SaaS Office Hours with Tomasz Tunguz & Hollie Wegman

Redpoint Ventures
Jun 12 · 27 min read

The following is a recap from our SaaS Office Hours on June 3rd hosted by Tomasz Tunguz who spoke with Hollie Wegman, Redpoint EIR and former VP of Marketing at Segment. The interview has been lightly edited for clarity.

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Travis Bryant: Good morning, afternoon, evening to all of you. Thank you for joining our first virtual Redpoint Office Hours with Tomasz Tunguz and Hollie Wegman. I’m Travis Bryant, and I lead our Founder Experience Program at Redpoint, which is the set of services and practices we deploy to support entrepreneurs through their journey and all of their interactions with Redpoint. Like many, we’ve had to evolve our events structure and so this is the first virtual office hours event that we’ve ever hosted. Just a few notes on logistics since we’re using a new platform called Airmeet to host this virtual event.

Of course, all of you are muted and video off by default, but there are a few ways that you can interact with Tomasz and Hollie. There’s a chat available for you to communicate that’s global for the entire group so use judiciously. If you have a specific question, you can use the questions icon there in the right hand column.

I’ll be monitoring and sharing those questions with Tomasz and we’ll work to tackle those during the discussion. And then at the end, we’ll save some time for open Q&A, and you can use the raise hand feature, the small icon there, and we’ll be able to hear and see you directly while you ask your question.

If you have any technical issues or need support, you can voice via chat or jump back into the tables section after this session and join table one to get support from the Airmeet team. Hopefully, we will have a smooth and fun session here. So without further delay, I’ll turn it over to Tomasz to kick things off.

Tomasz Tunguz: Awesome. Thanks, Travis.

Welcome everybody to SaaS Office Hours. We are thrilled to do this. Thank you so much for joining us, Hollie. Just a little bit of context, we’ve been doing SaaS Office Hours for about two years. We used to do them at the San Francisco office for Redpoint in a small room format and those have been a huge success. Now the world has changed and it’s an opportunity to change our format and reach more people.

We’re going to do about 40 minutes of Q&A, and as Travis said, we have some prepared questions. The audience members were wonderful and provided hundreds of questions, and so we’ve aggregated those, and I’ve got some terrific answers for you. Then at the end, we’ll save a couple of minutes for open questions. Afterwards we’ll send out a survey for feedback so if you have questions, comments or suggestions on how to improve this, please let us know. We’d love to hear!

Welcome, Hollie, you have an amazing background. You have worked at early stage companies and mid-stage companies through IPO and Fortune 500. You’ve done, I think, every single role within a marketing function, which is rare, and that gives you an incredible view of marketing and next generation marketing.

We’re also really lucky that you joined us as an Entrepreneur in Residence a few quarters ago and have benefited from your experience tremendously. We’re so lucky to have you. A couple of things I’ve learned about Hollie over the past couple of months is she’s deep into macro photography.

Hollie, tell us a little bit, what is macro photography?

Hollie Wegman: Macro photography is when you take a photo that’s really zoomed in, really close up, and you can buy some great macro photography lenses that’ll clip onto your iPhone. You can take incredible photos of flowers, of botanicals, anything really — and it looks like you’re looking into a microcosmos, another world, a level which you can’t normally see things. It’s really cool.

Tomasz Tunguz: That’s so awesome.

Hollie Wegman: I want to thank you too, Tomasz, for having me. I’m a big fan of Office Hours and all your content. I’m just really excited to be at Redpoint and to be on the show!

Tomasz Tunguz: I remember the first time we met, you showed me a photograph of a little cactus that was blown up at some huge magnification and it was spectacular. I’m a big fan. Okay, great. Let’s jump right in. By far, the most popular question from the audience was “What is the first step in selling to a technical buyer?”

And the reason that this question is so popular is that the bottoms up motion we’ve seen is incredibly powerful. We see an open source product like Growth DevOps. You’ve been marketing to technical buyers for some time, and, obviously, you’re an incredible expert in it. How would you counsel the audience to market successfully to a technical buyer?

Hollie Wegman: I think the first step is to get really clear on who the buyer actually is and what matters to them. A common pitfall I see with startups is where there’s not enough precision on who the customer is when it comes to a technical buyer. That’s because I think there’s a bias that the technical buyer will inevitably be an engineer. What you need to do first is you need to dig in a little bit. You need to ask yourself, “is the technical buyer even an engineer?” The reason I say this is because now there’s so much technology inside of a company.

Just myself as a marketer, I might have a stack with 40 or 50 marketing technologies. There are technical buyers, people who are buying technology, that are not in engineering. The first step is to figure out with your technical buyer “Am I even speaking to an engineer?”

Let’s just say they are an engineer and then let’s think, okay, well, what kind of engineer? You can have engineers with different goals and challenges. You can have front end engineers that will care about certain things, and you will have back end engineers that will care about other things. DevOps will care about different things. I think that the first step is to work out really carefully who they are, what their concerns are, what stage of their career they’re in — that can affect things as well — and then with that level of clarity on the buyer, you can better understand what matters to them and how your product might fit in.

Tomasz Tunguz: That makes sense. One of the things when you start marketing to a technical buyer is you’re actually trying to penetrate the company or the customer through the bottom, meaning through the technical buyer, through those engineers that you just talked about, but then they also want to sell a larger contract. They might want to sell an ELA or they need to involve a business buyer at some point in order to grow the contract.

That’s a two-prong go-to-market with potentially two very different marketing messages. One to the technical buyer and one to the business buyer. When you have one website, one marketing team, and one sales team, and you’ve got only one shot to talk about your product, how do you balance those two things?

Hollie Wegman: Yes, this is a genuine challenge and I’ve faced it in basically all of my companies. I have this concept that I talk about called “The Developer Duplex.”

If you think about a duplex, the duplex is a house with two units and one roof. They share the same roof. It’s one building, but it is two separate units. In one unit, there’s a family with certain concerns, and in the other unit, there’s another family with different concerns. When you think about “The Developer Duplex,” one unit is the developer and the other unit is the business buyer.

They have different concerns so you are going to have to bifurcate your message. You’re going to have to message to the developer a little bit differently than the way you’d message to the business user, but the roof is the same. So there is some level of high level messaging about what your company does and what your product does, which is the roof over the top. And then, don’t be afraid to have different conversations with the two different units.

Tomasz Tunguz: Have you been a real estate landlord in the past, Hollie?

Hollie Wegman: No, I don’t have enough money to be a real estate magnate, but I’m working on it.

Tomasz Tunguz: That’s awesome. So one of the questions that a lot of startups ask is “Which message should I have on the website?” Does it change as the company evolves? For example, if I’m initially starting out going bottoms up, mostly product led, and then at some point I bring in a heavy sales team, do I then change? Do you have a point of view on that?

Hollie Wegman: I do, and it kind of dovetails back with that first thing about understanding who your buyer is. If you’re doing bottoms up and that’s where all of your deals are coming from, your ideal customer profile — meaning the profile that’s leading to the most efficient fat deals — is bottoms up and is a developer, then you speak to that buyer on the website. If that starts to shift over time to be a business user and the developers are more stakeholders, but not necessarily buyers, then you’ll shift your messaging on your website to that ideal profile. I think that the tough point is the kind of purgatory where you’ll be making that transition.

And in that case, I think it’s really important to realize that the homepage of the website isn’t the only place where you get to have conversations with people. The website will say something, but you need to give people access to other messaging, whether that be through a channel or whether that be through a tab on your website.

There’s also some really interesting experimental ways to surface different messaging on the website, depending on where you see the buyer coming from.

Tomasz Tunguz: And then solutions pages. Do you see that often, you know, here’s a product for one particular industry or one particular buyer or by role? If I’m an engineer, I should click here. If I’m a VP of X, I should click here. Does that work?

Hollie Wegman: I do see that, and I think that those are valuable to have on the website. All the conversations that you can have, that you can push people to are good, but inevitably people are going to land on your homepage. The homepage is the one you want to serve your most ideal customer.

Tomasz Tunguz: That makes sense. Awesome. Moving on to the third question. Many of the people in the audience are early stage companies. We actually looked everybody up and tried to figure out what the composition of the audience is. A lot of them are just getting started and they were asking, “If we could take you back to your early stage startup days, Hollie. If you were starting at a Series A company today and you had to focus on one area of marketing, given a limited budget, what would that be? And why?”

Hollie Wegman: My early stage experience was Envoy, and if I go back to where we were, we had a product that we could sell. That was good, and we had really good product market fit. What we didn’t have yet was as much customer penetration as I would have liked. The first thing that I wanted to do was to work on that and that meant building out the acquisition machine and in our case, we were self-serve.

Making buying easy through the website was a big push for us. I think in general, in an early stage company, you’re really just trying to push the gas on getting more customers. More of those first customers and then, simultaneously, spending a lot of time really understanding who those customers are.

At Envoy, we originally sold to receptionists, but I think over time we realized that the buyer was really more a facilities type person.

Tomasz Tunguz: And just to clarify for everybody, what does Envoy do?

Hollie Wegman: It is a visitor registration tool. I wonder how many of you have signed in on Envoy? It’s an iPad. You walk into a building and you sign in on Envoy.

Tomasz Tunguz: I’m sure the vast majority of the audience has used it.

Hollie Wegman: People think, okay, the receptionist is the person who buys it. One of the things we had to figure out was, okay, well maybe the receptionist actually doesn’t have the budget. Maybe it’s really more somebody concerned with different things and facilities. The key things we were thinking at the Series A, which were different from a later stage company, was working through the early product market fit, expanding into that customer, understanding that customer.

Tomasz Tunguz: Take us back there for a second. Initially you were focused on receptionists and I’m sure you were running demand generation campaigns to those receptionists, maybe webinars or education, and online ads. At what point did you realize that they weren’t the right target buyer? Did you look at the metrics coming back from those campaigns and say those aren’t the right target numbers?

Or was it something that came back from product or sales? How did you, as a company, decide that the ICP profile had changed and it was a little bit different?

Hollie Wegman: I mean, it was a lot more basic than that. It’s funny. I mean, we were 14 people. We were small. I sat and said to this other person, “Hey, this seems like maybe the facilities person signed the check and not the receptionist who I was talking to,” so I think it was more basic than that. But, I do think that it really was just by looking at the deals, talking to the customers, and understanding what was happening inside their company. We had the bandwidth to do that because we still had a small customer base.

Tomasz Tunguz: A lot of companies are in this situation where they’re figuring out who the ICP is. Did you see an immediate pull when you made that shift or was it more sort of a leap of faith and you kind of bet on it, and then it started to take off after a couple of months or a couple of quarters?

Hollie Wegman: I mean even that evolved over the time that I was there — for a couple of years — from facilities to other people that might be interested in buying as well. But, it wasn’t something immediate, no. I think it’s always an evolution. I think this is the key thing where any marketer needs to always be working closely with product and sales, to really hear the voice of the customer and listen to what’s happening. You’re going to be continually evolving and refining your point of view. There wasn’t some hard fast shift or some kind of magical moment, at least not in any of the cases I’ve seen.

Tomasz Tunguz: Another company that you’ve worked at, that’s been hugely successful, is a company called Segment. You’ve seen the progress of that business. One of the things in the past that you’ve said about Segment is “If you’re growing fast, you have a different company every quarter.” Right? A part of it is because you’re hiring the team, there are all these people that you need to communicate to, the business is changing a lot because of the customer base and all the demands on the company, and anybody who’s experienced hyper-growth knows that feeling. It’s an addictive feeling for sure. As you’re going through that evolution as a company, how does the marketing tactics of the business change in order to meet the needs of a company that’s growing that fast?

Hollie Wegman: Yeah, I mean, you basically nailed it. That’s exactly how I think of it. It’s when a company is growing so quickly, it is a different company every three to six months.

And so how does marketing keep up? I think marketing needs to be very tightly tied, rafted, really closely with the other growing functions — product, sales, success, and so many other parts of the company — and needs to be very deeply dialed into “What is the goal right now?” and that goal might be changing. The one key thing I would say is just continual and open lines of communication. Keeping that startup feel as long as possible, staying rafted, and talking to a lot of people often, and then trying to maintain that clear thread on what the goals are and then reorienting the team around those goals as needed.

That might mean that at one point you make that shift that we kind of touched on earlier between maybe this is not about bottoms up right now. Maybe we’re going to do some top down and we’re going to experiment with that. And it may mean then thinking through, okay, marketing, we just hired all these people that are really good at bottoms up and now we’re going to do this totally other thing, and we’re going to support a sales team to do this totally other thing. How do we do that? It means, putting heads down, learning, understanding, and working with other teams. At Segment, we spent a lot of time talking to other companies who had been there and done that, and learning from them. And we would just sort of reboot and try the new thing and see how it worked. And if it worked, we would do more of it. And if it didn’t work, we would reboot again.

Tomasz Tunguz: One of the things that we have talked a lot about with early stage companies is demand generation. If you have a sales person, there’s always a lot of pull on demand generation. You talked about the focus of the marketing team changing with time. Is there ever a time in a company’s life where demand generation isn’t top of mind?

Hollie Wegman: Yeah, I think there is and I think it depends how far out the company is looking. Think about a company that’s in a highly competitive space. I always imagine Slack in the very early days when there were a lot of chat tools. I mean, demand gen was definitely important, but building their brand and connecting with a particular community was also really important.

I’m guessing some other things were important to them in those early days. I do think there are times when demand gen is not the first focus. In fact, if you think about what ads work best on the web, it’s the ones with the flashing bananas and the belly fat and the, you know, all kinds of weird stuff that people are going to click on.

A company that’s going to build just around demand gen is going to end up just trying to get clicks and it’s going to leave their brand in the dust. I don’t think that is going to be a good strategy, even if you can make a few dollars.

Tomasz Tunguz: You got a lot of love on that answer. Fantastic.

You know, we love benchmarks. We read a lot about benchmarks. One of the questions was about the marketing budget to support different companies at different sizes. Is there a one size fits all? If you’re at a million in ARR, you should be spending 15%. If you’re at 10 million in ARR, you should be spending 30%. You’re hired again at this hypothetical Series A or Series B company. You go to the CEO and the board and say, “I need X million dollars in order to achieve these goals.” How do you think about that and what are the rules of thumb for the marketers and the audience?

Hollie Wegman: Yeah, I wish it was so easy that when you raise this much at this stage that this much marketing budget is thus granted with this much headcount. It would make my job a lot easier. Unfortunately, yeah, there isn’t a formula. Again, you’re going to have to go back to the goals. If the goal of the company in that year is to drive tons of self-service, then marketing isn’t going to be as well funded as say product because some of that work is going to happen in the product.

You’re going to need to look at the budget as a whole budget across the company. You’re going to need to think through, alright now, given that we have this one budget at this juncture and we have these goals, where should it get allocated across the company? And then, when you think about marketing in a kind of narrow way, I think about marketing budget as a function of what ROI we can achieve.

If we can definitely acquire a customer for a certain amount, and they’re going to have a certain lifetime value, meaning if it’s a subscription and they’re going to be around for awhile, then I can start to experiment with spend and make a case that for every dollar we spend, we’re going to get some return.

At that point, after just a few quarters of doing some testing, I can come up with a budget that’s repeatable, and then we can keep trying to put more budget into that. But it’s definitely not a perfect science.

Tomasz Tunguz: That makes sense. You touched on one thing there at the end of your answer which was around measuring ROI.

If you’re going to ask for a budget, perform a series of experiments, and then you’re going to evaluate the effectiveness of those experiments, do you use particular metrics in order to determine ROI? Is it different for developer focused businesses versus sort of more traditional companies?

Hollie Wegman: I don’t use different metrics. Most of the companies I’ve worked in have been SaaS companies so the kind of benchmark that I use is some kind of ratio between customer acquisition cost, which is how much I’m spending over how many customers, and then the ratio of the LTV to that cost.

The LTV, meaning the lifetime customer value, is going to tell me that I’m doing things efficiently. I suppose other metrics are important besides just cost when we’re setting aside a budget. And then one thing I think about when it comes to developers is the size of the community and the activity within that community.

A vibrant community that’s very active answering forums, that’s doing things that are stars and all kinds of exciting, flourishing signals is not necessarily in itself generating a dollar, but it’s certainly going to matter to us as time goes on.

Tomasz Tunguz: Yeah, that makes sense. There’s a question from the audience that’s related to this line of what we’re talking about, which is, “Do the metrics suddenly change when you achieve product market fit?” Do you see a discontinuity, like all of a sudden your CAC to LTV improves or the lead velocity rate or pick some other metric, do they suddenly improve or is it a gradual thing?

Hollie Wegman: Yeah, I think there’s a really strong tie between product market fit and inbound signal. If I’m not doing a lot to build the brand and I’m still getting inbound, then I’m like, wow, okay. We have some product market fit going here and you’re in happy days. I try to join companies that already have signaled product market fit because it makes my marketing job so much easier.

I think there’s definitely a relationship between product market fit and inbound. I don’t know that there’s some kind of magic moment where just having product market fit is going to cause my efficiency to be great. I suppose there’s definitely a relationship. I think things do catch fire and then acquisition will get more affordable.

But, I don’t have a precise pattern.

Tomasz Tunguz: But that point about inbound is really interesting. You’re totally right. If you’ve got a ton of inbound and no brand, clearly you’ve got some magic happening, right?

Let’s talk about narrative. A narrative is super important for business. Every sales pitch, every recruiting conversation, every fundraising pitch, anytime anybody’s talking about a company, might be your own company, the narrative is really critical.

It’s something that’s really hard to do when you see a lot of companies with a really great product, but they don’t have that narrative behind the business to sort of fuel it and build a brand that we were talking about just a second ago. How have you done it in the past? Any tips that you can share with the audience?

Hollie Wegman: Yeah, I love this question. I’ll just give you a quick story. I was at Salesforce, which has one of the best narratives ever. Marc Benioff is a beloved character. Everything is goals, right?

I left that company to go to a company called MuleSoft. MuleSoft was eventually acquired by Salesforce, but at the time it was a standalone company. I remember when I left Salesforce, I had some people looking at MuleSoft, looking at the network architecture on their homepage and the name. They were making donkey noises at me and saying “I can’t believe you’re doing this. Do you really think this is a great decision to go from Salesforce to MuleSoft?” I believed in the vision and I believed in the CEO, Greg Schott, and I joined the company. I also felt like, look as a marketer, it can’t get any worse, it can only get better.

I’m going to go, I’m going to try and do something. The thing I did, along with my team, was build narrative. We built a narrative about this underdog muley, that’s a hybrid of a donkey and a mule, that went out and…

Tomasz Tunguz: So you embraced the brand?

Hollie Wegman: We built the whole thing from the ground up, and we had a whole story behind Max, the mule. We had a mule mascot. We had mule squishies. The squishies went on world tours. As a developer brand, we tried to make MuleSoft sexy because it’s integrations. What developer wants to build integrations? Right? It’s all narrative. The fact that we even had one developer was because we could convince people this might actually be worthwhile.

Everything about MuleSoft was brand and narrative, and the company went on to be really successful. I’m really, really proud of everything that company’s achieved and so privileged to have been part of that team that built it.

Tomasz Tunguz: Yeah, that’s amazing. I mean, one of the things Marc Benioff is known for is getting everybody to say exactly the same thing whenever they speak publicly. One of our colleagues, Alex Bard, used to work there and he was telling me a bit about the press training that he went through. Anytime you were interviewed, it’s a little bit like a politician where when you’re asked a question, you answered a little bit, and then you immediately went back to the narrative and gave a customer example that reinforced the narrative. That’s a skill. It’s really important for us to learn as we’re building businesses because you have to tell people a hundred times before it really becomes cemented and that’s ultimately the brand of the company.

Hollie Wegman: A hundred percent. And the thing that you mentioned, which was really important to Salesforce, is the customer narrative.

That was something that Salesforce really taught me as a marketer. Anytime you’re going to have an event or talk about something great, get a customer to do that talking for you, and that’s going to be much more powerful. That was a really big insight for me from Salesforce.

Tomasz Tunguz: One of the things that’s really important with marketing to developers is these kinds of communities. We’ve got Hacker News and a bunch of others. Many developer-focused businesses also create docs, the documentation for a building on an API or building with a product. How do you think about the importance of community marketing and what’s worked for you in the past?

Hollie Wegman: Community marketing or just docs in particular?

Tomasz Tunguz: Well, maybe we can touch on each.

Hollie Wegman: I’ll just say really quick it’s an unsung hero of every company. Amazing docs and the people who build amazing docs inside companies should win awards. To get the clarity and precision, and then to actually build the infrastructure to house those docs, and to get the feedback on the docs from developers is really key.

Going back to the developer community, I think it is important to build a community and similar with how you speak to them through docs in a plain-spoken and helpful way is how you want to approach everything with the community. These are builders. I sort of think of them as people in a workshop that are making things and need to have the right information. They’re running into trouble. They want to get help from the community. They want to get help from the company. Making it really seamless for them to get the help they need to build whatever it is they’re building and creating a raft for them where they are a community is really important. I also think making it fun is important. The gold standard brand for me is Github and Octocat; making it fun and creating sort of a playful brand, even within the community, but not making it about marketing. No gated forms, no slick advertising campaigns.

The community is a special place, like a neighborhood, where you can just be yourself and you don’t necessarily have to dress up for the neighbors. You just kind of go, be yourself, have a beer, and it’s fun. The community is different from the marketing side of the house, which is more along the lines of “we need a campaign” or “we need this to look really cool.”

Tomasz Tunguz: Great answer. I think you’re right. Slack has a personality. The brand has a personality. GitHub definitely also has a personality. You can see it everywhere and that’s marketing, but in a sense what really matters a lot to developers is this notion of authenticity.

One of the things we talk about internally is when you meet a developer, they’ll ask to see your code repository before they ask where you work, because they want to get a sense of how credible you are before they invest in whatever it is that you’re selling.

Building that credibility through docs or through an authentic brand is super important, particularly when going after really technical buyers, because they don’t want to get on the phone with a salesperson. They don’t want to go through a classic sales process and so it’s about building that authenticity. And the trust.

Hollie Wegman: Yeah. I completely agree.

Tomasz Tunguz: We’ve got a couple of questions coming from the audience, but before we’ve got one more question which came from a recruiter that I thought was a really good one.

“I recruit for CMOs for B2B SaaS companies. Often when there’s a CMO search, the CEO wants a demand gen oriented CMO, the product leader wants a product marketing focused CMO, the team wants somebody who feels right culturally, and the investors want somebody who can talk at the board meeting. We’re looking at four or five different elephants. What’s your advice if you’re a Series A founder, you’re hiring your first CMO or VP Marketing or marketing leader. How do you figure out if you need a primarily product marketer, primarily demand generation, primarily brand builder, or community builder?”

Hollie Wegman: First of all, God bless this person. Your job is actually really hard. I have a lot of empathy for recruiters. I think it varies depending on the stage. If it was an early stage company, a Series A, that’s going to be a different hire. When it comes to specifically CMOs, I think the key thing is that a CMO has to be all things to everybody and an expert in all the things, be that unicorn, I think. A CMO is a person who comes in and helps build a company. They’re not a product marketer. They’re not necessarily a growth marketer. They’re not a brand marketer. They’re at first and foremost a company builder.

When you think about how to hire a really good CMO, you’re actually thinking about how to hire somebody that’s gonna do that. Not somebody that’s going to come in and fix a pillar level problem. And when I say pillar, I mean like a product marketing problem, a growth problem, or brand marketing problem. They may fix those problems, but they’re maybe going to do that through hiring. If you’re hiring a sales leader, you don’t pass up an awesome sales leader that has a killer track record of closing deals just because in their previous company they sold success software, and then with your company, they’re going to sell MarTech. You know that they’re a great leader and that’s going to translate. You don’t pass up an engineering leader because he or she didn’t code in the language that your company codes in. A CMO is a company builder first. And so you hire for that. You hire for strategy.

Tomasz Tunguz: Awesome. Okay, cool. We are going to open it up to the audience. This is the first time we’ve ever done this.

In the meantime, while I’m figuring this out, one of the questions was around sales and marketing. There’s always a tension between sales and marketing, right? There is always a tension because marketing generates a pipeline six to nine months from now, and sales is closing the pipeline that’s in this quarter. Have you found any tips on how to manage that?

Hollie Wegman: Yeah, I actually would say I almost found the solution. Marketing usually either has trouble with product or trouble with sales. It can never be perfectly harmonious between both. I think that for sales, you need to benchmark and goal marketing farther down the funnel. A lot of marketers will goal marketing on MQLs. This is very top of the funnel. Then it’s sales’ problem to take those names and basic information and turn them into closed deals, which is a long arduous process. I think by setting marketing’s goals lower in the funnel at the sales accepted lead or the qualified opportunity lead, you’re going to create a lot more alignment. I actually think it’s helpful to co-locate them. I love seeing sales and marketing sitting right next to each other. At one of the companies, my early stage company, I ran both sales and marketing to get them both up and it was small . What I would do is have daily standups with sales and marketing together. I just think having them and their goals close together is going to make them move together better.

Tomasz Tunguz: It makes sense, like product and engineering, right? Daily standups, collaboration. That makes a ton of sense. Awesome. We’re going to welcome Travis back. He’s going to help us with the live questions.

Travis Bryant: I thought that was a good visual metaphor as a former VP Sales that we could show Hollie and I getting along together. Okay, we’re going to try the hand raise here and we’re going to have Aron, a group product manager from Dropbox. So I will hand the mic over to Aron. Aron, are you there?

Aron Solberg: Yes. Hello. Good morning!

Hollie Wegman: Hi, Aron.

Aron Solberg: Hi. So first of all, thank you so much for this conversation. This is really awesome to hear your thoughts, Hollie. My question is around developer relation programs. I’m curious to hear from you, how effective have you seen developer relation programs be for a company who is selling a very technical product, like say an API for example, and what are some of the components that you’ve seen help developer relation programs be successful?

Hollie Wegman: That’s a good question. I can give you some perspective on what makes a developer program successful. I think that it’s not approached as a normal marketing function. I almost think, don’t market to developers. It is a community. It’s similar to what we talked about earlier. That neighborhood kind of idea, giving them access to information they need, making sure that you understand where they’re spending their time. Does this developer wake up every morning and the first thing they do is Stack Overflow? And the last thing they do is Hacker News?

If that’s true, then you need to figure out how to get yourself into those channels and different developers spend time in different channels. It could be It could be any number of different things where they’re spending their time, depending on whether they’re front end, back end, dev-ops oriented. Understanding where they spend their time, getting yourself inserted into those spots, and then creating opportunities to have conversations with them and nurturing them to have conversations with each other — making that facilitation there is the way forward.

Aron Solberg: Cool. Awesome. Thank you very much.

Hollie Wegman: Thank you, Aron.

Tomasz Tunguz: Thanks for the question.

Travis Bryant: Okay. Well we’ll have Ron, who was the earliest to raise his hand at the beginning of the session. Ron Jacobson from Rockerbox, we have time for one last question here. Ron, are you there?

Ron Jacobson: Hi, can you hear me?

Travis Bryant: Yeah.

Ron Jacobson: Awesome. Thanks so much for this. I raised my hand actually, before anticipating to ask a question, but I’ll happily ask the question anyway. So I’m on the spot here. Rockerbox is marketing software. As a marketer, I’m wondering, how have you thought about marketing to marketers in a way, like another level of developers? I know developers are very skeptical, but I’m interested in, at least I know it’s a very broad question, but how would you think about best ways to market to marketers?

Tomasz Tunguz: Wait, can I just jump in? I remember one day I asked Hollie to show me her inbox and the number of emails marketing to her, and literally it was 10 in the morning and there were three pages on Gmail of marketing material coming to her. It was staggering. I’ve never seen anything like it.

Hollie Wegman: Yeah. I actually let Tomasz look at my mail. Don’t tell anyone, but it was pretty boring. It was like outbound, outbound, outbound. If you see the MarTech LUMAscape, all the different marketing tools, 8,000 tools — it looks like continence of tools. It’s really hard to stand out. I would say you have a very difficult job ahead of you with how you’re going to get the attention of marketers.

I think what gets my attention is when somebody really understands a pain point that I’m having. That could be that I have adopted one tool, let’s say I have adopted a chat bot or something. I now need to adopt the adjacent tool, the next kind of natural thing. What you can do is research what tools people are adopting. If you see that one adoption pattern, and then you go after that and say, “Look, I noticed you just got said chatbot and you’re going to now need my thing that I built.” That level of personalization and timing is really key. If you can figure out with Rockerbox what it is that’s the trigger, that compelling moment that makes people need your product, then you can create really personalized outbound around that. That’ll be one really interesting strategy. And one way that I’ve ended up buying a lot of products.

Ron Jacobson: Okay, thank you. That works for us actually.

Tomasz Tunguz: Thanks, Ron. Awesome. That’s all we have time for today. Hollie, I want to give you a sincere, thank you. This was exceptional. I learned a ton. I’m sure everybody else did too. We’re really grateful to everybody who joined for SaaS Office Hours and we will be sending out a survey. If you have feedback or ideas on how to improve this, I know we had lots of questions and we were only able to get to a subset. Thank you all so much for attending.

Hollie Wegman: I just wanted to say thanks to everyone. These were amazing questions and I’m really excited to be here.

Travis Bryant: Yeah. Thanks to both Hollie and Tomasz. Have a good week, and see you at the next SaaS Office Hours.

*Transcription brought to you by Descript which lets you “Record. Transcribe. Edit. Mix. As easy as typing.”

Redpoint Ventures

Since 1999, Redpoint Ventures has partnered with visionary…

Redpoint Ventures

Written by

Redpoint partners with visionary founders to create new markets or redefine existing ones at the seed, early and growth stages.

Redpoint Ventures

Since 1999, Redpoint Ventures has partnered with visionary founders to create new markets and redefine existing ones.

Redpoint Ventures

Written by

Redpoint partners with visionary founders to create new markets or redefine existing ones at the seed, early and growth stages.

Redpoint Ventures

Since 1999, Redpoint Ventures has partnered with visionary founders to create new markets and redefine existing ones.

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