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PODCAST 91: First Step in Good Category Creation with Scott Olrich

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This week on the Sales Hacker podcast, we speak with Scott Olrich, the Chief Operating Officer at DocuSign.

Scott is the Chief Operating Officer at DocuSign, where he focuses on orchestrating DocuSign’s vision strategy, marketing, and enablement efforts around the world. Scott brings over 25 years of leadership experience, and a proven track record for driving innovation, market adoption, and hyper-growth to his role at DocuSign.

If you missed episode 90, check it out here: 90: Key Mistakes Companies Make while Building their Skills or Revenues w/ Justin Welsh.

What You’ll Learn

  • What the agreement cloud is
  • How to get started in category creation
  • Changing the sales game for smaller companies
  • How to know what you’re good at

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Show Agenda and Timestamps

  1. Show Introduction [00:05]
  2. About Scott & DocuSign [2:35]
  3. What’s the agreement cloud? [8:13]
  4. First steps in category creation [10:25]
  5. Changing the sales game [15:29]
  6. It’s time for category creation when… [20:04]
  7. How to know what you’re good at [26:22]
  8. Scott’s shout-outs [35:42]
  9. Sam’s Corner [39:16]

Show Introduction [00:05]

Sam Jacobs: Welcome to the Sales Hacker podcast. Today we’ve got Scott Olrich, the Chief Operating Officer at DocuSign, on the show. He’s just got incredible insights and expertise, so it’s great. Also, DocuSign is a sponsor of today’s episode.

Now before we get there, we want to thank our sponsors.The first one is a company that everybody’s heard about — DocuSign. Every sales org feels the pressure to close deals faster. Take control with the DocuSign agreement cloud, a suite of tools that automates sales contracts and quotes ,all right in your CRM. Create custom contracts in a click, sign them digitally, and automatically pull data back into your opportunities. See why more than half a million businesses use DocuSign with a free trial and discount exclusively for Sales Hacker listeners at go.docusign.com/saleshacker.

Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Our second sponsor is Outreach, the leading sales engagement platform that enables sales reps to humanize their communications at scale, from automating the soul-sucking manual work that eats up selling time to providing action-oriented tips on what communications are working best. Outreach has your back.

Now, without further ado, let’s listen to this interview with Scott Olrich.

About Scott & DocuSign [2:35]

Sam Jacobs: We are honored and excited today to have one of the leading executives in Silicon Valley and in the enterprise software space. Scott is the Chief Operating Officer at DocuSign, where he focuses on orchestrating DocuSign’s vision strategy, marketing, and enablement efforts around the world. Scott brings over 25 years of leadership experience, and a proven track record for driving innovation, market adoption, and hyper-growth to his role at DocuSign. Typically, the way that we start, is, “We like to contextualize your expertise.” How big is DocuSign as an organization, roughly?

Scott Olrich: We’re over 4,000 employees, and we actually were just ranked number three on the Best Places to Work for large sized companies, in Glassdoor, just on Monday.

Sam Jacobs: I’m sure you had a lot to do with that. That’s fantastic. Tell us how you got to DocuSign and how you evolved into COO of a major public company.

Scott Olrich: I see myself as a demand generation person through and through. I had a successful career at Anderson Consulting, and then I went out and helped create a company called Topica, and then eventually joined Dan Springer at Responsys, which we built that company from approximately seven million in revenue to a large, public company that we ultimately sold to Oracle for $1.6 billion. Then I founded another company called Heighten in the sales tech space, and we ultimately sold that to LinkedIn, and then I rejoined Dan Springer about three years ago to help drive DocuSign, not only in rethinking the category, but more importantly to drive the growth to ultimately taking it public where we are today.

What’s the agreement cloud? [8:13]

Sam Jacobs: When you talk about an agreement cloud, you mentioned a few use cases or maybe just part of the customer journey as it relates to this concept of agreement cloud. But what is the agreement cloud?

Scott Olrich: Increasingly, companies want to buy into platforms. Every one of those front office platforms — think about Sales Force, or back office, like SAP, Work Day, Service Now — they all intersect with one thing: agreements and agreement processes. The agreement cloud is the underlying platform because businesses run on agreements. Those agreements have to intersect with business processes. The goal is, if you’re in sales and you have a sales agreement that you need to create, you should be able to do that with DocuSign, with our agreement cloud. When you need to get a sales agreement signed, you should use DocuSign to get that signed. Once the agreement is signed, you shouldn’t have to actually take the agreement and have to recode everything that was agreed to in that agreement manually, that should automatically be distributed into the right systems.

Our goal as an agreement cloud company is to help you automate and connect every part of the process of agreement, from preparing, signing, enacting, and managing agreements, and connect those to every core business process in a company, whether it’s across the front office or back office.

First steps in category creation [10:25]

Sam Jacobs: Just diving into a little bit on category creation. Why do you think it’s so important? If you’re an early stage company, what are the first steps you need to be thinking about when it comes to good category creation?

Scott Olrich: Category creation starts with the narrative. When I’m creating a narrative, what is the narrative that I want our sales people to talk to our customers? What is going to make sense to them and is going to paint a picture of what the bigger problem’s going to be? It’s about reframing the customers and getting them to see the problem from your worldview, and you really want to get them to believe what you believe. If you get your customer to believe what you believe or you’re prospering, you’re going to win. It starts there.

For me, I really see myself as a chief orchestrating officer of DocuSign. My job is really to create the narrative. The narrative at DocuSign is that we want to help people be more agreeable. What do mean by that? Well, we believe that every single company needs to be easy to do business with. They need to be easier to do business for and they need to be easier on the environment. Then we said, “Well, how are we going to help companies be more agreeable?” We said, “Hey, we’re going to help them modernize this entire agreement process across preparing, signing, enacting, managing.” And then we said, “How are we going to do that?” Well, we’re not just going to do it with e-signature, now we’re going to do it with the agreement cloud.

The key thing is being able to create that narrative and then drive that all the way down into every single part of your business. All of us have experienced what it feels like to actually be on the receiving end of an orchestrated company or experience, and that’s exactly what you need to do in these businesses.

Changing the sales game [15:29]

Sam Jacobs: How do you think the sales team needs to adapt when you’re selling a new category, and how does it benefit the sales person?

Scott Olrich: You need some early success stories. I’ve been involved in big companies like DocuSign and Responsys, but I also have a lot of experience working in the early companies. You need some of those early initial wins and that takes a lot of effort. Sometimes you’re going to come in second. The answer is not trying to do the same thing the larger incumbent is doing in the category. You won’t win that way. You need to change the game.

You need to figure out a couple of the unique things that you’re going to be able to deliver on that are going to be really important and create narrative that drives the prospect and customer to believe that those unique two or three things that you can do are more important to their business. Too many times I see small companies try to go battle straight on with the competitor versus figuring out those two or three things that you can do uniquely. Make sure you create a narrative that elevates those into the priority of what the customers going to look for in that product or service.

Sam Jacobs: What’s your advice besides lean into category creation?

Scott Olrich: I think you need to understand what is going to help you win in the future. What is that unique difference? Then put everything you have, go all in on those things, and then train your service organization, train your customer success organization, your SEs. You’ve got to stand out, but you can’t stand out just by marketing. It takes the strategy, it takes the sales reps being highly educated and being able to challenge your customers that that’s how they should view the world, and then you have to deliver on it. You have to deliver it from a product perspective and a customer success perspective. That’s why I’m such a believer in orchestration. You’ve got to get all this stuff orchestrated. That’s the hard part, but once you do, it’s hard to lose.

It’s time for category creation when… [20:04]

Sam Jacobs: Is category creation the right strategy for every company? Are there signs or indications that a company should take a leap?

Scott Olrich: The first thing is to get the right narrative that’s going to get your prospects and customers to buy into what you’re doing. Ultimately that will lead to a category. You don’t just set the narrative and category from day one. It constantly evolves. Figure out what’s the right message and narrative to get customers to buy into your vision today, and that will continue to evolve.

Sam Jacobs: What are the lessons as you reflect back on your career? What do you think are the skills that enabled you to become a chief operating officer?

Scott Olrich: I was always trying to think about the future. One of my skill sets is I can see things before others can see them, and then I am able to put them into a package, a narrative, and then drive the orchestration of whether that’s sales, marketing, product, customer success. I have a really strong knack for that.

I built up a strong team. I don’t necessarily hire that just have the skills that I have, I look for people that are very analytical because I feel I have a lot of intuition. If you really want it more, the people that I’ve seen that have been really successful, that’s what it really takes. At the end of the day, just like a great athlete, you’ve got to put in the time. I’ve attacked my career just like an athlete would, and I’ve really focused on getting good at what I do.

How to know what you’re good at [26:22]

Sam Jacobs: How have you figured out what you are good at? Some people are advocates of identify your weaknesses and work to improve them, and then the other point of view is to double down on your strengthsWhere do you fall out on that?

Scott Olrich: If you’re spending all your time thinking about things that you’re not good at, your life is going to be pretty stressful. I just don’t spend a lot of time stressing out about things that I’m not good at. If you don’t stress out, you’re probably doing things that you’re good at. When you’re stressed, you’re probably working on things that you’re not so good at. You need to be very self aware and you need to be truthful with yourself. My coaching is, “Hey, find out what you’re really, really good at and spend your life accentuating that gift. Find people that can help you and support you in the areas that you’re not at gifted at.” You’ll be a happier person.

Sam Jacobs: Are there certain things that if you’re not good at, it’s disqualifying to being an executive at a public company? Or do you feel if you’re good at enough things you can always find ways to complement your areas for development?

Scott Olrich: You have to look at who you’re going to work for. You want to find people that actually understand your unique strength and appreciate that strength. I have people that have different strengths that work for me. I really appreciate their strength, even though their strengths are different than mine. My business partner, Dan, has strengths that are different than mine. When you go look for a job, make sure that whoever you’re working for understands and values your particular strengths and will make sure that they will support you in the areas that you’re weaker. That will set you up for success. That would be the coaching that I would give to any young person early in their career.

Scott’s shout-outs [35:42]

Sam Jacobs: Whether it’s a favorite book or a favorite entrepreneur or CEO, when you think about some of those influences, who are some of the folks or the content or the ideas that come to mind that you want us to know about?

Scott Olrich: Geoffrey Moore is a guy that I think has done and contributed a ton to Silicon Valley. His book Crossing the Chasm has arguably been one of the best books in Silicon Valley and still sits on my bookshelf today. Marc Benioff has done an incredible job as an orchestrator. Narrative drives everything he does in that company. He’s arguably one of the best category creators out there. My hat goes off to him.

Sam Jacobs: Any guiding principles or a life motto you want to share with us before we sign off?

Scott Olrich: Focus on what you’re great at. Everybody should write their own narrative. We all have our own personal narratives, so decide what your narrative and write it. Best of luck to each one of you.

Sam’s Corner [39:16]

Sam Jacobs: Hey, folks. Sam’s corner. I had a fantastic interview with Scott about how important the narrative is. He talked about Marc Benioff’s V2MOM, so when Scott’s talking about narrative he’s talking about vision. The vision of where you want the organization to go, what you want to have accomplished for your customers in the future. That vision of putting yourself into the future determines what your strategy is.

First you articulate that vision and then your values. Those two things in combination, the vision and the values, should be your flashlight and your compass for when you’re lost in the woods. It’s exciting to hear companies that are trying to change something big. When you’re pursuing a goal of category creation, you’re really pursuing a multi-year journey. That’s what Scott was talking about.

What We Learned

  • What the agreement cloud is
  • How to get started in category creation
  • Changing the sales game for smaller companies
  • How to know what you’re good at

Don’t miss episode 92 next week!

I hope you enjoyed the show. Before we go, let’s thank our sponsors.The first is DocuSign. Execute contracts and get to revenue faster with DocuSign, used by employees in 90% of the Fortune 500 businesses. Learn more at go.docusign.com/saleshacker. Our second sponsor is Outreach, the leading sales engagement platform.

If you want to reach out to me with feedback, you can reach me on LinkedIn. If you want to become a member of Revenue Collective, check out revenuecollective.com. If you haven’t rated the show, please give us five stars on the iTunes rating system so that we can remain in business and continue to bring you this show.

As always, thanks so much for listening, I’ll talk to you next time.

This is a sponsored guest post from a Sales Hacker partner.

Sam Jacobs is the Founder of Aqueduct Revenue Advisors and the New York Revenue Collective and regarded as one of the top start-up CROs in the tech community.

He has has over 15 years of experience scaling companies from post-revenue to ~$300M, has helped raise over $400M in institutional capital, and has helped companies of all sizes achieve an average annualized revenue growth rate of 48% over the last 15 years.