The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

clear all ✕

why aren't all 13 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

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 Taylor Jul 21, 2022 ▶ 18:12 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
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 Taylor Jul 27, 2022 ▶ 24:35 20VC: 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
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 Taylor Jul 21, 2022 ▶ 11:15 Sam 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 Taylor Jul 21, 2022 ▶ 33:54 Sam 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 Taylor Jul 21, 2022 ▶ 37:01 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Early PLG sales reps should act as workflow therapists for organic users
“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 t…”
Sam Taylor Jul 21, 2022 ▶ 5:56 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Taylor: To convert PLG power users, ask what stops them from spreading product
“Particularly when we are using data effectively as our sales team, which means that we're trying to talk to heavily engaged users, power users, if you will, those that have the potential to be champions internally like to ask. What's preventing you from sharin…”
Sam Taylor Jul 21, 2022 ▶ 7:05 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Sam Taylor: Recording calls is the best way to document GTM
“I think the recording of calls Is actually where the most value can be had. And only because it's so rare in my experience that the founders are actually recording that and then making it available to the rest of the employee base because it's really personal …”
Sam Taylor Jul 21, 2022 ▶ 14:00 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Transitioning to an outbound sales motion requires a 12-to-18-month runway
“In my experience, that's a 12 to 18 month. Runway of actually getting the learnings, getting the motion, and getting the fruit of that labor, so to speak.”
Sam Taylor Jul 21, 2022 ▶ 22:37 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Taylor: Early sales hiring interviews require a 50-50 evaluation and selling split
“I'm a big believer that whoever the hiring manager is, whether that is the CEO, whether that's going to be another member, like there should be a very much like fifty-fifty split in terms of time of getting to know one another and feeling out the two-way stree…”
Sam Taylor Jul 21, 2022 ▶ 27:50 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Taylor: Passive engagement from new sales hires is an early red flag
“Those that are coming in that are great hires are asking really high quality questions, and they're not just asking them of their team. They're going on a frickin fact-finding mission cross-functionally, and they're building relationships to go and do it. And …”
Sam Taylor Jul 21, 2022 ▶ 44:10 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Taylor: Customer support is the best product knowledge source for sales reps
“I think a center of absolute unbelievable treasure trove of knowledge sits within a support organization, if you have one, just because they're hearing both the blemishers as well as the praises of the product on a daily basis, and typically at a much higher v…”
Sam Taylor Jul 21, 2022 ▶ 46:26 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
Insight
Sam Taylor: Analyze early power users to document founder sales playbook
“There's like an eighty-twenty value approach here, absolutely, of who are the folks that you've engaged with where there's just been an unlock. They get it. Like, I think in most companies, you find that there's going to be certain customers that just, that th…”
Sam Taylor Jul 21, 2022 ▶ 13:09 Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908 · 20VC with Harry Stebbings
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