Sam Taylor, VP of Sales and Customer Success at Loom (previously at Quip and Dropbox), discusses GTM discovery strategies for product-led growth companies transitioning to enterprise sales.
“I refer to our early sales team as workflow therapists. Like, lay on the couch. Tell me all your problems. Like, let's understand, like, there has to be an innate reason of why has someone individually gone and signed up for your product and inserted it into their day, and how do you find the trend lines between those?”
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More from Sam Taylor
Insight
Taylor: Organic user engagement drives enterprise sales faster than security features
“Product leads everything. And the more compelling thing, in my view, if you're going up into the enterprise, having depth of engagement, having there be masses of folks that are gravitating towards your product, regardless of even talking to someone, and that …”
Sam TaylorJul 21, 2022▶ 18:12Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Taylor: Every founder who raises capital has already done sales
“I'd kind of call bullshit on the founder can't create it. Like, if you raised money, you started a company, and you have the capital to hire anybody, you're in sales. So you've already created that sales pitch.”
Sam TaylorJul 21, 2022▶ 11:15Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Taylor: Asking candidates to solve company problems on the fly fails
“Asking somebody to solve your company's problems on the fly in real time is broadly not setting anybody up for success.”
Sam TaylorJul 21, 2022▶ 33:54Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Startups should avoid heavy variable compensation for their first sales hires
“Variable compensation is an excellent lever at the right time, and I don't think the right time is going to be your first couple of hires, because you got no data, and if we're looking statistically at someone having, you know, let's call it between 50 and 30%…”
Sam TaylorJul 21, 2022▶ 37:01Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Opinion
Sam Taylor: Startup founders who raise capital have already proven sales ability
“I'd kind of call bullshit on the founder can't create it. Like, if you raised money, you started a company, and you have the capital to hire it, you're in sales. So you've already created that sales pitch.”
Sam TaylorJul 27, 2022▶ 22:2420VC: The Memo: What is a Sales Playbook? Does the Founder Need to Create It? Should the First Sales Hire Be a Leader or a Rep?
Insight
Sam Taylor: Early sales teams must deliver customer insights alongside ARR
“With these early hires, and I still repeat this, and my team, if they listen at some point, they're going to go, oh man, there he is saying it again, but I really view that our team is on the hook for two things, ARR and Insights. And the insights are almost a…”
Sam TaylorJul 27, 2022▶ 24:3520VC: The Memo: What is a Sales Playbook? Does the Founder Need to Create It? Should the First Sales Hire Be a Leader or a Rep?
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