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After landing back at SFO airport at 2:30am last night from Philadelphia, I got up, dressed up, and showed up to SaaStr Scale in San Francisco today. Following lunch and hearing Aaron Ross speak, SaaStr CEO Jason Lemkin presented his playbook on getting from $1M to $10M ARR faster. I'd imagine every B2B SaaS founder that has yet to do a Series B (maybe even up to C) round would have wanted to be in the room when he presented. As such, here is my post and my takeaways on Jason's seminal playbook.

SaaStr Scale: The Playbook to Getting From $1M to $10M ARR Faster - My Takeaways

SaaStr Scale: The Playbook to Getting From $1M to $10M ARR Faster with Jason Lemkin "Buying should be easier than deploying." (Jason Lemkin)

Here are my takeaways from Jason Lemkin's presentation, The Playbook to Getting From $1M to $10M ARR Faster:

  • Hire all the VPs as soon as you find them after $1M ARR. It doesn't matter which VP you hire, just get them.
  • Most of the good up-and-coming VP of Sales are now tending to wait on the sidelines until a startup has crossed $8M-$10M ARR
  • SaaS enterprise workflows get complicated. Don't wait to hire a VP of Engineering
  • 2 additional six-figure deals can easily justify a VP of Product hire
  • The best VPs of Engineering are always recruiting
  • All VP hires can be accretive to the business
  • Make driving up NPS a Top 3 Company Goal
  • What's great about NPS is that it's measurable
  • High NPS leads to lower marketing costs
  • Relentlessly remove friction out of the sales process: Let customers buy the way they want to buy.
  • "You can't treat your buyers like idiots." (Jason Lemkin)
  • Consider auto downgrades as a method of removing friction from sales. Slack does it and it certainly works for them.
  • The best companies convert pilots (i.e. Proof of Concept) at 80-90% success rates
  • "Buying should be easier than deploying." (Lemkin)
  • Specialize sales team earlier. Especially by $2M ARR.
  • "Not only does sales specialization work, but you should do it far earlier in your company."
  • Segment AEs into at least 2 groups: SMB, Mid-Market, Enterprise, etc.
  • Move away from a "full-stack salesperson" model as soon as possible
  • Segment sales team by vertical, not by geography
  • Buyers want to hear from someone who has already solved their problem in their vertical
  • Outbound always works. The same is true for webinars.
  • Events always work
  • Field marketing is always a large marketing spend
  • It turns out a lot of the world does not immediately want to buy after clicking to your Contact Us page. That's where webinars come in. "If Twilio does it, you should do it." (Lemkin)
  • Spend 20% (or more) of your time as CEO recruiting
  • Hire an internal recruiter as soon as you are making 1.5 hires a month
  • "There are some folks that love doing recruiting. But that's not most of us in this room." (Lemkin)
  • You have to interview at least 30 candidates for each senior role
  • Invest heavily in brand as soon as you pass $4M-$5M in ARR. And go long.
  • "90% of the world wants to buy the default choice." (Lemkin)
  • As CEO, you want to do whatever you can with whatever you have to build your company's brand
  • "Brand is everything in the long run." (Lemkin)


SaaStr Scale: The Playbook to Getting From $1M to $10M ARR Faster with Jason Lemkin SaaStr Scale appeared to be another sold out SaaStr event


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