Mike Clayville, Chief Revenue Officer at Stripe

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The sales profession is changing more than ever as more buying behaviors turn digital. Forrester calls it the “Death of a B2B Salesman“, but I see it as an exciting opportunity for sales professionals to have more impact and use more creative skills.

One trend from the growth of the digital behaviors is the morphing of a “VP of Sales” into a “Chief Revenue Officer.” A CRO is a C-suite position not only just over sales but also over marketing, pricing, service, and product strategy in some cases.

Mike Clayville is arguably the greatest Chief Revenue Officer of our time having launched the enterprise sales team at AWS that took them from $1.8 Billion to $43 Billion over 8 years, and oversaw the growth of VM Ware becoming the largest acquisition in tech history.

This article is my summary of the most comprehensive interview I’ve been able to find with Mike Clayville about his sales leadership process. The interview is from the Kleiner Perkins Podcast with Mike Clayville, CRO at Stripe.

Increase in search volume for “Chief Revenue Officer” over the past 17 years.

Mike’s Career:

  • Past three decades has focused on working for “tornadoes” or high-growth companies.
    • One quality of working at a tornado is “building something that has never been built before.”
    • At a tornado, you need to be a builder and an inventor. This means you need to be willing to be wrong because you cannot predict the future.
  • VMWare, AWS, and Stripe. Did time on the product team with VMWare. 
  • Took Amazon Web Services (AWS) from 2013, $1.8 Billion – 2020, $43 Billion (350 – 22,000 reports).
  • IBM was the most profitable company in the world when Mike Clayville joined, and then the year after, least profitable. Days of Ross Perot. 
    • Did first reductions in company history. 80% of his team. 

Values

  • One thing that’s true, we all need to be part of a community. 
    • Whether they ask or not, you’re there. That is what the cowboy hat represents. 
  • When thinking about change, consider the customer first. 
    • Consider first principles.   
  • How to find great people for go-to-market
    • Loving change: There is a Darwinism about sales. If you’re not evolving, you will die. You have to change every day. Must change in the right way. 
    • Innate curiosity: it helps them ask that next question to the customer to uncover the big problems from the customer. 

Sales Methodology

  • Convince Customers Using Proof points: Proof points are the demo, peers (other customers), 3rd party analysts (Let me tell you why your current IT infrastructure is not optimal. This is what your competitors are doing.)
  • Bring in lighthouses: General Electric and Capital One were mine for moving to public cloud for AWS. (A big turning point was CIO of GE saying they are going all in to public cloud because they can go faster and save money) Lighthouses sway both other customers and your employees internally. 
    • Build lighthouses by developing a relationship with the senior most executive.
    • Create engagement across the entire client organization to spur on change management.
    • Sales is always about change management. The “frozen middle” management will slow things down. Your job as CRO is to support your executives at the client with change management.
  • Customer Centricity: If you make the customer successful, the business will take care of itself.
    • Often, executives get off topic on client calls. One strategy to be more customer-centric is to redirect the executive by asking a question from the client’s chair that needs to be asked on the meeting.
  • Prospecting: Is the calisthenics of sales. It must be a daily practice. Call coldest prospects first. The most likely sale should be the last call you make.
    • Targeting is the first part of prospecting. Understand the use case and the customer you are selling to.
    • First contact is needs to make contact. It is the “meaningful interaction”.

Leadership Methodology

  • Decision-Making: As a leader, you make two types of decisions every day, those you can and cannot reverse.
    • Reversible Decisions: Need to be made quickly if you want to operate at speed. Be comfortable making decisions with 70% of the information rather than 99% because it will build agility.
    • Irreversible Decisions: Pause before making these decisions. They must have a high win-rate. Do not take the same amount of time with every decision.
    • Example of Irreversible Decision: AWS did not have an enterprise sales organization, and he made the decision to build that out. It was an irreversible decision based on how it impacted morale and culture at the company.
  • Tactics Inform Strategy: CROs have to go deep into the tactics that is informing their strategy. What is slowing people down?

Amazon’s Secret Sauce

  • Time Horizons as a competitive advantage. Jeff Bezos believes that something truly pioneering will not be obvious. You have to be willing to wait longer than most people will wait to get an outcome. That is one of the secret sauces of Amazon. Are you willing to be misunderstood for a long period of time? This also helps keep an innovative culture. 
    • Example of Time Horizon: One of big negatives in software sales is the concept of ‘Shelfware’. How do you align sales compensation for longer term success of company? We don’t do enterprise license agreement. Every hour, you can fire us. I get economic value when you get economic value. I only get paid when you get a transaction. 
  • You Should Be Failing. If you’re not failing, you’re not innovating. Product development starts when the product gets released. 

Extras:

  • Executive briefing for customer meeting: Executives need to know what are the three things the customer needs out of this meeting. 
  • Made mistake of keeping technical team separate from sales team. 
  • Don’t make an investment by giving it away for free. Make investment by finding the value your product brings to the customer. 

Cancer Fight:

  • Cowboy hat came after the cancer fight of his late wife because it represents ranching community. Everyone was there to help. You didn’t have to ask, and they just showed up. 
  • Kept optimism. We know the chances, but we are going to be the one in a million that makes it through this. 

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