Oct 19, 2022 · 50m · news
Fivetran's Lauren Schwartz: Must-Ask Questions to Identify Potential Sales Talent | 20VC #939 · 20VC with Harry Stebbings
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode, Fivetran's VP of Enterprise Sales Lauren Schwartz shares her comprehensive playbook for B2B sales success, covering value-driven discovery, strategic partner co-selling, and rigorous hiring methodologies. She details how to build highly effective sales teams and navigate modern enterprise SaaS motions to accelerate business growth.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 22.3% of the talking time here. How this is scored →
Harry as informed peer 4.3 Guest teaching 5.0 Guest disagreement 1.9 Harry pushing back 3.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 44:11 Lauren corrects Harry's management premise
Lauren directly refutes Harry's pushback on deal inspection transparency, explicitly pointing out that he is confusing candidate interviewing with team leadership.
Hardest push from Harry ▶ 43:41 Harry defends withholding intent in deal reviewsHarry forcefully rejects Lauren's advice to explain the 'why' during deal inspection, offering a counter-argument that transparency lets reps tailor answers to what leaders want to hear.
Biggest teaching moment ▶ 18:35 Lauren dismantles artificial urgency tacticsLauren corrects Harry's proposal of discounting and relationship-based begging, demonstrating how to construct genuine deal urgency using backward timelines and mutual action plans.
Harry holds his own ▶ 8:02 Harry challenges early-stage co-selling feasibilityHarry demonstrates strong industry awareness by pushing back on Lauren's playbook, asking how early startups without market leverage can realistically co-sell with giants like Snowflake.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Google Takeaways & Uncomfortable Discovery Conversations | 4 | 4 | 1 | 2 | Harry probes Lauren's Google takeaways and asks her to roleplay a first-day sales rep scenario. Lauren explains how to navigate uncomfortable customer discovery conversations. | |
| Modern Outbound, Partner Co-Selling, & Playbooks | 5 | 5 | 2 | 5 | Harry challenges Lauren's recommendation of partner co-selling by pointing out that early-stage startups lack leverage with big tech partners. Lauren reframes outbound around community warm introductions and ecosystem leverage. | |
| Sales Playbooks, Career Transitions, & PLG vs. Enterprise Sales | 4 | 5 | 1 | 2 | Harry asks about sales playbooks, PLG versus enterprise sales models, and multi-threading. Lauren explains why playbooks are too rigid early on and why top-down sales must complement PLG. | |
| Creating Urgency & The Backward Timeline | 4 | 6 | 3 | 3 | Harry suggests using discounting or personal relationships to create deal urgency. Lauren explicitly rejects these tactics as cheapening product value and advocates backward timeline planning instead. | |
| Structuring the Hiring Process for Sales Talent | 5 | 5 | 2 | 3 | Harry brings up industry hiring models like Jason Lemkin's two-rep 'Hunger Games' and sales attribution edge cases. Lauren reframes hiring two reps as separating signal from noise and outlines interview strategies. | |
| Case Studies, Role Plays, & Hiring Mistakes | 3 | 4 | 1 | 2 | Harry asks about candidate presentations and Lauren's biggest hiring mistake. Lauren critiques traditional candidate presentations and recommends off-the-cuff roleplay. | |
| Onboarding, Ramping, & Assessing Sales Reps | 3 | 4 | 1 | 2 | Harry asks how to evaluate sales reps during long enterprise sales cycles before deals close. Lauren explains leading process indicators like trial resource discipline and economic buyer alignment. | |
| Best Practices for Deal Reviews & Sales Leadership | 6 | 7 | 4 | 6 | Harry directly opposes Lauren's advice to share the 'why' during deal reviews, arguing for keeping mystery to avoid leading the witness. Lauren corrects him by noting he is confusing interviewing candidates with managing a team. |
Statements from this episode (22)
Schwartz: Curiosity and asking for forgiveness are essential sales skills
“The best skill you can develop in sales is an insatiable curiosity about what's possible. And truly the instinct to ask for forgiveness rather than permission.”
Schwartz: Sales teams heavily overlook the value of ecosystem co-selling
“So I think actually the value of co-selling with sales teams at other businesses that are in your ecosystem, where a customer would benefit from the compilation of what we call a modern data stack. Is, is really overlooked in sales.”
Schwartz: Startups are never too early to build go-to-market partnerships
“So I don't actually think there is ever a time that's too early in a founders in, in a startup's life cycle to lean on the connections you have in your community to start developing those partnerships.”
Schwartz: Early startup salespeople are equal parts sellers and product R&D
“The role of the salesperson, especially in an earlier stage startup is equal parts sharing the story and the vision of your product, but also doing research and development, right?”
Schwartz: Fixed sales playbooks are too prescriptive for early startups
“I think that the word playbook is like a little prescriptive for super early stage startup. I think If what we're thinking about is first couple of hires and what they actually need, their job is to go out into the market and collect information about your add…”
Schwartz: Combining top-down sales with PLG drives true enterprise momentum
“That like top-down sales combined with product-led growth is how you truly drive momentum.”
Schwartz: Enterprise deals lacking a clear 'why now' were never real
“At Fivetran we say, why do anything? Why do it now? Why do it with Fivetran? Right. And those are the questions that you need to be answering on every deal. And if you don't have an answer to why do it now, slipping isn't even the right term. It was never goin…”
Schwartz: Discounting and relationship-based selling cheapen your product's value
“I don't really buy into discounting or relationship selling personally to me. That's a sort of cheapening the value that this company is going to get from their investment in your product.”
Schwartz: Early-stage startups need scrappy reps, not tenured sales leaders
“You don't need someone who has spent their career scaling sales organizations and building out a ton of process. You need someone who is willing to get out there And kick down doors and ask the hard questions that will allow you to have to take that feedback a…”
Schwartz: Startups must hire two sales reps simultaneously to test market demand
“You do want to have multiple sellers going at the same time. Otherwise, you know, let's say it's Lauren and Harry and If it's just Lauren and Lauren is a terrible salesperson, then you didn't really learn anything about your product or your messaging or your c…”
Schwartz: Sales interviews must target specific metrics over open-ended storytelling
“What's really important when you're interviewing salespeople is that you don't leave it open-ended for storytelling because any good seller can sell you a dream, right? And so unless you are testing for the specifics and the metrics and the repeatable performa…”
Schwartz: Segment initially rejected her because her Google background lacked scrappiness
“I was actually rejected when I first interviewed at segment because one of the pieces of feedback was, well, you came from Google. We don't think you're likely to be that scrappy.”
Schwartz: Asking candidates about lost deals reveals their internal locus of control
“And then I do this a lot when I ask about, tell me about a deal that you lost. And the reason I want to learn about that is because you get a really good signal about someone's locus of control. Either they're, they have an internal locus of control and they'r…”
Schwartz: Having sales candidates pitch prior products in interviews is ineffective
“I've spent a lot of time hiring people with, when they had to come pitch their product, That's not usually that valuable because often the people in the room like on the panel don't, they haven't been in the seat of the buyer. And so no one really knows what t…”
Schwartz: Spontaneous role-plays reveal if sales candidates can listen and pivot
“I often will just do a role play with them that they're not prepared for. So something like, all right, real life situation that I'm facing. We're deep in procurement with this customer. Here's a situation. Okay. You're the sales rep on procurement. Let's go. …”
Schwartz: Sales hiring fails when leaders assume deal experience from titles
“Making assumptions about their experience. I hired someone once. Who did this was back when I was doing, we were doing pitches and his pitch was so smooth. And I was like, oh, great. You know, he's very comfortable off the cuff, blah, blah. And I had asked, bu…”
Schwartz: Managers can gauge a sales rep's eventual success within 30 days
“I'd say in the first 30 days you can get a sense of whether they're going to be successful because you're looking for things like what are they doing to What are they doing to get organized? What are they doing to start to learn about your product?”
Schwartz: Unsolved prospect problems represent sales qualification failures
“If it turns out that we don't solve the problem that they're trying to solve, that means we missed on qualification and quality qualifying them out of our pipeline.”
Schwartz: Losing to customer inertia means reps targeted minor practitioner projects
“If that happens, my reaction is what was the identified pain, how painful was it? Did we miss an opportunity to attach to a bigger business problem? Cause a lot of times when you're selling technology, you're like, oh, I found a practitioner who wants this thi…”
Schwartz: Black-box subscriptions and shelfware licensing models are becoming obsolete
“Pricing that's not aligned to value. Black box subscription shelfware, licensing. That, that model is, is moving in the past.”
Schwartz: Tying sales compensation to product adoption aligns incentives better than bookings
“A traditional bookings quota and a variable compensation structure, what that does is it drives someone to land a deal and nothing else. When you start to align compensation with the actual adoption of the product and consumption of what you sold as a salesper…”
Schwartz: Top sales performers excel in category-creating, unbudgeted environments
“I think the best sales teams are people who have had to be in a category creating environment. So people who like the real hustlers that I've seen be successful are people who are selling Products where there isn't already an identified budget and it's, it cre…”