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PODCAST 21: The Making of a Top-Producing Silicon Valley VP of Sales

Sam Jacobs

August 22nd, 2018

Key elements of sales leadership

On this 1×1 interview with Mark Cranney, the Chief Commercial Officer of SignalFx, we chat about the key elements of sales leadership and his journey to being a top VP of Sales. Tune in!

If you missed episode 20, give it a listen here: PODCAST 20: How to Negotiate More Effectively to Close More Deals

What You’ll Learn

  • How to find success in sales management
  • What criteria to look for in sales leaders
  • What sets great executives apart
  • How to be a “pro not a schmo”
  • What changes have occured in the sales world over 10-15 years

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Show Agenda and Timestamps

  1. Show Introduction [0:10]
  2. About Mark Cranney: A Brief History [3:00]
  3. Be a Pro, Not a Schmo [6:06]
  4. Top 3 Criteria For Sales Success [11:34]
  5. The Difference Between First Line and Senior Executives [15:01]
  6. Evaluating Internal Promotion Vs External Hires [18:18]
  7. ARR Milestone Breakdown [20:15]
  8. The Changes In and Evolution of Sales [34:06]
  9. Being A Student Of The Game [40:03]
  10. Sam’s Corner [42:30]

Sales Hacker Podcast — Sponsored by Aircall and Outreach

Sam Jacobs: Hi folks. Welcome to the Sales Hacker podcast. Super exciting week. We’ve got Mark Cranney on the podcast this week, which is amazing. The first thing we want to do, as always, is thank our sponsors.

The first is Aircall, the phone system designed for the modern sales team. Aircall seamlessly integrates into your CRM, eliminating data entry for your reps, and providing you with greater visibility into your teams’ performance through advanced reporting.

Our second sponsor is Outreach.io, the leading sales engagement platform. Outreach.io is the leading sales engagement platform. They make customer-facing teams more effective and improves visibility into what really drives results.

Without further ado let’s listen to Mark Cranney, famous Silicon Valley CRO, and VP of sales. Super honored to have Mark on the show, so let’s take a listen.

About Mark Cranney: A Brief History

Sam Jacobs: I’m really delighted and honored to share the microphone today with Mark Cranney.

Currently, he’s the chief commercial officer at SignalFx. But prior to joining SignalFx, Mark was an operating partner at Andreessen Horowitz, a Silicon Valley venture capital firm.

He’s also held senior executive positions at Hewlett-Packard and was in leadership roles at Opsware.

Welcome, Mark, to the podcast.

Mark Cranney: Thanks, Sam, for having me!

Be a Pro, Not a Schmo

Sam Jacobs: How did you figure out that you wanted to be a manager? What were some of the tools, the tips, the strategies that you used to be successful in those first managerial days?

Mark Cranney: I say this to my team all the time, “Be a pro, not a schmo.”

Particularly early in your sales career, I see a lot of the younger crowd don’t approach the job as their profession. A lot of people really don’t understand that it’s not just the product that can set you apart, it’s you.

You are the big differentiator as an individual contributor. And you have the ability, even as an individual contributor, to be in a leadership position. Master that first, and then enjoy helping other people from a team standpoint: teaching, coaching. If I hadn’t of gone into this path I have probably ended up in sales coaching.

Top 3 Criteria For Sales Success

Sam Jacobs: What are the criteria that make a successful salesperson?

Mark Cranney: My criteria kind of falls in three buckets.

The first is you want to look at their track record. Leading indicators are past performance, that’s probably the easier thing to vet out in selecting talent.

Then comes the character bucket. Do they have the courage to push through resistance? How competitive are they? Is there focus and discipline to study, and drill, practice, and get better on a day-to-day basis? What’s their work ethic?

The last one is empathy. Do they have the ability to put themselves in the buyer’s shoes and understand what’s going on in their world individually and as a company?

Measuring Courage In Sales

Sam Jacobs: How do you measure courage? I was struck by the use of that word.

Courage, like, jumping in a river and saving someone is different type of courage than when I’m talking about. It’s business courage — pushing through the resistance from a seller’s standpoint.

Mark Cranney: There’s different types of courage. If you’re an SDR, do you have the courage to get some height and width in the account? Do you have the courage to push through resistance?

Sometimes you have to go above, around resistance. You have to address an enemy in an account, or you have to challenge a prospect or customer if you truly believe. If you’ve done your homework you’re extremely competent with your value proposition.

Getting competent gives you confidence, which gives you the courage to do the right thing, to push through the resistance.

Related: A Salesperson’s Go-To Guide To Improve Business Acumen

The Difference Between First Line and Senior Executives

Sam Jacobs: What are the critical differences that separate a senior sales executive from a manager and all of the tiers below?

Mark Cranney: The first line manager has to have mastered the value proposition, the market sales process etc. But they’re probably also somebody that has run somebody else’s playbook, from a process standpoint.

A great CRO is somebody that can come in and they’ve really created a from-the-bottom-up playbook and process at a very detailed level. They’ve got the feel and the situational awareness to go figure out when and where and how to go put things together.

That’s probably the biggest difference — the playbook. Can they run one? Running somebody else’s system versus putting it together are two completely different things.

Related: The Best Sales Managers Don’t Chase Revenue: 6 Steps to Get Goal-Setting Right

Evaluating Internal Promotion Vs External Hires

Sam Jacobs: How do you think about helping founders evaluate when is the time for an outside hire vs. an internal promotion?

Mark Cranney: I love seeing the high potential grow into the role. The thing they bring to the table is knowledge of the solution, the value proposition, the customers, and advising the founder or the CEO.

A lot of it probably depends on them and their ability to essentially coach them up and help them grow. Where do they hit a wall?

You’re going to probably have help from your board. But reach out and build a team of advisors that are best in class from a sales and marketing standpoint. It could be customer success, that could go help that executive grow, and help you assess if they can make it to the next level or not.

Sometimes though, you have to go fast — you don’t have time to let them grow.

ARR Milestone Breakdown

Sam Jacobs: What are the natural ARR milestones that seem to be indicative of something shifting?

Mark Cranney: $0M to $10M is probably the toughest and where you’re really trying to find that recipe to systematize. I think once you crack $10M, I can typically see the path to $100M from $10M.

I think that’s probably where the breakdown is. Having been in all the different phases from $0M to managing a few thousand people at complete scale helps dramatically. You then know what needs to come next and you’ve got that awareness of the building blocks that need to be there.

Getting up to that $100M, I’m looking at a billion. You do or you don’t, but you can start to at least understand what needs to come next. Breaking it down into the smaller buckets, I think’s tougher.

Sales Now Vs. 10 Years Ago

Sam Jacobs: What’s stood out to you as some of the biggest changes in the sales world from now, versus maybe 10 or 15 years ago?

Mark Cranney: Oh, I think a lot’s changed. The customers are armed with way more information prior to the reach-out. So I think ABM and account based sales are super important.

And the tech is just so much better, right? The tooling has changed from a Customer Relationship Management and marketing automation standpoint.

The biggest thing is just the power and knowledge that the buyer has. Marketing and customer success are really being able to take the iron out and just flatten everything. I don’t have three functions that are pointing fingers at each other.

Related: PODCAST 10: Using Data to Align Marketing, Sales, and Customer Success

Being A Student Of The Game

Sam Jacobs: Is there something that’s had a big impact on you over the last couple years?

Mark Cranney: Look, be a pro not a schmo. Become a student of the game is what I suggest with everybody. Consume data, study, practice, drill, rehearse.

Sam’s Corner

Sam Jacobs:  Hey everybody, it’s Sam’s Corner. We just continue to get amazing guests here on the Sales Hacker podcast.

Mark Cranney is somebody that a lot of people know. He’s featured very prominently in The Hard Thing About Hard Things, and now he’s chief commercial officer at Signal FX.

Just a quick interesting point that Mark said is that there’s a lot of pushback against celebration, particularly for the sales team.

And what I try to convey to people that I work with, particularly CEOs, is there are different cultures, and sales teams need to be motivated and people need to celebrate.

What we do is hard so when we do get that win, I think it’s okay to celebrate.

It takes a lot of different types of people to build a company, and let’s make sure that we empower the salespeople on the team, whatever gender, race, ethnicity, or age. This has been Sam’s Corner, I’ll talk to you soon.

Don’t Miss Episode 22

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

You can also find the Sales Hacking podcast on iTunes or Stitcher. If you enjoyed this episode please give us a share on LinkedIn or Twitter.

Finally, a special thanks again to this month’s sponsors, Outreach and Aircall. If you want to get in touch with me, find my social handles in my bio below.

I’ll see you next time!


Also published on Medium.

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

About the author

Sam Jacobs

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.

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