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How DocuSign Defines Digital Experience With Robin Joy

Digital experience is all about giving people the best experience with as little friction as possible. DocuSign uniquely excels in this regard with a core product that is itself digital. Through its well-known eSignature product, DocuSign has become an early adapter of product-led growth before that very concept even existed. As people started to find themselves working remotely in the context of the pandemic, the company experienced an unprecedented growth in sales as people began to appreciate the pain point that it addresses. The company’s SVP, Robin Joy believes that even when the pandemic goes away, DocuSign will retain its command of its market because of the ease and efficiency that it offers. In this conversation with Rico Mallozzi, Robin shares how DocuSign defines digital experience, how her team has helped introduce millions of people to the platform through compelling web experiences, and how the company is gradually expanding its niche as a broader agreement cloud platform. She also discusses the role of performance marketing and enterprise tech and how best to manage leads between marketing and sales.

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How DocuSign Defines Digital Experience With Robin Joy

I'm extremely excited to have this conversation with Robin Joy, the SVP and General Manager of Small Business and Digital Sales at DocuSign. She leads a team focused on demand generation, digital experience, eCommerce, marketing and analytics. Her team's work has helped introduce millions of people to the DocuSign platform through compelling web experiences and award-winning mobile apps. In this episode, we discuss how DocuSign defines its digital experience, the role of performance marketing and enterprise tech, and how best to manage leads between marketing and sales. I hope you enjoy this episode as much as I did.

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Robin, thank you for joining us.

It's great to be here, Rico.

This is going to be an interesting conversation as your experience blends marketing, sales and also the SMB segment, which for some enterprise companies is its primary segment. For others, it's one that they expand to overtime, or start with and then expand out of. It’s relevant for a lot of enterprise technology companies. With that being said, could you give us a high-level background about yourself, your experiences and your journey to DocuSign?

Maybe starting with DocuSign because I have been here for several years. I joined the company when we had 150 employees and we're up to 5,600 now. We were $30 million in annual revenue before I joined and we're now at $1.5 billion in annual revenue. It's been an exciting journey here at DocuSign. I have had a few different responsibilities while I've been here, including our digital business, which is focused on helping our customers try and buy DocuSign online.

Over time, I have put more emphasis on also trying to identify those customers that might be right for other channels as well. I’m helping them through the funnel and getting them to the right person and the right opportunity so that they can purchase what's right for them for DocuSign. Prior to DocuSign, I worked at several different small and large companies, a mixture of startups and larger companies. My longest stint was at Intuit where I lead marketing for QuickBooks, which was a great introduction to small businesses and all that is important to those businesses.

Can you talk about the marketing activities you own in your role at DocuSign and the revenue numbers that you own from a sales perspective? It's an interesting blend of both. You own the BDR team, which in some companies is put in the marketing division, and in the sales division in other companies. Can you explain the rationale behind where you have it?

To answer the last part of that first, we call them sales development reps rather than BDRs, SDRs. Those are owned elsewhere in the organization although I partner closely with them. We do have some offshore reps, which are managed by my team. We have a combination of reps who are full-time employees as well as some supplemental reps who are offshore. My team manages the offshore reps there. The team is focused on the end-to-end journey for our customers as they think about wanting to get introduced to DocuSign. How do we best reach them? How do we help them get started in a trial? How do we get them through that trial to purchase? What are the analytics and the signals that might suggest that they're larger companies and that we might want to have a human talk to them? How do we help route them and get them to the right place to do that?

DocuSign was a pioneer of product-led growth before people call it product-led growth in a sense. What are some of those key demarcation points along that journey that you've developed to properly route customers to the right path? Maybe you can give us some examples at the front end of that journey, and then as they go along the pipe.

There are signals throughout the journey as you've indicated. Some of them are pretty standard demographic signals that oftentimes you can learn either because your prospect has told and informed you that you've had them fill out, or because of other markers that you can leverage things that you can append data to. Some of the basic demographics and then there are technographic. If you can understand what other technology those prospects are using, that can be another good signal. Those are all signals that you try to get as quickly as possible in the journey.

Because we leverage our trial for our signature product as part of the prospect journey, that's also a great source of signals. For example, if someone has used the trial, if they've sent a document to somebody else to sign, that's a key signal. We know they're more engaged and can respond accordingly and help make sure that they're getting the help that they need to get through that journey and hopefully become a paying customer.

That's helpful. I know free trials are an important gateway for a lot of product-led growth companies. When you identify that a customer has been in a free trial, at what point do you insert the engagement? Is it after a certain time of usage? Also, do you then make that decision? “This should go to an enterprise sales rep based on the firmographics. This should go to an inside sales team.” How do you make those decision points?

There are multiple triggers across the journey. Upfront, when they are filling up and signing up for a free trial, we are getting some information that can tell us right away if we think that they should talk to a sales development rep who can help qualify them further. The faster that you can do that, the more responsive that prospect is going to be. That's something that we try to do as quickly as possible. We get those leads routed and responded to as quickly as possible.

The initial touch is important. There are triggers across the journey and that includes after they're a paying customer. One of the things that we've gotten better at over time is identifying once someone is a paying customer. Perhaps through our digital business where they're more in a self-service motion, we can still get signals as a paying customer. At that point, you're truly trying to encourage them and reward them for being a good customer, but also signaling that they might be able to take advantage of our different offerings as they move upmarket.

One of the things that are unique about DocuSign’s approach is that it has this natural network effect. Most likely, if you're using DocuSign, you're sharing that with another company that could be another potential customer of DocuSign. It has its product virality loop. Can you explain how you approach that at DocuSign and how you use that to your go-to-market advantage?

One of DocuSign’s greatest strengths is that its core e-signature product is very well-suited to businesses of all kinds and sizes. Click To Tweet

For us, people are signing an agreement. As we think about that agreement process, oftentimes, other people have to sign that same document. First and foremost, making sure that it's a great experience for the other people who are touching the product. Oftentimes, this is the first awareness point that people have of DocuSign. The product team does an excellent job of making sure that the experience is as simple and straightforward as possible, which leads to a moment of delight for those prospects.

We try to take advantage of that moment of delight and help them understand how we can help them even in a simple free plan where they might be able to save a copy of the document they've signed. They can more easily access it in the future. If there are multiple signers, they can manage and understand who else has signed and where it is in the process. Over time, it also allows them to become a user and send their documents for signature to other people as well. We try to think of both their needs as a signer and the person who's received this document or agreement to sign, as well as somebody who could be a potential initiator of an agreement in the future.

Not everyone is in that second category. We are always trying to look for signals that help us suggest what's the right way to nurture those signers. It’s a massive and important segment for us. A lot of why our product has been well received is because it delights the person's customers and clients on the other side. How we then can help them through a journey and perhaps a deeper relationship with DocuSign is core to our business.

It's a great point because oftentimes, it’s the first experience for that signee. It can be an important point for them to engage with the product. Do you insert people in that go-to-market process for the signee? Do you hope that they log in and then start the sales cycle themselves? Do you try to intervene at that point as well?

That's where the scale is such, as well as the fact that these folks aren't ready to talk to a salesperson. It's a self-service, low-touch motion for them, completely digital. That is as it should be because of where they are in their journey. They're trying to get the document completed. The person who's sending them the agreement would not be happy if we were sending them off to a sales rep right away. Part of the reason that the product took off in the first place is we created as little friction as possible for that signer. That's still the case. We're focused on making that experience great for them.

There's some benefit for them if they create an account. Creating this free account does enable them to more easily access this document to be able to have future documents in the same place, and to be able to manage them. If they need to get signatures from other people, that gives them the ability to get started on that front as well. In that regard, it's a completely digital journey. If we see that they’ve started to send the document or even further, we might get them triggered to do a more full-featured trial of the product, which then gives us signals that they might be interested in something more. We might insert some more human touch into the process. We're letting the end users’ actions and behavior help guide that journey.

Let the end-user guide the interaction because they're an experiencer of the product at that point. They haven't shown any intent for it. To insert them early in the process could be disruptive. Especially for the customer too who's sending that document, their job is to make it as easy as possible for the person signing that document. I want to talk about the SMB business at DocuSign. A lot of companies have trouble augmenting enterprise sales with SMB or vice versa, whichever one they started with. How have you successfully operated these go-to-market motion simultaneously? What are some of the keys to success in your mind that other companies could take away who are selling enterprise SaaS across customer segments?

One of DocuSign’s greatest strengths is the product. We have multiple product offerings, but our core e-signature product is well suited to businesses of all sizes. We started trying to solve a pain point in the real estate industry. The founder of DocuSign, Tom Gonser, his wife was a real estate agent. He understood the pain of real estate agreements. Early on, he was focused on solving that pain and we continued to cater to the real estate industry but have expanded into many other industries, including financial services, healthcare, life sciences, public sector, you name it.

We have a product that can serve an individual, small business like a real estate agent, all the way up to a global enterprise. That is pretty unusual from a product offering perspective. We are fortunate that the early work done on the product to make that easy enough to use for a small business, but also secure and robust enough for an enterprise customer was a critical foundational work that we continue to leverage. Not every company has a product that can scale across business sizes in the way that DocuSign has. Some of the things that are important to small businesses like ease of use are also important to enterprise customers. Things like security, which is a no-brainer that an enterprise customer cares about are also quite important to a small business. They may not need quite as many certifications or they're not going to go as deep to understand how secure the platform is, but they still care about it.

The good news for us is the core benefits and attributes that are important to customers are somewhat consistent across small businesses in the enterprise. Although the way that you message that, the way you bring it to life in the product, we do think about that segment and try to cater to them differently. As we've learned, we put a lot of focus early on our small business customers to make our trial as easy as possible for them so they could get started on their own. We learned that there were some things that we did well in that trial experience that we're carrying through and bringing to our enterprise customers. Everyone wants things to be as easy to get started and easy to use as possible.

Oftentimes, the actual core values of what you're delivering may be the same for SMB and enterprise rather a nuanced way to communicate it to be effective with each one of these customer segments. Sometimes we try to over-engineer serving these different customer segments. I want to move up the sales funnel to the demand generation side. Demand gen was impacted pretty greatly in 2020. Enterprise SaaS companies rely a lot of times on in-person events for that top-of-the-funnel activity. Can you talk about how you've managed the mix of lead generation activities through this period and what you found to be most effective for an enterprise technology company?

This is where our investment in the digital experience has paid off for us because we already had a lot of the fundamentals. In our case, our business experience had accelerated growth as people move to work remotely. We were able to handle that velocity and scale because of the strength of the digital business. Simultaneously, we scaled up our sales team, although that takes more time to hire people and train them and get them. Fortunately, some of the motion that I was describing with our free trial and some of the work we do to automate the process of lead scoring, lead routing, and also to be able to do a lot of email nurturing and things that don't require as much human touch. All of those items were in place. We continue to try to optimize them and improve them. We were fortunate that the strong digital experience helped us serve our customers well.

On the event front, we had to make a shift. Our big annual customer event was scheduled for the Spring of 2020. We quickly had to make a shift to digital for that event. What we found is that people were interested in attending digitally. In some ways, that allowed us to reach a broader community of customers and prospects because they didn't have to travel to be part of the presentation. We've had our momentum of that, which is our annual customer event. We got more sophisticated in how we delivered that digital content. The quality of that content and that event improved as we had more experience over time.

We've learned that digital can be a fantastic way to have events that have a much broader reach of customers, particularly as we think about small businesses. It can be tough to take a couple of days out of their work. The expense of traveling and staying somewhere else can be prohibitive. That event in the past was focused on our larger enterprise customers. Now we've been able to broaden the appeal and reach to extend to customers of all sizes.

Has 2020 impacted the way you go about paid performance marketing versus organic marketing leads? Any insights there? Did the mix change? You don't have to give exact numbers but did the strategy change at all?

The tension between marketing and sales teams can be reduced if the marketing team is as focused on sales as the sales team is. Click To Tweet

Every marketer and every CEO loves organic leads. We're always trying to do everything we can to optimize organic leads, which are incredibly cost-effective. We want and need to supplement that with pay programs as well. We still spend the majority of our budget on digital advertising. We are experimenting beyond that. We are starting to consider some even further top-of-the-funnel advertising. We're focused on making sure that our investments are ROI positive. We're doing a lot of testing our way into new channels and new opportunities in terms of our marketing mix.

By and large, with the big shift being away from in-person events to digital events, we still are spending on events. It's a little bit of a different type of spend because it's digital. We do a lot of paid searches. We do some YouTube advertising. We're expanding into other areas of advertising as well and lots of email marketing, which years ago, people were thinking that email was dead. It's not the way you get the initial contact with your prospect, but it is a great way to continue to nurture your customers. That still does factor into our mix as well.

I don't know if you do this at DocuSign, but I've even heard targeted direct mail campaigns have been quite effective if it's the right lead at the right stage of the process. I don't know if you're doing the same activity as well.

It's interesting because back in my days at Intuit, direct mail was an effective way, particularly as we were reaching out to our accountant community. We don't do that very much at DocuSign. People are at home. If you happen to have their home address, it could be effective. A lot of times, people are still giving their business address. Sending a bunch of direct mail to an office, which people aren't in is not going to be effective. If you have the right information, then people are certainly in their homes and probably opening their mail more than ever.

I haven't thought about that. I imagine my mail pile back at the office is going to be quite large. I haven't checked it in a year.

You’re not sure if it'll still be there or what's happening.

They might have recycled it. Oftentimes, there is this inherent friction and we see it with a lot of companies between demand gen and the sales team. What's a qualified lead and the KPIs around that? Have you found an effective way to rectify that at DocuSign? What are some of the strategies you've used to make sure that marketing qualified leads are up to stuff for the sales team and the marketing team feels like their leads are getting the attention that they deserve?

That can be tension and part of how we tried to reduce that tension is to make sure that the marketing organization was as focused on sales-qualified opportunities as the sales organization was. That was the common output metric of success. The salesperson is the person who decides that it's a sales-qualified opportunity. That allows there to be no friction, although, we do still also measure marketing qualified leads and that's where the lead scoring is.

Making sure we continue to optimize that with input from our sales development reps as well as our account executives. Making sure that the lead scoring and up funnel marketing qualified leads are the quality that we all would expect and want is also important. We're doing both. We measure every step in the funnel. We're trying to make sure we have alignment across the funnel so that we can look at those conversion rates. When we think there's an opportunity to improve those conversion rates, we get everyone aligned on that and working together on trying to make the improvements and optimizations that we think are possible.

In that scenario, does the lead scoring framework dictate whether it's a sales-qualified lead? Does the salesperson have to make that decision because the rules and parameters have already been defined I would imagine?

The lead scoring is more focused on the marketing qualified lead. The lead scoring is what determines that something is what we call an MQL or marketing qualified lead. That lead score is more upfront. The initiative was led by our sales development reps with partnerships across sales and marketing to make sure the definition of a sales-qualified opportunity was being applied uniformly. Reps wouldn't just decide that something's a sales-qualified opportunity when they're about to become a close one deal. There's work that we've done to try to standardize that definition across.

It is still the AE’s responsibility to determine that it's an SQL, but we've tried to standardize the definition. We do leverage some best practices and metrics that we get from places like SiriusDecisions that help us know what's an industry standard. You want your close one to be as high as possible. On the other hand, you don't want it to be so high that it implies that people aren't turning enough things into sales-qualified opportunities. Some of those standard metrics can help you know where you may have room to push harder on some of those opportunities and those leads.

I would imagine if you had a high conversion to the Q1 stage, you may think that you might not be exploring enough of those leads to potentially convert. You might be leaving some on the table that could have been sales-qualified leads. They may have been a little bit tougher to get to, but you invested in those leads. You should probably turn those rocks over.

That’s where you need to be careful of how people are being rewarded and measured. If they're only measured on their percentage close one, they're going to be less motivated to turn something into a sales-qualified opportunity. You want to make sure that there are incentives and you're looking across the funnel. As you get larger, that’s where it can also be helpful because you can look across teams and see differences and start to understand why there might be those differences. Some of it can be because of lead quality, but some of it can be because of the behavior of different teams.

We're all trained as individuals to think that 100% is the best number. There's a healthy number of not achievements because that means you're stretching the goals there and covering a wider universe of potential opportunities. In our prior conversations, you mentioned sales ops being critical to reducing this friction. How do you work with the sales ops? What's the interaction there? Are they the ones who are helping analyze all these metrics for you? What's the relationship?

Digital experience, in the broadest sense, is about getting people to have the best experience possible with the least friction possible. Click To Tweet

We have analysts spread across the business. The sales ops team is critical in helping to set the plan. They play a critical role in planning and have been collaborative across teams to try to understand all the inputs. They're trying to be as aggressive as possible, but make sure there's no point of failure in that planning process. They have been important and great partners at DocuSign.

One of the things we've touched on previously in the conversation is DocuSign’s digital experience. It's paramount to the company's go-to-market strategy, the marketing strategy. What are the core pillars of a great digital enterprise experience in your opinion?

At DocuSign, we use the word digital experience to mean different things. We have a team that's called The Digital Experience Team. Our product itself is also a digital experience. When we think about the digital experience in its broadest sense, it is about how do we help people have the best experience possible with as little friction as possible? That's true of both the product itself and the product experience. I talked about how important that work we did early on with the trial experience was and how important the work that the product team does on our signer experience. Those are digital experiences because the product itself is digital.

There are also pieces of the infrastructure that help enable the digital experience from more of a marketing perspective in terms of being able to make sure you are capturing all your leads and that you're able to route those leads. From an eCommerce perspective, you're able to complete a purchase that your website has the content that your customers want, but that also has the performance that you need and that is as fast as possible.

There are multiple components of digital experience and a lot of it has to do with making sure that you're thinking both outside-in and inside-out. Outside-in meaning that you're thinking about the prospect and customer who is touching that and making sure that their experience is as good as possible and they're getting what they need out of that experience. The inside-out part is making sure that you have the infrastructure, the dashboards and metrics that show that your performance is where it needs to be. It helps you identify opportunities where you can continue to improve and optimize.

One of the challenges for a lot of organizations is to aggregate all that data from those systems and the importance of integration. Everyone knows that DocuSign is an eSignature company. As you mature as an enterprise technology company, you spread that product breadth. Can you talk about that at DocuSign and where that stands now and how you manage that process of expansion?

Our e-signature solution is still the center for what we're calling the agreement cloud. It's the way that most people know DocuSign. That's the way that most people get started with DocuSign. We've started to paint the vision of DocuSign as an agreement cloud company, and trying to think about the agreement process from end to end. What are the different needs that our customers have as they're initiating and completing agreements? A few years ago, we purchased a company that was in contract lifecycle management. We've also purchased a company that was in document analytics. Some of those expanded offerings are a little more targeted to our enterprise customers. We want to think about the agreement cloud for customers of all sizes. We'll be continuing to expand that.

As we think about the opportunity, we have more than 750,000 paying customers. To be able to sell more to those customers, the good news for us is we’re uncovering new use cases for those customers even with our core e-signature product. We have been able to expand our relationship with those customers even with our core product. We believe we have an opportunity as we've developed this trusted relationship and this platform as we can expand to the agreement cloud into additional product needs. That's a huge opportunity for DocuSign to expand and continue to grow from $1.5 billion to $5 billion to $10 billion. We are always looking for ways to expand our growth. Expanding our relationship with existing customers is a critical part of that.

It’s an enormous opportunity if you can expand the product footprint at these accounts. It sounds like an incredible opportunity. It sounds like an incredible journey from here. It sounds like it's only going to get even better as you expand the story for DocuSign.

We were talking about this a lot in the pandemic and working from home. That’s obviously where we are now. If we get lucky and this show lives on, there may be people who are tuning in after we’re all back to work. We had such impressive growth in 2020. We do sometimes get lumped into these work-from-home companies. We were very vital and instrumental in helping people work from home, but we believe that once people are using DocuSign, they’re not going to go back to pen and paper. We now are talking about it as the anywhere economy. The fact that DocuSign as well as some companies have products that are enabling people to work from anywhere. We were vital as people move to work from home, but we’ll still be vital as people go back to the office or whatever flexible arrangement they may be looking at in the future.

DocuSign will not just remain relevant in the context of remote work. It will be a critical part of the anywhere economy concept. Click To Tweet

What happened in 2020 accelerated a lot of trends for companies and people are trying to figure out what is going to be the enduring impact of that. Companies like yourself, DocuSign, Zoom and others, how do you look at the post-pandemic world as it relates to DocuSign and its relations to DocuSign’s growth?

You're right that 2020 accelerated our growth. DocuSign played a vital role in helping people make the transition. We feel like every signal that we're having from our customers is that they don't want to go back to the old way of doing things. We're framing the future for us as the anywhere economy and that applies to companies beyond just DocuSign as people want products and services that help them be able to work from anywhere. That might be true if they go back to the office or if they're working remotely or some flexible arrangement in between. People value those tools and those products that help them be on the go. Hopefully, people will be more mobile going forward, but that doesn't mean that they won't still need these services. We're excited about this concept of the anywhere economy. DocuSign is a product that will be critical for it.

That's a great point. A lot of the SaaS companies have benefited as a result of this. What's key for them is to find out what's the enduring impact from the customer behavior and how can, not just benefit from that, but use that for their company as they tell their story moving forward. That's insightful. I’d like to end these interviews with one question that has nothing to do with technology, but a better way for the audience maybe to get to know a little bit about you. The Bay Area has been impacted by COVID and the remote work experience. I want to show the Bay Area a little bit of love. What's your favorite thing to do in the Bay Area when you have a weekend or so?

I love to cycle. It's a great thing that I've been able to continue doing throughout COVID. I also have a Peloton, which I love. That's indoor cycling. It has been a bit of a lifesaver during COVID as well. I've also been doing a lot of hiking in my neighborhood and expanded beyond. It has been wonderful to explore all of the great open spaces that we have in San Francisco. To your point, there are lots of stories about people moving out of California or moving out of San Francisco. We have so much here that helps us, the outdoors, places like Ocean Beach, which is a short drive away.

I can't think of many places where I could be to the beach in twenty minutes, up to Tahoe in the mountains in a few hours, up to Sonoma or Napa, the wine country. All of those are places with fabulous outdoor activities. It's been important to me. None of us have enjoyed some of the limitations that we've had on travel and other indoor restrictions. In terms of group gatherings, I feel fortunate to have been in an area where there are many wonderful places that you can be outside. I love being able to explore, both places that I already knew and loved, and then to be able to experience some places that I haven't explored before because of the desire to be outside and moving.

It’s important that we get outside. We're now spending most of our time inside and secluded. I agree with you, some incredible hikes that are ten-minute drives outside of the city or right in the city. It's a nice luxury to have. Do you cycle up the Marin Headlands? I see people doing it and that looks like one tough cycle. Also, not a lot of room there between cars and bikes.

One of the things that were great for a while was a lot of those roads were closed off to traffic. I do cycle up there. I do some in the city. I got Twin Peaks, into the beach, some in Marin, some down in Woodside. I was up in Sonoma as well. I do love cycling up there in Sonoma and Napa as well. There are lots of great places to explore. Pretty much anywhere you go in the Bay Area, there are going to be hills but that's part of the fun.

It's also rewarding once you get to the top and you get some epic views up there that are quite beautiful.

Even the downhill.

That's the nice part, although some of them are pretty steep. You got to watch out. Robin, I want to thank you so much for your time. This was a great conversation about all these digital experiences, product-led growth, lead scoring and pipeline management. I enjoyed this conversation. The readers will as well. If people want to get in touch with you, what's the best way?

They can find me on LinkedIn. I'm not as active as I'd like to be on Twitter, but I’m @RobinJoy on Twitter as well. Thanks so much. I enjoyed speaking with you.

Thank you so much, Robin.

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About Robin Joy

Robin Joy serves as Senior Vice President and General Manager of Segment Marketing and Digital Sales at DocuSign, the #1 eSignature and agreement cloud solution. Robin built DocuSign’s high-velocity Digital business, introducing millions of people to DocuSign via a compelling web experience and award-winning mobile apps. During her 9+ years at DocuSign, Robin has helped scale and grow DocuSign from 150 employees to 5,600 and from $30 million annual revenue to $1.5M, with a successful IPO in April 2018.

Robin is passionate about building great businesses and great teams. In addition to her work at DocuSign, Robin is an Executive-in-Residence at Bessemer Venture Partners, serving as an advisor to their portfolio companies.

Prior to joining DocuSign in 2012, Robin served in leadership positions in marketing, sales, and general management at companies including Intuit, AltaVista, Clorox, Odwalla, and Caring.com. Across companies, Robin has developed strategies leading to sustainable, long-term growth while successfully driving quarterly results.

Robin graduated cum laude from Dartmouth College and received her MBA from Stanford University. She was awarded a Rotary Scholarship to the University of Melbourne where she received an MA with honors in Women’s Studies. From 2008-2016, Robin served on the Board of Directors of the non-profit Full Circle Fund.

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