Maintaining Developer Trust While Scaling Upmarket

Michael Grinich (00:02):

Welcome to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving upmarket to serving enterprise customers. I'm your host, Michael Grinich. I'm the founder of WorkOS, which is a platform that helps developers quickly ship common enterprise features like single sign-on. On this podcast, you'll hear directly from founders, product leaders, and early-stage operators who have navigated building great products for enterprise customers. In every episode, you'll find strategies, tactics, and real-world advice for ways to make your app enterprise ready and take your business to the next level.

Today, I'm joined by Helen Min, co-founder and managing partner of Phenomenal Ventures, and formerly the Head of Marketing at Plaid. Helen spent over 13 years leading marketing at some of the top tech companies, including places you might know, like Plaid, AngelList, Quora, and Dropbox. She's thought a lot about developer-focused marketing and how it's different than traditional B2B marketing. I'm really excited to talk with her about this and more today. Helen, welcome to the podcast.

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Helen Min (01:04):

Oh, thanks for having me.

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Michael Grinich (01:05):

You have a really impressive resume, spanning a bunch of companies that folks know. I want to talk about Plaid specifically. Let's go back to 2017 when you joined Plaid, what was the state of the business and marketing then? What was it like on day one for you?

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Helen Min (01:20):

When I joined Plaid, I think they were doing about $30 million in revenue. They had hired Paul Williamson, who has also been on this podcast, and I think is an advisor to WorkOS at this point.

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Michael Grinich (01:30):

Yep. Know Paul very well. Yep.

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Helen Min (01:33):

Yes, Paul's the best. He was scaling his sales organization, and I think that that was the time to really think about what does marketing look like running alongside a rapidly-scaling sales organization that is moving upmarket? So, I think this is probably very relevant for your audience here. So, Plaid had a really strong brand among developers and I think they were trying to figure out how they go the next phase. And so, what marketing looked like when I joined, there was a Head of Comms, there was a Product Marketer and there was somebody doing Demand Gen and starting to test campaigns.

I would say that the biggest thing that we did just right off the bat was build that relationship and define the working relationship between Marketing and Sales. And so, Paul and I and somebody from Biz Ops, we got together and made sure that we were defining MQLs the same way, and defining what sort of engine we wanted to build. I think the analogy I used was like, "You want to make sure that the gumball machine is working before you keep putting quarters into it." And oftentimes, I hear founders say, "Okay, I just hired a Head of Marketing, so on day one I need to see all the numbers go up because they were such an expensive hire," or something like that. And I think something that I was really grateful for at the time is Zach gave us a quarter to figure out the plumbing on all of that. Yeah, so that's kind what happened right when I got there.

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Michael Grinich (02:59):

I want to ask you more about this developer marketing specifically, but I wanted to ask, before that, about something you just said. I think people are really familiar with product marketing and familiar with demand gen, but they're maybe less familiar with comms. Having a Head of Comms at that phase is pretty different. What was the head of comms doing at the company? What was that role?

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Helen Min (03:19):

That's a great question. I think that that's actually specific to Plaid. I mean if you remember, Plaid, they were very developer-focused, but they're a fintech company, and so existing within financial services and figuring out how to communicate with a lot of the more traditional financial publications that would be reaching banks and helping banks think about how Plaid works, or regulators from that perspective. So, I think that that Head of Comms hire was pretty specific to fintech.

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Michael Grinich (03:46):

Got it. And definitely, I mean brand with those types of institutions is really important, really, really important too. Let's talk about developer marketing because the other side of the marketing talent coin was not those institutions, it was reaching developers, building stuff, writing code, actually pushing forward fintech. As you think about marketing to developers, what are some of the rules you live by there or things that you've seen absolutely work super well or things that you definitely shouldn't do?

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Helen Min (04:10):

So, I think at the time, and so where we were was really knowing that we had high trust and affinity from developers, and we didn't want to lose that and we didn't want to sacrifice that as we moved up market. And the reason and the insight behind this is that even when we closed large enterprise deals, like I remember there was a utilities company that we had just won, and when we investigated how did we ultimately win there, it was because the developers inside of that organization, even though they weren't the decision maker, they loved Plaid. And so, there was this idea that if you think about developers as this sort of self-service, smaller accounts, that wasn't true because building that brand, there are developers inside really large organizations that can ultimately impact how enterprises buy.

So, that period, it was important to build that brand. And some things that we talked about on how to maintain your developer cred while moving up market were like, ‘show don't tell’. Don't tell me how great this product is, just show me. So, when you went on to the website, for example, everywhere you navigated across the website, we always had this button that was ‘download API keys’, because we think developers, they don't want to be told how great the product is, they just want to get their hands on it and see for themselves.

Another rule, ‘features not benefits’, which as a marketer, that is the opposite of what you're told all the time. You talk about the benefits and have them imagine how much better a world is when you're using this product. It's the opposite with developers, again, because they want to see for themselves. And then, I think another principle we had was just ‘be genuinely helpful’. Being genuinely helpful, that shows up in a lot of forms, usually in content. So, it doesn't have to be so transactional. You can create really great docs, you can create videos, help center guides, et cetera, et cetera, really helping developers finish their projects or get started. And it doesn't have to have a zippy call to action or anything like that. So, those are some of the things that we kept as rules, regardless of the type of content that we were creating.

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Michael Grinich (06:13):

Is there one or two things you see companies always get wrong when they foray into this? Maybe folks that don't have experience selling to developers, it's a new motion, a new part of their product where you just see them consistently fall on their face at the first step?

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Helen Min (06:28):

Good question. I really think it's delicate in this transition from if you got a lot of traction initially with developers and you built this great organic developer brand, usually because the founders are developers themselves and they did a lot of the heavy lifting in creating content, being active and engaged in the community. And then, maybe you raise the next round and you hire a marketer and you hire a salesperson and you feel this pressure to go up market and really multiply a lot of your metrics. It's almost like you have to abandon the past or it's one or the other. And I think that that's actually a misconception I see over and over and over again.

And I will actually just say that the time that I was at Plaid, like 2017 to '19, they were definitely going through this transition, where it was like, how do we have our cake and eat it too? How do we have a business that looks more like an enterprise software business? I think thinking about it sort of black and white, like, "Oh, we have to abandon the way that we talk to developers, or the channels, or the content that we create for them in order to win enterprise customers," I think that that's a false choice. So, at the time though, we were going through a transition where we were starting to hire more salespeople. And I think this is what happens, where you're hiring experienced enterprise salespeople who are used to having a marketing team that was generating content that was more traditionally enterprise marketing. So, trade shows, white papers, webinars, things like that. But all of those things felt very inauthentic to what Plaid had been doing previously, and definitely inauthentic to the core developer audience that they had.

So, it was really about how do you make that transition smoothly? Because if you look at Plaid today, they're doing all of those tactics, but at the time, it was like that sort of, "Okay, how do we get to the next step?" So, one thing that we did was get on the same page, that developers are at the heart of everything that we do, and the brand has to very much, first and foremost, speak to developers, because of the example I just gave on the why we win enterprise deals. But we could try vertical by vertical. I remember when Plaid started getting into lending, we said, "Okay, can we try to do this very targeted webinar with a partner in the mortgage space and just see how it performs?" And because it was so targeted and it wasn't going to reach a bunch of developers, Zach was fine with that.

And so, there were great results from that initial test. So, we did a little bit more and a little bit more and a little bit more. And I think then Zach started to feel more comfortable with like, "Oh, okay. I see in this very focused vertical how some of these marketing tactics are performing. What would it look like to do that with another vertical?" And so, the importance here is really the transition and how a marketing team continues to have the trust of whether it's the CEO or whoever ultimately they're reporting into, to be able to try to push without losing themselves, or frankly, losing trust that they're not great stewards of the brand.

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Michael Grinich (09:29):

Making that transition is definitely a thing that needs to be done intentionally it sounds like. When do you think is the right time to start thinking about that? I know you advise a lot of companies, we'll talk about that in a bit, and invest in folks. When do you think is the right time for an organization to start experimenting or investing in marketing that's maybe adjacent to their core developer roots? Is there a business phase or something you see in the product or the customers?

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Helen Min (09:53):

Yeah, so I mean a typical path... You mentioned all the companies that I've worked for, I think that they all follow this path. And the other thing that they have in common is they've all got technical founders, and a lot of them delay investing in marketing as long as they can. So, I know this phase really well because I think the growth trajectory is usually organic growth starts to plateau and, "Oh no, we need to hire somebody to figure out how to pick this back up again." And so, I think that one of the signals for when to start being more intentional about investing in marketing, perhaps with some specific marketing hires or investment, would be like when you start seeing organic start to plateau a little bit.

I think another time that we typically see companies invest is when they get a new round of funding and they're like, "This is something that we've ignored for a long time, but now we can do this." I think what's interesting about marketing is that it doesn't have the best sort of reputation, especially among technical founders, but you're doing marketing from day one whether you know it or not. So, it's not like, "Okay, now I'm going to start marketing." You've probably been creating content or talking to people and being thoughtful about your messaging and how you present the product from day one. And so, the thing that I always say is recognize the things that are working well, recognize where marketing already exists on your team, and then make sure you don't lose what is already working well.

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Michael Grinich (11:19):

So, you mentioned that Zach, when you started making this transition at Plaid, that he was hesitant to do this or didn't feel right for the culture necessarily of the company. But eventually, obviously it's what the company's doing now, it's driven a lot of impact, it's expanded. Do you have any words of advice for maybe those technical founders that when they see anything related to marketing just go, "Ugh, I don't want to do any of this stuff"? And yet, it's exactly what you're describing, where it's time for the business to do that, maybe exhausted the organic growth or they just want to accelerate in a different way.

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Helen Min (11:51):

I think so much of what I talk to founders about who are going through this one-on-one is that this is an exercise in change management and trust is really paramount. And so, advice I have to founders who are hiring a first Head of Marketing and a little bit nervous about handing over the keys, so to speak, literally in some cases. It's like, "Okay, here's the Twitter handle. Please do not tweet anything crazy." Is that hopefully you're hiring somebody that you really trust their taste and trust their judgment, and they understand what is really important to you. And Zach was really great at that. He did a great job translating what he thought was good and what he didn't like, and me having to continually demonstrate that I understand that. So, how do I balance that with pushing the sort of pressure that we get from people like Paul or Sima on the Biz Dev side because we were also serving banks.

And I think that's a really great point. A lot of these developer-focused companies, they have multiple audiences as their business grows. Plaid is definitely that. Yes, we were serving developers, but we were also serving maybe product managers at larger enterprises and we were also serving banks and we're also being watched by regulators. For us, we had to create this brand that was developer first but also it was good for all these other groups. And so, I think prioritization and being on the same page is really just key to that. And so, how do you start taking some of that risk? Well, you're going to enable somebody you trust to take risk more than someone you don't.

And so, I think really spending the time to understand how they make decisions, what their tastes are and what they're going to do with the brand. Because at the end of the day, I always tell founders, "This is your baby. You should care as much as you do. And I'm sure everybody gets really irritated with you sometimes that you care too much or that you're obsessive, that's fine. Brand is so important." And there are zero exceptions to this rule. So, I always say that the founder's brand is the company's brand, full stop, because they're ultimately going to have to feel comfortable with what's out there.

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Michael Grinich (13:56):

Let's talk about taste some more. You said that a couple of times. What does that mean to you and how do you find people with whether you call it good taste or taste that matches what you're trying to achieve?

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Helen Min (14:08):

Thanks for asking this question. Let's acknowledge that taste is extremely subjective. And that gives, I think technical founders in particular, a discomfort, because you really want things to be quantifiable and measurable. And also, especially given budgets are tight and people are trying to run leaner than they ever have before right now. And so, investing in something like brand or content that's more in that taste category feels precarious sometimes. So, I think this is really just part of the long getting-to-know-you process when you're bringing on somebody like a Head of Marketing, or just any person to join that team, to get to understand how they make decisions and what their tastes are.

It's really just talking through and sharing, if you're the hiring manager or you're the founder, what you like and why. And I mean everything from other SaaS websites and brands to the sneakers that you wear, or what artists you like, or anything that really just gets a sense of where that marketer can really curate what you would choose. Because what they're doing is they're making choices on your behalf, and hopefully, you're choosing somebody that you think has better taste than you or you respect their decisions. So, maybe they have a good track record of working on brands that you respect and admire. And you should be very specific and deliberate about like, "Oh, I liked this aspect of that brand," or, "The work that you did here, I thought that that was really smart for X, Y, Z reason."

It's really trying to dump all of the thoughts in your head about brand, and taste, and decisions to help onboard that person. And I cannot stress enough that you have to spend a lot of time with this person so that you guys can mind meld almost, and then get them off to the races because then they'll have a playbook that they can scale. And you don't have to spend time with everybody on that team, but really invest in one person that you're trusting as the taste-maker for that team's activities going forward.

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Michael Grinich (16:06):

You mentioned brand is really about the founder brand. And taste here, sort of mimic the founder's tastes or in some way be able to be in tight resonance with that. Talk more about that with brand. Brand, founder brand, how do founders discover what their brand is? Or maybe there might be technical founders listening to this saying, "I don't even have a brand. I'm not posting hot takes on Twitter or blogging or anything." What does founder brand mean? How is that the anchor of the company brand?

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Helen Min (16:31):

When I work with founders specifically on this, I spend about an hour or two just asking them a whole bunch of questions. "Why do you think this is cool? Why don't you think this is cool? Name some celebrities you think are cool and why not? What did you eat? Where did you go on vacation last? Why did you choose that place?" Really getting them to explain in their own words why they think something looks good, or is cool, or something like that, that is actually curating what I think that their brand and their taste is.

And so, it's not as straightforward as like, "Here's a list of 10 enterprise and software websites that I think are great that our company should emulate." That actually tells me very, very little and in fact I can get a lot more information that you think that this person is cool because they work in tech and they wear these sneakers that no one's heard of that they got in Japan once... Those inputs are actually a lot more helpful than being more literal about, "Here are some companies that I like," as part of the brand exercise.

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Michael Grinich (17:31):

I want to ask about something I think you have really good taste in, which is companies. Obviously, places to work, you've nailed it and hit a bunch of really great places early on and helped them grow. But also, now you've moved into this role where you're investing in companies and advising, what do you look for in founders and companies when you're looking to work with them, in the past, maybe join, now invest? What do you look for in those teams, or products, or founders?

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Helen Min (17:55):

Oh, thanks for asking. So, I mean I think investors don't ask themselves enough this, and maybe it's because not all of them have operating experience, but it's like, would I join this company? Are they working on a mission that is exciting to me? Do they fit a lot of the patterns of some of the companies that I've worked for that, as you mentioned, some of them were big hits, so do I see a great technical founder here that is going to sort of take the company all the way to the end? But I think the other stuff that is also pretty unique about the companies that I've worked for and the companies that we invest in from Phenomenal Ventures is that a lot of them, if they're an enterprise software company, they have aspirations to build a brand that looks a little bit more like consumer.

So, let's take Dropbox, great example, and Plaid, and Quora, frankly, and Facebook, because both of those are consumer internet companies. They have a really great business and strong go-to-market motion, and it looks like marketing and enterprise sales now. But all of that is basically built on a foundation of either having massive user adoption in the case of Facebook and Dropbox and Quora, or being intentional about a B2B2C sort of motion. So, Plaid, for example, when I first met the founders, I didn't really know a ton about fintech or Plaid at the time, but they were very clear that they want to build a brand that consumers will trust and love. And how do they do that right now when they're not consumer-facing? And so, even just knowing that that is something in the back of their minds is actually really useful. And so, I think the types of companies that we look at are, I think, technical founders that have an appreciation for brand at the end of the day, and those are things that we can be uniquely helpful with.

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Michael Grinich (19:32):

All right. So, last question for you before we have to wrap up. If you were in the shoes of an earlier stage founder looking to make their first marketing hire, maybe someone like Helen five or 10 years ago, what would you look for? What do you think makes a really great first hire as they're starting to build that marketing team? And specifically, for these developer-focused products, maybe more technical founders. Is it someone from a DevRel background, more traditional marketing, someone not from marketing at all? How should founders think through that?

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Helen Min (20:02):

Oh, great question. And you saying someone not from marketing at all is super interesting. I'm going to answer this question in a couple of different pieces. So, one, if it's a first hire, first marketing hire, they don't necessarily have to have the title of Head of Marketing. You just want to put somebody on that full-time for the first time. I generally advise founders to hire a really smart generalist over a specialist. So, somebody who doesn't have any previous experience with a marketing title or doesn't even self-identify as a marketer in some cases. I think finding people who are really curious and experiment-driven, because when you're starting out and investing in marketing, you don't know what channels are going to be the ones that really deliver for you. So, if you don't know what channels are your channels yet, you actually need to just hire somebody who's going to be very driven to run as many experiments as possible to unlock what that is ultimately going to be.

And smart generalists, they're going to get bored once they figure out the answer to the question of, "Okay, great, these are the two high performing channels for us. Now that I've figured that out, I want to go move on to some other sort of problem to solve." And then, you can hire a specialist to run those channels because they're going to be more used to you just doing repetitive work day in and day out. I think if you've got folks on the marketing team already and you're looking for a leader, but you're not quite massive scale, maybe more around the time that I joined Plaid, where there's a couple folks and then you're bringing in a leader for the first time, I recommend T-shaped hires. So, a marketing leader who's got experience leading, building, developing a team, but can also play the role of a super IC that maybe the team doesn't currently have.

So, when I joined Plaid, I was very honest. At the end of the day, I'm a product marketer and I think that that is going to be very critical to develop that team as we scale, and especially as we grow alongside the sales organization. But because I identify as a product marketer and that is something that I have tons of IC experience in, I can do a lot of these basic things in the beginning as we hire. And so, that sort of helps you grow different facets of the marketing team at the same time and be efficient about it. And then something that I've written a blog post about is the first Head of Marketing or the second Head of Marketing, there's going to be a lot of trial and error, so don't put so much pressure on yourself to go hire that perfect first Head of Marketing. And then, go easy on yourself if it doesn't work out.

It's one of those roles, I think marketing is super unique because one, I mentioned technical founders in particular tend to wait as long as possible to hire for that role, but the other is that unlike any other function, secretly everybody at the company thinks that they can also do it. So, I'll give you an example. I remember if there is Super Bowl season and there's a bunch of Super Bowl ads, everybody has an opinion about what the best Super Bowl ad was, or whether a billboard on the 101 was clever or not. And I think that that's sometimes conflated with like, "Oh, I know how to do marketing because I thought that was clever or that was not." They have got an opinion about it.

Whereas you would never go to your head of engineering and say, "I don't understand why we write code in this language." Or you wouldn't go to somebody on the legal team and disagree with their judgment on something because they went to law school and they've got all this experience. Marketing is something that everybody is interested in, and so it's awesome in that case because everyone's interested in it and they're leaning forward and they want to be a part of it and they want to know what the company is doing, but it's also kind of hard.

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Michael Grinich (23:36):

For everyone listening, Helen mentioned her blog, definitely go check that out. We'll make sure to link it in the description and comments. I've learned a bunch of stuff from you in that blog and even just from this conversation, even more. I wish we had more time. Thanks so much for joining us on the podcast. It's been really great to catch up with you.

You just listened to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving upmarket to serving enterprise customers. Want to learn more about becoming enterprise ready? The WorkOS blog is full of tons of articles and guides outlining best practices for adding features like single sign-on, SCIM provisioning, and more to your app. Also, make sure to subscribe to this podcast so you're first to hear about new episodes with more founders and product leads of fast-growing startups. I'm Michael Grinich, founder of WorkOS. Thanks so much for listening and see you next time.

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