PODCAST 53: Transitioning to Move Upmarket from SMB to Enterprise w/ David Katz

This week on the Sales Hacker podcast, we speak with David Katz, Senior Director of Sales and Customer Solutions at Intercom. David discusses his impressive career, beginning with a productive stint at LinkedIn, remarking on what special skills he has to maintain staying power and tenure amidst a fast-paced, ever-growing organization. He also gives us a framework for how to move upmarket, and the requirements for taking a company from the SMB space all the way to the enterprise.

If you missed episode 52, check it out here: Building Sales Coaching and Training Framework w/ Rob Jeppsen

What You’ll Learn

  • The key tenets of managing a large team.
  • How to have the right impact at each stage of your career.
  • Strategies for moving upmarket, and how to transition from SMB to enterprise.
  • Why the word “no” should be embraced within a sales process.
  • How to help transition your buyer’s journey to a more positive B2C experience.

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Show Agenda

  1. Show Introduction
  2. About David Katz: An Introduction
  3. Focus on the Customer
  4. Moving Upmarket
  5. Meet the Customers Where They Are
  6. “No” Is a Blessing, Not a Curse
  7. Connecting the Political Dots
  8. Mentors and Multipliers
  9. Sam’s Corner

Show Introduction

Sam Jacobs: Hey, folks. It’s Sam Jacobs. You’re listening to the Sales Hacker Podcast. We’ve got a fantastic show today. We’ve got David Katz, who’s a senior sales director at Intercom. One of the things we’re going to be talking about today is how to move upmarket and how to take a company that’s been focused on high volume SMB, high velocity sales, and move them into the enterprise. And what tools and methodologies you need to make that successful.

Now of course, we want to thank our sponsors. The first is Chorus.ai. Chorus records, transcribes, and analyzes business conversations in real time to coach reps on how to become top performers. Our second sponsor is Outreach.io. They are the leading sales engagement platform. Outreach supports sales reps by enabling them to humanize communication at scale and by automating the manual work.

Lastly, a quick plug for Revenue Collective, the business I run when I’m not hosting a podcast for Sales Hacker. We’re in six cities: Denver, Boston, New York, London, Toronto, and Amsterdam. If you’re in a city where there is no Revenue Collective chapter, just know that we’ve plenty of remote members, people in Paris, Indianapolis, Manchester, UK, Sydney. Folks who want to build highly engaged communities of sales and marketing executives to collaborate and help each other succeed, improve in our day jobs, and achieve our career goals.

About David Katz: An Introduction

Sam Jacobs: Today we are excited to have the senior director of sales from Intercom, David Katz, on the show. David is responsible for global sales and customer solutions teams across Europe, Asia, and the Americas. Welcome to the show.

David Katz: Sam, thank you for having me and making me sound really fancy.

Sam Jacobs: You are very fancy. Tell us about Intercom.

David Katz: My official title is Senior Director of Global Sales and Customer Solutions. We bring personalization back to internet businesses, and have a platform that lets you communicate with prospective and current customers across all segments of the customer journey. Our customers experience faster growth with better customer relationships. We help communicate with prospective customers, new customers, and customers who have been around for awhile and need support.

Sam Jacobs: Walk us through your background and career.

David Katz: I’m originally from New Hampshire. I thought I wanted to study law and public policy. When I look back on it now, I think I just loved debating and conjecture. I liked to win, which is probably part of the reason I’m in sales now.

I was fortunate to get a job with J. Robert Scott helping research technologies. After moving to the west coast, I cold called a guy at LinkedIn with a background similar to mine. I left a voicemail and said, “We have similar backgrounds. I see you recently joined the Linkedin sales team, I’d love to talk about what that was like for you.” And he actually called me back. They were hiring like crazy. They took a bet on me as someone who didn’t have software sales experience, and I wanted to make sure I didn’t let them down. My experience at Linkedin was transformational. It changed the trajectory of my career and I’ll forever be in debt to them.

Over the years, I was very fortunate to work with some incredible partners who really knew how to sell. And more importantly knew how to listen.

I took some of those things to Dropbox where there was no blueprint, no playbook, and rolled out some basic methodologies there. There are things I’ve learned along the way that I have brought to Intercom.

I try to be conscientious, not just force a sales methodology. I want to listen to customers, understand our position and the relationships we’re trying to build, and work to find a methodology that AEs and RMs can use to guide them. But I don’t want to be overly prescriptive.

Focus on the Customer

Sam Jacobs: Tell us about Intercom and the different functions that are encompassed in that.

David Katz: There are four different roles. We have account executives, who are purely new business acquisition. Once people become customers, we introduce them to relationship managers who are responsible for onboarding new customers, making them successful, and renewing that business. The third component is sales engineers who are primarily pre-sale focused. There are occasions within some of our larger customers where we bring them in to help us with a new evaluation. We also have customer success managers who are product consultants. These folks do a lot of training, implementation, and ongoing education to make sure our customers are successful with what they currently have, and understand things that are coming up.

Sam Jacobs: So the account management team at Intercom is the daily point of contact for questions that the customer has?

David Katz: Yes. They are the quarterback, and bring in the appropriate internal folks as necessary to solve customer needs.

One of our mantras internally is “focus breeds excellence.” Having relationship managers who own that relationship but are very revenue focused, whether it’s retention or expansion, has served us well.

Moving Upmarket

Sam Jacobs: What are your strategies for moving upmarket and how do you shift an organization either from a self-serve model or from a high-velocity transactional model to a much longer, more consultative sales process?

David Katz: When I joined Dropbox we started at square one. People were using Dropbox for business purposes, not just personal. If we could understand why Dropbox was valuable for business purposes, that’s a story that we could tell to the appropriate audience of something they’re missing in their stack.

Through that process we were able to put together our initial sales playbook. It was focused on certain industries, selling where there was a real need in their business, where their current solutions weren’t meeting muster. We went from closing deals for a couple thousand bucks to a $10,000 deal. By the time I left, we were closing multi-million dollar deals.

A lot of it was working with the product team to help them understand the problems we needed to solve for larger customers and why those requirements were important. As the product evolved we were finding increasingly better product market fit for larger and larger companies, and we were able to solve larger and larger problems.

RELATED: Moving From Mid-Market to Enterprise

Meet the Customers Where They Are

Sam Jacobs: What are some of the common mistakes you saw at Dropbox?

David Katz: Make sure you build very strong relationships with the different cross-functional partners who are going to help your team be successful. Prioritize those. I had to go from defense mode for the sales team, to business leader. If I’m not able to accomplish the things I think are important for our customers from a product perspective and from a roadmap perspective, why is that?

I had to prioritize relationships with R&D to make sure they understood the increasing complexity of the customers’ needs, and make sure we were building the right things. Someone told me the best thing I can do is go out on the road with R&D, and let them meet and hear from the customers. When I got to Intercom, one of the first things I did was have folks jump on a plane to go meet with some customers.

“No” Is a Blessing, Not a Curse

Sam Jacobs: You’ve said, in sales, “no” is a word reps should embrace, especially for upmarket customers. Help us unpack that concept.

David Katz: At Intercom we’re constantly A/B testing and figuring out how can we make this more streamlined. How can we remove friction in the buying process? As you move upmarket, and have more human interaction, you need those points of friction to figure out if we’re both aligned in our expectations. You want to make sure you understand a customer’s needs and can meet them.

That might require some work or modifications to longer term roadmaps to win that business and make them successful. You have to bring a high degree of scrutiny to that deal evaluation early on and make sure that you’re aligned and honest with what your product can accomplish and what it cannot. It is a huge mistake to oversell because they’re worried about killing a deal. From my experience, it’s usually the opposite. Technical buyers understand when they’re buying software that’s meant for a broad audience, it’s not going to accomplish everything they need it to. And you’re going to have to make trade-offs. Don’t oversell.

Connecting the Political Dots

Sam Jacobs: How do you build the width and the depth of buyer preference into the sales cycle so that you can make sure that the reps are getting not just to the E in MEDDIC as economic buyer, but also to the wide range of support you need in an organization in order to move a purchase forward?

David Katz: It’s a great point. Something when you get into these more complicated deals you need to understand the political environment within that customer. We try to map out what we think the organizational structure looks like, and understand the people we are working with. It looks like some TV crime show where you have the detective in a back room drinking coffee with a cigarette and they have a big board with their connecting yarn dots. We are trying to understand real influence and the underlying motivations of the different people we’re working with. We literally map out an organizational chart of decision makers and influencers and motivation. And across those three things for each person we’re talking with, we try to strength test and verify who else needs to be a part of this. We really try to understand each individual’s motivation and what they’re hoping to accomplish, and try to make our best judgment as to what we think their core motivations really are.

This goes right back to the Sandler fundamentals. As you’re going through the pain/gain funnel, there’s the different levels of pain and gain, and the deepest level, level three, is personal pain or gain. And so we’re teaching our team to try to get to that point where you understand not just the financial impact of this decision, but what does that impact actually mean to this person? Whether they’re the decision maker or an influencer.

Mentors and Multipliers

Sam Jacobs: Are there any books that you’ve read that have really impacted you, or a couple of mentors whom you really respect?

David Katz: I look back to Dan Shapiro at Linkedin who’s now the vice president of global sales. He is one of the most incredible leaders I’ve ever witnessed. He had the rare ability to have a conversation with you at ground level, and then take it up to 30,000 feet and then back down to 10,000 feet really quickly. He had this very rare blend of analytical capability, raw intellectual horsepower, and insanely high situational awareness and EQ. He knew exactly what wasn’t being said, and therefore always knew what needed to be said. And it was incredible to witness.

A favorite book that he gave to a lot of us was called Multipliers. It talks through two different types of leaders. The empire builder is someone who might be very successful from a performance perspective by bringing very talented people into the organization and then keeping them there. The second group is the multiplier who brings in incredibly talented people, but knows when to move them on to a new role that might be outside of their organization and might mean a short term hit to the performance of their org.

I’ve always kept that in mind as I think about our team and their career development, and encourage my leaders to do the same. In doing that you become known as someone who has the best interest of their employees in mind, and is keeping a lookout for what is really important to them in their careers. You will always be able to attract the future talent that you want by using that method. People know that when it’s time, you’re gonna help them get onto that next role

Sam’s Corner

Sam Jacobs: Hey folks, it is Sam’s Corner. Another really great interview with David Katz, Senior Sales Director at Intercom.

Things We Learned:

  1. The key tenets of managing a large team.
  2. How to have the right impact at each stage of your career.
  3. Strategies for moving upmarket, and how to transition from SMB to enterprise.
  4. Why the word “no” should be embraced within a sales process.
  5. How to help transition your buyer’s journey to a more positive B2C experience.

Don’t Miss Episode 54

If you wanna check out the show notes, see upcoming guests, or play more episodes from our incredible lineup of sales leaders, visit gtmnow.com/podcast-subscribe. You can also find the Sales Hacker podcast on iTunes or Stitcher. If you enjoyed this episode, please share it on LinkedIn, Twitter, or elsewhere.

If you’ve got a great idea or a guest for the show, or if you want to get in touch with me, find me on Twitter or on LinkedIn.

Finally, thanks again to our sponsors: Chorus the leading conversation intelligence platform for high growth sales teams, and Outreach the leading sales engagement platform.

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