PODCAST 25: From SDR to VP of Sales at Lucidchart w/ Dan Cook

Have you ever dreamed of becoming a VP of Sales? This is the podcast for you. This week on the Sales Hacker podcast, we speak to Dan Cook, SVP of Sales & Success at Lucidchart, one of the fastest-growing SaaS companies in the US, about what it takes to become a sales executive at a top company.

If you missed Episode 24, check it out here: PODCAST 24: Building a Tier 1 Saas Company From the Investor Perspective

What You’ll Learn

  • The merits of a background in Finance when working at a startup
  • Why culture eats strategy for breakfast
  • Using your competitive advantage to your strength
  • The importance of execution over the perfect idea
  • How to use skip level meetings to drive alignment
  • Using quotas as a motivational tool

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Show Agenda and Timestamps

  1. Show Introduction [0:09]
  2. About Dan Cook: An Introduction [2:45]
  3. Dan’s Management Hypothesis and Principle [24:52]
  4. Skip-level Meetings Lead To Better Communication And Drive Alignment [30:56]
  5. 4 Decisions That Led To Success [33:09]
  6. Attainable Quotas Boost Confidence And Create A Winning Culture [39:37]
  7. Sam’s Corner [48:17]

Sales Hacker Podcast — Sponsored by Aircall and Outreach

Sam Jacobs: Hi folks, it’s the Sales Hacker Podcast. We’ve got Dan Cook on the show this week, the SVP of Sales and Success at Lucidchart. It’s a great interview so I’m excited for you to listen to it.

But first, let’s talk about our sponsors. We’ve got two–the first is Aircall. It’s a phone system designed for the modern sales team. They seamlessly integrate into your CRM, it eliminates data entry and it provides you with greater visibility into your team’s performance through advanced reporting. Really impressive business and so I encourage you to check them out.

Our second sponsor is Outreach.io, the leading sales engagement platform. Outreach triples the productivity of sales teams and empowers them to drive predictable and measurable revenue growth. By prioritizing the right activities and scaling customer engagements with intelligent automation, Outreach makes customer facing teams more effective and improves this ability into what really drives results. Without further ado, on with the show.

About Dan Cook: An Introduction

Sam Jacobs: I am excited to welcome Dan Cook to the podcast. Dan Cook is the SVP Sales and Customer Success at Lucidchart. It is a 350 employee SaaS business based in Salt Lake City, Utah, one of the sales capitols of the world. Dan, welcome to the show.

Dan Cook: Hey Sam, thanks for having me. It’s great to be here.

Sam Jacobs: We’re excited to have you. So, you’re in a very senior position at a pretty well known company, how did you get here? Tell us a little bit about your origins.

Dan Cook: At BYU, I got exposed to some really smart people that all said “Hey you should go and get into investment banking.” I hated my investment banking job, but I worked with the technology group, which basically helped tech companies raise capital, go public, or engage in mergers and acquisitions.

That, to me, was a pivotal experience. I realized that I didn’t like being in situations where I wasn’t engaging with other people and I was working 80 to 90 to 100 hours a week. I realized that wasn’t sustainable, nor was it a lifestyle that I really appreciated. While the experience wasn’t always fun, I did feel like it taught me this principle of compound interest. I felt by investing heavily in my career early, it actually helped catapult me faster than maybe if I had taken a more traditional job.


Dan’s Management Hypothesis and Principle

Sam Jacobs: One of the big questions we often get on the podcast is that leap from individual contributor to manager–what did you do to make sure that you did a good job? What’s your approach to management?

Dan Cook: From my perspective, I felt like there were a few things that I had to do early on.

One was be directly involved with the reps themselves and make sure that everything that I thought I had figured out was being implemented to some degree and I wanted the process to be pretty consistent across the four reps.

My hypothesis and this kind of management principle for me, is that, first of all, people like to hear the sound of their own voices, and so anytime you can ask a question instead of telling somebody something, you’re always going to be better off.

Secondly, if you learn to ask the right questions, you can generally guide people to your same conclusion, and so my management philosophy early and certainly still today has been ask a lot of questions.

The follow-up question “tell me more” has got to be one of the best questions ever invented. I think I learned a lot that way and was also able to direct the team to make them feel like they had buy-in and ownership of the program, while guiding them towards the things I wanted them to do.


Skip-level Meetings Lead To Better Communication And Drive Alignment

Sam Jacobs: Communication is what either enables or prohibits scaling. What are the specific strategies that you use?

Dan Cook: We did a few things. First of all, the weekly one-on-one is fundamental, and you have to find time to sit down with your direct reports and make sure you’ve got that one-on-one scheduled. That’s just 101.

The second thing that we did that was really helpful for us was we incorporated what we call a skip-level cadence. The way you might think about this is if I’m managing a manager who has a team, then I would find once a month, or once a quarter, to actually have a one-on-one with the skip-level individual.

I don’t meet with the manager, I meet with the direct report. And what that allows you to do is filter through the B.S. and say hey, tell me how you’re really doing, and tell me how things are working on your team. It tightens or allows for that communication gap to really shrink.

We also have our managers do skip-level reports so the guys that report to me, skip-level to our CEO. Again it shrinks the distance, so to speak, between the managers, the executives, and the sales team and, for that matter, the customer.


4 Decisions That Led To Success

Sam Jacobs: You’ve been a banker, you’ve been a VC, you went to Harvard, and now you’re helping scale some large organization. When you reflect, what do you think are the main differentiators that you embody, or that are advantages for you?

Dan Cook: There’s a few decisions that, when I look back on, were made that I think certainly helped me.

  1. The Theory of Compound Interest. There are individuals who are working very hard and putting in a lot of time, and, if that time is used wisely, they’re growing and they’re getting exposed to things in a way that will ramp their career more than if they just worked the standard 40 hour work week.

And don’t get me wrong, there is a time and a place for finding balance, but I do think early in your career, if you want to have success, that’s the time to invest. Generally speaking, you might not have a family yet so I think early investment in your career is first and foremost really important.

  1. Finding Balance. At the end of the day, no matter how hard you push yourself earlier in your career, or even later in your career, if you don’t find balance in what you’re doing, you won’t be happy, and if you’re not happy in what you’re doing, you won’t be good at it.


  1. Asking The Right Questions. There’s a professor named Clayton Christensen, who had this concept about how 99% of the battle is learning what questions you should be asking. And learning how to ask the right question.

When you see someone around you who’s really successful in their role, you should reflect and say, “What question did they ask in their brain that got them to ask those questions or to do that thing with their prospect?” That practice is really great because once you start to do that exercise instead of just copying someone, if you actually ask “why are they doing that and what did they do to get there?” your brain learns faster and you become better.

  1. Don’t Be Defensive In Your Career. Always be looking to hire someone that’s better than you. Generally speaking, not always, that will actually elevate you. Go and work somewhere where you can surround yourself with people who are better than you, who are smarter than you, who are more experienced and have been more successful. And don’t let your ego get in the way. And I think that sets you up for a lot of different success.

Attainable Quotas Boost Confidence And Create A Winning Culture

Sam Jacobs: What’s your point of view on sort of how to incentivize a sales team?

Dan Cook: My point of view is that quotas should be set in a way where everyone can attain them and where everyone does attain them. What happens in sales, is there’s this confidence concept. When you’re able to perform, your confidence is through the roof. You start to believe in yourself. Sometimes irrationally. But confidence is so critical in what we do.

When you set quotas in a way where people can achieve them, their confidence goes up. They want to come to work and, when they go home from work, they’re happier. Which means when they talk to their significant other, their partner, their boyfriend, their girlfriend, they’re saying how much they love their work, which breeds even more satisfaction with the job.

We’ve also found there’s this other positive, which is that as soon as somebody starts having confidence, they go and tell everyone. All of a sudden our recruiting effort is enhanced significantly.

So what does that mean? How far do you go? Do you really want 100 percent of your reps to hitting the number? There’s certainly a little art to it. If you create that winning team and winning culture, I think it covers a multitude of other sins, so to speak. We think it’s one way that we can make sure we’re building a winning culture and team.

Sam Jacobs: Wonderful. Dan thanks so much. This was a great conversation.

Dan Cook: Thanks Sam. Thanks for having me.


Sam’s Corner

Sam Jacobs: Hey folks it is Sam’s Corner. Dan Cook, really dynamic individual. Dan mentioned that one of the greatest challenges was becoming a manager of managers. He employs quarterly skip meetings between the rep and the manager’s manager so that they can all stay kind of in communication. It provides an ongoing story of the business that kind of reinforces the main themes that you might be trying to instill.

I’m a big believer in daily huddles. I believe in the rhythm and the motion of the business and you talk, every day. You figure out that rhythm of being accountable for what you’re doing and then have different mechanisms, like a skip-level meeting, or a weekly email that ties the day back to the week, which ties up to the quarter, which ties up to the year because that’s how things get done. Every day, every moment, and then, slowly, that builds to a multi-year journey.

This has been Sam’s Corner. Thank you so much.

Don’t Miss Episode 26

To check out the show notes, see upcoming guests and play more episodes from our incredible lineup of sales leaders visit gtmnow.com/podcast-subscribe.

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Once again, a huge shout out to our sponsors, Outreach and Aircall. If you want to get in touch with me, find my social handles in my bio below.

Thank you for listening. I will see you next time!

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