Crossing the Enterprise Chasm

WorkOS CEO, Michael Grinich, and Augment Code Acting CMO, Francois Dufour, discuss the enterprise shift during Francois’ time at Twilio, B2B marketing that is actually helpful for developers, and early signals that indicate the right time to build for the enterprise.

What is Crossing the Enterprise Chasm?

Crossing the Enterprise Chasm is a podcast on how high-growth startups prepare to build with enterprises and Fortune 500 companies. Each week WorkOS founder Michael Grinich is joined by founders, early-stage team members, and product leaders who lead the charge to go upmarket. In every episode, you'll find tactics, strategies, and actions on how to successfully sell to and serve your crucial early enterprise customers.

Michael Grinich (00:02):
Welcome to Crossing the Enterprise Chasm, a podcast about software startups and their journey moving up market 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 Francois Dufour, CMO in residence at Decibel Partners. Decibel is a VC firm that invests in early stage enterprise software companies focused on developer platforms, cybersecurity, machine learning, and AI infrastructure apps. He's also an advisor and coach to CMOs and VPs of marketing across the valley. Prior to this, Francois was actually head of marketing growth at a company you probably know called Twilio from 2015 through 2017 driving the growth in developer sign-ups. They 3X-ed those during that time, grew revenue by 2.4X to over 400 million through the IPO. Francois has also been a part-time CMO at companies you probably know, like Algolia, Apollo GraphQL, and a bunch of other dev tool and SaaS players. Super excited to dig into this and more about Francois' knowledge about marketing to developers. Francois, welcome to the podcast.

Francois Dufour (01:27):
Thank you, Michael. Great to be here. I look forward to the discussion.

Michael Grinich (01:30):
All right. So we've talked a bit about Twilio in previous episodes, but I want to talk about your time there when you were VP of global marketing. The company went through a pretty tremendous growth sprint during those two and a half years. Bring us back. What did the company look like when you started working at Twilio?

Francois Dufour (01:45):
Yeah, so when I joined, it was pre-IPO, a year before the IPO, and actually literally two weeks before starting crafting the S1. About 450 employees, $160 million of revenue, handful of quota-carrying reps and a really, really great developer brand and a great playbook to go and do developer relations, developer evangelism, et cetera. And then literally two weeks after our start, I get pulled into S1 prep meetings and this is where the process starts. So I had to learn to talk about Twilio the right way quickly. I was brought in because, and Sara Varni, who you also had on your podcast, tells a similar story, on top of this really strong self-serve, developer-focused playbook, we wanted to build an enterprise marketing and enterprise sales motion as well and make them work in harmony together.

Michael Grinich (02:32):
So it sounds like the developer marketing stuff, the brand of Twilio, was just kind of firing at that point. People know Twilio from their DevRel work and community work. What wasn't working as well when you look at as Twilio is looking to move into enterprise growth, enterprise customers and enterprise marketing?
Francois Dufour (02:47):
Well, one thing that people may not realize, we IPO-ed and at the time we were not really able to have a sales motion that was top-down. So out of the only, I guess, 10 quota-carrying hunters that we had, there's really only one or two that were able to get new deals because they needed the foundational usage first, the understanding of what their category was first, and a lot of times they were going to companies and they either didn't have the right sales enablement, the right awareness of what CPaaS or a cloud communications platform was, and we had not yet built the right way to track all the usage and give them just the right information about who was using and for what or the sales enablement around use cases. That came later. So that was one of the things that we needed to build with better bridges also between the developer marketing side of marketing and the more business product-centric and IT-centric side of marketing, as well, with sales as well.

Michael Grinich (03:43):
As you started layering these things in, moving from that developer growth, that bottom-up developer growth into something with more of an enterprise spin to it or focused more on those enterprise customers, what were the first things you did? Bringing us back to that moment, the very first things you started trying. Eventually Twilio built this really successful larger enterprise marketing strategy across the whole company, but maybe talk about the first couple things that you were experimenting with and trying back then.

Francois Dufour (04:08):
So one of the key things was really being use case-centric. A lot of developers would adopt Twilio because they were looking at one of the APIs, think of that as Lego bricks. I could do through voice, I could do text messaging, et cetera. They really understood what to do. For an enterprise buyer, we needed to showcase a lot of stuff through the lens of a use case they were interested in. Again, going back to our mission with developers was to put Twilio in the toolkit of every developer even before they had a use case or a need. So the day they would have that, they would turn to us because they liked the brand, trusted the brand, loved the developer experience.

An enterprise buyer comes to you not just because they're curious. They come to you because they have a need and if they have the need, that means they're really trying to build a use case, either an IVR [Interactive Voice Response], a contact center, an alert system, a better engagement with the customers, better authentication. And so that's one of the first things we did in creating content for that, in creating the right dimension activities for that, being at the right events, doing the right outreach, and also even on the developer side, doing more use case-centric type of activation onboarding to also pick up what use case are we trying to build, and as a result we were able to identify another champion in the company to go and talk about that. That's one.

The second thing I did was I brought together the growth marketing team and demand gen under one leader and to try to instrument more of what was going on. And another thing we did was also get really close to the technical BDR function, at the time called BDRs, really work well in unison with them so that they would be equipped to understand what the developer was doing initially, and from there, grow the understanding and the targeting into these accounts.

Michael Grinich (05:51):
I want to talk about both of those things, unpack both of those last two. This is really interesting. So consolidation of the growth marketing role and demand gen. I've talked to a lot of different companies where demand gen is sometimes owned by the marketing team. Occasionally I've seen it owned by a sales team or a CRO. What did it look like at Twilio? Why consolidate them and what did you converge to? What was the thing you were working towards by doing that?

Francois Dufour (06:13):
When I arrived, there was a funky situation where for instance, all the paid spend SCM was managed by the head of brand who was a fantastic head of brand, also developer himself. So for some reason, it was being managed there and there was a demand gen team that was doing a lot of field events and experimenting with these use case-based marketing, but there was no, yet, harmony in terms of tracking all this. So what was important is to every time you do PLG, that leads to PLS or product-led sales into potentially ABM within your target audiences, collecting all the signals into one.

And so that's why bringing in a marketing ops leader so a head of growth marketing and demand gen, who underneath, had marketing ops and data analysis and working closely with data engineers was really key to get a 360 view of ideally by account, but someone, a developer coming in, who very often wouldn't even use our coupons or vouchers was using a personal email address. But at some point, we had some signals that it was a company or which company it was, and the understanding of the use case, letting a technical BDR or sales team know, hey, that's what they're trying to do and creating the right nurture stream to do that was really critical.

Michael Grinich (07:21):
I was going to say, what is a technical BDR?

Francois Dufour (07:23):
Okay.

Michael Grinich (07:24):
Yeah, that term, I haven't heard.

Francois Dufour (07:26):
Yeah. By the way, Twilio, we call them at the time technical BDRs. Vercel calls that product advocates, but they basically do the same function, which is for a developer who comes in, signs up, usually doesn't want to talk to sales, especially the sales is going to be about qualifying them, understanding what's your budget, what's your timeline, who are going to be the key people? They just want to start using the product fast. And if they talk to a human, it means either they're stuck, they need help or they are asking for discounts or pricing information, et cetera. And so a technical BDR is someone who looks at the signups coming in and is going to be either reaching out to the active or not active signups, especially active if possible with the right information to help them on their journey to building something.

So they're usually early grads. They're interested in learning the tech. They're not developers necessarily, but we give them enough tools to understand how to help developers signing up and trying to build their first apps or scaling their first apps and they do discovery by just figuring out what are you trying to build I can help with, and as a result, they're giving more information than they're extracting and it's really someone instead of doing ongoing outreach, “I want to talk to you to qualify you and sell you something”, was offering help. Vercel also has done that very successfully by scaling these product advocates who I think specialize in helping both media and e-commerce companies build their better apps on top of Vercel.

Michael Grinich (08:56):
The helping phrase, I've heard a lot. I think in the first or second season of this podcast, we had Paul Williamson as a guest who led Plaid's revenue team from I think like 3 million to over 300 million, and their mantra was not “always be closing” like the Glengarry Glen Ross. It's “always be helping”, always be helping developers, always be guiding them, assisting them, and then the deals would sort of come from that.

Francois Dufour (09:19):
It's super necessary with developers and any technical audience. I would claim it even extends into all of marketing B2B marketing. It's all about education. People will follow the brands that educate them and the mission for instance, for developer relations at Twilio was to inspire and equip developers. And that's really, really important to unpack that I think and extend that into all B2B marketing you do because your content is about that. Inspiring means showing them what's possible, what others have done, what you can dream of doing, what you didn't realize you could do with this platform, especially if you've got a horizontal layer platform. People want to see their inspiration of what others do. And ‘equip’ is just making sure you help them do that, the right documentation, the right connection to the right people, et cetera. And this is what Vercel product advocates for instance do. By helping “here, oh, this person has a big enough app or big enough audience that maybe then I can act as the gatekeeper to the solutions architect”.

So it's our solutions engineer whose time is very precious, so this is the product advocates, the technical BDR just gives as much information as they can and if they see there's a big opportunity, then they pass to someone more knowledgeable, more senior to go and consume the critical and rare time of your either AEs or sales engineers. But it's through giving value instead of extracting information that typically developers don't want to give or maybe sometimes don't even have. I don't know what volume I'm going to get on this, I'm prototyping, so help me do that and then if it's successful, we may scale, but for the meantime, just help me build my app please and make sure I'm not going to get clobbered by your cost. And this is what Twilio was designed for, just making sure it's transparent, predictable and developer-friendly.

Michael Grinich (10:58):
When it comes to marketing, especially B2B, enterprise-focused marketing, I feel like the sentiment that I hear from a lot of developers and what they see is that it's not helpful. It's usually content that's gated behind putting your email address, having to get on a call and those calls you might have feel very extractive. You can tell you're being qualified versus them figuring out what you're building. I would love for you to walk through specifically for this enterprise angle, how you think about marketing being truly helpful, genuinely helpful for those folks versus I think for smaller companies getting started, developers, DevRel, just answering support tickets. That's one thing. Maybe it's more around these use cases. I don't know. Unpack that for me.

Francois Dufour (11:38):
Yeah, well, there's the trend in general just really gate something where it's going to be really great value, long, but as much as possible just try and ungate and help because that's how you build a brand and ideally you optimize everything to get hand-raisers. People want to talk to your experts or sales instead of just getting contacts and leads, which frankly don't convert as well anyway, so the thing in the way you help is typically start by understanding what are the personas beyond the one that assuming you start with PLG self-serve, what other personas get added to the mix in the discussions, who are they, what are their questions? So we see the questions they ask to your technical BDRs or support, et cetera. So make sure you have content first that answers these questions, whether that's online, whether it's delivered through webcast, whether you give that to the rep so they become more consultative. Train the reps like crazy on these personas, the questions they have, the objections they have and the information they need to have.

And so at every point you not only build reputation, but also you have a really good engagement that helps basically the buyer and the set of buyers do their job, which is they have a really difficult job and you should always remember that. If they're making a buying decision, they're putting a piece of their career at stake and it's a complex decision. It's one thing when you are a developer, you want a prototype and in 30 minutes, maybe two days, you get an idea of the product and how it works. It's another if you're going to be buying a product or a new service and you need to enlist your colleagues to go and vet it and to then go use it. So you need to build a lot of confidence over time and your job as product marketer or marketer or DevRel is to help them understand what you're good at, what you're not good for, and just help them make the case internally, which is a very difficult decision for them.

So keep that in mind all the time. If you have a really developer-centric mindset as a marketing team, first of all, it's a lot more interesting and empowering to serve people, but two, you really will ask questions about what do you need to know, what do you need to decide? How can I help you? Gating it is serving yourself, whereas giving good education and good help is helping others and this is how you build great brands. Companies are there to provide value to their customers and when you're in marketing, the value comes from the right information at the right time.

Michael Grinich (13:53):
I've been on the receiving end of people when they do sales like that and it's amazing. It doesn't feel like sales. It doesn't feel like you're being sold to.

Francois Dufour (14:00):
Yeah. One of the best things that sometimes what salespeople can do for you is within five minutes after listening to you like, "Hey, I'm sorry, we're not for you. We're really good at this, but what you need is this." And orient you to maybe another vendor or another category. That saves you time as a buyer and saves reputation for the team and their time as well.

Michael Grinich (14:15):
And it builds trust too. You'll come back when you say, "Hey, I actually think I do need this and I trust that this person is actually on my side. They're looking out for me. Yeah." I want to jump back to Twilio. So you joined in 2015. One year later, 2016, Twilio launches Twilio Enterprise, the enterprise plan. What signaled that it was the right time to do this, to go after the enterprise segment and even build sort of a product for enterprise? This podcast is called Crossing the Enterprise Chasm. What was happening then when Twilio began crossing it?

Francois Dufour (14:44):
Yeah, so after the IPO and the category gets better understood by more people and there's more energy from buyers to just go figure that out. Basically that is certainly what happened. We're seeing deals discussed and developers are still in the discussion, but there's more people we see happening in this discussion. There's IT folks, product folks, sometimes compliance. Folks who understand that if they really build mission-critical engagement communication system based on Twilio, they'll need the ability to be secure, compliant, have access to data, maybe having sub-accounts there. And so as that comes up again and again, of course we needed to package and build these features, which at WorkOS, you're very familiar with, and so that's one of the signals of multiple personas involved in these deals and the need for more advanced ways for or at least proof points that it's not just going to be a developer is a fan woman or fanboy of Twilio trying to play and do prototyping.

No, it can really scale. So we needed to do that. Internally also, the need for us was to know that someone, a company is serious about using us and because they could start and spend $1 a month for years, we wanted to also see the commitment from them through usually the initial purchase of that subscription that they were serious and therefore we could really invest the time of our sales engineers and solutions consultants to go and help them prototype something that could sometimes take months or years if it was very complicated, for instance. We also heard they wanted extra support, so it was all packaged in this enterprise deal that was also helping get more urgency from an account initially. They start paying for the subscription or they're about to do that, then it helps them just scale the app faster and scale the app a little faster since there's already a spend there.

Michael Grinich (16:32):
So it sounds like a lot of changes across the board for enterprise. You had pricing changes in terms of looking for that committed type of spend. You had packaging changes for support. You had sales changes in terms of navigating multiple stakeholders, more than just developers. Break down what had to change on the marketing front a little bit more and maybe thinking about this through the lens of people listening to this who are thinking about how to evolve their marketing to go after the enterprise audience. What's inherently different about launching features for enterprise?

Francois Dufour (17:02):
You talk to more personas, you talk to more audiences, and that's actually where you need to be very clear for each channel who you talk to, first of all. And it's really interesting if you look at the evolution of just the homepage of a Twilio or a Stripe and you see the evolution of initially there was a lot of code on the homepage to there's a little less code to at some point they even go like there's no code at all. They all reverted back to code, thank God, and it's showcasing stories of IT people, product people instead of developers. But the thing to think about is finding the right message and the right tone. Another is in the case of a horizontal platform that can do so much like Twilio, a big shift for us in marketing is the shift to talking a lot more about use cases and having basically mini teams in product marketing, content marketing and even demand gen focused on the use cases that also map to some of the organization of the sales team.

We had overlays that were specializing in contact center for instance or security, and so that was very different from selling a horizontal platform and its different API bricks. And then also the, oh yeah, analyst relations also becomes a little more important. Initially we don't care at all about analyst relations at Twilio because a developer can start in 30 minutes and get a very good idea of what Twilio is and how it works. After a while when you get to engage and you go after bigger budgets and a set of people who need to CYA, analyst relations also really matters.

Michael Grinich (18:27):
Meaning like Gartner, Forrester, that type of analyst. Yeah.

Francois Dufour (18:30):
Yeah, yeah, exactly. So that all changes and also beyond use cases, sales development becomes super key as well. You talked with Sara about the fact that the quota-carrying reps at some point just tripled in the span of four months, so that really meant investing big time in their enablement so they could have consultative and really good discussions with the buyers, with the set of buyers, could talk about not just the products but also the different use cases you can build and also the different companies and who had built these use cases and how they came to do that, and talk to different personas and not just the head of product or head of IT, but potentially someone in security and compliance, et cetera.

Michael Grinich (19:08):
I want to jump a little bit ahead. There's so much stuff we can cover here. We don't have too much time. Jumping forward to Decibel. So with Decibel, you focus on helping these companies that are technical founders driving growth certainly earlier, much earlier than Twilio, and you mentioned content being really important and this is something you've written about, about how key it is getting started for content to be the anchor for a lot of marketing for technical developer products. What's the best way that you've seen companies do this to produce that technical content? Maybe give some examples.

Francois Dufour (19:37):
Yeah, there's multiple playbooks, so let's assume that Decibel and also the work that I do on the side, it's technical founders building technical products sold to a technical audience. So therefore what they need is same thing, information about what it is, how does it work, how do I use it, et cetera. And when there's the equivalent of a DevRel team, one of the playbooks that usually, and you've got developers who need to build with your product, one of the playbooks that's always there, usually, is a set of tutorials or blog posts. At Twilio, we call them stories with code that explains how do you do XYZ use case or job to be done in XYZ, complete this with tech stack or programming language, et cetera. Basically it's capturing a developer or builder that is looking for the information on Google or elsewhere, how do I build this? How do I build this app in Python for instance?

And so that playbook of writing these very good tutorials is key. You got the model where you're going to do this all in-house. Algolia did it initially themselves with their own engineers who crafted all the content plus thought leadership content. At Twilio, we had DevRel leaders do that themselves. DigitalOcean is famous for having scaled that like crazy with an external community and the set one or two editors who were reviewing this. And remember it's not just a blog post you write. It's also an app initially. It's making sure the code works, make sure you have a good story where you present this, you point to the right GitHub repos and there's the hybrid model where you've got a mix of internal people and community contributors doing that.

It's basically when the developer or technical lead is looking for information about how to do XYZ in their tech stack, you want to show up in the source results and that was the playbook that is essential to nail for most of these players. Then this thought leadership around understanding deeply the pain points, the challenges. Using that stack, this is happening, let me explain why this is happening and the typical symptoms of your pain.

Michael Grinich (21:31):
The step after that. So say companies get this going. I mean creating content is hard enough, it's a big jump of course, but for folks that have say a PLG motion that's going, they have strong inbound, they're starting to think about commercialization a little bit more. They're in that transition phase. What do you recommend they focus on first? There's so many different things to do. We talked about where Twilio converged eventually, but maybe in that first few months after they're moving beyond just pure PLG, where do you think they should focus?

Francois Dufour (21:59):
After that, it depends what type of PMF you already have. If you're convinced you have product market fit, you can invest more in amplifying your content in different channels, in nurturing, in selling, and by selling, I mean helping and selling to the people who are coming through this channel. Or if you don't believe you got product market fit, then what I would recommend is having... And maybe that's a product advocate, maybe it's a fairly technical salesperson, maybe it's a product marketer who just goes and really talks to the people interacting with your content and understanding, okay, what do you do next? What do you need next? What you need to provide in terms of the right product, the right pricing, the right collateral enablement, et cetera. So that really could take different roads. Is there one you want to talk about more than the next, given the questions you're getting?

Michael Grinich (22:47):
Oh gosh, there's so many there. Yeah. I think it's mostly just from hearing from folks as they're like, "I have PLG. Now what? Now what do I do?"

Francois Dufour (22:54):
Oh. So yeah, if you're PLG, the next one is how do you monetize that better? And this is going back to understanding your ICPs. PLG, true PLG self-serve is going to be great when you've got a very, very large TAM [total addressable market] in terms of logos or users. Very often, especially these days, you need to get quickly to getting larger deals. So you either need to do product-led sales or quickly apply account-based marketing based on that first user base. And so what's really, really critical is getting the right data, the right telemetry and understanding which accounts are coming. So there's a big exercise of tracking data and account consolidation to understand “do I have accounts here that correspond to the ICP I need and if so, how do I activate them?” Which is understanding how do I get to the champion, how do I identify the blockers, how do I partner with the champions to find who are going to be the decision makers, economic buyers, what questions do these guys have and how do I have content, programs, events to just engage them at scale?

Michael Grinich (23:56):
Last question for you before we wrap up. Thinking back on your experience and also for this next generation of founders of entrepreneurs, what's one single best piece of advice you would give them that you would share with them as they're going up market, developing their business, thinking about how to make this transition?

Francois Dufour (24:14):
The transition from what moment do you have in mind?

Michael Grinich (24:18):
From PLG going up into enterprise, starting to think about adding their first enterprise customers, their first enterprise version.

Francois Dufour (24:24):
Yeah, first go… Don't try to get the top of the very, very, very large enterprises first. Their requirements are really different. The deals would be very long. The number of people you need to talk to will be many. And so probably experiment first with the top-up in market or the low-end on enterprise before going too deep. And to really spend the time understanding beyond the first one or two personas that you engage, what are going to be the other ones, what do they care about? Which questions do they have? So it's a really fundamental product marketing exercise of understanding audience pains and proceeding with a lot of discussions and finding it's almost as you're starting again from scratch and finding the lighthouse customers and understanding what they care about and understanding how you scale that first. Knowing that building one go-to-market motion is really difficult. Tackling another one on top of that takes time and will need different cultures, different metrics, different people from the first. So you need to be very aware of that.

Michael Grinich (25:25):
I like that. Pick one, do it well and figure out the future from there. Francois, we got to run. Thanks so much for spending some time with us. This has been great.

Francois Dufour (25:32):
Thanks, Michael. It's been great being here with you. Thanks you so much.

Michael Grinich (25:35):
Take care.

Francois Dufour (25:36):
You too.

Michael Grinich (25:41):
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.