559 Jen Grant:

What’s your next act if you’ve built businesses to billion-dollar Unicorn status as a CMO… and what does it take to transition from there to an early stage startup CEO?


I’m Melinda Wittstock and today on Wings of Inspired Business we meet an inspiring entrepreneur who has spent 15 years building companies from the ground up, several of them to billion dollar valuations – and now Jen Grant has stepped up to the CEO role at Appify, a no code platform for businesses needing mobile apps.

Today Jen Grant shares what it’s like “shifting stages” from post Series D investment round when the focus is all about fast scaling and operational efficiency to that earlier scrappy startup stage when you’re still perfecting product market fit and laying the foundations for scale.

You won’t want to miss this conversation about how to co-create with your customers and master sales and marketing in the age of Covid. First…

Jen Grant has spent the last 15 years building companies from the ground-up and taking multiple companies to over a billion dollar valuation. As a CMO, Jen Grant led Looker’s marketing until its 2.6B acquisition by Google in 2019, led the rebrand of Elastic and built the team that took the company public for 2.4B in 2018, and grew Box from a small start-up to an industry-leading enterprise content company with a 1.7B IPO in 2015. Prior to that, Grant spent 4 years at Google leading the Google Apps EDU, Gmail, and Book Search marketing teams. She holds an MBA from Wharton and a BA from Princeton.

Today dig deep into the secrets of scaling, what it takes to stand out from the crowd with a differentiated message that resonates with your targeted customers, and create repeatable sales processes built on authenticity and trust. And much more including how women can help other women succeed as entrepreneurs and CEOs.

Take out your phone and join the conversation over on the Podopolo app. Ask any burning questions you have about finding produt-market fit, marketing, team building – and how you can best lay the foundations for scale.

Jen Grant has been there, built that, and has so much to share with us today so you can change the game in your business – plus everything she is up to at Appify, where you can take advantage of a offer to get started on your mobile app there for free.

Let’s put on our wings with the inspiring Jen Grant.

Melinda Wittstock:         Jen, welcome to Wings.

Jen Grant:                          I’m so excited to be here.

Melinda Wittstock:         Me too. Well, it’s such a delight to talk to women who’ve scaled into the billion-dollar range. There’s not that many that have done that, so congratulations.

Jen Grant:                          Thank you.

Melinda Wittstock:         We’re going to get into everything that it took to get there with your previous companies, but I want to start with Appify. That’s what you’re doing right now. Tell us about Appify.

Jen Grant:                          Yes. I’m the CEO of Appify and it’s been a wild ride. Just to give context on leading through crisis, I started at Appify at the very end of February of this year, so it’s been a wild and rough run. But Appify is what the industry might call, the tech people will say, “A no-code platform.” But really what that means is if you remember way back when we had to hire developers to create even websites, HTML, all sorts of developers to actually create the websites.

Now we have Wix and Squarespace and easy tools that help anyone make a website really quickly, and that’s what we’re doing for business apps. So if you’re a company and you have maybe your sales force is meeting with customers and putting together proposals for them, you can easily create an app that’s customized specifically to what your business does, that your rep can be out there, collect info, search up availability. They can map things. They can put it on a calendar, and then they can send a quote and put it in the inbox of the potential customer that they’re talking to, as one example. But really, any business can really create anything. So it’s a platform for everyone.

Melinda Wittstock:         That’s wonderful. So how much does it stretch? Does it stretch to doing, if someone comes and says, “Okay, I want to build my thing on Appify but I want to add all kinds of other stuff to it,” can it stretch that way-

Jen Grant:                          You bet.

Melinda Wittstock:         … or is it really more turnkey?

Jen Grant:                          Yeah, no, that’s a great point. I think that’s actually one of the important pieces of having an app platform, is that typically with software, you’re buying something that’s very purpose-specific to you are going to do XYZ with this piece of software. In the case of Appify, we don’t assume that we know what you’re going to do with our product. Now, we do have some prebuilt apps as starter points. But as an example, we had a healthcare company come to us and say, “We want to create an end-to-end experience so we can offer in-home testing to people.”

So we were  able to help show them with the platform how they could create seven different apps that touched all of the parts of this process, whether it was the person who was driving out to the test, to the consumer who was saying, “I would like a test,” or the lab where they did the test. That’s a fairly complex kind of experience. We have simple apps that people create. We have one app that’s really just an NPS. It’s a Net Promoter Score. They say, “How likely are you to recommend us to other people?” They collect their answer, and they’re done. That’s pretty much all that the app does.

Then we have these very complex, multiple different people having different views on the process that we’re enabling through the technology. So it’s all across the board.

Melinda Wittstock:         So how did you come to join Appify? Appify was already going. It had a different name before and then you came in and-

Jen Grant:                          Changed everything.

Melinda Wittstock:         … changed everything. So you’re a change management expert as well. Let’s talk about that, because that’s not easy.

Jen Grant:                          Yeah. Yeah. I think a lot of what made it easier is my relationship with the founder. In retrospect, I think about I got very lucky for this to happen so fast. But I think the process that we went through was really important. So Hari is the name of the founder. Hari and I spent about six months talking and getting together. Sometimes we would talk about ourselves, our lives, our values, culture, things that we hated in our previous jobs, things that we loved. We also talked about the business and, well, how would you go to market with this?

He is really a product and engineering leader, so his instinct is all around what to build, whereas my instinct is how do you communicate it to the world? How do you get it in the hands of people? How do you go to market? We spent the time. I think that made all the difference. Hari has been incredibly supportive. He, by no means, wanted to be the CEO. He did not want to be the CEO. I think that was a big compelling reason that I joined the company is he kind of emphatically said, “I don’t want to lead this. I want to focus on building an amazing product, and I want to bring someone in who’s excited about getting it to market and being the CEO.” So I think that was how I got in.

At that stage, you’re so early. I think we had about 30 employees when I started, but we had sold to about 25 customers. At the time, they were fairly small and they were still figuring out. With a platform like this, you sort of go out there and you say, “Okay, what do you want to build?” You’re learning as you go. So I think the key for anyone else in this situation where you get in there and it’s early but it’s not the beginning, it’s the listening. It’s the listening to what are customers saying? When do they buy? How do they use the product? Really going towards how do you coalesce an opinion about who is our ideal customer, because that’s the stage that we’re in or were in back in February is who is this ideal person that we offer so much value to that we can really help them be more efficient, and that they will be thrilled with the product and then will tell all of their friends?

So it’s all about this deep listening to employees, to customers, listening in to sales calls, going out on the internet. What are other companies saying? What are we saying? Does it resonate? That was where I started and started to plant those seeds of change of these are the things that we’re going to need to do to be successful because I’m hearing from customers. I’m hearing from prospects. We’re seeing in the sales cycle that these things work and these other things don’t.

Melinda Wittstock:         It’s so astute, what you say. On one level it’s so obvious. It’s about the customer. Does it solve a customer’s pain point? Is it really urgent for them to solve it, number one, and to solve it in the way that you’re offering, right?

Jen Grant:                          Yeah.

Melinda Wittstock:         This conversation is very top of mind for me right now because we’re hiring a senior product manager into Podopolo, my podcasting network and platform. It’s interesting. Some people come at it from a vision of what they want to build, but they haven’t actually really talked to a customer or-

Jen Grant:                          No, it’s so important, so important.

Melinda Wittstock:         There’s so many people in technology that, “I’m just going to build it and they’ll come.”

Jen Grant:                          Oh gosh. Yes. You know what? What’s crazy is so I was at Google back in 2004, right after IPO. I will say a lot of it is the culture of Google that has kind of spread out through technology companies. It’s this idea that I will build it and they will come. It was sort of the culture of Google at the time to say, “Well, just come up with crazy things and people will like it.” I mean yes, Google obviously hit on some things that worked. But if you look at how many things that didn’t work or that they went to market and someone else, like YouTube’s a great example.

There was Google Video. I worked on that product way back when. But there was so much hubris around we know how this product should be. We know what technology should do, without realizing that if you listen, that your customers or your potential customers or the people who are responding will tell you what to build. I’ll add to that because I think, as I know you have many listeners who are in the middle of this. I think there’s a second order of that. It’s listening to the customers, but it’s also spending the time to really unpack because sometimes you’ll get, and this happened to us, you’ll get people who buy your product and they’re just being nice.

Melinda Wittstock:         Yeah. They tell you what you want to hear because they don’t want to hurt your feelings.

Jen Grant:                          Yeah. They’re like, “Oh yeah. That’ll be cool.” Especially in the beginning when you haven’t figured out your pricing. In our case, we were priced too low effectively. We were priced so low that people were like, “Well, okay. I’ll try it.” So realizing that’s not them saying, “This is a meaningful product to me. Oh my gosh, if I can get it working in my business, I will either make money or become more efficient, lower my costs. I have this deep desire and understanding how this product will help me.” It’s not when someone says, “Oh yeah. I’ll give it a shot.” That’s not a signal.

Melinda Wittstock:         Yeah. Because there’s a nice to have and there’s like, “Oh my God. I’ve got to have.” So how do you go about that customer validation? Because it’s tricky because, say for instance a founder has this vision and you see something that other people don’t see. It’s born of your expertise and experience often or it’s just your mind thinks differently or I don’t know, a billion things. But you come at it and you have this vision. The vision’s a hypothesis. But often, visionary founders can get very attached, emotionally attached to their ideas.

So how do you balance that vision and gut feel and intuition with the data that’s coming from customers?

Jen Grant:                          I have a really good story because not only in my current role in Appify, but throughout my career as a CMO of a number of companies, I am always talking to founders, CEOs that have sometimes rigid thinking around this is what it is and this is what we’re going to do. As a marketer, you have to communicate where people are, not where you wish they were, but where they are right now. Right in the beginning when I joined Box in 2008, so now Box is this big-

Melinda Wittstock:         It’s huge.

Jen Grant:                          The content of your business.

Melinda Wittstock:         It IPO’ed, didn’t it?

Jen Grant:                          Oh yes. 2015, I think. It’s a wonderfully successful company. But in the beginning, it was a bunch of people in a room kind of trying to figure it out.

Melinda Wittstock:         They all are.

Jen Grant:                          Yeah, they all are. Yeah. We’re all sort of like, “Wait, does this work?” When I first joined Box, one of the things that I noticed was there was this massive difference between what our CEO wanted us to be and what we were actually selling because his vision was competing against SharePoint, the file system for a Fortune 500 company. But there’s no way this tiny little company could actually be the file system of a Fortune 500 company at the time. This is 2008. As I sat and did the listening, I spoke to many of the customers that were happy. And then I listened to the sales call.

What I realized is we had hit on three really important pain points that were super boring, not sexy at all. At the time, the most boring one was at the time, I don’t even know if you remember this. People used FTP to send-

Melinda Wittstock:         I do.

Jen Grant:                          … files, and it was horrible.

Melinda Wittstock:         I created a whole business that was around FTP when FTP was new.

Jen Grant:                          There you go. And then it was a thing. So people struggled with FTP. “I can’t figure out my password. It always fails, dah dah dah dah.” We had made a really simple way to send a big file. You can send it to an external person that’s internally through your company or externally. So we were selling a replacement for FTP. That was one. The second is someone was trying to literally just send a big file. We had one customer in the early days was in Los Angeles. It was a digital agency of some sort.

They would put their files on a CD and put it on a bicycle and ride it across town. We were like, “He solved that problem.” And then the third problem was we called it … when everybody gets on the phone and nobody knows what the latest version is. The sort of, “Ugh, what’s the latest version of the file?” It’s like everybody’s got a different version of it. It’s flying all over the place.

Melinda Wittstock:         That costs businesses millions of dollars right there.

Jen Grant:                          Yeah. Because it’s just a waste. We solved that. You have this little online folder. You put the latest file in there. Everyone can see it. They can then update it. So you have this consolidation or workspace that everybody can use. Those three pain points were why we were doing deals. It was in no way interesting to the founder to talk about it, which in the end was okay because what we did is we said … This is where I sort of stepped in and said, “Okay. So where in our messaging are we selling to buyers?”

It’s on the homepage, the website. It’s in the sales cycle. It’s in our digital advertising, any sort of place where we’re trying to bring in leads to the sales team and close deals. So those are the places where we’re going to talk about these less than sexy use cases. But the CEO, he’s going to talk to the press. He’s going to talk to Forrester and Gardner and other industry analysts. He’s going to talk to other CEOs and he’s going to keynote at this or that. He’s going to do all of these very external-facing things.

That’s where he can talk about the vision and he can talk about the file system of the Fortune 500 and the cloud and how this is fundamentally changing everything in the world of technology. I think that’s really important because often people come into the company and they think, “Well, there’s only one thing. We need to find that one tagline or that one use case or the one buyer.” It’s like, “Nah, there’s more.” It’s okay to have a vision and tell it in the space where people want to hear your vision and then have the practical reality of this is how we’re closing deals.

Okay. So let’s double down on making sure we close more of those deals so we can build an actual business.

Melinda Wittstock:         Something that you really talk about there, Jen, is alignment, people really knowing their roles and this gap between vision and reality and how you start to close that gap. Often, it’s an incremental process, but it requires everybody to really be bought in. I’m fascinated by your role as a CMO in a company where sometimes companies get really siloed between the marketing effort and the sales effort and the product and the engineering.

Everybody’s kind of going in a slightly different direction. As a CMO, how did you take on that challenge-

Jen Grant:                          It’s so true.

Melinda Wittstock:         … to make sure everyone’s actually really aligned in their various and necessarily different areas of expertise?

Jen Grant:                          Yeah. It’s a hard challenge. The bigger your company gets, the more people, the more ideas, the more it’s harder to kind of get everyone back together and say, “Okay, let’s all focus on the same thing.” I think I probably did the best job of that at Looker, which was later in my career. Looker’s a business intelligence platform, so that kind of gives you a little hint as to how I did it because we were able at Looker to have dashboards for everything. We truly understood exactly what was going on in the business and we had access to be able to go, “Well, wait a minute. If sales says they don’t get enough leads, what exactly does it mean? Does it mean that the leads aren’t good? Or they haven’t called the leads?”

We had the SER function in, so the initial sales conversation isn’t converting. Where exactly is the problem? That ability, certainly between sales and marketing, the ability to so deeply understand the data starts to remove the emotion stuff, the finger pointing and it’s your fault, it’s my fault. Whose fault is it? What are you not doing for me? Because you can very much pinpoint, okay, in marketing, here’s where we have a gap and we need to work on that. That’s not working right. But you know what? Over there in sales, you have one of those too.

So as I started working with the sales leadership, it was about looking at the data and then having a much more productive conversation around, “Okay. What are we going to do about this, this, and this? These are the problems in our funnel.” I think in the product, again, at Looker was another situation where we had lots of data so we could tell how people were using the product, when they stopped using the product. So the more we could pull in that information and say, “Huh?”

In the case of Looker, the data analysts who usually were the champions within the company because they’re the ones that are supposed to build dashboards for everybody, they loved Looker. We were there for them. We made it easy for them. They were able to build these dashboards. But we did realize over time, “Well, hang on. We’re not helping them sell their dashboards to their company. We’re not helping the people that look at those dashboards really understand what their value is.”

Melinda Wittstock:         What they’re seeing. Yeah, or what they’re even seeing or what to do with the information.

Jen Grant:                          Right. We could see that through the data. We could see, “Oh.” They come in and they look at it and they leave, but they’re not exploring the data. They’re not digging in. And then there were certain people who would and we’d figure out, “Well, who’s that in an organization?” So then talking to customers, once you see the data, you start to talk to customers and realize where your pain points are and you shift. You say, “Okay, product.” We on the marketing side, we started creating more materials for our end users, more training, more here’s how to look at data. Here’s how it can help you.

On the product side, they started to think about how do we make the UI easier? When you first click into the product, how do we make that experience better so that these people that maybe aren’t data analysts but they want to see the data can more easily be captured into the product? I mean I think the thing about Looker that was so amazing, it was the amount of information we had about every single thing that was going on. I miss it, to be honest. I’m at a much smaller company right now. So we’re not quite as instrumented.

If you can get that know of fidelity into what is happening in your business, it starts to remove a lot of the emotional politic conversations.

Melinda Wittstock:         Absolutely. But I think from the perspective of a lot of female founders at the very early stages of their company, just even looking at their financials, looking at their numbers, it’s sometimes a challenge. It’s not just women. I mean there are a lot of people who have this thing where they don’t really know their numbers on a financial level, let alone really knowing their customers. At that early stage where you don’t necessarily have the funds to invest in all the systems are like social listening or really good AB testing or let alone multi-variant testing… So you’ve worn the hat from early stage startup right the way through to these bigger companies. How do you get people invested and even looking at it?

Jen Grant:                          Yeah. I think that the early stage, it’s hard because you’re so small and you don’t quite make as much noise.

Jen Grant:                          So I would say it starts with the foundation. Like we talked about before, it comes to the point where you can say, “Okay, who is our ideal customer that really gets into this product? Okay, let’s get a sense of that. Let’s make sure our positioning and our messaging kind of reflect something compelling.” A really good example, I’m currently into a company called Calendly. If you-

Melinda Wittstock:         I love Calendly.

Jen Grant:                          You’d love it.

Melinda Wittstock:         I use it for everything.

Jen Grant:                          If you go to their homepage, the sentence on their homepage is brilliant because it is exactly the words I would use to describe my problem. I hate the email back and forth of scheduling, full stop. That’s what their homepage says. That’s a really great example of if someone comes to that website and has that pain, you are speaking to them. They will go, “Oh, maybe I should look at this product.”

Melinda Wittstock:         Exactly. Well, it’s just very crisp and very clear. It cuts right to the heart of what they do.

Jen Grant:                          Exactly. And it’s hard. It’s hard to get there. I mean it seems easy when you see it because you go, “Of course that’s they would put on their website.” But you struggle a lot internally in a company when you have a new idea like this because partly you’ve got the founder who’s like, “Here’s my grand vision.” An example would be at Appify if we said, “We’re the no-code platform of the future.” People would be like, “What problem does that solve for me again?” They’re like, “Well, I don’t understand.”

And then they’d have to click things and read things to get there. So how do you step back and say, “Hey, we make it easy to build a business app. You need a business app? We can make it easy to do that? Okay, now we’ll get into the details.” So there’s a little bit of that foundation-building so that when you get people to come, you catch them. I’d say very specifically I’ve seen three different methods for starting that initial top-of-the-funnel excitement, getting people to come.

At Box, we did a lot of press. So we put Aaron out there. He spoke at every event we could find. He was on all sorts of panels. He was constantly saying interesting things. At the time, the press was really interested in technology and the cloud and what was happening. Aaron Levie, the CEO of Box, is amazingly interesting. He was 22 at the time.

Melinda Wittstock:         I remember seeing him speak at a whole bunch of things in the Valley. I can’t even remember. But I remember that period where he was everywhere.

Jen Grant:                          He waves his arms around and he’s super charismatic and crazy. He says things that are very not offensive, but they’re pointed. So for us, it was really around the PR, brand, cloud, making noise in the space. That was how we sort of started our getting people to come to Box. And then I would add to that, the other thing we did was we gave away free storage. As a consumer, if you needed to send one big file, we’d give you a Box account for free. Well, now we have your email and you’ve heard of us. So those are two good things.

So that helped as well is just building that awareness even if it wasn’t in a business context. It was in a Box is easy to use. I still keep my pictures and all of the receipts that I need for taxes and all that crap that I know that I’m going to lose if I just leave it on a desktop, so getting people in that way so they hear about the product. Those two things were the beginning for Box. In Looker’s case, we had an SER team that was excellent at outbound calling. They really found a couple of threads of working … When they would talk to someone who was XYZ, they could get them interested in Looker.

They started with VC-backed companies. So they basically went to the websites of all the VCs and just went down the list of their companies and called them all. The reason it worked is because what they had discovered is smaller companies can move faster and buy a product faster. Often the founder or the CEO is the one who will make the purchase decision. So that speeds up the sales process. And then the second thing is tech companies love data. If you say, “Data-driven. We have a platform. We can make it easy, blah blah blah.” That’s compelling.

Melinda Wittstock:         It’s music to any tech founder’s ears. Listen, I’m just rapt in this conversation for that reason. I mean yeah, it makes a lot of sense. I think also the PR, getting a lot of earned media, that’s a great top-of-funnel strategy, for sure, because it’s just people are already warmed up.

Jen Grant:                          Yes, exactly.

Melinda Wittstock:         Podcasts, coming on podcasts.

Jen Grant:                          Exactly. Everyone should do podcasts.

Melinda Wittstock:         Exactly. Everybody should.

Jen Grant:                          That’s nowadays. I think back in Box, it was 2004, 2008. It was like, “I don’t know what a podcast is.” But now, we’re all at home.

Melinda Wittstock:         Exactly.

Jen Grant:                          It’s a really exploding means of getting information and having conversations.

Melinda Wittstock:         Also developing that trust because that old, say if you’re selling B2B in the old way. It was all the relationship sale and knowing the person’s hobbies and what they did and just interacting and all that stuff. With the pandemic, all of that is gone. I mean actually this is a little bit of a detour, but how has the coronavirus really impacted marketing?

Jen Grant:                          I’ve seen two major ways. The first is, and this is a little bit specific to Appify, is that we were so successful at events. The particular markets we were reaching out to are typically field service or these aren’t the VC-backed tech companies that are used to Zoom. The face-to-face was so helpful, so critical. There was half of the sale was do I trust you? And then the other half was, okay, now tell me about your product? We don’t have that anymore. I don’t think we have found an equivalent yet. I’m sure there’s many startup companies that are like, “We’ve developed the digital event of the future.” Hopefully, someone has. We haven’t found it yet.

Melinda Wittstock:         Zoom can get you a long way, but I mean I come at Zoom as this person who is a deep introvert and I’ve learned to be extroverted because I go out and I speak and I do all the things to grow my companies over time. As a podcaster, obviously, I can get a sentence out and all that. But Zoom calls I find more exhausting than actually meeting people in-person.

Jen Grant:                          Yeah. I literally said to my founder, we had scheduled a one-on-one at the end of the day. I said, “Hey, we know what we look like. Can we just do a phone call? My face is tired.”

Melinda Wittstock:         Exactly. It’s like the phone-

Jen Grant:                          He was like, “What?” I was like, “No. Literally, my face is tired.”

Melinda Wittstock:         Right. Exactly. It’s true. So I mean to get that relationship, I mean we’re all hoping the coronavirus ends soon. Events are a great way to just, yes, to get that relationship. And then for now, there’s all kinds of other ways to reach people online. There’s increasing numbers of strategies. I mean I think, and this is relevant to you with Appify, there’s all the ASO stuff or app store optimization. There’s all these deep techniques around you get into schema.org and all these really cutting-edge things.

Jen Grant:                          The assumption is because people, which is likely true, people are online a lot more often=

Melinda Wittstock:         Yeah, they are.

Jen Grant:                          … because they can’t go out.

Melinda Wittstock:         So reaching them though with a message, and this was where the writing and the way it’s communicated becomes so, so critical. But on the flip side of it, there’s so much information out there. I think when you add to it this layer of all the, I don’t know, the disinformation, the fake news, the conspiracy theories, and all that sort of stuff, people have just lost trust generally. They just don’t know what to believe and to what extent that bleeds over into marketing for businesses.

I think we live in a really weird environment. How do you stand out and develop trust in that context?

Jen Grant:                          That’s a really, really good point. I hadn’t thought about it for that reason, but I 100% agree with you is I think it’s … Maybe it’s the podcast is one example. It’s from a me as the leader of a business, when you see someone speaking, when you hear the passion in their voice or the authenticity. When I get on the phone, much more often I get on the phone with customers. It’s not necessarily that I’m pitching them on this feature or that feature. They just need to see and hear me and hear the authenticity when I say, “We’re going to be there for you. We’re going to make you successful.”

That’s what they need to hear. It’s all we have since we don’t have face-to-face. But I think it’s that being more of a person in the public versus a digital ad or obviously you need to do all those things too, but also developing that persona of the company through the people that are speaking to the public. I think there’s something in there that I think helps.

Melinda Wittstock:         Absolutely right. So I want to talk to you about what it takes for women in particular to scale because there’s a terrifying statistic that only 2% of female founders make it to a million dollars, which is crazy low. And then we also have these things that only 2% of female founders actually get funded and, again, qualified for VC funding. They have an idea, a system, a business, the IP, whatever, to actually potentially be a unicorn, right?

Jen Grant:                          Right.

Melinda Wittstock:         But only 2% of those get funded. So in that context, you have a lot of women who are creating businesses that sustain them. They’re potentially good businesses, but they’re stuck in that bootstrapping thing and can’t quite break out of that. So I come at this with you in the sense of who are you being at these different stages of growing a business in terms of the mindset you need to really adapt as you go? Because in my experience, say, getting to seven figures and eight figures in some of my previous businesses, there were different things required of me.

Jen Grant:                          God, that’s a really good point. I think my experience as a CEO, it’s been a long time since I’ve been at this small stage. I think one of the mistakes I made right at the beginning is my what you might call post-series B hat was on.

Melinda Wittstock:         Right. Which is like a total disconnect from that early stage.

Jen Grant:                          It’s totally wrong. Right. Typically when you’re post-series B, that means you found product market fit. You know what you need to do and you just need money so that you can hire sales, hire marketing, grow fast, fast, fast.

Melinda Wittstock:         Yeah. Seize market. Yeah, exactly.

Jen Grant:                          Mm-hmm (affirmative). I think I was quick to say, “Hey, look at those 25 customers, 20 of them look the same. We have product market fit.” This is where it comes back to the listen harder feedback is, well, let’s take a little pause. Now, luckily, it was the middle of the pandemic, so I didn’t spend any money.

Melinda Wittstock:         Right.

Jen Grant:                          So the hat came off pretty quickly. To some extent, the silver lining was it forced me to slow down to say, “Okay, let’s be really sure that we’re ready.” And we weren’t. The answer was we were not ready and we needed more time. So the hat that I wear in the early stage is now it’s that’s listening to customers, listening to the sales calls, really getting the positioning, really thinking about that ideal customer and continuing. I mean even this last week we’ve continued as I got my leadership team together. We’re refining who is that ideal person?

We’re getting this cool deal. Why? What was it that made that work? That is a very different hat from when you shift to the growth stage. It’s funny. I had this experience too trying to recruit many of these amazing women friends who are ready for VP titles, for CMO titles even. I’m like, “Yes, come. You’re amazing.” There’s a lot of risk aversion. It could be the coronavirus. It could be the economy. They’re like, “Well, even though my job isn’t this wildly, crazy growth career, but it’s safe.” I think there’s a knee-jerk reaction that women have where they slow down a little bit.

They’re worried and risk-averse, particularly during the coronavirus. I’ve seen this with people that I’ve known and loved for many, many years who should be CMOs or who should be CROs or who should be leading companies and they’re worried to take that next step, to take the risk and to kind of go. I wonder if that switch from where I am, which is the sort of series A product market fit, finding that ideal customer stage, when you switch to that growth stage, it is really different, as you said. You’re no longer thinking about, “What exactly are we selling?”

You’ve hired someone to think about that. What you’re thinking about is, “How do I make sure every single person we hire is amazing? How do I add process and recruiting and culture and all of the things that people need to kind of build this thriving group of people?” You’re no longer driving the details of the interaction.

Melinda Wittstock:         You have to let things go. I think what’s interesting at all these different stages that I’ve learned is just at the point of you get to mastery and you’re doing what you’re doing and it’s working really well-

Jen Grant:                          And it changes.

Melinda Wittstock:         Man, it changes. And then you’ve got to get out of your comfort zone again and again and again and again. But that’s actually what I love.

Jen Grant:                          I think it’s the changing. Yeah, me too.

Melinda Wittstock:         I enjoy just the intellectual challenge of it, the fact that over my entrepreneurial career, it’s led me to really grow as a person as well in so many areas. There’s this really interesting connection between, I think, your personal growth, call it mindset or consciousness or whatever kind of paradigm we want to put on it, and your business growth because you get challenged by all these things.

It’s like, okay, challenges, setbacks, things beyond your control, how do you react to those things? What do you take away from them? What do you learn from them?

Jen Grant:                          Yeah. It is hard to change. From a personal perspective, from a leadership perspective, I think there’s both the making sure you have time for yourself, whether it’s meditation or yoga or running or where you get out of your day-to-day jazz and you get into calm space to say, “What is the most important thing for me to be working on right now?” Because very often you accidentally will go back to the things that you’re comfortable with.

Melinda Wittstock:         Yes, that’s true.

Jen Grant:                          I’ll do things like, “Let me change the brand and worry about what the logo looks like.” It’s like that is not the most important thing for me to be doing right now-

Melinda Wittstock:         A couple years ago-

Jen Grant:                          … as much as I love it.

Melinda Wittstock:         A couple years ago I started specifically on some of the entrepreneurial masterminds or groups or things that I’ve been involved with over the years. I actually specifically started doing things that would get me out of my comfort zone, whether it was learning how to play polo in Argentina. That was hilarious. I was not good at it, but it was hilarious. Or literally swimming with sharks, say, in the Bahamas. We were all terrified and then we got into the water. We noticed the sharks couldn’t give a crap about us. They were just completely uninterested.

Jen Grant:                          Right. And they’re beautiful. You’re like, “Whoa. What is this experience I’m having?”

Melinda Wittstock:         But specifically seeking out things like that to develop that muscle within me because sometimes the lesson or the epiphany comes from outside your business or doing something completely different. Or in my case, I get a lot of my best ideas about my business when I’m walking the dog.

Jen Grant:                          Yeah, yeah. And when I’m running, I have the same thing. When I’m running, finally my brain starts kind of wondering. And then all of a sudden, you come back to, “Oh.”

Melinda Wittstock:         Right. Right. I remember I met Sara Blakely from SPANX a few years ago. She was saying that all her best epiphanies have come while she’s just out driving mindlessly. So we all have our things. What are some of the lessons, Jen, that you’ve learned along the way, setbacks or things, challenges you’ve had to overcome in any of the different companies that you’ve built?

Jen Grant:                          Well, I’ll start with the one I just mentioned, which is really reflecting on what stage you’re at and trying not to … It could even go to when you go from one job to the next job, you have to let go of everything that you were doing before and not just sort of go right in and go, “Well, I did it at that company so I’m going to do it at this company,” that you have to slow down and say, “Okay, no. I need to know what the current situation I’m in requires of me, not what I wish I could have done at that last company I was at.” So that would be one thing.

I think the second thing is really go with the people. Actually, twice in my career I went to companies where literally one of them I was there for maybe 15 days and I was like, “Oh no. This was a mistake.” It’s because I didn’t go for the people. I went for, “This seems really cool. They’re going to pay me a lot of money. Wow, I’m going to get this new title.” Those things don’t matter at the end of the day. What matters is when I joined Box, I went because a good friend of mine was there. She said, “Jen, I know it all seems crazy and chaotic, but get in here. We need you.” And I did. It was a really good choice.

Melinda Wittstock:         Well, the people are everything.

Jen Grant:                          Everything, yeah.

Melinda Wittstock:         I think when investors look at companies, really, it is the people. It’s the founder. It’s the team. It’s all of that because there’s going to be all kinds of things beyond your control. There’s a whole bunch of things that you haven’t validated yet and that’s just part of the territory. So it’s how is the team going to deal with all that stuff. Now, for me, back at the early stage again, one of the things that I’m determined to do is get right from the outset, being focused from the get-go on the culture. Being very, very intentional about it. The right people are showing up without as much of an effort because there’s clarity right from the get-go.

Jen Grant:                          I love that. I 100% agree. It’s really hard to do.

Melinda Wittstock:         It is.

Jen Grant:                          I don’t feel like I’ve gotten there with Appify yet, but it’s definitely one of those things that I kind of, God, I need to get that clarity of purpose, that mission that feels so strong that people go, “Yes, I want to be on that mission.”

Melinda Wittstock:         Well, part of the big challenge, and actually this seems so simple, but it’s actually knowing what you want. What is success? What do I want? What’s every day like? How can people enjoy the journey and whatnot? So tell me about Appify and where it’s going. What’s the big vision? Where do you intend to be? Is this a company that’s going to be bought for billions of dollars or IPO or what’s your vision for where you want it to get to?

Jen Grant:                          Yeah. I mean I think I want to grow. That’s for sure. I think that having been a CMO for 15-plus years, getting to be able to lead a company through that process myself is very exciting for me. I think both personally but also because when I was talking to Rajeev, who’s a VC for Mayfield who funds Appify, he asked me three times in a row because he knew that I wasn’t giving the right answer, “Why do you want to be CEO? Why now?”

I came up with all sorts of other answers. And then finally, I was like, “Look, Rajeev, there aren’t that many women who get to the position where they could be CEO and I feel a responsibility to take up this role, even though it’s hard, even though I still have kids in high school, even though it’s not going to be the simplest things and I could fail. I feel the responsibility because more women need to be in this seat and I’m in the position to do it. I need to do it.” It was a weird moment because I was like, “Well, I just said that out loud.”

Melinda Wittstock:         But how beautiful and how beautiful still that it was the right answer?

Jen Grant:                          It was. Well, and that’s part of what made me realize this was the right company because the main investor was like, “Yes. That makes perfect sense to me.”

Melinda Wittstock:         This is so important that women do this. It’s really the reason why I started this podcast is that the more we actually share our journeys and help other women, promote other women, buy from other women, invest in women, one of my dreams is to get more women investing in other women, first off. I mean that’s huge. But there’s myriad ways to do it, just mentoring and whatnot. But just showing up and being, I guess, maybe a little bit vulnerable because we come at it thinking that we have to be perfect and nobody is.

Jen Grant:                          Nobody.

Melinda Wittstock:         So for the women who are succeeding and to the outside world, it makes other women think, “Well, I’ll never be that.”

Jen Grant:                          Right. It looks so easy for her.

Melinda Wittstock:         Right. But I don’t know how I can do that. But by really sharing openly what it’s actually like and being there for other women, we can do that. So I think, wow, what a great story. Hats off to your investor. Were there more investors that were aligned in that way, although I think that’s coming. I think that is coming.

Jen Grant:                          I think it is. I do get the feeling that there are more and more investors that are more engaged in diversity and the true value that it’s not just, “Oh, I guess we should do that,” that it’s like it will make everyone more successful to look for more diverse folks and founders and CEOs and leaders.

Melinda Wittstock:         Absolutely. The data does bear it out though too. There’s been all these studies. NASDAQ-quoted companies, for instance, that have women on their boards or on their executive team wildly outperform those that don’t. Startups that have women on their founding team, whether the CEO or in another C-suite position survive. They’re 99% more likely to actually survive. So this is really important. There’s a whole series of data points on that. But I think my spidey sense is that it’s time for us now.

Jen Grant:                          Yeah.

Melinda Wittstock:         So hats off to you for everything you’re doing in the world. I want to make sure people can find you and find Appify, anyone listening here that needs an app for their business. What’s the best way to connect with you?

Jen Grant:                          Appify.com, of course. And then appify.com/demo to come talk to us if you have something you need. Of course, I’m on Twitter at @realjengrant, Twitter.

Melinda Wittstock:         Fantastic. Jen, thank you so much for putting on your wings and flying with us today.

Jen Grant:                          It was lovely. It was lovely. This conversation was so much fun. I’m inspired.

Jen Grant
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Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
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Review on iTunes and win the chance for a VIP Day with Melinda