323. Box’s Go-To-Market Strategy, Building the Enterprise Sales Motion, and When to Bring on a Sales Leader (Karen Page)

Karen Page on The Full Ratchet

Karen Page of B Capital Group joins Nick to discuss Box’s Go-To-Market Strategy, Building the Enterprise Sales Motion, and When to Bring on a Sales Leader. In this episode we cover:

  • Building Box’s GTM Strategy
  • High Touch vs. Low Touch Investing
  • Tips for Selling to Enterprise
  • Making the First Sales Hire

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Transcribed with AI:

Karen Page joins us today from San Francisco. Karen is general partner at B Capital Group, a multistage tech investor with more than 3.5 billion under management. She has led investments in Anvyl, Satori, Precent, Centivo, Plastiq, and Kandji. Karen, welcome to the show.

Hey, Nick, great to be here. Thanks for having me.

Yeah, it’s good to have you! Tell us a bit about your background and your path to venture.

My path to venture is quite a bit less typical than most I would say. I started in sales, and worked my way from sales to marketing to business development to partnerships, landed at Prosper as a very early employee, and then made my way to Box also, as a very early employee, and one of the founding members of the executive team there where I was all go to market. I mean, my whole entire responsibility while I was there for almost a decade was to help box get on the map make us look bigger than we were at the time. And then as we grew to negotiate and navigate continue to put us in a prime position to sell.

Mission accomplished.

Well, thank you for that. Yeah, it was that was a good, that was a really, really fun part of my journey. After I left Box, I made my way to Apple, where I ran the US enterprise partnerships and commercial channel business where I have responsibility for about $4 billion in the commercial channel working with partners like Deloitte, SAP, IBM, and others, before I decided that it was time to try something new altogether and started doing a lot of angel investing and joined a few boards before I was recruited by B Capital.

Amazing. So you’ve been with B Capital for a couple years now, is that right?

I joined three years ago almost to the day.

And the firm has grown quite a bit.

It’s really fulfilling because it does feel a lot like the box experience, you know, how do you grow as fast as we have, while building incredible teams, making sure that you’ve got the right path in front of you so that you’re tediously directed while building out the infrastructure to support that growth. So it’s been really fun to be part of that. One of the most fun things for me personally has been, you know, joined as a growth team investor, I was writing checks for B, C, and D stage companies. And about a year and a half into my tenure, we decided that it would be time for us to start an early stage effort. So I worked with Howard Morgan, we brought on Gabe Greenbaum to to launch an early stage effort. So now I’m writing checks at the preseed, seed, and A stage.

It’s like back to your angel investing roots. Right?

It is it’s kind of full circle, maybe my whole career has been a full circle effort.

That’s always makes sense. Looking backwards, right? So I want to talk more about B Capital, but you were an early employee before then at Box. What would you say was sort of the most impactful learning from that experience running, go to market at small team that’s going through, you know, hyper growth phases?

Yeah, I mean, the learnings I could honestly I feel like I could write a book about it. I think some of the the learnings include, you know, you have to hire the best people you can hire for the stage of growth that you are currently in, and the team and the the leadership around, that is an absolutely critical part of success. And being able to look at that as the company grows, and make sure that you still have the right people in the right seats as you grow. And scale is critically important. And of course, that’s hard, because you build relationships with your team. And you have to make sure that like I said, as you’re scaling that those people are still the right people in those roles. And sometimes that means hiring above someone, sometimes it means switching someone from one role into another role entirely. And sometimes that you know, if the path has come to an end, and you need to, you know, separate and launch that person into something else entirely. So I think those ideas around managing growth, understanding leadership, and in particular, the difference between leadership and management in a company that is in such hyper growth mode over the better part of a decade was interesting. And a lot of those things hold true at B Capital Group, you know, you hire the best that you can hire at the stage of growth that you’re in. And then you make sure that those people have everything that they need to continue their growth, and that you’re providing the infrastructure to enable them to do the best that they can do. And always monitoring, you know, are people sitting in the best seat for them and for the company.

So angel investing and venture investing are quite different. Talk to us a bit about your early approach. You started as an angel investor, you moved into growth investing, you’re now doing early stage, give us some thoughts on high touch versus low touch investing and sort of how the role has evolved. You’ve sat in different seats.

My angel investments were almost 100%, relationship based, a friend of mine started a company or there was a network of executives who were trying to launch another female founder into into our first round of funding. And almost always it was, as you mentioned, low touch, certainly low diligence, more relationship based. And often, the reason that I was sought out was because of my experience and go to market. And the idea that I could be helpful to that founder over time, I’d say about 75% of my angel investments were with female founders. And when you then put your hat on as an LP funded venture capitalist firm, you know that you have an obligation to look across a wider spectrum to think through what the rationale is behind this. And certainly a relationship isn’t the only factor that’s going to be important as you navigate that. So the responsibility that comes with investing other people’s money is a very different approach to take. And one that I think benefits from having had the angel experience, but one that is, is much more complicated, I would say.

Tell us more about your focus, Karen at B Capital. And you know, you talked about stage, are there sectors as well or their technology types? Do you consider yourself a generalist or a specialist?

I would consider myself a generalist moving towards greater focus in some specialty areas. The reason I consider myself a generalist is because I believe that what I bring to the table is that expertise that we have mentioned during this conversation, which is go to market expertise. So I tend to look for companies across the spectrum that have an enterprise go to Mark sales approach, because I really believe that I add a lot of value when thinking through that, as a result that fits nicely within tech companies, or health care companies, or even a cybersecurity company, I was very deeply involved with a box went to market, how we approached influencers and leaders and founders and CEOs and what the personas were that we created to go after those markets. And I believe that’s super helpful to every company that I’ve invested in today. And think that’s really a helpful approach. One thing that we have noticed, as we’ve gotten started is, you know, the relationships that we’ve built have been critical and crucial to our success and to meeting other founders. But as you break it down and understand the various businesses that you want to partner up with the idea of how to go to market how to sell and how to be efficient in all of that is a critical underpinning for success.

How do you think the the enterprise go to market motion has changed?

You know, since you were a box to now, she’s it’s so much more digitized and scientific and analytic, then certainly than it was when I first started at box. And I think the ability to understand not only the approach, but most importantly, the outcome, what are you trying to achieve? You know, what is the most important thing I’ve got, I’ve got some companies who are selling to just one buyer persona in the company, that’s a different approach. I’ve got a company who is really trying to create a new market, that’s a completely different approach that requires multifaceted top of the funnel, educational relationship based approaches. And so some complicated and complex models for doing that. But the end of the day, the basic premise is the same. Who are your buyers? And how are you going to reach them in a way that makes sense for both parties? And how do you find over time, the logic behind that so that you can replicate it? It’s got to be emotion that’s repeatable over time? And how do you find that? So discovering that and paying a lot of attention to that, and those learnings that come along with each approach, I think is a make or break.

You work on go to market motions that are top down, bottom up, middle out all of the above? Or is there you know, one in particular that you have more expertise with?

I would say all of those approaches are very commonplace. And I’ve mentioned a few of the companies that I work with that have those different approaches, you know, I’ve got a FinTech company that is fairly consumer oriented. And its model, however, relies on a b2b approach to be successful. So understanding in that case, what are the benefits to the end user? And how do you create a business model that embraces that? So I would say yeah, all of those approaches become really important to the sales effort overall, just a bit more on B Capital Group.

So there’s a relationship with BCG, can you give us some color on what that is and how it works?

Absolutely. Early in our history, we knew that it would become really important for our companies to have access to some of the most strategic minds in business, both for the purpose of understanding markets and also for having access to the relationships that have been built by those folks. BCG was a natural for us. They’re world class in what they do. They represent some of the biggest most impressive companies in the world and their people are also some of the most impressive people that you can meet. So we wanted to form a relationship with them. And we do we have an exclusive relationship with BCG, their LPs in our funds. But we are most importantly partnered to help the portfolio companies that we represent scale and grow as efficiently and effectively as they can. They provide us with insights on markets, as well as on particular problems that they’re seeing their clients face. And then we address those collectively to try to solve the problems. And we often will bring in our portfolio companies for those conversations.

So is there a shared service component then for the portfolio’s where they can leverage some of the brain power BCG?


And what does that look like? Is that, like you said, you can bring in the portfolio companies? Or is there kind of a systematic way that that’s done?

Yeah. You know, we’ve seen all different sorts of approaches, we’ve seen companies that are working hard to determine whether they should put their resources behind say, you know, a deep partnership strategy, or should they focus instead on international expansion? What are the best pricing or monetization strategies that they could deploy? What would be the best, you know, structure as they continue to scale and grow? And where should they focus their resources in terms of hiring and team. So we’ve had companies that have looked across all of those various problem sets, and we’ve partnered them up with BCG to get to those solutions.

Awesome. You know, talking a bit more on enterprise, one of my favorite areas, I spent my career mostly in corporate America working in enterprise domains, I’d love to hear your thoughts on how legacy industries are changing, and sort of what trends you’re seeing in enterprise transformation.

My goodness, the past couple of years have certainly been transformational. We always used to joke at box that we were just hitting, you know, enterprise transformation levels. And we were at the time, but we couldn’t have known what we can see today, and how you particularly over the past few years, with COVID, how barriers have been forced to be broken down. Due to the change in our entire society. I think one area for sure has been healthcare, it’s been on the verge of transformation forever. And I think most of us would agree that it has needed that transformation. But it has been very slow. It’s a complex, high stakes industry. And the main product, of course, that they produce is health and well being but the complexity of the systems in place today have made it extremely difficult to enact that change. And COVID came along and broke down all of the barriers accelerated digital health at a pace that nobody could have imagined. And it was really out of necessity that the change was was sort of forced. And you know, overnight, we began to rely on care delivery, being delivered electronically, digitally, through zoom and through other sources and companies that had solutions and tools in that space, found themselves in a very, very good spot to have conversations that were able to escalate and be pushed to the system much more quickly over this need. But you know, it also has caused very different situations in terms of the employer markets and the criticality of care. And, you know, I don’t have to tell anyone this, it’s very obvious. But think what we are seeing now and the future of healthcare is going to be much more convenient in a lot of ways. It’ll be virtual first, and we’ll see a be designed around consumers and their needs. You know, the explosion of telehealth puts a premium on digital engagement. But it’s really time to rethink the entire customer experience. I think the next few years in healthcare are going to be absolutely fascinating. Can the legacy players, institutions and insurance carriers and whatnot, keep up with the rapidly evolving tech landscape and the expectations of consumers and other stakeholders, what I hope we’ll see is that consumers will drive that forward, they’ll demand that and when it impacts the wallets of the payers and the providers who must create new tools and solutions. It’s all going to drive that change forward. I don’t know how fast it’ll go. But I certainly know that leveraging the technology to deliver these solutions is going to be a cornerstone. And we’ve seen that already. Healthcare has been hot.

I love it. I mean, we’re bullish, we just closed the preseed investment in a remote patient monitoring integrated, you know, service and system. There’s a lot of players out there. And of course, we picked our horse and have a lot of belief in the team. But yeah, you know, there’s so many trends in the space, especially going to value based care and more continuous monitoring instead of just episodic guessing, which often happens when patients only go to a doctor once every couple of years and be diagnosed accurately.

Yeah, totally. I totally agree. And I think the idea of picking a horse, you know, is an interesting way to phrase it because the market is it’s very rich with companies in the space right now. There are a lot of experts, a lot of people with tons of experience a lot of people with fantastic ideas, all trying to push forward on this notion of revolutionising and transforming healthcare. So I think we need every single one of them all of those companies can play a role and obviously it’s going to then realize, what we started with is how do they go to market? And how do they define themselves? And how do they partner? And how do they they also have to be able to create their their moat in their niche in the market?

Karen, what observations have you come across or maybe experienced firsthand, it could be at Box. Let’s say it’s an enterprise software business, you’re selling into legacy spaces, you’ve got tech averse buyers, slow adopting organizations, what in your experience, have you seen founding teams and tech companies do to sort of drive velocity adoption engagement in these classically slow legacy spaces?

I think one of the key things that that founders need to be able to do is to connect and build relationships over time, even if you just can understand what your various market segments might be, and then divide those in terms of the size of the companies that you’re going to reach. So you can draw some conclusions around like a smaller company is going to be able to make a decision faster, medium sized companies may have various stakeholders, and decisions may be just a little bit delayed as a result of navigating, and very large institutions may very well take a longer time to close the deal. So creating a pipeline that takes all of that into consideration, that has room for quick sales, as well as you know, medium and longer term sales and can carry through as you’re navigating, negotiating and closing those various deals, I think makes makes for a reasonably good formula. There’s also understanding from the company’s perspective, not only the size of the companies that you’re selling to, but also the industries that they’re in. And how do you have a combination of those industries now, that that may not be the case for every single company out there, but often see companies and they’re just looking for people who will buy where the right approach may actually be to concentrate in certain markets and try to own a market and then move along. So I think it’s really the founders that are able to get a strategy in place around some of those concepts, I think are going to do well. What have you seen at the seed stage, you’ve got a lot of founder selling and founding team selling going on. And then as you get to Product Market Fit beyond series A and Series B, there’s this transition that happens, you have to build a sales organization and learn to delegate and empower and find some common areas to sell on, how have you seen teams make that transition? And what advice would you have for early stage companies that are going through that transition point from small, scrappy team to we’ve got to build a muscle on a machine here? It’s probably one of the most complex periods of time for a lot of companies, you know, you’re still small, you want to hire a sales leader? How senior Do you hire? What’s the best talent that you can find at that stage, when you don’t even have a clear understanding of the go to market motion of the sales process? How many leads do you have to have coming in the door, in order to close X dollars per month? Those are all things you learn along the way. So I think it’s critically important as the founder is working hard to close deals himself or herself and to figure out what is working and then bringing on someone else. And having that mutual that shared relationship as you’re building the muscle on sales. And the ability of a founder to both hold on and let go during that process is really a testament to the leadership abilities of a founder? How do they navigate that? How do they think it through? How are they kind of there with while the training wheels are on? And then how do they let go the bike and let the training wheels fall off as that sales leader gets up to speed and then knowing along the way, what those metrics are, and and being there to be able to help along the way or to determine whether or not this is a good fit or not, because it may not be may not always get lucky on the first round of your sales leadership hire. If you’re in a situation at let’s say series A or Series B, where growth is not at the level, it’s not at plan. It’s not at where you want it to be. When you’re on a board as an investor, you know, you’re not in the weeds, you’re seeing things that usually 30,000 feet, 10,000 feet, you know, how do you tease out whether there’s a fundamental product issue? Or if it’s just a sales in or go to market challenge? Really in question. It’s clearly very nuanced. And you’re totally right, as a board member, I don’t want to be in the weeds. It’s not my role. I want to be able to help and advise on those things and hopefully shed light on those questions. What seems to be holding back the sales process and navigating through that. Now there’s a lot of things that you can do along the way to help diagnose one of which would be working through Why did a customer say no? Was it a product oriented reason? Was it financial? Was it people driven? You know, why are people not buying and to the extent that you can dig into that and understand whether it’s through materials that are provided by the company or whether you’re kind of taking some steps on your own to figure that out, I think it’s critically important to know that the other side of the equation, if you’ve got what looks to be a robust funnel and a pipeline, and maybe things aren’t closing fast enough, what can you do to understand that is there some sort of friction that can be understood and removed, I had one company that was having a slower sales cycle than they wanted to have. And we talked through it, what happens when they click, you know what happens next and what happens next. And it turns out that they had a major friction point. And we talked through it together and got to a point where we could implement a different cycle, and it had an impact. These past few months since that has been implemented, he’s close twice as much revenue. So it has had a major impact. But sometimes it’s just slowing down dissecting and diagnosing to understand what the options are, wouldn’t want you to reveal that specific circumstance. But is there a way you can generalize or give us an example of what a friction point might look like in the sales cycle, that is something that’s addressable versus just customers not ready to approve the budget. In this particular case, there was a requirement after sort of a POC, that some information was to be provided. And oftentimes that that space, that chunk of time, during which the buyer was being asked to provide this information, you know, sometimes weeks and weeks we go past. So we just cut that out, we didn’t make that part of the the closing cycle, we would close the deal. And then and then bring on that information. And so there was a huge incentive, because then the customer was already bought in and signed up. And so we just changed the progression and made a lot of difference.

Love it. Karen, are there any repeatable processes and or behaviors that enterprise founders and sales leaders should be thinking about incorporating from day one, there’s more to think about, then most people would believe I think, you know what I mean?

It’s everything we’re looking at, from the positioning of the company in the space that they’re in to how to build an exceptional leadership, Team Two, how do you define your advantages over other players? And how do you have impact on the market that you’re in? Everybody wants a bigger pie? What can you do to grow the pie? And how will your product and your services really be transformative in the businesses and the industries that you’re serving. So those are pretty big thoughts in and of themselves. And they are just the top of the iceberg, when it comes to all of the various things that you need to think about. I love to work with founders on team and strategy around who to bring on and what the right person might look like. And often, I am brought in to help in the interview process on executive team members or board members. And I think it’s important to really think about the building of the company as a puzzle with an awful lot of pieces. But they’ve got to fit in nicely. And even if you’re just thinking about the skill sets of your executive team, the ability to have diversity and skill sets that are complementary, without too much overlap. I mean, obviously, there’s going to be overlap in the skill sets. But you know, the knowledge base is to the extent that you can really compile a group of people who are complementary at a massive level, you know, the better your odds of solving problems, because you’re going to have so many different perspectives.

Is there a go to resource or anything with regards to talent in building out that organization over time that you rely on or suggest to founders?

As a founder, you have to rely on your network and, and you have to rely on your networks network. So what I want to bring to the table is a range of ideas and options. So if someone says to me, I need to hire a product leader. And I think that these qualities would be very important. Well, I may go to my rolodex and spin through and see who I think might make a good fit based on that, and provide the profiles. And every type of person has a product person may be an introvert or an extrovert. And maybe you want one or the other, because somebody else on your team has a different set of, you know, personality and skill set. And again, you’re trying to piece them all together so that they’re complementary, and they all work. So, you know, I can provide a couple options here. So here’s a few folks that might be good for the role. What do you think about these profiles, and then from there, you just build it out. But hiring remains one of the most critical components, one of the more opaque areas and I think the ability to at least be able to extract from your network, people who might be a good fit, at least cuts down on some of that uncertainty.

Another key focus area for you at B Capital is democratizing Innovation for SMBs. Karen, do you think that large company tech can be optimized for small and mid market players or do they need their own sort of purpose built solutions if a startup wants to access them do they need to develop sort of custom solutions?

I think it really depends on the company, we certainly have lots of pattern recognition around companies who have started selling to SMBs, and work their way up to enterprise sales, Salesforce, Box. You know, many, many, many other companies have gone that route as well. And primarily, the rationale behind that is if you can learn from those early customers and maximize the product enhancements, so that you can sell through to the enterprise. It’s an incredible process of learning for those companies, you can’t always start at the enterprise level, obviously, there are many, many, many companies who have launched directly into enterprise. And that’s always been their sale, probably a lot of the AI tips, companies that we’ve been talking about have chosen that that go to market route. However, the approach to selling to an SMB, and then working your way up is long proven to be effective. And as you grow and scale your company, and you add on those various services and product enhancements that enterprises require, you’re able to leverage that previous history and growth as you’re selling through that period of time.

So Karen, this question is called three data points. I’m going to give you a hypothetical situation with a startup. And you can ask three questions for three specific data points, let’s say your approach to invest in a Series A enterprise SAS startup companies in New York, the sector is digital health, they have a million of ARR. And they’re growing 3x, year over year. Again, the catch is you can ask three questions for three specific data points in order to make your investment decision, what three questions you ask?

Who is their target audience?


What is their business model? And what makes their founders the team to beat? What gives them an unfair advantage? Why are they going to win?

What are you looking for in the target audience just focus in a specific segment identified? Or is there you know, another aspect to it?

We really believe that we’re seeing, you know, the transformation healthcare that we’ve already talked about, we think that there are lots of areas that are worth focusing on, you know, leveraging technology to deliver personalized care to expand access into various markets to reduce the administrative overhead that exists and a lot of the legacy care settings and making sure that incentives are aligned between suppliers and the consumers of health care. So to kind of see, does that fit into the way that we’re thinking about digital health? Understanding the target audience, I think is a critical component, you know, are you trying to reach out to caregivers is your primary audience, you know, psychologist, because you’re a behavioral health company? Is it the consumers of behavioral health companies that are going to buy those services? So in order to get a good sense of what that company does, and how difficult it’s going to be to hit their objectives, I want to know who they’re going to sell to.

Karen, if we could feature anyone here on the show, who do you think we should interview? And what topic would you like to hear them speak about?

I have to say, you know, my partner, Howard Morgan, who I look up to as a mentor and a friend and has had such an incredibly rich history in investing from founding Renaissance Technologies to idea labs to First Round Capital, and now is our chairman as well as my partner on the ascent investing team. He brings such a wealth of knowledge, and I learned from him every single day, so he’d be great to share his knowledge with your audience.

Karen, what do you know, you need to get better at?

You know, there was a lot in venture that is experienced base. And sometimes you just can’t, you can’t rush that forward, I recognize I’ve got a long way to go, I learned something new every single day deal structures and how funding rounds are transpiring, and all of that. So I’m here for it. I love the learning. I know I have years of experience ahead of me where I can, I can learn and become a better investor. But one thing I really want to be able to do is to continue to nurture the relationships of the founders that I come across, hopefully, becoming a resource to them, whether we invest or not, and just continuing to build out the network and helping founders as best I can in all of the areas that we’ve discussed today.

And finally, Karen, what’s the best way for listeners to connect with you and follow along with B Capital Group?

Absolutely. All of the social channels are open and available. My email is Karen@Bcapgroup.com.

Perfect. Well, Karen, this is a real pleasure looking forward to finding a digital health company to partner up on one of these years through it.

Let’s do it.

Let’s do it. Thanks so much for your time and in all your insights today. Really appreciate it. Thank you so much.

Thanks, Nick.

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