for the life of me, I would say, where did it all go? And it became this frustrating for me and I really wanted to become involved in understanding that funnel from the ideas that you have to, the products you decide to build to the software that you deploy and how it's adopted by many different people. And I wanted to get into that next lane where I could start to say, these are the reasons that all these ideas dropped out of the funnel, and these are the ones we've built.
And so I really wanted to get my hands on them, the answer to this problem. And I think it's been my quest for the last few years to if not solve that problem, at least provide transparency to people around it and how the decisions are made and where the inefficiencies are. And so that's the reason that I moved into product operations, and I think the key to my moving in that direction was to be pretty vocal about my interests. I was pretty vocal with a few different folks. I really said, you know, this is something that frustrates me in the business. And I think I've proven that I can do this job in a few different categories. I also would say that there's definitely a tradition of, you know, moonlighting in jobs that you don't have yet. So offering to help here at help there and add some value to it. Roll that you're not yet playing helped me prove that I can do that job if I were given the opportunity. So that's really how I was doing well to move out of business analytics, into product operations.
Nick (Flux): It's a great way obviously to test if that's a move you want to make. Right? Some of these things are such big leaps and investments of time and emotion to take and then to land and be like, Oh, wait a minute. This is not what I thought it was. It's good to find that out without having totally jumped in the pool yet. And I think the other interesting thing thinking about this is we've both had the good fortune to work environments where when a company is growing, like a startup does right where the relative change is significant. Your role itself grows the whole time. It's why leveling is so hard and early companies and titling is so hard because you might be the VP right now, but it's actually this director level role two years from now when the company is three times bigger and finding people who are able to grow with that is really hard. Let alone be able to transition between a bunch of these things because it's really a moving target. It's like your understanding of what this is right now it may be totally different 18 months from now, depending on what the company is going through. I think you did a really good job navigating through those things. I think it's almost fitting, you've kind of ended up in this operations role. Beause I feel like with a lot of this, it was following where the squeaky wheel or problem was where you were working and then uncovering that, oh crap it's actually pretty big and we need to deal with this. So let's stand something up and work on it. And then once that's there and can run itself, I'm going to find the next thing. And I think you're a showcase of that within Freewheel.
Kate (Cockroach Labs): Well, thank you. And I think that's also one of those things we're spending the time as a person to examine yourself and what you like and where you flourish and what gives you agita and what makes you happy is really important. Because if that, if the sound of what Nick just described makes you. Just want to curl up in a ball and hide don't no worries. I think if you want the reliability of being in tax, for example, and you know that every single April, it will be terrible, then that predictable cyclical business might be for you. And I think there's a, there's a person for every job. And I think for me, the idea that things in 18 months could be completely different. Makes me so happy and I don't think everyone is like that. So I think, you know, spend some time thinking about how you feel.
Nick (Flux): Yeah, that's great advice. I think this is the challenge generally with job descriptions sometimes in the high growth environments If the context of the work is not being explained, like job descriptions really focus on what you need to do, what you need to have, maybe what you'll get you know, doing it, but usually not. There's usually very little insight on the context of the work, the instantiation of this role. That same job description could be applied to a product role working on something brand new versus working on something that's existing, but maintaining and optimizing. And the responsibilities might read the same on paper, but those are two totally different jobs based on the work environment really dictating the types of skills and the working styles and things you need to not just be comfortable, but to really be good at it.
Kate (Cockroach Labs): Totally. And I think that's why I think every single guide to interviewing says have questions prepared and you know, every interviewer is disappointed. When you say, do you have any questions for me? And they say, no, it's because that's your opportunity to say, you know, who is this job today? Are they good at it? Like what makes them good at it? Why is this a new job that didn't exist before all these questions where you can really dig in and. Say, you know, am I going to be deprecating products for a living or am I going to be starting from scratch? those are two very different job descriptions and it's important to understand that,
Nick (Flux): Yes. So we're coming full circle to where you are now. Let's talk about product operations specifically or more broadly business operations style roles. What do you think is an important attribute in your current role that most people wouldn't typically associate with it?
Kate (Cockroach Labs): I really had a struggle with this question when I saw it. I think to be honest with you, product operations is such a new field that it's a little bit people even still don't really know what it is. So it's hard to expect. I think the flexibility aspect is a huge piece, which I mentioned earlier on, especially if you're taking this on in a technology or in a smaller company. But I think having a good grasp of data and executive reporting has become a mainstay of this responsibility for me personally. I believe there are probably more junior operations roles where that's less the case, but I do believe that. Reporting on a product organization, providing insights to boards and executive team meetings is a substantial skillset that if you're taking a senior product operations role will certainly be part of the job. And I think that's the only reliable piece that I can really grasp because those job descriptions do vary quite widely.
Nick (Flux): Yeah. And I'd imagine too, in a lot of environments, just given the newness of the role and usually where it's popping up part of your job is getting to be able to get to a place where you can do that because the first step is just making sense out of the chaos or just, what's not there. Right? And what are the things we're trying to measure? And where is the squeaky wheel or thing that we'd need to focus on and visibility . Where you kind of are starting from there's some things here to react to, but I'm the one putting the structure and this isn't about optimization yet.
Kate (Cockroach Labs): Absolutely. I do think a big piece of any operations role is walking into the chaos of a business and trying to make sense of it. I think operations people in a lot of ways are ambassadors for their departments. So whether you work in operations and engineering and you're explaining why the sprint velocity is the way it is or whether you're in product and you explain why the initiatives that you've taken on are the top three. Overall, what I would say, especially in the technology sector, is there so many pressures on our executives to appear at AWS conference to speak at this conference and that conference, regardless of whether you're a CTO or a CPO. This is going beyond the CEO's, these external commitments and priorities. And I think having operations people to structure the work and make sense of it on behalf of that executive is extremely valuable.
Nick (Flux): And I think even just listening to you talk about this obviously the paths out of a job like this there's the obvious ones, right? Becoming COO or operational leader within a business unit. But even the things you're touching in terms of going more into a product role or to a GM type function. Given what you're touching again, it sounds like it's very dependent on an environment, but it feels like you're getting such a broad exposure to the business. It's almost like this operational MBA in a way, in terms of all the things you're getting to learn and touch. So that's really cool.
Kate (Cockroach Labs): Yeah, I think I've seen operations folks go in a few different directions after this role. Obviously going into COO is one option, becoming VP of product for product operations is certainly one. But also migrating to a higher level operations functions. So working in internal consulting or I've even seen one of my colleagues jumped to the VC space. I think they're the operations discipline is really growing. There's a few groups now. One is called the Operator's Guild, which I recommend where people like myself are starting to congregate and make sense of what is operations? What is our job? What's the standard? What should we be saying the standard is and how do we make moves from this role? So it's definitely a new and exciting job description in my opinion.
Nick (Flux): It is. And I'm happy where we're talking through this. So tell me if you were going to hire somebody for your role, what would you look for?
Kate (Cockroach Labs): I think the biggest piece which I have returned to before is flexibility. And that is because this role is operations. I like to say, it's like looking at Swiss cheese, there's all these holes in the Swiss cheese and that's your business. And someone says to you, your ops. You're responsible for filling all the holes. And that means that one day I work on analytics. The next day I work on process. If you're not a fan of context switching, if you need a single project to work on, that stays the same. Maybe not the job for you. I think the other piece is being able to work cross functionally. I do think there's a lot of EQ required in this job. I talked to sales, I talked to engineering, I talked to marketing. I'm all over the place. So if you have a very particular style that you like may not work for you, but if you like talking to everyone, it's probably great for you.
And then the last piece is the overall operations is about making things more organized. I don't like using the word process because that makes start up people cringe, but I say, I'm going to make it more organized for you. And they say, okay. And I do think that that means you have to be one of them.
Nick (Flux): So your next role might be in marketing. We have a marketing role opening up. That positioning is great. This has been super insightful. I think both in just understanding a discipline that's developing and becoming so much more present and you've had such an interesting path of going from one thing to another and then returning to it and enhancing it or doing it in a different context . Or doing it at a different level.
So, let's just say someone wanting to make a similar move given what we've covered, from a product or a business analyst oriented role into more of a bus op product ops. What advice would you give someone wanting to make a move like that?
Kate (Cockroach Labs): I do think two of the techniques that I've mentioned already are one is that moonlighting. So offering to help in areas. If someone already has the job I'm offering to help them out, asking them for coffee, all these techniques that I'm sure folks are aware of. The second piece is when someone presents you with optional work, that might involve more exposure, especially to the groups that you're interested in. Get involved, take it on. I know it's tough to add more to your plate, but it definitely will help you meet new people and gain exposure in places that you wouldn't. The third piece that I would say is some companies, not all companies, but at Cockroach, we do have this where we do rotations. So if you say to your manager, I really want to move to this group that they might give you to that group for a month or two months and give you a small piece of work full time to see at sort of a, on the job interview a little bit. We still do make folks go through the full interview process against external candidates. But I think pitching that to someone is always a good option. And then the last piece I would say is just start doing the work. I definitely have just started doing the work. And then someone said who, it seems like that's a whole job. And I said, I think it is, you should give it to me. And I think that depends on the size of the company. I think if you're at a larger company, that's potentially not a great tactic, but the first three are probably suitable for companies of all sizes.
Nick (Flux): That's really insightful. This was great, Kate. Anything you want to plug or is Cockroach doing any hiring? Anything you want to share with people while we've got them?
Kate (Cockroach Labs): Yeah, Cockroach is hiring. We have openings for front end and backend engineers, as well as SRS. We do have limited business roles available, like every time tech company out there. But we also are releasing our latest version in October. So feel free to check that out. But last but not least, I just want to say thanks so much, Nick, for having me on. I think it's really important to know that Nick was one of the people who saw me and said, Hey, I think you'd be good at this. And I'm always eternally grateful for someone taking that step. And I think if you're in that position to take the time out and do that for someone who's more junior. I really encourage you to do that.
Nick (Flux): Well, thank you, Kate. I mean, the pleasure's all mine. I've been looking forward to getting to reconnect and obviously walking through this with you. So thanks. This was super insightful. Really appreciate it.