When companies achieve product-market fit and really start to scale, they have to make some tough strategic decisions. Brianne Kimmel, an angel investor and startup advisor, helps them make the right calls. Read the full transcript of her chat with us. 

Eric Boduch: Welcome, lovers of product, I am here with Brianne Kimmel. Brianne has a storied history, some great companies, Expedia, Zendesk, and now doing some work as an investor. Brianne, why don’t we kick this off by you giving us a little overview of your background.

Brianne Kimmel: Nice and thanks so much for having me, Eric. I started out my career as a product manager, I was at Expedia in a number of different roles. I first started on the consumer side of the business, focused on more performance marketing, and then moved into end product personalization. I then worked on the B2B side of the business, which is actually how I got into Enterprise software. I started working on building internal tools, a lot of it was focused on, basically stitching together various different parts of the Expedia Inc. organizations. I was there during a pretty crazy time, that’s when there was a lot of hotel and OTA consolidations. 

Brianne Kimmel: During that time I was fortunate to work on Orbits, I worked a little bit on Travelocity and then I worked on the HomeAway acquisition, which is a company that was based in Austin, and throughout my journey there spent a lot of time with startups, very much early-stage travel companies, but also looked at software as well. During that period of time that’s when early influencer marketing started taking off, we wanted to figure out as a broader Expedia Inc., how do we get great travel photos at even a destination or neighborhood level? 

Brianne Kimmel: I spent a lot of time with a number of different startups that were working on programmatic content, working on user-generated content platforms, and that actually took me to Zendesk, where I got more and more interested in both B2B software but also B2B to C business models. Zendesk is a great example where during my time there we went to one to seven products, a lot of individuals know us for Zendesk support, but we also had live chat, we had more robust datalytics. It was a pretty crazy time there as well as we started to move upmarket and wanted to spend more time on expansion opportunities outside of just core customer support. 

Eric Boduch: Awesome. Let’s talk about Expedia a little bit first, it had to be interesting tackling kind of a large, I would say, antiquated sector, I think maybe you used that word actually, talk to me about the challenges there. 

Brianne Kimmel: Yeah. A lot of folks know Expedia as it is today and fun fact, a lot of people don’t know that Expedia actually started as an internal project at Microsoft. Essentially it was one of the first, I would say, software applications to really focus on tackling a very broad and antiquated sector, hotel chains, airlines, tourism boards had historically used really outdated software, and this software was only available to agents. I remember reading, if you read about the history of Expedia, what was interesting is, for those individuals that were working in travel, there was a lot of controversy on do every day people have enough knowledge and can they actually book their own flights? 

Brianne Kimmel: Cause historically you had to go to the local travel agent, you had to spend time and go to someone who was technically trained, these are people that studied travel and hospitality or these are people that became trained agents, and they were responsible for booking your flights. It’s funny when you read about the history of Expedia and sort of how we operate today, but it turns out consumers are very good at booking their own travel. In fact, they’re very good at identifying travel discounts and ways to optimize their trips, and now we are fairly self serve in the way that we do things. 

Brianne Kimmel: I think that model really applies to a lot of the trends that we’re seeing today in software, where essentially, over time people are getting more and more sophisticated in the way that they choose and use software. Which was a great learning at Zendesk as well, where we started out with primarily self serve business model, it’s been great for me as an investor now to really understand bottom-up product adoption. It’s been helpful to have platform experience at both Expedia and Zendesk, and now applying it to investing. 

Eric Boduch: Talk to me a little bit more about working with the underlying providers, what was it like changing the paradigm with the airlines, you were talking about booking tickets and having to have very … You had to have expertise in their systems right? 

Brianne Kimmel: Yeah. It’s really interesting cause I think a lot of folks, I’ll get asked the question a lot, well Expedia’s a large consumer platform, what was it like and does it make sense to move into software? It’s really interesting because when you look at the B2B side of Expedia Inc. our hotel account managers use Salesforce, you actually have hotel account managers that are based in various different neighborhoods. They own a portfolio of accounts, they actually are strategic for more of the B2B or enterprise terminology, and they essentially work directly with hotels and do everything to inventory optimization to pricing and packaging at the chain level. 

Brianne Kimmel: It actually is, behind the scenes, while the output is a consumer app and it’s great for us to book our travel, behind the scenes to actually make this work you have a very large sales team and very large global sales team who deeply understand their individual market and they’re able to actually develop very deep relationships with the hotel chains, the airlines, the tourism boards as well. 

Eric Boduch: And when you first approached them with the concept were they receptive to it? 

Brianne Kimmel: I was not there very, very early so I think what’s interesting is I’ve been able to see a lot of the transitions that have come later. It’s been funny to really see where Expedia has unlocked a lot of opportunities for hotels to increase their utilization of their property. What we’re starting to see now, which I think is a cool trend in travel is, there’s a lot of next-gen boutique hotels and this is sort of the Airbnb mindset, whereas consumers want to stay in very cool and trendy neighborhoods, one of the challenges for an OTA like Expedia is that historically there aren’t a lot of hotels in the really cool neighborhoods. You’re kind of stuck, if you wanna book with a large hotel chain, you’re kind of stuck in a financial district. You’re stuck close to the airport. 

Brianne Kimmel: By having Airbnb inventory and by having like a HomeAway on the platform you actually access a lot of non-traditional inventory and then that allows travelers to stay in cool and up and coming neighborhoods. 

Eric Boduch: That’s very interesting. Let’s jump to Zendesk next, talk to me about Zendesk for startups, that particularly interested me. 

Brianne Kimmel: Yeah, Zendesk for startups is awesome. This was a program that we had re-launched while I was at Zendesk, it’s very similar to AWS Activate, Stripe has their own version which I think is called Stripe Atlas. It’s great to see software companies as they start to mature, there is an appetite to not only give back to the next generation of great software companies, there’s also a really nice way for you to continue to innovate by talking to startups who are moving a lot faster than you as you start to mature as a company. 

Brianne Kimmel: For us it was great, it was sort of a twofold thing, where we actually started seeing a lot of low-end competition or new and emerging competition. It’s a great way to actually play defense against some up and coming software that typically is less robust in terms of feature set, but also they tend to discount a lot more heavily. It’s a great way for us to say, if you are a seed-stage company, if you’re like we want you using Zendesk because that’s a product that can scale with you over time, and we want to invest in your business, meaning we are willing to give you free software and services to be successful. 

Eric Boduch: Talk to me a little bit more about how you structured that program because I think it’s interesting as kind of the larger player trying to make sure that there’s no low-end competitor that gets a solid foothold, that’s one of the reasons I assume is behind it. Tell me a little bit about how you thought about it, the strategy, the positioning, the structure. 

Brianne Kimmel: Yeah, it’s a really interesting model. It’s almost similar to … The way we ended up structuring it was very similar to almost a marketplace model. What we had on the supply side was that we had a lot of great pre-seed and seed-stage startups who essentially wanted access to free software, that was very easy for us to provide. On the demand side, we also had a great partner ecosystem built out where because Zendesk had such great exposure to very early companies, our early, early customers were Uber, Airbnb, Dropbox, and now we’ve just scaled really well with these hyper-growth startups. 

Brianne Kimmel: It was a great opportunity for us to also build a network of essentially VCs, I spent a lot of time with incubators and accelerators. Part of it was actually building out partnerships where we could essentially have a portfolio of Zendesk for startups, startups and we could connect them with the right funding, we could connect them to the right incubators and accelerators. There was more of a high touch model, where in addition to giving free software, we also wanted to make sure you were getting supported to get you from your seed to your Series A. We played a more active role in certain parts of that puzzle. 

Eric Boduch: That’s very interesting, not only did you provide software in your area, but you provided business connections in help making them successful as a company, I like that. 

Brianne Kimmel: Yeah it’s really interesting and I like it’s a model that … I learned a lot from the AWS team. AWS Activate has done a great job where in addition to giving you free services and free access to the platform, they also have their AWS Loft, which is just that additional way to provide support and to bring a lot of startups together is by giving them space.

Brianne Kimmel: We actually launched this model in Paris with Station F and I partnered with Rachel Delacour, we … Zendesk had acquired Rachel’s company called BIME Analytics and that was a company out of Montpellier. After the acquisition Rachel transitioned into a startup evangelist role, which is a great role for her, she’s very active in the startup ecosystem and she actually built a really great accelerator model inside of Station F, where there were desks available for the Zendesk, for startups participants. And you could also get connected to any VCs in her network, and that sort of thing there. It was sort of more a high-touch model that is still running today. 

Eric Boduch: And so one of the things I hear from a lot of startups and companies out there, that are looking to provide kind of that Zendesk for startups equivalent, right? Is worrying about cannibalization or leaving money on the table, how did you balance that? 

Brianne Kimmel: Yeah, that’s a really great question and I think that’s something that became a lot more complicated as we were going from one product to seven products. Historically Zendesk for startups was limited to Zendesk support. One of the questions that came up as we started to think about various different expansion products is, at what point do we actually migrate startups into our full … Like our bundled solution, and what’s interesting is that with the startups that we were working with, primarily venture-backed startups, it was almost something where we knew organically they were going to grow into increased utilization of the product. 

Brianne Kimmel: For us, it was a lot less about the short term gains and more about investing in startups that we believe we’re going to be the next Uber, Airbnb, Lyft, Dropbox. For us, we were willing to make … software in terms of margins, it was worth us actually giving away the software for 12 to 24 months, rather than missing an opportunity and then having these companies potentially go to a competitor. 

Eric Boduch: Okay, interesting. From growth and marketing at Zendesk to becoming an angel investor, what’s the transition like? What made you want to become an investor, I mean specifically in early-stage companies too. 

Brianne Kimmel: Yeah, absolutely. Well, it’s been interesting because I think I’ve always had an operating role plus done side projects in the startup ecosystem. I started teaching at General Assembly about five years ago, I actually started when I was living in Sydney. As it goes with all startup things a friend of a friend was working at General Assembly, they needed some teachers that were willing to launch an Apack so I created some curriculum around go to market strategy, early user acquisition, and just started spending a lot of time with startups on evenings and weekends. 

Brianne Kimmel: As I continued to do that and started meeting interesting companies, it became very natural for me to start advising, which I think this is a question that I get asked a lot from operators and from CEOs as well is like, at what point do you start advising or investing? And I think a lot of times it just happens organically. You just start spending time with great companies and then it makes sense to formalize the relationship. For me, I started out as an advisor, when you start advising a lot of companies you then become very time poor, the only way to solve that is to start investing. I started with really small checks, I started … 

Eric Boduch: If you give them money you get time back? 

Brianne Kimmel: Yeah, basically you either have to give startups time or money. Once you run out of time it’s usually a little bit easier to find money than time. 

Eric Boduch: I got it. In order to get that share of the company, it’s time or money. 

Brianne Kimmel: Of course, yeah exactly. Of course. Well, I think for entrepreneurs as well, I think there are a few things, you either want access to someone’s network, you want their operating experience, or you’ll meet entrepreneurs where, you know, they know exactly what they’re doing, they’ve done it before and all they want is money. 

Brianne Kimmel: There are three different types of companies that you can work with and I think to start I was helping a lot of pre-seed companies or companies that were just getting into YC. They needed a lot more help and expertise in terms of advising and network. And then as you start doing later and later-stage investments, like I’m in a few series A companies, they’re already on the path to success, they either just want quick help when they need you, but for the most part, it’s a little bit less hands-on. 

Eric Boduch: Got it. What qualities do you look for in early-stage companies? 

Brianne Kimmel: Yeah, it’s a great question. I think for me, I have historically, coming from a growth product background, I typically invest in companies that have some traction. I’m usually like a post-product-market fit investor, what that means is typically when I invest I also want to be as helpful as possible. Typically I will invest in companies that have very much product lead founders, they typically want help on more the go-to-market side, pricing, packaging, early customer introduction. That’s usually my sweet spot is, really spending time on more the business side before you hire a CMO, a CRO, someone to lead the more technical functions. 

Eric Boduch: It’s interesting you mentioned post-product-market fit, how do you figure that out? 

Brianne Kimmel: Yeah that’s a good question. 

Eric Boduch: This is something I think a lot of companies themselves struggle with, are they really at product-market fit? 

Brianne Kimmel: Yeah and it’s an interesting point because I think that what’s different about consumer versus B2B startups is that, I almost feel like … And B2B companies are always trying to find product-market fit and product-market fit actually may never exist. Cause I think for every company I talk to whether you’re seed-stage, whether you’re post-IPO, you’re always trying to find the balance of self-serve versus sales assistant or at what point are you actually moving at market? 

Brianne Kimmel: I think that’s something that’s kind of a funny conversation to have with companies because it’s something where you always have multiple different go-to-markets and that’s okay because it turns out, you know this very well, enterprise product is very different from consumer product. Where, essentially, you’ll start getting hit with various different feature requests or if you have an account-based marketing strategy and there are a couple of logos that you wanna land, as an enterprise PM you basically build whatever you need to build to make this account successful. 

Brianne Kimmel: It becomes more of a very customer-centric and a customer-friendly role, I would say, as a product manager or as an engineer when you’re working in an enterprise company. I think for me, post-product-market fit, I usually am looking for 500K to a million. That’s just kind of a number that I use as an initial starting point, but I would say as an investor as well I’ve done a couple of pre-traction, pre-launch investments as well, and these are enterprisers that have … You know, they’re working on their second company or just the vision that they have is so strong that it’s one of those things in the seed landscape, things move very quickly and there isn’t necessarily as much time for diligence. 

Eric Boduch: Yeah, absolutely. I completely get that. The other thing that you mentioned about, value-add, was about pricing, and that’s another area I think product teams, product managers, product leaders, and entrepreneurs tend to struggle with, do you agree with that? 

Brianne Kimmel: I do. Yeah and I think that it’s a conversation that for a long time … It’s a tough conversation to have cause it really depends on the type of product that you are building, it depends on who your buyer is. Are you going more bottom-up where you wanna make sure that it’s very easy for the end-user to put this monthly subscription on their personal credit card and expense it, and how do you scale that all the way up to large enterprise contracts where potentially you’re selling to a CIO or to someone in the C-suite. Those are two very different conversations. 

Brianne Kimmel: I think historically what’s been interesting is, I think in the last five years we’ve seen a number of great companies who have started with primarily self serve and then the question is at what point do you move upmarket or at what point do you have enough seats within a company that you can start having a more C-level conversation. I think that’s one common strategy. I think what I’m seeing more and more is a shift towards giving company-wide access, that way you can get as much data and insights upfront as possible. 

Brianne Kimmel: I think there’s a number of different models that people are testing, which I think is great. I’m starting to hear more and more conversations around pricing and packaging, but oftentimes it does take a mix of experienced folks who’ve done it before, plus testing an understanding who is our customer base and who are we ultimately selling to? 

Eric Boduch: Yeah I did a podcast with Kyle from OpenView on pricing and I feel like there needs to be a master class on pricing podcast coming up soon because it is something I hear people struggle with a lot, and more often than not I see enterprisers underpricing. 

Brianne Kimmel: Yes. 

Eric Boduch: Which, that’s generally easily remediable, but often has impacted their numbers. 

Brianne Kimmel: Yeah, absolutely. 

Eric Boduch: By definition or by extension their ability to raise funding, right? 

Brianne Kimmel: Yeah that’s a really good point. Well and I think so highly of the work that Kyle is doing because, essentially, in previous years you’d have to pay a very expensive firm, you’d have to pay Churchill managing consultants to come in and do a pricing exercise or they’d help you with packaging. I think historically pricing is not something that you wanna get wrong because once you have a low price point it’s very hard to increase pricing over time. 

Brianne Kimmel: This is something that if you Google Zendesk pricing, one of the things we did very early on is … At the first point when we started to increase our pricing, you don’t want to make your first power users, your first batch of customers angry when you start to increase your pricing. I think that’s when you start to think about grandfather clauses or making certain custom packages and arrangements with existing customers, which if you’re an early-stage startup, that starts to get very time consuming and it’s also not something you wanna mess up early on. 

Brianne Kimmel: I think it’s great to see the work that Kyle’s doing at OpenView, just having conversations on what is the right way to think about pricing? Patrick from Price Intelligently, he does some great work as well as far a really driving the conversation around usage-based pricing and how can you actually scale it based on the features you’re using. I think that’s really compelling as well, because I think for a long time, companies in particular, we were pricing things based on per user, per seat, but I think what one of the risks or challenges there is you actually wanna … You want people to use as much of the product as possible. I think for a lot of companies that are thinking about a “land and expand” strategy, if you want a lot of people using the product within a company it doesn’t necessarily make sense to charge per user, per seat, where you’re technically de-incentivizing growth … 

Eric Boduch: Absolutely. 

Brianne Kimmel: Depending on the product and how you actually want it to grow within an organization. 

Eric Boduch: Absolutely. And finding that metric that aligns with the value it delivers is difficult. 

Brianne Kimmel: It is. 

Eric Boduch: In that pricing metric sometimes. 

Brianne Kimmel: It is and I think you wanna have enough … You wanna at least have enough leeway in your margins to allow for customer success. I think that’s something I see a lot of times, especially with bootstrap-sass companies or I think sass companies outside of the Bay area, where if you are incredibly capital efficient that’s awesome, but one of the challenges is that there are often times ways that if you increase your margins just slightly, you could actually add a lot more value in terms of having more customer success people. You could have richer programs around growth and retention, which I think a lot of times startups are very much focused on user growth and there’s an opportunity to actually really drive feature adoption, individual feature level adoption.

Eric Boduch: Well it’s great to hear, like you and Kyle, and other people are helping out on the pricing side because even, you mentioned, the expensive management consultants … I even see them off … Pedigree was like, yeah I helped Microsoft do pricing when they were selling their boxes in CompUSA, it’s a different world now. Having the exposure to people like you and Kyle that can help startups out there think through pricing I think is huge because you’ve been through it in the SaaS world recently, right? 

Brianne Kimmel: Yeah, very much so. Well, and I think having the platform experience was very helpful at Zendesk because I think when you have a singular product, self-serve is a very easy way to grow quickly. When you start to have multiple products, that puts a lot of pressure on an end-user if you expect them to adopt multiple different product lines. That’s when you actually need to have strategic AEs, you need to have customer success. Having someone who’s a thought partner can be really helpful for your customers, rather than relying on emails, push notifications, there’s only so much you can do as a project manager. There’s actually a nice shift where if you can marry your self serve strategy with really strong technical counterparts, in a sales war, that’s when you can start to see strong expansion revenue. 

Eric Boduch: Great. Let’s talk about mistakes you see. You’ve done the start-up thing yourself a number of times, for a number of years, and you’ve done some of the investing now. You talked to a lot of start-ups. What are some of the common mistakes they make? 

Brianne Kimmel: I think you touched on it very briefly. Underpricing your product? 

Eric Boduch: Yeah, that’s one I’ve definitely seen. What else? 

Brianne Kimmel: I think that with underpricing your product, I think that typically is a byproduct of not doing enough research. I think there’s also a piece as well, and this is just speaking anecdotally, but I think as entrepreneurs, when you’re focused on building something. It’s helpful to really understand the overall value of the product, and what … Basically determining what is your initial wedge into the market versus where you will actually see the most amount of value delivered. I think time to value is a really important metric. I see this a lot where Bay area companies are famous for this. It’s very easy for a SaaS company to sell to other start-ups. 

Brianne Kimmel: And one of the challenges there is, start-ups are incredibly sophisticated in the way they choose tools. They are great because they are primarily self-serve users, it’s easy for you to communicate from a product marketing standpoint because it’s like talking to your friends. Start-ups understand other start-ups. One of the challenges there is that start-ups typically turn at a much higher rate. You know we saw start-ups and went free software? And you also find that start-ups are very quick to adopt the next cool tool. So you do have problems in terms of self-serve users actually turning to something that’s a lot easier or next-gen or newer. 

Brianne Kimmel: So it’s interesting to see. I encourage a lot of start-ups to actually start having conversations outside of the Bay area, sooner rather than later. Because a lot of the enterprise … A lot of things that make a company enterprise-ready are things that we don’t necessarily think of inside of the Bay area. Such as HIPAA compliance, such as SOC compliance, there’s a number of different things where … There are certain things that you need to be enterprise-ready. And a lot of start-ups don’t think about that early on, because they see at least short term traction, with selling to other companies of the same size. 

Eric Boduch: Okay. I like that. So you had a tweet I really liked. I was thinking about this when we started, thinking about what types of companies people start. And to read the tweet, I have it in front of me here. “As a founder, you may never know how much impact you have on the lives of individual users, there is so much more to life than curing cancer. Anything that makes someone smile and feel better about their current situation, is worth building.” Talk to me about that. 

Brianne Kimmel: Yeah. Thank you. So that was a tweet … I primarily do B2B software. I think what’s interesting about the B2B landscape … I think B2B founders are very humble. And I think one thing that you’ll notice is like within the first one or two conversations, there’s always this conversation of, well, I’m not curing cancer. So and so that I know. Or I should be working on something in health care. I think it’s very easy as an entrepreneur to start comparing yourself to other types of companies or other founders, who are currently building something. 

Brianne Kimmel: And I don’t know if that’s just a byproduct of everyone spending time together and sharing insights, and you start to get … Not necessarily envy, that’s definitely not it, but I think it’s very easy to kind of say, “The thing that I’m working on, it’s interesting, but it’s not as interesting as it could be.” And I think for me … I’ve been spending a lot of time really … As I’m talking to a lot of SaaS companies that I’ve worked with, once you actually have HIPAA compliance, then you’re actually starting to power some … Like the back end, and some really powerful parts of the next generation of medicine. 

Brianne Kimmel: I’m an investor in a company called Box Seat, that’s a video, API company. The minute that they added HIPAA compliance, they then started powering a number of different telemedicine companies. So while you’re building a software application, it’s more of a B2B use case. Once you actually start building these features, where you’re plugging into … You’re powering the next generation of hospitals or you’re increasing innovation in telemedicine. Like there’s some really great things you can do with your product. I think that oftentimes, for entrepreneurs, when you’re building, once you have a vision and have an idea for your product, that in itself is adding value to the start-up landscape. 

Brianne Kimmel: You also are never quite clear on the impact your product is going to have. And I think we saw this a lot at SunDesk, and I definitely saw this at Expedia, where for a while I was working on internal tools and kind of infrastructure at Expedia. One of the things that we were working on, was essentially building our own internal version of Zendesk. So I worked on the customer support and ticketing side of things, especially in some of … We basically had the traditional tiered model where we had some agents that were overseas in Manila. We also had onshore agents as well, in different parts of the country, and when you think about travel in general, you usually think about the vacation side of things. 

Brianne Kimmel: But we actually started to dig in and you could see all these different use cases why people travel. People want to spend time with their family, they want to go to weddings, there’s a number of reasons why people travel. And when you start to dig into the customer support side of things, that’s a great way for companies to really be human and to actually demonstrate their vision and their purpose. And I’m seeing that a lot in the customer support space today, where historically customer support agents have been viewed as not a core function of the business. Customer support is viewed as being a cost center, not a profit center. But I think those conversations are starting to change, as the next generation of companies wants to be more customer eccentric. 

Brianne Kimmel: So it’s been cool to watch how that’s evolved over time. One thing that I really like is, we saw this a lot at Zendesk, where a lot of the gray direct to consumer brands all use Zendesk. So whether that’s AllBirds, Peloton, is a great example, where Peloton is just so customer eccentric in everything that they do. That it’s actually created a whole new next generation of people who are not only talking about customer support, but it’s actually understanding the relationship between brand, product, customer experience. Because they all tie into each other really nicely. 

Eric Boduch: So let’s talk a little bit now about product management. So in product management, what’s a product problem that fascinates you these days? 

Brianne Kimmel: There’s a lot happening in the product space. Like I think for a long time a word that was very much overused was personalization? So one thing that I’ve been thinking a lot about and really spending time with companies on, is what data sets do you need? How much data do you actually need to personalize the experience? And I think my counter to that, and sort of a controversial point is, I think oftentimes, I’m not sure how much we actually have to personalize the product. 

Brianne Kimmel: Like if you build a great, easy to use product experience, you have a great UI, like it’s very clear in terms of how you onboard users? I’m not sure how much you actually need to personalize it. What are your thoughts? 

Eric Boduch: On personalization? 

Brianne Kimmel: Yeah. 

Eric Boduch: Oh, you know I envision a world in the future that’s both adaptive and personalized. So I look at them in two different ways. Like I think of how I want to interact with certain applications, I’d love to adapt to my role in what I usually try to accomplish in that application. And by that I mean there’s usually three or four areas of functionality that I use extensively, and there’s probably two or three that I never use. It’ll be great to hide that stuff from me in the adaptive way. And then it would be great to personalize the functionality I do use, based upon how I use it. So I would love to see personalization, maybe not in the, hey Eric Boda kind of personalization, like they don’t need to use my name. But I want them to personalize the application in a way that makes it easier for me to use that area or functionality. 

Brianne Kimmel: Yeah, that’s right. 

Eric Boduch: And then also adapt their application, so it’s not necessarily cluttered with things that I never am going to use. But at the same time, I still like to have the power to pull things back. 

Brianne Kimmel: Yeah. 

Eric Boduch: So here’s a great example of something that I think can be personalized. In fact an application I’ll pay for, maybe it’s out there. And it’s like my iPhone. iPhone’s great, great design, great product, but I use ear pods. I also have a car that has a Bluetooth connection. I can never get it set up right, so that the music is coming out of the right place when I want it. As soon as a phone call comes in, goes in my ear pods, and the music starts coming on my ear pods, which I want to go back on the car vice versa. Where I’m on a phone call I hang up on and then … Or I’m on a phone call and I jump in the car and it starts coming out of my car, where I still want it on my ear pod. You know, the one that’s in. 

Brianne Kimmel: Yeah. 

Eric Boduch: So there are things like that, I would love to have personalized to me. And I do it the same way every time. Like I always want my music in the car, I always want the phone call in my ear. And no matter how I do that, there is no way to personalize my Apple integration that way. Just for the audio. And then, have maybe the exception be, the rare instance where there’s someone sitting next to me, that actually wants to talk too through the Bluetooth through the car. But that’s rare. 

Brianne Kimmel: Yeah. 

Eric Boduch: It’s usually all in my ear. So like I can use … That’s an example of the personalization I would love to see. 

Brianne Kimmel: Yeah, that makes sense. Think another area I’ve been thinking a lot about is like, how do we build more consumer applications for work? And I think what’s interesting is that as more and more companies, Pendo is a great example, as more and more companies are increasingly distributed, I think that it’s going to become increasingly important for people to feel like they can be themselves. And one company that I recently invested in, I spent a long time with, is called Dev Dot 2. And they are a platform for developers. It’s essentially more of a social network. 

Brianne Kimmel: So the idea is that LinkedIn is basically resume focused, it introduces to an extent a number of biases when you want to hire someone. Because it’s based on lagging indicators. It’s things you have done, it’s limited to the company you were at. The role you were in, where did you go to college. What Dev Dot 2 wants to do is there actually … 

Eric Boduch: And also really how aggressively you networked too, right? 

Brianne Kimmel: Oh, for sure. Yeah, for sure. 

Eric Boduch: There’s a lot of people that just don’t click connect to every single person. 

Brianne Kimmel: Well, and I think that raises a really interesting point because I think … When I think about remote teams and I think about distributive work, I think it actually introduces a lot more opportunities for individuals who potentially have been underserved in a company. And I’ve heard this specifically applied to people who identify as being an introvert. Because introverts, one of the challenges, is you will get into a meeting, and maybe your boss is there and other peers, and it’s usually whoever is the loudest talker or someone who is very extroverted who ends up dominating the conversation. 

Brianne Kimmel: So one of the things that I’ve read recently is, oftentimes actually now that we have Slack, now that we have all these different ways of communicating with distributed teams and employees, it’s actually great for people who identify as introverts. You can contribute a lot to the conversation, you can actually communicate in a new way that doesn’t involve being the loudest person in the room. Which doesn’t work for everyone. And I think what’s interesting about Dev Dot 2, is when you have a profile which basically talks about the things that you’ve done to an extent, but it’s more focused on the things that you’re learning now. Like you can actually write blog posts, you can start to host your own discussions. When you have a way to actually drive conversations about the things that you’re thinking about, it promotes active learning and ongoing learning versus the things you have previously done. Which I find to be a much better indicator of talent, then simply looking at a resume. 

Eric Boduch: I like that. So let’s talk about growth, right? Because growth is all the buzz these days. I know you’ve talked product growth before, and companies are actively hiring for that role. And it’s just not the funnel optimization, the growth hackers we saw before, what are your thoughts on the growth trend? Are people prioritizing growth correctly? And do you have any advice on that? 

Brianne Kimmel: Yeah, it’s really interesting, because I think historically growth has focused, as you mentioned, on everything from performance marketing to funnel optimization to hacking your way into new segments. I think there’s a lot of discussion in the broader growth community on how do you evolve the discussion from where it was historically. Which was primarily like quantitative marketers, plus data science, plus a few new functions that have popped up. How do you evolve the conversation into becoming a core part of the company’s strategy? I think software companies have done this really well, by having a self-serve team and eventually layering on an enterprise go to market team. 

Brianne Kimmel: I think one of the questions that I have, and this is something that I am still actively exploring, is what’s interesting in software is that I think oftentimes it’s very easy to get started on the product-led growth side of things. Because you typically have product minded founders, you have a core engineering team. So organically you start experimenting, and it’s a lot easier to build the self-serve part of the experience. I think what is a little bit harder for start-ups, especially more technical and product minded founders is, at what point do you actually start building your next phase of growth? Which typically is less scalable, you start hiring salespeople, which one of the things I hear a lot from companies that I talk to, is when you hire salespeople, you also want to maintain your initial core culture. 

Brianne Kimmel: And I think that’s something where you want to make sure that … That’s when like you start to see this sort of weird position where companies identify as being product-led, or sales-led, and we’ve talked about this before. Where I think if you’ve come from a more technical background, or if you’ve been focused solely on product, to actually hire individuals who join on the sales team, you’re actually not really sure how that’s going to work. Like what do you call them? What do they do? Are they doing inbound? Are they doing outbound? And proactively reaching out to prospects. 

Brianne Kimmel: So it’s been interesting to see the evolution of early-stage companies, and when you actually start to think about, when should we hire someone? And it’s been great to see … I think there’s a whole next generation of great companies, and Pendo included, where I think there’s a great opportunity to hire, what I call product minded sales reps. And they’re basically more consultative sales reps, who understand product, they talk like a product manager, maybe after a few years, as a sales rep, they actually move into product management. I don’t know. But it’s great to see that. That’s what customers are ultimately looking for is someone who can give them the data that they need, someone who can empower them, and help them be better at their day-to-day. 

Brianne Kimmel: Especially large companies. Because large companies don’t typically have that sort of counterpart internally. As you’re in an increasingly large number of meetings, and you know … Especially at big companies, you spend most of your day in meetings. Having someone that’s more consultative on the vendor side is really helpful. And I think oftentimes start-ups undervalue that early on. 

Eric Boduch: Yeah, it’s interesting, you talked about this label of product-driven or sales driven companies and I think some people describe Pendo as a sales-driven company, which I think is ironic, in the sense that we were started by four product guys. None of us had ever been in a sales space. Maybe Rahul did. We did some biz dev, Rahul and I. But we were product, maybe a tinge of marketing here, engineering there, but product people. Yet still, we’ve been labeled that way from time to time. So it’s interesting. But you started talking about this whole product-led growth, sales not being mutually exclusive, and the product minded salesperson, can you dig in a little bit deeper to that? I mean, is it really important for companies that have started with product-led, to look at sales assisted? I feel like if they don’t, they might hit that plateau so to speak. 

Brianne Kimmel: I think so. I mean I think it’s interesting that it all comes down to looking at your product usage. So great conversation to have with Pendo, once you really start to understand how your customers are using your product, that’s when you can actually figure out, where does a human touch make sense? Because I think historically, we’re now mature in terms of understanding marketing automation, and building out life cycle programs and lead nurturing. And a lot of these terms we throw out on the marketing side of the business, we are all using some sort of marketing automation. I think what’s previously been missing, and still missing today to an extent, is actually really deeply understanding which features are your customers using? Because I think organically if you’re coming through a self-serve funnel, you’re likely using one or two key features. You haven’t been fully onboarded to use the full sweep of features, or maybe like one or two worked for you for the first 12 months, but now it’s time to mature in your product usage. And oftentimes that comes down to a more consultative conversation. 

Brianne Kimmel: I think one of the interesting things that we did very early on at Zendesk, and still do today, is for our self-serve users, we will still do account optimization calls. So we’ll actually hop on the phone, we’ll go through how are you using the product? What are some areas that you’re getting stuck? And more importantly, you’re digging into their goals and you’re understanding, what are the things that you’re currently focused on, and what are things you should be measuring and tracking over time. So I think having a good understanding of your customers’ KPIs is really important, and then you can start to layer in additional features or additional ways for them to use the product, to tie into those goals. 

Eric Boduch: Yeah, I think that’s a great point that you brought up is that you see people that will come in and will use like two features, two areas of functionality, out of a vast area of value they might be able to get out of it. And they stay there for a long period of time, and it was product-driven, which was great and all. But if you’re not giving that, if you’re not adding reoccurring value to the customer, or if that value kind of stalls, or deteriorates over time, then it’s hard to see that reoccurring revenue continue to go, or that expansion revenue continue to go. So you can add to that by either teaching them about all the additional product in-app, or via customer success, or sales. I think that’s where you’re going with that, right? 

Brianne Kimmel: Yeah, very much so. And I think it’s interesting, too, because when you empower specifically the sales team with relevant data, they can have much more productive conversations. So I know a number of companies are using, they’re using G2 Crowd data, they’re using technographic data coming from any of the data providers. They’re using Clear Bit for enrichment. I think there’s a number of tools in the broader B to B landscape now, whereas a product minded salesperson, you can understand not only how users are adopting your product, you can also understand the other technology that they’re using across the business. 

Brianne Kimmel: So I had worked on the Zendesk app’s marketplace for a while. And one of the really interesting insights that we found, is having the marketplace is a great data point to really understanding what other technologies are they using in addition to Zendesk. And we found that a lot of the early-stage start-ups, they were using the Trello integration. Which we … And then in doing additional user research, and really spending time on this, we recognized that in the early days of your company, customer support can’t sit in a silo. It’s less about … It’s less about more product related topics, and more about these early data points that are coming from support should actually be passed to product and engineering. So by having a Trello integration, by integrating with basically the full suite of tools that a product manager is using, that actually adds a lot of value across the company. 

Brianne Kimmel: So while Zendesk gives very much a solution for customer support agents, by using these various integrations, we actually could track how customer feedback was being spread across an organization. Which was really compelling. 

Eric Boduch: Interesting. So let’s talk about the future. What upcoming trends do you see in product, product management, or in SaaS in general, and why do you think they’re trending? 

Brianne Kimmel: Yeah, I mean I spoke to this a little bit earlier. I’m seeing a very clear shift from customer support being a reactive conversation, to a proactive conversation. So I think as more and more companies like Peloton, like Allbirds, you have these great direct to consumer brands that really invest in building relationships with our customers. And that’s becoming something that’s increasingly contagious across even large companies. Where I think historically customer support has been tied to someone is emailing our company with a complaint. Whereas now I’m seeing start-ups and large companies build really robust programs around customer engagement, they’re investing in … I’m seeing a lot of corporate gifting apps. So there are all these applications where people proactively want to do nice things for their customers. And they’re also ensuring that they are fairly defensible in terms of ensuring that customers write a positive review on a G2 Crowd or any of a number of review sites. So I think it’s been great to see that shift from, how do we create customer eccentric companies from day one. And what are the tools for us to do that successfully? 

Eric Boduch: I like that. Let’s wrap this up by talking a little bit more about Brianne. So tell me what’s your favorite product and why? 

Brianne Kimmel: Oh. Favorite product and why? That’s a good question. I think lately … I’m a huge fan of reviews. So I actually spend a lot of time on G2 Crowd. 

Eric Boduch: Oh, yeah? 

Brianne Kimmel: Yeah. I love looking at customer feedback, what are people saying about different products. As far as seeing how do people choose software and what is some of the feedback at an individual company level. So I kind of geek out on that, which is quite funny. 

Eric Boduch: Totally an investor thing. Given that you’re not talking about reviews on Yelp or Zagat, no you’re talking about reviews on G2 Crowd. 

Brianne Kimmel: I’m talking about reviews on G2 Crowd, which I think is really interesting. Like I love this whole space of how do we build consumer applications for the workplace. Because I think there’s a lot of cool stuff that we could do. 

Brianne Kimmel: I’ve seen like with Airtable and with Notion, you can see some really cool applications where people are planning their wedding, they’re planning parties. I love actually going through some of the Airtable templates and seeing how people are using the product, ’cause there where people are increasingly obsessed with productivity, there’s a whole suite of various different productivity tools out there. I think it’s also funny to see that everyone’s making the Marie Kondo joke now. 

Brianne Kimmel: Let’s just simplify things and make things as easy as possible. So I’ve been looking at that as well. If we’re moving into this world where people are looking at looking to become increasingly productive, they also wanna remove things that don’t bring joy. I think it’s kind of a funny space to be in where it’s kinda like personal but also professional-ish. 

Eric Boduch: I like it, it is a huge trend, going about organizing, optimizing, removing, focusing on what you do. 

Brianne Kimmel: Yeah and I’m like super optimistic that someone will do this for calendars. I really want someone to Marie Kondo my calendar. 

Eric Boduch: How so? Tell me what you want.

Brianne Kimmel: Well, you have Calendly now which is great because it’s easier to schedule meetings, but what you’re actually doing is, you’re sending your calendar to someone else and giving them complete control to book a meeting whenever they want. So I mean, I’ve heard this from friends where they’ll say, if it’s a salesperson that send you a Calendly link, you’re gonna book it two months, three months out because people try to avoid sales conversations or they hold off until they have to talk to a salesperson. So, I almost wonder if there’s a smarter way for us to do calendaring, where it’s a lot more people=centric, it’s a lot more human. Are there easier ways for us to actually manage our time? That I don’t know, I think there hasn’t, there’s been a number of tech companies that have done sort of Robo Executive Assistant or this sort of like Robo Advisors, which I don’t think that has historically worked very well but I’m optimistic that someone’s going to figure out the whole calendaring thing. 

Eric Boduch: Interesting. I would be up for it. Final question for you, three words to describe yourself? 

Brianne Kimmel: Oh, wow. That’s a good one. Hm, three separate words or we want like a sentence? 

Eric Boduch: I think you can, I’m giving you creative license to go with that. 

Brianne Kimmel: Yeah, okay. I think my latest thing is to always be helpful, I think even if I am incredibly time poor or not sure how I can help you today, I just always want to be helpful. So that’s what I’ve been working towards. 

Eric Boduch: Awesome. Well, thank you, Brianne. This is a blast. 

Brianne Kimmel: Thanks, Eric. This was great. 

About the Author

Eric Boduch is the Chief Evangelist for Pendo. Previously, he served as the CEO of Brainstorm SMS Technologies LLC (dba SMaSh, Inc.) and was the co-founder and CEO of several other companies. Eric holds a Bachelor of Science from The School of Computer Engineering at Carnegie Mellon University in Electrical and Computer Engineering and is a graduate of its Executive Management Program.