Kerry Bennett — Upfront Ventures

Wednesday, May 25, 2022

Loved talking with Kerry about how startups should think about their marketing org and how that has changed.

Also fun to hear about Upfront’s brand and the brand of the partners at Upfront.

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Hello and welcome to the LA venture podcast. This is Minnie Ingersoll host of the podcast and partner at TenOneTen. TenOneTen is a seed stage fund here in LA. All opinions expressed on this show by me and my guests are solely our own. 

Kerry Bennett is a passionate brand builder and head of marketing at Upfront.  Upfront is probably the fund in LA with the best known brand.  Before upfront, Kerry was SVP  of marketing at a variety of top startups, including DogVacay and HauteLook. I’m excited for her perspective on upfront her advice for startups and her thoughts on brand building for venture funds. Kerry, I’m so glad we’re doing this.

I’m so glad we’re doing this. Thank you for having me. 

Oh, it’s great. so I thought I would start by saying like, what’s your job? What is a head of marketing? Is it the same as head of platform? Anything you can share? 

It’s a great question. And there’s no one way to define that. So what I would say broadly speaking is it’s providing leverage and marketing support to the firm and sometimes to the portfolio.

So what is upfronts brand? What do you think upfronts brand is? 

I asked you first. 

Well, so I think Upfront’s brand really starts with the name it’s about. How you’re going to experience us and how we work with portfolios or LPs or other VCs. And so that’s something we all really value as partners being honest and not hiding behind any sort of niceties or, , hiding behind, uh, the mystery of VC.

Hmm. do you think of the upfront brand in relation to anything else, like in relation to other LA funds or in relation to sort of the venture ecosystem as a whole? 

That’s a great question. I mean, I certainly think of the upfront. Experience in relation to all of that. One of the things that upfront really values is community then.

So one of the things I really like about my job as head of marketing at upfront is obviously I want upfront to win. I care about upfront I’m team upfront, but I really do think about adding value to the community. And I assume that it will pay off to upfront in the long run.  

Yeah. Uh, when we were talking about fundraising, my partner, David Waxman was like, we should call Mark suster. And I was like, you think he’d help us out. And he’s like, yeah, he’s interested in helping the ecosystem.

And how do you think about lax brand? Just in general or for tech I’m ending more for tech, but you know, wherever you want to weigh in, 

I think there’s a real spirit of collaboration and support, like. I think everybody really still feels excited for everybody else to win. 

I really think everybody’s excited for everybody to be successful. I think everybody shares their information. What do you think, how do you think it’s changed over time? 

 Oh, I would echo what you said. And in the Bay area, being a BC is a negative thing. And in LA you say I’m a venture capitalist and people say, Oh, how cool.  And we need to be deliberate in maintaining that.

let me stick in LA and if I think about LA venture and think about the different firms and sort of put them on a continuum of, maybe bam or M 13 or over here on the consumer side and over on the other side, there’s embark or Lux capital on the frontier tech, uh, where would you say upfront fits in, in that sort of continuum?

You’re talking about categories then.

Yeah, I think we’re probably in the middle and it’s probably. I don’t know, less of a spectrum and more of a quadrant. And I would say we’re certainly category agnostic. , we’re deep in SAS. We’re deep in enterprise. We’re deep in commerce, both B2B and B2C. Certainly some of our more well-known investments are in the consumer space, whether that’s goat or parachute home or threat up or even bird.

But that’s often because consumer businesses are more well-known But. We have, ag tech investments. We were invested in,  a company called appeal sciences, , which is a big ag tech company where in future of work, we’re in FinTech. So we’re really across the board in terms of categories, 

Okay. What if you stay with my continuum for a second and put the partners from upfront on this continuum and sort of say who’s the most consumer focused and who’s the most tech focused 

oh, well, okay. First of all, I think I’m going to take issue with the fact that consumer isn’t tech. Right? I think that people think that a lot, , it’s the same way that everybody thinks marketing is not a technical thing, right? So I’ve been at up-front for almost five years and what’s been interesting to see is  that most partners have evolved the areas of focus that they are investing in, that they’re enthusiastic about.

And I think that just speaks to, you know, people learning and. Finding new things and finding new passion points and the industry evolving. ,  certainly Greg   is deep in commerce and experience. Prior to coming to upfront. He was the CMO at HauteLook where I worked with him. , and a lot of his portfolio has commerce , and I would say consumer elements to it.

So whether that’s goat, which is a  sneaker, resale marketplace, , and that is consumer facing, but also really about sort of fans and communities. But on the flip side, he’s also invested in companies like in via robotics, which is. Warehouse automation, that’s commerce related, but it’s not consumer or happy returns, which is enabling in-person returns or online purchases.

That’s kind of B to B to C. So nobody really has only consumer focus or only software focus. I think everybody really just. Is excited about different areas as they sort of grow and evolve as,  investors. 

Let me change gears a little bit off upfront and how you work with your portfolio. You know, I’m a seed stage company.

Do I need to start thinking about my brand?  How does that process  evolve? How do you coach people. 

 So the answer is you think about your brand starting from day one. , I’m sure maybe you find the same thing with startups is they’re really good at telling you what they do. They’re not as great as at telling you why that matters, who they do it for, what problem they’re solving and walking you through a narrative that if you’re not an expert in their space that you can’t understand.

Right. And so I think part of, , What a startup should be doing early on is really thinking about that narrative and that storytelling. Then down the line that turns into logos and brands and website and press releases and content and all of those things. And each startup has a different timeline as to when they do those different things. 

and are there exercises or like workshops you’ve seen that really help startups crystallize that narrative or, or, or define their culture?

 We’re rarely running into somebody who’s like starting from nothing. Right. And so part of it is just, how are you putting this, this raw material together in a way that is consistent, that articulates , how you want to be perceived and is an actionable thing.

 I’m sure. A lot of people listening have had brand experiences where you get, you know, you go through this brand exercise and then you have a 200 page brand book, and there’s a lot of mission statements and nobody ever uses it. But to just be really clear on what’s your two line elevator pitch that encompasses not only what you do, but who it’s for and why it matters.

It’s we all think we know, and then we start talking about it and you know, it’s really hard to articulate. 

Okay. So everyone needs a to line pitch. Everyone needs a two-line pitch. What are other actionable things I can get out of this exercise? Yeah, absolutely. I think, brand values is a really key one, one exercise.

I really like is we’re this not this, um, we’re playful. We don’t take ourselves too seriously. We are knowledgeable, but we’re not experts. Sometimes people like to do that exercise where they say, We’re fun. We’re not silly. And I’m like, well, nobody wants to be silly, but like, you know, what’s a, what’s a good thing.

You don’t want to be making those decisions about what aren’t you. And I think with startups, 80% of what you do and how you do it is pretty consistent because you have not that many people. And you’re, you know, you’re kind of all looking at the same stuff. And so it’s not that it’s going to go. So crazy, but it’s at 20% on the margins where you’re inconsistent  or it’s not, user-focused, that’s another thing that I think startups can really do is who is your user?

And I actually say, let me revise that to say, who is your customer? I think a lot of times startups think about who their user is. Who’s clicking, who’s buying, who’s using the software, . But , that’s a very company focused way to think about it. And that’s valuable. That’s one way to look at it.

But who are these people as humans? What else does their life look like? What other brands do they experience? What is the problem that you’re solving for them and how have they solved it to date? You know, are they, are there other buyers or influencers in the mix? What do they care about? And so really understanding that human, , with your company as part of their lives, but not at the center of their lives is a really valuable exercise.

Interesting. So that’s the consumer, not the user. Well, reframing it to 

rewrite could be the same person by the way. Yeah. But yeah, every, I think a lot of people think about users and like, how do I get this click to do this thing and drive this dollar? And that’s a very, how do I get you to do what I want versus what do you want and how do I give you something that will, that you many consumer wants?

Okay, that makes total sense to me, but that also sounds a lot like what product teams do. And so where do you define, what is marketing? What is product what’s brand? Where does this all fit into the organization? And when do I go out and hire specialized people for specialized functions? 

Uh, this is the million dollar question mini, how long do we have and let’s do it all right.

Get out the whiteboard, right?  no, we could get out the white board, but the, the spoiler is there’s no one right way to do this. That used to be, and I think , you’re landing on this. There was marketing and it encompassed all of those things. . And I think because marketing covers so many different verticals of expertise. It’s very hard to have one organization that does all of those things. And so by nature marketing started fragmenting off. Now I personally think marketing perhaps has fragmented a little bit too much because, you know, I think you see organizations that have product and they have sales and they have technology and they have a CEO and they have customer success.

And then at some point they hire marketing and they’re like, well, what do you think marketing is? You obviously think it’s. Ad campaigns or some sort of tactical thing versus a strategic piece of the business. But to get back to your question, I think certainly there are parts of business strategy that product can cover or marketing can cover.

And there’s no necessarily one right way to do that  probably the standard is that products thinking about. The user. 

Totally. So product has to think about the user and how the product and the user interact. But then I feel like marketing people very like growth marketing peoples sometimes are very funnel focused 

Very funnel focused, very funnel focused. You know, I think when you’re funnel focused, again, it’s very conversion focused. And so it tends to.

To be, how do I get this action that I want? And that’s the worst kind of growth person, right? The worst kind of product person is how do I get them to click this buttons? I’ll just make the button bigger. I’ll just put an interrupting page. I’ll just whatever. And the worst kind of brand people are the ones who are so precious about the fact that it needs to be this kind of brand that they don’t ever think about the business needs.

Right. Everybody can go down the wrong path.  But hopefully everybody’s keeping the user in mind. Hmm, the consumer in mind, even though I’m doing it. 

And so in your waving magic wand, you would have more sort of centralized marketing, CMO level leadership that, well I’m putting words in your mouth. 

Well, I’m a marketer, so I would say that, right.

Um, I do think that centralizing a little bit more. Ensures consistency and it, and it ensures everybody, it is working together, that there’s not sort of redundancies in what people are doing. And also that there’s not siloing, but four 50 person company having various teams, having the comms team and then the design team, and then contents in a different place with social and then SEO is product.

And then your product marketing over here. That’s I think you end up with a lot of different, Activities and no sort of centralized strategy, the difference. What is comms? What is it? A subset of marketing, 

as a great question, mini,  it can be, or it can not sometimes comms live separately from marketing because it’s, narrative storytelling, investor relations PR sometimes social goes into calm.

Sometimes it doesn’t, I think a lot of. Enterprise and B2B comms can be separate because it’s covering different things versus in a consumer business comms and marketing and campaigns, maybe tied together a little bit more again, there’s no one right way to do it, but you want to have it. 

Got it. Yeah. I think I knew that comms was more storytelling, when you’re working with portfolio companies, are you coaching them on their marketing? Um, what are you doing there? 

Definitely. And, you know, I would say all of our partners are terrific marketers.   Coby and Greg were both CMOs at DT was in product. And I think where, I’ve seen real success with startups, whether it’s ours, whether it’s how we interact or others is really thinking through when they’re, before they’re going to fundraise, what is the story?

What do people care about? How do I make this important and how do I tell it? You know, one of the things that I observe with startups is that as they grow, as they’re lucky enough to grow right, and raise a, B or a C and become a big company, They’re often still using the same stories and proof points and, and communication style that they did when they were just like the scrappy little, nobody.

Right. And that’s not helpful. That’s not representative of the business and that’s probably not helpful to the company. And so one of the things that founders really need to do as they go on that journey is think about how did they. Evolve as a, as a storyteller, how do they evolve as the face of this brand, if they are in fact, the face of the brand 

Do you have any good examples of that or, or can you explain it more?

 You still have the same pieces, um, who are you and why did the, how did you start the business and what do you do?

But, you know, I think early in the seed stage, the origin story and the Genesis of the pro of your discovery of the problem and your discovery of the solution. That’s basically the whole story. And as you get down the line, continuing to sell the vision without selling, without also explaining how you’ve built the business and what the business success metrics are and, what the team looks like.

And, and sort of how you’re building a market, not what it could be, and you’re going to solve this problem, but you’re building a market. You’re creating a movement. People love you, and the proof points to share that that’s different. And also, I think there’s a difference, you know, if you think of a founder over the course of say five years, When you’re nobody and you’re begging, you know, you’re not begging for money, but you’re, you’re convincing people to buy into this.

Sometimes harebrained scheme of yours, that’s a different way of speaking and presenting yourself than somebody who’s heading up a $500 million business,  you are a different kind of leader.  Are, you conveying the gravitas of, of somebody. Who is, might be an acquisition target for, you know, multi-billion dollar corporate organization.

Those are two different ways of communicating. 

Okay. So presumably that’s something the CMO could help coach them with or do startups even have CMOs anymore?

For awhile. I think the CMO is not something anyone wanted to be CRO chief growth officer. But nobody wanted to call themselves a marketer.

And I think that was a hangover of like CMOs of consumer packaged goods brands that were just like talking about advertising and didn’t understand data. And was not able to speak in any technical kind of way. And so I think all of that to say, I think marketers now, as they’re coming up in the world, do really need to think of, need to be at least burst  in the technical side of the business.

You need to understand where your data is. You need to understand how you’re tracking things that can’t just be handed off. And so I think that’s one trend of a sort of technically versed marketer. 

Okay. So the marketing team needs to be technically savvy, but why did the marketing org fragment so much? 

One of the reasons that I think. Marketing fragmented so much is because I actually think marketing unlike maybe any other discipline and a startup is very specialized.

You mentioned there are so many platforms. There are so many this, and it’s true. And you know, 10 years ago when I was working at an e-commerce business, um,  Facebook was still really exciting and new and you could innovate on it and you could come up with new things. There are no sort of big silver bullets right now.

Um, I, I think as soon as there is one, everybody figures it out. Everybody is quick to jump  on that  and mind that for results. And so. You have to be in the platform every day. You have to be really well versed in, I think that’s very hard for a smart, small marketing team. So a better way to say when I was, what I was trying to say is I think that marketing requires a lot of specialization.

If you’re an SEO specialist and then somebody is like, Hey, can you do this press release? You’re like, I don’t know what you know, or if you work in Facebook and somebody wants you to do events there, they’re very different categories. But also, I think people are going to become a handful more of generalists and pull in specialists that are outside, that are agencies, 

hmm.  just to be really tactical? When, , when does it make sense to hire an agency and what sorts of agencies have you seen work really well? 

It depends for everybody. That’s my answer for everything. It really depends on the organization. I think bringing in an agency can be really useful when a few things are in place.

One is you have somebody that can dedicate the time to manage an agency. I feel like you get the agency that you deserve both in terms of the process you went through and picking them. And how you manage them. And I think so often people think I’m going to hire an agency, so I never have to think about it.

And you’re like, well, that’s not going to work out well at all. I think when you’re testing things out, that’s a really valuable time to try an agency or, um, or you think there’s something there, but it’s a specialized skill that maybe you don’t have.  I’ve seen some really great growth agencies because they’re really specialized in Facebook and Instagram, and that’s what they specialize in.

And that’s what they do all day long. PR agencies as well. I think they get a bad rep, but I think having a PR partner, if that is not a core competency of whoever’s inside the organization, That’s something that I think people think, well, I, how hard can it be?  I can just email someone and they’ll cover my news.

And like, that almost never works. 

Okay. So I can’t just write a one pager on my seed round of financing and hope that tech crunch writes about it. Um, and then on the other extreme, you’ve got a 16 Z now has more news staff than tech crunch does. How do you think about VC funds becoming the content creators?

That’s a whole other podcast, I think for any kind of content creation, whether it’s in a VC firm or at a startup, what purpose is it going to serve? What are you trying to do? What can you dedicate the time to, and. Where’s your best focus. I mean, you know, you’re, you’re creating a podcast and that is a lot of work.

Yeah. But I enjoy it. Yeah. 

And that’s it. That’s a great place to, so I think a lot of people say, Oh, I want to blog. And I want to be really active on social. And I want to do all these things, but they don’t actually like writing. So why would you want to blog? But, you know, they want the end result of having this content and not the content creation.

And so I think that. Thinking about what are you trying to communicate? Who is the audience? And what can you commit to doing is the best place to start. 

Well, and I look at Mark sister and I’m in awe of his communication skills.

How do you think about his brand

1000%. He is an incredible content creator that the speed and clarity with which he can create content is amazing. And I think that’s a perfect example of, he loves to do it. He loves to write, he built a platform. It took time. Yeah. 

and Michael Carney was a reporter before becoming a partner right upfront,

Yeah. Yes,  , there is a trend in, journalists moving into VCs, which is so smart because journalists having. , the ability to synthesize think critically, gather information, tell a clear narrative. If no, if you take one thing out of this entire conversation, I hope it is figure out a clear narrative that tells civilian people what you do and why it matters.

I think journalists are really excellent at that. So I’m not at all surprised that we’re seeing more of them moving then to the VC space. It’s a 

great pipeline to mine. And it’s a diverse pipeline. Um, at least gender diverse pipeline, 

gender diverse. It’s often not like it’s not consultants 


right? Not consultants. I actually don’t dislike consultants, but still staying with journalists. Uh, are there any really good shout outs recommendations you have for people we should follow on Twitter or newsletters?

We should be reading. 

Oh my gosh. 

Um, I’m a big fan of Webb Smith and TPM. I didn’t even know it. Great web Smith. Hold on. Pause, I’m sorry. I got the website wrong. So web Smith, 2:00 PM, Inc. I think he’s done such a great job of synthesizing trends in retail and commerce. And do you see, and brand, and growth and everything that goes into that.

So that’s a great one. Great. 

Any favorite Twitter accounts? Uh, podcasts you listened to? 

Oh, my gosh. I read a lot and I share a lot of book recommendations and my friends are always like, what business books should I read? And I’m like, I don’t, I don’t know. Life’s too short. I do. Hi. I spend all day in business.

I want to read novels and nonfiction. When I am not. Looking at my zoom. 

Well, maybe that’s a good transition from things we enjoy doing to conferences. We actually enjoy attending. 

Maybe just talk a little bit about the upfront summit. Okay. Um, because it’s, it’s incredible, Carrie, it’s a really incredible, uh, you know, I’ve been to a bazillion conferences, some fancy ones.

  I mean, just to set the stage, you’ve got John legend. You’ve got ice cube, but you’ve also got Josh Koppelman, , and Jeff Jordan. So, , uh, what’s my question are VCs easier to deal with than celebrities or harder.

Thank you so much for saying that it is absolutely a labor of love. And what was the question? 

Um, who’s been really hard to deal with with the question, but that’s a bad question. Have there been any great moments that have really, like, I know some speakers that I thought like melody, , Hobson, Hobson.

Oh my gosh. She 

was incredible. She was incredible. I thought the team at bad robot, uh, Katie McGrath and JJ Abrams, of course they’re going to be great. And they were, um, I thought Reese Witherspoon was fantastic. 

That one was awesome. And just funny, people should look up Reese Witherspoon and Marc Seuster. Uh, one thing I think a lot about is, is do you coach people to be better interviewers 

like I’m trying to learn to be a better interviewer. You’re a great interviewer. Well, thank you. But are there,  do you help people learn to be a good interviewer? 

This past year was the eighth upfront summit that we had. And so now we know. What the audience is and what they care about and what they’re going to respond to.

And so we can always provide that insight to the interviewer and interviewee to say, these are the things that people are really going to have on their mind. So let’s make sure that we talk about it, but yeah, I think a great interview is a conversation. , and we’ve been really lucky at the upfront summit or other,  events.

To have a lot of great conversations where, , some really nice nuggets come out and people really speak honestly about their experience. 

Okay. Quick.

Wrap-up I’m going to give you a name and you have to tell me their brand. I’ll start easy. Karen Norman.  


doesn’t love Karen Nortman.

Everyone loves Kara. If I had a dollar for everybody that I meet in my life that says they love Kara Norman, I would be starting my own fund too. Right. Best in Karen Norton. Um, yeah, I think Tara is. Super high IQ along with her super high IQ. I think she’s really all about making sure that we have a tech community that’s inclusive and representative all, and  such a joy to work with her sister.

How do you characterize him? 

He’s a visionary and he is an incredible leader. Um, he is an incredible leader of up-front and he’s an incredible leader of the tech committee. Unity. I think he’s a great advocate.  He says what he thinks. He’s up front. He absolutely is. I think it’s not a surprise that he’s been a face about front for so long.

I think the two are, really are mirrors of each other. . 

Okay, great. I’m going fast. Coby fuller. I don’t know. Coby at all. 

 You die, 

you should know Kobe, Kobe podcast mini. 

It takes some time once a week. 

Yeah, he’s been and, um, he’s been an operator. He was the CMO of revolve before. Um, Long before he joined upfront and he’s really focused on future tech and he was an early investor in Oculus.

He also invests in marketing technology and communities, and he’s really has his finger on the pulse of building community building event. Events, and how people use their community to build a bigger business. So 

Carrie what’s, what’s your brand? 

Oh my gosh. My personal brand, you know, it’s funny that you say I’ve been thinking about this a lot and it’s, it’s like, I don’t.

Ad agencies always have the worst brands because they’re like, , you know, the cobbler’s kids have no shoes. Right. It’s so much easier to do for somebody else. But what I will say is this, the thing that I love most about my job is that I get to just be. And advocate and support for portfolio for the firm.

Like I want everybody to win. I want everybody to succeed. 

. And Curie. I see that so much. And, , , so thank you for the role that you play in the community and,   and things would be on the podcast.