How aligned is your organization when it comes to driving growth—are internal silos or misaligned goals or expectations holding you back from reaching your full potential?
Today, we’re joined by Robert Chatwani, President and General Manager of Growth at Docusign.
Before joining Docusign in 2023, Robert was the Chief Marketing Officer at Atlassian, where he helped scale the business to nearly $3 billion in revenue. He also held leadership roles at eBay, where his teams supported $35 billion in annual trading volume.
About Robert Chatwani
Robert Chatwani leads Docusign’s Marketing & Growth organization to scale its digital strategy across marketing, product, technology and sales and is responsible for Docusign’s product-led growth and execution. He also leads all CMO functions, including product marketing, field marketing, communications and public relations, content, creative and brand strategy.
Before joining Docusign in 2023, Robert served as Chief Marketing Officer at Atlassian, where he oversaw teams across marketing, brand, communications and data science, and worked with the product organization to help scale Atlassian’s business to nearly $3B in revenue. Prior to Atlassian, Robert served as Chief Revenue & Marketing Officer for social e-commerce platform Spring. He also spent more than a decade at eBay, ending his tenure as CMO of North America where his teams supported $35 billion in annual trading volume.
Resources
Docusign website: https://www.docusign.com
The B2B Agility podcast website: https://www.b2bagility.com
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Transcript
Greg Kihlstrom:
How aligned is your organization when it comes to driving growth? Are internal silos or misaligned goals or expectations holding you back from reaching your full potential? Today, we’re joined by Robert Chatwani, President and General Manager of Growth at Docusign. Before joining Docusign in 2023, Robert was the Chief Marketing Officer at Atlassian, where he helped scale the business to nearly $3 billion in revenue. He also held leadership roles at eBay, where his team supported $35 billion in annual trading volume. Welcome to the show, Robert. Thank you, Greg. Great to be here. Yeah, looking forward to talking about this with you. Before we dive in, though, why don’t you start by giving us a little more about your background and your role at Docusign? Yeah, you bet.
Robert Chatwani: I have a mixed background in consulting. I started my own company, it’s what moved me out to Silicon Valley, but spent most of my time in consumer e-commerce at eBay and other e-commerce companies where I really fell in love with marketplace business models and the role of using technology to help entrepreneurs be successful. But then soon ported that expertise over to an enterprise software company, Atlassian, where we took a lot of the principles that helped build some of the world’s most powerful consumer platforms and applied them to an enterprise software business. And now at Docusign, really figuring out and finding ways in which to take some of the best of growth principles from B2B and consumer and bring them together to help grow the Docusign business.
Greg Kihlstrom: Great, great, wonderful. Well, yeah, let’s dive in here and I want to start by talking about expanding a brand. And, you know, Docusign is certainly a brand known. I know it well. I feel like I use it almost every day. Yeah, a brand known for leadership in e-signatures, for instance. What opportunities and challenges arise when expanding a brand and marketing beyond that singular product focus?
Robert Chatwani: Docusign is a company that’s 20 years established and pioneered what we call the e-signature category and has been wildly successful in sort of doing that, both in terms of market share, the number of signers and senders who’ve engaged with our platform, over a billion people globally have signed with Docusign. But as you know, technology companies really need to think about how their roadmap and technology vision can continue to serve their mission. And so that’s exactly what we’ve embarked on here at Docusign is defining the next act for the company. And so our mission is really redefining how the world comes together and agrees, you know, making agreements smarter, easier, and more trusted. And so while signature is certainly part of that, the change that we’ve embarked on is really thinking about uh, agreement management and specifically intelligent agreement management as a pioneering new SaaS category for DocuSign. Um, now the unique challenge we have there is, um, we are known for signature and it’s certainly something that is the core of our business. Uh, but with a company that actually has sign in its name, when you embark on something that stands for much broader than just signature, in this case, intelligent agreement management, or what we call IAM, We really have to think about a combination of taking the existing customers we have, both those who sign with DocuSign and send with DocuSign, and introducing them to sort of this new frontier of where we’re headed. of bringing them along and also helping them succeed in what we think is a really exciting new way to look at agreements, which is the way people and companies create agreements, commit to and sign agreements, and then manage agreements. And that’s certainly a lot more than signature. And so we have a number of challenges around repositioning the brand. uh, telling a new company narrative, reframing the product strategy, thinking about international expansion that markets at different levels of maturity. And hopefully we’ll unpack some of this, but this is a challenge we’ve embarked on.
Greg Kihlstrom: Yeah. And so, I mean, in, in doing that, it sounds like the one, one good way of doing that is the framing it as agreements. You kind of broaden, it doesn’t, it doesn’t get rid of your core offering or it doesn’t, uh, you know, but, or it doesn’t diminish the core offering, but it kind of expands it, you know, how, how should, you know, there’s marketers listening out there that might be in similar enough, uh, situations where, uh, you know, they need to expand. How should they be thinking about. expanding without diluting what, you know, what you just said, what people are really, what people know them as. Yeah.
Robert Chatwani: Look at the brand equity is extraordinarily difficult for most companies to create, preserve and then grow. And so this is really the heart of the challenge that we have here. Um, and I think there’s, you know, a few lessons. One is, um, we decided that, um, it was time to really shape and create a new category of software. And so what does that actually mean? Um, one is it allows organizations maybe who are, you know, existing companies who want to reframe what their market opportunity might be to really, uh, think about a new problem or a new challenge to solve. And so for us, it was really trying to identify, looking at our existing customers, what is it that they struggle with? What is the opportunity, the challenges that they have to face and how can we better articulate and name that, what that is? And so for us, we decided and discovered that our companies do business with DocuSign and have agreements, tens of thousands, often hundreds of thousands of agreements. They have a lot of information trapped in those agreements. A lot of value and a lot of information that’s trapped, and there’s no organization or company that’s really serving that need. And so, we started by really naming the villain. What is it in this new frontier that we want to identify that our customers are challenged with the most? And so, we call that the agreement trap. And so, you know, one step around thinking about reframing the opportunity for companies and organizations is looking at the next frontier of problems, often creating language that doesn’t exist in the world to name that. Secondly, we sized it, which is how big is that problem? We did some research work that ended up sizing that global economic opportunity of value that’s trapped in agreements at nearly $2 trillion, right? So you could start measuring that as a set of global GDP and break that down by industry vertical and function like HR, procurement, or sales. and then effectively creating stories around why it’s so challenging and why it’s so complex to solve that problem. And earlier this year in April, we decided to have what we call a lightning strike moment, which is the convergence of our research, our new product strategy, those stories of both challenges and opportunities, sizing of that problem and bring it all to life at an event. Our annual customer event is called DocuSign Momentum. And it was a convergence of all of those things I just described. unveil and reveal the new journey that we’re on to create this new SaaS category. And so this category creation process has been tried and tested at a lot of remarkable companies, companies like Qualtrics, like CloudFlare, and elsewhere. And we were fortunate enough to work with a fantastic team called Play Bigger. And they were our partners in this journey, but really, I think it starts with conviction and ambition, the senior leadership team, any organization or company, or even the founder, to say, we want to reinvent and challenge ourselves to dream one size bigger about how we can fulfill our mission and rethink what that future could look like.
Greg Kihlstrom: Yeah, and I think, you know, what makes sense to me about it is that it feels organic. It doesn’t feel like all of a sudden you had another bright idea and it’s all the way over here and wouldn’t it be nice if we also did XYZ or whatever. It feels like an organic expansion. Was that part of the thought process as well?
Robert Chatwani: You know, it was, and I think that is important to have and hold two things equally true, which is to think about reinventing your company or your business unit, even, in a way that is authentic and credible so that you have the capabilities to deliver on that new promise. And simultaneously, be audacious enough to think about the opportunities as it met the company type move. meaning it’s all or nothing. And it is really hard to reconcile both of those because one might lend you to incremental thinking and the other might lend you towards an existential crisis of a company not existing. But if you could manage the tension between both of those things simultaneously and say, how do we do this credibly such that our customers will not only trust us, but bet on us, and it’s not so far afield that we don’t have that authenticity to the core brand values while still thinking and dreaming big enough to bet the company. And I think that’s both the art and the science of how to do this.
Greg Kihlstrom: Yeah, yeah, love it. So another thing you touched on was geographic expansion. And, you know, certainly in your experience, not only at Docusign, but in some of your past experience, certainly led teams doing campaigns and marketing across the globe. Scaling digital strategies across geographies, industries brings both internal as well as external challenges. In your experience, in your career, what are some of the key hurdles that you’ve seen in these kinds of challenges and how do you think about approaching them?
Robert Chatwani: Well, one is just to acknowledge that it’s hard, difficult, right? There isn’t a go-to-market leader that I’ve met who doesn’t tell me that they’re in the and business versus the or business. So what I mean by that is, hey, we’re pursuing large enterprises and mid-size and small companies. Or we have a growth strategy that requires us to accelerate growth in our most mature markets, let’s say North America, and invest in emerging markets to think about planting seeds for future growth. Or we have a core platform strategy that’s designed to scale and help us reach as many customers as possible. And we’re targeting industries and verticals. And folks listening to this, and the endless can go on. And by the way, that’s true in enterprise businesses and it’s true in consumer. Back at eBay, it was like, we’re about fashion, motors, electronics, and sporting goods. every country in the world and building a global marketplace. And so one, just acknowledge that it is fundamentally hard. I believe that there’s nothing more powerful than prioritization when it comes to thinking about how to balance delivering the present and creating the future. And my brain tends to simplify things into categories. And by that what I mean is inevitably you want to build a business that’s going to deliver on the commitment that you make to your investors or to your employees or to your stakeholders or to yourself if you’re a private company or founder-led company. in the short term, right? You have those milestones that are effectively non-negotiable, whether it’s around growth or efficiency. However, it’s also your responsibility to ensure sustainable long-term growth and create that future. And so I like to think about these two categories. And for every company, what’s present and what’s future might vary. But to think about resource allocation, people and dollars across those two buckets, and then within them, get down to a point where you are force ranking your prioritization of what’s most important, and then aligning those prioritization decisions across functions and teams in the company. And it won’t be considered a success, meaning this exercise shouldn’t be considered a success until it’s painful, where you are making decisions of what falls below the line or what gets under-resourced relative to the things that you’re gonna bet on. And I have yet to find a company or a team that is successful without going through the painful exercise of making tough choices. Ultimately, it’s what separates the companies with the most successful strategy and execution from those that do a lot, but can’t seem to win.
Greg Kihlstrom: Yeah. Yeah. Totally agree. I mean, it’s, you know, if everything’s a priority, nothing’s a priority. Right. So it’s definitely important to be able to do that. But, but to your point, it’s tough to be able to do that because there always is that. And we also want to do this or what about, what about this? Or, you know, there’s, there’s a lot of those kinds of, um, kinds of things. How do you. I think a lot of this also comes from, from leaders showing by example as well of, of how to do this and how to make, make good decisions. How do you think of it as a leader, you know, to kind of set an example of doing the right things, you know, finding the right priorities and, you know, what are, what are your thoughts there?
Robert Chatwani: Yeah, I think strategy and prioritization is a team sport. And so we’re going through this at Docusign, my team’s at Atlassian and at eBay, typically do it in the annual planning process. I think some of the world’s most agile companies do it as an ongoing process and that’s what I encourage. But I say it’s a team sport because the decisions that emerge from prioritization strategy exercises Um, in most companies, they affect a lot of people. And so some of the principles that we use here is, uh, progress over perfection, meaning it’s, you know, continuously iterating on the thinking, um, uh, in really being willing to challenge that and drop assumptions at certain points in time when you get new data. Second is to manage the process radically open, so with extreme openness. So even teams who are not directly involved in some decisions have visibility into the journey by which those decisions and trade-offs get made. And I think that one, fosters a lot of trust once those final decisions are made and maybe not everything on people’s wishlist Our expectations made it to the biggest bets that a team or a company is going to make. And I think it is clarity around what success looks like, whether that’s using an OKR methodology or measurement so that folks know, okay, if we’ve decided to pursue something, How do, what’s the yardstick by which we can measure that? So this is the approach we take at DocuSign. Flexible, agile, open, and transparent, and then measured. And then, you know, one of the risks is when priorities are communicated, that There’s a clear understanding of what that means, which is just because something might not be on a go-to-market leader or company’s top priority list doesn’t necessarily mean that those things aren’t getting done. It simply means that the things that we choose to invest in get a disproportionate amount of investment focus. And when trade-offs have to happen, these are the things that we make sure get resourced first. And I think it really gives permission to leaders to ensure that all teams working on important projects and programs in a company still feel connected to what needs to get delivered today and then for the future. And so that clarity around communication and understanding if something’s not on that priority list doesn’t necessarily mean It’s not critical and important. That’s separate. That’s a stop list, right? Or a reduction in investment. And so, just having parameters around the stuff is important.
Greg Kihlstrom: Yeah, yeah, I love that. So the last topic I want to talk about, it’s a big one, but I want to talk about product-led growth and team alignment to help lead that growth as well. So, you know, first thing there is just breaking down some of those silos. And, you know, you’ve talked about the importance of aligning product, engineering, data, and operating teams to execute this product-led growth strategy. How do you think about breaking down, you know, some of those traditional silos to achieve this level of, of cooperation?
Robert Chatwani: Well, maybe what I’ll, I’ll focus on is, you know, agnostic of the go-to-market motion, um, whether it’s sales-led, partner-led or marketing-led or product-led, um, Every organization and company will have sort of a unique go-to-market formula that works for them. And what I’ve typically seen is that changes over time. Now, you know, in the consumer world, back in my eBay days, it was very much traditional marketing lovers that would drive a lot of growth, plus organic traffic. At Atlassian, intensely centered on product-led growth, and product is the vehicle by which to make that top line and customer acquisition number grow. Here at DocuSign, it’s a real hybrid. We’re very sales-driven and that has incredible advantages. We’re introducing product-led motions and product-led sales now, which is sort of a convergence of both of those. A bit agnostic of the go-to-market motion, I think a few things hold true, which is one, um, this question of how do you, um, create, retain and grow a customer? And in most complex organizations, that’s going to require teams across an organization and company rowing in the same direction. And that is incredibly hard. And in fact, the larger an organization, the harder it is to get that alignment. So, um, to your question, how do you break down those silos? There’s a few things that I think are really powerful. One is whenever possible, have a North Star metric or a set of metrics that can be shared between teams, ultimately meaning aligning those goals. The second thing I love to think about is we use a DRI model here at DocuSign, which is an individual is effectively the directly responsible initiative owner. And effectively what that means is the point person that gets to play the role of orchestration and choreography of all the people and resources needed to achieve that shared outcome. And typically it means it’s a person who might sit somewhere in a product team or a growth team or in a sales team. And frankly, often doesn’t matter where they sit. They influence more than they control, but they’re effectively the leader who is responsible for bringing together all the resources needed to support the outcome. And then, you know, the last thing I would say is really powerful. This is something I learned from teams over at Airbnb, which is looking at the handoffs between teams and whenever possible having a shared metric intersection where let’s say a marketing team and a product team intersect or a sales team and a growth team and finding ways to look at that end-to-end customer journey with a shared metric. and that handoff metric so everyone understands how their work contributes to the overall growth and to delivering a unified customer experience. And this is, I think, the real magic happens when you can share metrics across teams, share the journey across teams, and you can build a lot of empathy when teams across that journey really understand what does it take in the step prior, the step after, whatever they’re responsible for.
Greg Kihlstrom: Yeah, definitely. I mean, I see, I think a lot of what creates silos or at least perpetuates them is different goals and incentives and things between teams, right? For those listening and, you know, listening to this and they’re like, wow, this sounds great, but I’ve got like super entrenched silos and, you know, I’d love to do this. Like, what would your advice be? Like, what’s maybe a practical step or two to like get there? You know, cause I, I would imagine, you know, it’s not going to happen overnight for, for organizations that are really kind of stuck in their ways, but there are some steps they could take. Well, what might you recommend there? Yeah.
Robert Chatwani: Look, it is hard, but what I’ve learned and appreciated is most of the challenges and problems across teams and companies tend to be very similar across industries, across company size, and they often come down to things like team health. In my prior life, I did some research and some of the data showed that if you ask leaders and people on teams a very basic question, which is on a spectrum of health, is your team healthy? And only 13% of teams go back and say, we feel like we’re optimized and we’re really healthy. And if you deconstruct that and sort of what’s the root cause, then it’s the basics. It is, do you have a foundational model, like a DACI or a RACI model of who is a driver of a particular project, who is the approver, who should be consulted, who should be informed, right? Oftentimes those things don’t exist. And so it’s messy middles where you might have multiple people who think that they’re the owner or initiative driver of a particular project and You don’t have that uncomfortable conversation of clarifying that. That amplifies as the team gets larger. Or there’s a missing project poster, which is somebody new joins the team. What’s the one pager where they can look at and say, what’s this project about? What are the metrics? What are the measures? How long is it going to last? Or there is a lack of adequate accountability through retros, which is we’re going to deliver a project and then take time after that project to do a look back and to assess how well did we do? What could have been done better? What could we improve next time? And it’s not about fault finding, but really elevating the team’s capabilities. One of the things we’ve tried here at DocuSign is premortems, which is before you kick a project off, get all the key stakeholders in a room, spend 15 minutes going through all the things that can go wrong. And, you know, sometimes those end in feeling like this incredible disaster because you’ve just identified how everything is going to fail. And then you remind yourself, oh wait, we haven’t even started the project yet, right? But effectively what you have is a diagnostic of things that you can go improve. So we spend at Docusign a lot of time on not just what we do, but ways of working and how we do it. And to point to some assets that are available for free for those who are listening, and I’m very open about this, Atlassian, my prior company, shared something called an Atlassian team playbook. And all of these templates and resources are available for anybody who wants to discover them. And these are great ways to just spend five minutes finding some team rituals and practices that I think can make a big difference between a team chugging along and delivering on what’s expected of them versus a team that’s thriving and really has that force multiplier effect of achieving great outcomes that many people may have thought weren’t even possible. Oftentimes, it just comes down to ways of working
Greg Kihlstrom: Yeah. So the last thing I want to touch on here is the role of data in all of this. And just, you know, there’s a lot of emphasis on data-driven decision making and relying on this. A lot of what we’ve talked about just now is team collaboration, and a lot of that happens, you know, whether it’s virtually, but it’s still, you know, people communicating with other people. But data, you know, is playing a bigger and bigger role for lots of reasons. How should leaders be thinking about maximizing their human team members’ contributions as AI capabilities, you know, machine learning, predictive analytics, like all of these other things? are also making a bigger and meaningful impact. How should a leader think about balancing these two things?
Robert Chatwani: Greg, I think it’s a great question. If anybody listening, if this is at the forefront of something they have to think about, you know, monthly, weekly, or sometimes even daily, then they need to just pause and reflect. Because across every type of company, including B2B companies and SaaS companies, this is probably the most foundational shift, seismic shift around how to generate revenue, great growth, that is important, especially right now. One of the most important relationships I think that exists within.
Greg Kihlstrom: As some of you may know, I’m the host of another successful podcast, The Agile Brand with Greg Kihlstrom, Apple’s top-ranked enterprise marketing podcast. Three times a week, I talk with C-suite leaders from world-leading brands and platforms about the latest trends, issues, and challenges in marketing technology, AI, and customer experience. Be sure to subscribe so you too can join the thousands who have already followed to hear us discuss the top issues and challenges you need to know about and get real world insights and advice which you can quickly apply to your biggest marketing challenges. Check out the Agile Brand with Greg Kihlstrom podcast wherever you listen and make sure to follow or subscribe so you can catch the very latest.
Robert Chatwani: any organization is between the go-to-market or sales or marketing leader and both the CFO and either the CTO or the CIO, where data responsibilities often sit. And what I would say is, we think a lot about this at DocuSign, and there’s a maturity model of companies, and it depends on what type of company you are and where you are, the maturity model of having data as part of the culture of running the business. Um, so agnostic of that because companies are at different stages of maturity. Let’s take an example of a company that’s far enough along where high quality data is available to anybody who needs to use it to make decisions. And if you’re not there, that should be part of your journey. But assuming that’s the case, I would say, you know, what we do here at DocuSign is one, we spent a lot of time thinking about, uh, AI specifically, and in our go-to-market and sales teams, how can we identify use cases that we think can benefit from better data, or better automation, or better use of AI? And the good news is that exercise tends to be a lot of fun. There’s lots of different use cases that can be identified. And secondly, stack ranking those use cases, and then asking, how can we make improvements to use either data or applied AI to actually automate some of these capabilities to improve experience for team members or for customers? And then lastly, how do we translate a lot of those applications into results defined by better growth, which is revenue growth or customer growth, or efficiency or activity? It’s really translating the use of applied data and AI into business benefits. And a lot has emerged from that. We’re still very early in our journey here, but we’ve been able to identify a lot of experiments that we use to do inbound and outbound prospecting. We’re now embarking on how to use better product behavior data to inform better sales experiences and interaction with customers. Some of the table stakes of consumer platforms, we’re using data about product behavior and browsing behavior to drive better targeted personalized experiences, both on Docusign.com and our global properties, but also within the product. And so, you know, there’s an infinite number of use cases and applications, but I think this is a whole new exciting frontier where enterprise and software companies are headed.
Greg Kihlstrom: Yeah, definitely. Yeah. Lots and lots more to, to discover here. So definitely. Uh, well, Robert, thank you so much for joining today. Um, got one last question for you. Uh, I like to ask everybody this, this question here, what do you do to stay agile in your role and how do you find a way to do it consistently?
Robert Chatwani: That’s a great question. I would say, um, be open to a lot of new ideas that emerge that challenge conventional ways of working and conventional ways of operating. And I found that more so than having the answer or believing, you know, myself or anybody on my team knows what to do. Our superpower is the ability to respond to new information that comes our way and translate that into better execution and better teamwork.
Greg Kihlstrom: Love it. Love it. Well, again, I’d like to thank Robert Chadwani, president and general manager of growth at Docusign. You can learn more about Robert and Docusign by following the links in the show notes.
Robert Chatwani: Thanks Greg.
