Sunil Rajaraman (VP of B2B Marketing at GoodRx)

Hey everyone, this is Erik Torenberg and you're listening to Execs by On Deck. Execs is a show for founders, operators, and leaders who want to understand the playbooks, frameworks, and tactics that leading tech companies today have used to scale. Our guests are tech execs in key roles at top tech companies who share their hard-won, earned secrets on how to scale faster.

Sunil Rajamouhan is the VP of B2B Marketing at GoodRx. He also spent time as CMO at Mentormile, Head of Marketing at Radiance Labs, and SVP of Marketing at Replicon, among other roles. In this episode, Sunil shares guidance on how to navigate online versus offline marketing, how to market to a community, and the biggest mistakes that most marketers make. Sunil, when you look back at the arc of your career, you know, we have some aspiring marketers, we have aspiring founders listening to this, founders who are looking to build marketing teams, of course, marketing organizations. What has been your education of a marketer? Like, just give us a little bit of an overview.

Yeah. It's a good question. I mean, Erik, as you know, I've had kind of an unusual reverse career where I started as a founder and my education was as a founder. I started a company called Scripted, which was a marketplace for businesses to hire freelance writers, co-founded it with Ryan Buckley and worked with Jay Kring and some others on it. I kind of learned marketing from that company, if I'm being honest. And so, you know, and we kind of, we did a crash course of everything at once. And so in those days, I guess it was now like 10 years ago we started it, it was, you know, we were competing with the likes of oDesk and others. And so we had to be really scrappy about a few different areas. One was email marketing, other was SEO. And then, you know, later we expanded to things like paid media, but I learned on the job as a founder. And then joined Foundation Capital as an EIR for a bit, but decided against being a founder again for a bit. And now I've run marketing at a few different companies. Everywhere I've gone, I've learned by doing is what I would say.

Totally.

And you've seen kind of old school, new school, you've seen how marketing has evolved, you know, a decade ago to now. Why don't you give a little bit of an overview at high level, and then we'll go kind of in the weeds on some of the specific channels.

It used to be possible to be a step ahead of the Google algorithm. It's not possible anymore and everybody is looking for that exploit. One thing I'll share as an example that was commonly talked about amongst founders back then but not commonly talked about in the public is you could game Google search in such a way to basically pay for distributed clicks all around the world. To increase the relevance of your search result relative to others. Click-through rate mattered a lot. You could also do other things like create a lot of content with shady backlinks, et cetera. There was a lot of gray hat stuff you could do. Those loopholes have shut and the platforms are ahead of the marketers now. And so there's this weird thing that I'm seeing where old school marketing, like consumer direct mail, something that I've spent a lot of time on, is working really well right now compared to the auction-based platforms because ad inventory is not going up in price and it becomes more of a conversion and creative game rather than anything else. So it's weird because everybody's focused on digital, but the old school stuff is still tried and true.

For people who are new school founders themselves, what is the right way to get smart on some of the old school methods?

I think all of the old school methods come down to 3 things: data, creative, and logistics. If you know those 3 things, you're good. So the nice thing about old school is there's a modern twist now, which data has just gotten so much better. So, you know, even if you're working with, say, consumer direct mail, for example, you can use all of the data that served you well in the online world and take it to the offline world. And so, you know, there's plenty of vendors out there, uh, LiveRamp, Acxiom, etc., that will serve you with your data needs. And it is mind-boggling how much data is publicly available out there. So on the data side, there's that. On creative side, there's specific people and agencies that work to your medium and do a really good job with that medium. And on the logistics side, you know, again, I'm going to pick on the example of consumer direct mail, but It's a scale game, and it's one of those things where your costs actually scale down as you do more of it, which is unusual and like the exact opposite of what you see in the online world.

Yeah. Talk about the differences between consumer and B2B because you've done both.

Really, really different. And I've kind of, you know, gone from being a B2B person to primarily B2C. If I'm being totally honest, I think consumer is way harder. It's way, way, way harder. With B2B, having a good product marketer that can position against your competition, because every single granular area of SaaS is being taken. I mean, you just take one category, no-code. There are so many companies within there. Take another category, like some of the design stuff. You see Figma, you see Webflow, you see Notion and all of these different tools are positioning against each other. So having a really skilled product marketer in B2B is sort of what you need. There's so many different ways to purchase demand in B2B. Some people use your Capterras and your software advices to purchase leads and predictably get your SDRs, feed them and keep them busy. B2C requires Totally different skillset. Like, you really have to put yourself in the shoes of the consumer and capture that finite moment of attention at that moment and get them to think about you. Really hard.

Yeah. And so going back to Scripted, and you were saying you had to separate from oDesk, how did you do it? Or what did you find that was most effective?

Well, you know, a lot of credit goes to my co-founder, Ryan, who did figure out some tricks with email marketing in those early days. And he set us up with SugarCRM and was able to cleverly, I'll just say cleverly, scrape about half a million email addresses of directors of marketing back in those days. Totally legal, everything was great. It was a gray area, but I worked with him to set up, like, in those days, it was like really Marketo and HubSpot were just taking off. So we built our own, like, marketing automation And then eventually, you know, we started using some of the tools out there, Pardot, Marketo, et cetera. But that early start of email marketing, like there's so many companies, so many examples of companies that have been successful by basically emailing a shit ton of people. And we were one of them, and that was how it started.

Yeah. And what do you see other startups make mistakes when they do email marketing? Like what are the things to absolutely get right in terms of being most effective?

Oh my gosh. I mean, you probably get so many of these, 50 of them daily. The worst is, gosh, like these days when someone sends like a Calendly link and says, oh yeah, you can grab some time with me. I hate that. Pet peeve. Look, it's, it's really hard to stand out now, but the, and, and the generic personalization advice, you know, works, but like do things that don't scale with email marketing, go the opposite direction. It's, uh, It's not like, I know that it's very popularized to send out a lot of stuff right now. You're better off like, you know, spending that extra 10 minutes finding a personal connection to the person, encouraging your SDRs to do so, making sure grammar is perfect. Cannot tell you how often you see that one, but you don't want to be the person who's having your email screenshotted and shared on a group text thread because it's so ridiculous.

Or on Twitter.

Yeah, yeah.

You mentioned, uh, direct mail being sort of underrated. What are other channels you think are either underrated or overrated, uh, as, as we enter 2022?

You know, well, one thing that, uh, you know, GoodRx, my current place, has done, uh, successfully, which I can take absolutely no credit for because, you know, the company has been very successful for a long time, is figuring out how to— for us, the referral from a doctor is really important. And so this company figured out how to market to doctors, which are a consumer of ours, through like these doctor's kits. So if you go to a doctor's office, you'll see oftentimes at reception, there's like a GoodRx display where you can take away, like take a doctor's card with you. But that brings up a point, which is, you know, find who a key referrer is for your product. And, you know, that's the magic. If you can figure out, and oftentimes those people can be reached through offline channels. And so, you know, find your equivalent of a doctor's kit for your business. And of course, it just varies business to business. But, you know, like marketing through Jiffy Lubes, or, you know, where there's high foot traffic of volume and people just sitting there and they're, they're waiting for something. If you can find your equivalent of that for your business, the channel where people are spending a lot of time and not doing anything except staring at their phones, that's a viable channel.

At GoodRx, where have you explored or experimented, or what have you found that was particularly interesting?

Yeah, I mean, this company's been very successful for a long time. I've only been here a year and a half, but it's just with GoodRx, there's a doctor, there's a pharmacist, and there's a consumer. All 3 are very, very important to the business, and I just think this company has done a good job building relationships with all 3 and marketing to all 3 in such a way where the And so to any marketers sort of watching this, it's not obvious, but it's not just the consumer. There's probably 1 or 2 other people in your transaction that are really, really important. Find that dynamic and that network of people that will make the transaction really sticky and work.

Yeah, it's really interesting. I want to segue a little bit and give advice to the founder building a marketing org. Maybe they're just raising their Series A or something. They're just sort of scaling their team and they're starting to think about, okay, they have a product that's working and now they want to put some gasoline on the fire. What can they expect in terms of sequencing? And of course, it depends on the org, but how to build out a marketing org? Why don't you give out some of just the basics?

The biggest, biggest mistake unquestionably that I see every founder make is, you know what? I'm gonna find that unicorn marketer that can totally do it all. They're gonna know demand gen.

Right.

They're gonna know messaging. They're gonna know growth, and it's gonna be great. Every single time it fails. And so like what you should instead do is you should figure out on your own a channel that's kind of working and like you have an instinct about that's working and find the expert on that channel and blow it out. And that person is not likely to be your marketing leader, and they need to come in knowing and accepting that. But they're going to be one of the first employees at the company. Their equity is going to be immensely valuable in large part because of their skills. And, you know, you can have the conversation with them later about whether they're the leader or not, but they will get you so much traction so fast, you'll be far ahead of your competition that's searching for that unicorn marketer.

Yeah, no, that makes a lot of sense. Okay, so you bring in somebody who's got some special expertise around a channel or helps figure out what blows that out. Maybe they become a leader over time, maybe they're not. Talk about what that's like. When do startups, should they be looking for a leader? Or when do they realize that they need one? And how should they choose whether to promote internally or bring externally?

I don't think you need a leader until like Series B or later. I really don't. Like a CMO anyway. You could probably have a VP of marketing, but I would be very disciplined about titling in those early days because you do want the eventual leader to have optionality, and it is completely different. And one thing that I am fortunate is I have seen that $0 to $5 million scale, but I've also seen like $40 to $100 million, and now GoodRx is at the 500+ level. And, you know, the person who gets you from, you know, 0 to 5 is just not, it's just totally different. Even on the channel expert part of it, you know, the kind of person who plays with, you know, budgets much larger in Google and Facebook, it's not the same person. It's just different.

What should founders be looking for in VPs of marketing?

You know, you don't actually, it's overrated. You don't need an org builder. And so, you know, You just want a person up until Series B who can bring in and recruit, call it 5 to 10 people max. And these are other experts across different channels. Eventually later, you're going to want someone who can bring in a lot more people and maybe even mentor the VP and all of that, but you don't need a heavy marketing org. I'm applying this just generically as a rule. GoodRx was very efficient. Metric Mile, where I was previously at, was pretty efficient. But you don't need a gargantuan marketing org up until your Series B. After Series B, worry about that. Then you matter. Totally.

And so you've been a VP of marketing as well as a CMO. How do you think about, let's say when you hire a VP of marketing and start to scale, and is that person the CMO or not? What are the questions that you should be asking to determine whether that's the That's the right thing.

Yeah, that's a great question. And so that goes back to the, is where we're going gonna get us to where we need to be? And so, you know, you want someone in the channel who's expert in the channel of where you need to be. So for example, it might be Google or Facebook that got you to where you're going, but it ultimately might be TV that gets you to where you need to be. And, you know, we have a great CMO at GoodRx who's like a deep expert in TV. You know, in TV. And like, that's a, that's a big deal for us because of, you know, sort of broad reach consumer type of thing. You, you have to have an instinct about where you need to be and what's going to get you there. Oftentimes that's somebody who's worked with big, huge brands before, whether that's B2B or B2C, and has that like broad reach channel experience, uh, TV, out-of-home, something like that.

That makes a lot of sense. I want to stay with a little bit and talk about the intersection of marketing and community. Why don't you talk about what that looks like, marketing in the context of community?

Yeah, um, so, uh, in the Scripted days, actually, so, you know, what Scripted was before, um, you know, before it was Scripted was it was actually just a writer's side tool. We were building Google Docs for screenwriters, and we were trying to get writers to collaborate on screenplays. And there was a magical community that formed of about 80,000 writers on that side back, you know, in pre-Discord and all of that stuff. Without that community, you know, Scripted, you know, wouldn't exist. And I can't even imagine now in the hypercompetitive world of Web3, etc., matters even more. Here's, here's the things that I've learned about community is like really just engaging the first 200 people or so who are part of the community and making them feel like you're having a one-to-one relationship with them they will then pass that on to the rest of the folks in the community. After that, it doesn't scale, but really spending the time as either a CMO, VP of marketing, or founder preferably on those first people who are part of the community is what ultimately matters. And then it's a virtuous cycle. You know this better than most. I mean, you've built multiple communities. What's your take on that?

Yeah, I've built multiple communities, but I haven't— and I was going to ask, the next question was advice for On Deck on the marketing side. Ours has been mostly word of mouth. And so yeah, communities are critical, but one challenge is they can be slightly insular. And so for example, Product Hunt, right? We were early adopters within tech, but then we tried to expand to different communities like podcasting and gaming and books. And we realized the hard way that those are just different audiences. There wasn't a ton of adjacencies. in what we were doing. And we thought we kind of had just this like magic bullet of anything that we launched would just work because it worked in tech, why wouldn't it work elsewhere? And I think we, with On Deck, the lesson we took there is we're not going to launch anything new unless it benefits our core, like unless we have some advantage to launching it, and unless it makes what we're already doing stronger. Otherwise, it's kind of like doing multiple startups. And that's what we learned that in Product Hunt, we were like, trying to do multiple startups at once and even doing one startup is hard. And we've learned some lessons on the Y Combinator side too. I mean, we've launched maybe like 25 fellowships in the last 2 years and we sunset about 5 of them. And the ones that we sunset were the creator ones. It was like writing, podcasting, course creators. And we had a thesis that the people who were in those programs would bring distribution to founders and investors. And so that's how we would benefit. But turns out that while tech people are happy to pay for programs, creators aren't. And maybe it's obvious in retrospect, or creators that have distribution, I should say. The creators that we were getting to our programs were trying to get started or trying to build the habit, or they were tech people or whatever, but they weren't adding fuel to the fire, so to speak. And so we stayed true to the idea that, hey, and they were going well, but they just they weren't making the core stronger and opportunity cost is big, etc. So yeah, I think it segues to the next question, which is like, hey, Omdek's skill set is building communities and we are focused on tech, but even still within tech, we're focused among the Twittersphere, right? Twitter is our growth channel. And so if you were us or if you were leading marketing at Omdek, what might you experiment with? What might you explore?

Well, one, I mean, I only have really 2 bits of advice, but the one you're already doing, which is I really do believe that there is a massive difference between online and offline community. You just cannot, no matter how hard we want to try, as you and I, both people in the tech industry, to claim that, you know, building like online relationship is the same. It's not. It totally is not.

Yeah.

And so I think the companies that recognize that and do both, they're both important, are going to win.

Yes.

The second and perhaps more important point is mainstream America is like way bigger than people even imagine. And that's a lesson that I'm constantly taught every day here at GoodRx is we have our Twitterati that we interact with on the— who are, you know, quote unquote coastal elites, even, you know, whatever, Miami, whatever you want to call it. There are 30 million people in Texas, you know, and like between the coasts, The companies that realize faster that that's actually where a bulk of the audience is, they're going to win. And that's where, like, you think of things like offline channels or things that are a little less cutting edge. They're not participating in DAOs, you know, yet. They will maybe.

Yeah.

But, you know, I will bet if Coinbase, for example, sent out a piece of consumer direct mail offering $10 worth of Bitcoin to everybody in America, They will— I mean, everybody would be a crypto head. Everybody. Same thing for Ondec. There's so many people in Ohio. I went to high school in Cleveland, as you might remember. There's so many people in Cleveland who would want access to like the tech world. The sooner you reach them, you know, the faster this thing becomes like a $100 million run rate business. And I know some of your numbers. I won't share them on the pod.

Yeah, totally. And I appreciate you being a member and supporter of Ondec. So yeah, direct mail is interesting. We should go deeper there. I'm curious how you think about LinkedIn. We've gone deep on Twitter. We haven't done a ton on LinkedIn, although we do have a ton of people put On Deck in their bios on LinkedIn. And I wonder just how you— and we've started to do some sort of manual outreach for specific career programs and stuff, identifying, hey, customer success leaders, we should reach out to them. Are you interested in this? But any advice for leveraging LinkedIn as a platform?

A few years ago, I did like a super deep dive of LinkedIn. I actually became like a LinkedIn top voice one of those years.

Yes.

And I will say that I've not found a way to make it work. I find it to be very spammy, like extremely spammy, spammy. And so a lot of noise, not a lot of signal. With that being said, India, like you can reach a lot of international audience, like high-quality, great international folks through LinkedIn. If you put in the time and the effort, but if international is not a priority, I don't necessarily recommend it. Also, ad costs have just skyrocketed, and so unless you're a very special type of business, it just will not make sense. Inbox has gotten noisier, so I personally have not found a way to make LinkedIn work. I think the way to make it work is probably if you're like a LinkedIn influencer, if you were enshrined as an influencer or have access to someone. in those early days, that's truly a platform where that, if you were part of that group, that paid dividends.

Interesting. Yeah, interesting. When you're advising founders who are thinking about like best bang for their buck on paid media besides direct mail, what else are you advising them in terms of where to look or where not to look?

I mean, Google Display is great. One thing that is sort of, again, going back to the old school, I'm a big like believer in call center. And so Um, I mean, I can't— I won't share numbers, but like, you know, even MetroMile, Modern Insurance Company, etc., we got a large number of policies that came in through the call center. And so a lot of things— and so maybe On Deck falls into this category— but for a lot of things that cost, say, like $500 or north, people want to get on the phone and figure out what's going on.

Yeah.

So you can do a combination old school, new school. There's actually a Google Display ad unit that will route you through— like, you can Click on a phone number, literally. You'll see this if you— and actually, it's not even just a display unit, it's like a text unit. But if you Google auto insurance or whatever, some of the Allstate ads will actually have like a phone number by it. And if you click it, you're connected really fast to an agent. I will bet for Ondec or for other companies out there that are considered purchases, you spend that 30 seconds on the phone. And so you find them through Google, and you have the phone call to action. You will get a ton of customers that way.

Yeah, that's awesome. That's good to know. And zooming out a little bit and gearing towards closing, you've hired a bunch of people under you over the years. What are some of the characteristics that you're looking for in your marketing hires? And the flip side of that is for people who are looking to either break in or, you know, uplevel, you know, move up and apply for some of the roles that you hire for. What do you recommend in terms of how can they separate themselves from the pack?

Yeah, I mean, at this stage, like, really audience specialists are key and/or channel specialists. So whereas, like, as a founder, I would have, like, probably hired someone and taken a chance on them and, like, you're, you know, 1 or 2, a couple years out of college, boom, you know, maybe I find the next Erik and maybe not. But now it's, like, super deep expertise. With that being said, they also have to have and want to learn. And so the best hires, I oftentimes, they'll get bored after a couple of quarters and say, hey, you know what? I wanna learn a little bit about this other thing. That's not negative signal. That's in my mind, positive signal.

Yeah.

And so you can like, you can give them the opportunity to learn while still remaining a specialist at what they do and an authority in the company and what they do. So appetite to learn, but initially have to be a specialist at something. Yeah.

And so your advice is to pick a domain, pick a channel, and become an expert at it.

Become the best at one thing, and then the whole world will open up to you.

Yeah.

Because if you can become really good at one thing, then you can probably become really good at other things. If you remain kind of more of a generalist, like constantly, then people will just wonder where to slot you as your career goes on. There's nothing wrong with being a generalist. I have like a lot of different interests, but But you gotta work your way to that point.

So I could see someone listening in and say, okay, I'm gonna become a specialist, but based on where you see marketing going, what's a channel or domain that I should become an expert at that will become even more important in the future or not?

Gosh, that's a really, really hard question to answer because so much has changed over the past, like, whatever, several years. I do think that what I'm seeing is in the market, a massive shortage of people who are paid social experts.

Yeah.

And so, you know, that may sound like, yeah, sure, you can hire agencies to run your Facebook campaigns, etc. Hard to find individuals to work for a company who will do it. TikTok, Snap. But like, if you can— like, paid social is— it's here to stay, and it's going to be here for a long time. So if you can become an expert at, you know, Instagram, TikTok, etc., a few of these others— those are all very different, by the way. There's a shortage of those skills in the world. I think there will be a shortage of search experts in short order because it's not cool right now, and then it'll become cool again in a little bit.

Totally. So On Deck actually does nothing on Instagram or TikTok. Do you think that prospective entrepreneurs are there, that we should be doing something there?

I definitely think so. Yeah. I think that just by your very nature, your product is social. You know, I see people, for example, when they get into, you know, when they get into college these days, they're posting their college acceptance letter on Instagram.

Yeah.

What's your equivalent of that for Ondec? There's got to be. And you do that, you do a good job of this on Twitter, but what would it look like if you actually sent a physical acceptance letter, tying in the consumer direct mail thing, you've been accepted, and people share it on social? There is something there. And like, there's probably like a really interesting story to be uncovered there of somebody who's like, you know what, this is life-changing for me. I want to share it with folks in the world.

Yeah, no, that's really great advice. Yeah, I find it fascinating about the combination of offline to online. This is something that us and more startups should definitely take advantage of. Well, Sunil, this is a great place to wrap. You've dropped a lot of wisdom here. I appreciate you coming on. For people who want to go deeper and see some of your writing, et cetera, where can you point them?

For now, I'm cooling it on social these days. I think I just got worn down on the pandemic, and so I don't do Facebook anymore. I don't do Instagram anymore. Just follow me on Twitter, @subes01.

Awesome.

Sunil, thanks for coming on the podcast and all your support of On Deck.

Thanks for having me. Awesome.

Thanks for listening to today's episode. Execs is produced by On Deck, where top talent goes to start companies, find their next roles, or invest in their careers. If you're looking to start a company, uplevel your career, or navigate a career transition, I encourage you to visit beyonddeck.com. See you next time.