Fivetran's Lauren Schwartz: Must-Ask Questions to Identify Potential Sales Talent | 20VC #939
Harry Stebbings (host), Lauren Schwartz (guest)
In this episode of The Twenty Minute VC, featuring Harry Stebbings and Lauren Schwartz, Fivetran's Lauren Schwartz: Must-Ask Questions to Identify Potential Sales Talent | 20VC #939 explores lauren Schwartz Reveals How to Hire And Ramp Elite Sales Talent Lauren Schwartz, enterprise sales leader at Fivetran and formerly Segment and Google, breaks down how to identify, hire, and develop high-performing sales reps in both startup and enterprise environments.
Lauren Schwartz Reveals How to Hire And Ramp Elite Sales Talent
Lauren Schwartz, enterprise sales leader at Fivetran and formerly Segment and Google, breaks down how to identify, hire, and develop high-performing sales reps in both startup and enterprise environments.
She emphasizes curiosity-driven discovery, rigorous qualification, and multi-threaded enterprise selling, while challenging outdated tactics like discount-led urgency and black-box pricing.
The conversation dives deep into designing early sales motions, structuring interviews and onboarding, running effective deal reviews, and using sales feedback to shape product and go-to-market strategy.
Lauren also discusses leadership style, building psychological safety, aligning comp plans to consumption and value, and the importance of diversity and internal promotion in sales leadership.
Key Takeaways
Relentless curiosity and discovery are core sales superpowers.
Lauren argues the best sellers are insatiably curious about customers’ current and future states, ask open-ended questions, and ruthlessly qualify opportunities by tying pain to concrete business outcomes like revenue, cost savings, or risk mitigation.
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Create urgency by working backwards from value, not discounts.
Instead of relying on end-of-quarter discounts or relationship pressure, she recommends mutual action plans built in reverse from the customer’s target business outcome date, helping them see when they must sign to realistically realize value.
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Hire early reps who are both fearless and process-driven.
Founders should prioritize sellers who can operate in ambiguity, kick down doors, and still run a consistent process so the company can learn what’s working and build a repeatable playbook, rather than “artist” reps who do something different every time.
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Use precise, evidence-based interview questions to cut through performance.
Lauren avoids theoretical questions and instead probes attainment history, specific deals, the candidate’s exact contribution, and even asks for the ‘second favorite deal’ and real customer references to get beyond rehearsed stories.
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Enterprise selling demands multi-threading and deep stakeholder alignment.
She stresses mapping champions (including those for competitors and for ‘do nothing’), validating pain and desired outcomes with multiple stakeholders, and then presenting the synthesized picture to the economic buyer so they feel researched, not sold.
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Onboarding should maximize at-bats and codify learnings from the field.
New reps should quickly get exposure to customer conversations via recorded calls, shadowing, and low-risk meetings, paired with libraries of deal reviews and postmortems so they can pattern-match what works in that company’s motion.
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Align compensation and culture with long-term customer value.
Lauren critiques black-box, shelfware-heavy pricing and pure bookings-based comp, advocating instead for models that reward adoption and consumption so incentives for AEs, customers, and the company stay tightly aligned over time.
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Notable Quotes
“The best skill you can develop in sales is an insatiable curiosity about what’s possible.”
— Lauren Schwartz
“You’re not selling. You’re helping them participate in their own rescue.”
— Lauren Schwartz
“If you don’t have an answer to ‘why do it now,’ slipping isn’t even the right term. It was never going to be a deal this quarter.”
— Lauren Schwartz
“Any good seller can sell you a dream. You have to test for specifics and repeatable performance.”
— Lauren Schwartz
“There is no substitute for deep curiosity, which drives relentless discovery and ruthless qualification.”
— Lauren Schwartz
Questions Answered in This Episode
How would you adapt Lauren’s interview framework for hiring your very first, non-enterprise sales rep?
Lauren Schwartz, enterprise sales leader at Fivetran and formerly Segment and Google, breaks down how to identify, hire, and develop high-performing sales reps in both startup and enterprise environments.
Get the full analysis with uListen AI
What specific questions could you add to your current discovery process to better uncover ‘why do anything, why now, why us?’
She emphasizes curiosity-driven discovery, rigorous qualification, and multi-threaded enterprise selling, while challenging outdated tactics like discount-led urgency and black-box pricing.
Get the full analysis with uListen AI
If your comp plan today is bookings-driven, what would it take to shift toward consumption or value-based incentives?
The conversation dives deep into designing early sales motions, structuring interviews and onboarding, running effective deal reviews, and using sales feedback to shape product and go-to-market strategy.
Get the full analysis with uListen AI
How can you practically build psychological safety in a small, numbers-driven sales team without lowering performance standards?
Lauren also discusses leadership style, building psychological safety, aligning comp plans to consumption and value, and the importance of diversity and internal promotion in sales leadership.
Get the full analysis with uListen AI
In your current deals, who is the ‘champion for doing nothing,’ and how could you identify and engage them more deliberately?
Get the full analysis with uListen AI
Transcript Preview
Lauren, I am very, very excited for this. I've heard so many things from Jordan, from Zhenya, from th- your time together at, uh, Segment, so thank you so much for joining me today.
Well, thank you for having me, and likewise. Your reputation precedes you as well.
That is very kind. Uh, they're forced to actually say nice things about me. It's the joy of my business. But I would love to start with a little bit of context on you. So, we see the incredible companies you worked with from Segment to now Fivetran, but how did you make your way into sales first, and then come to be an enterprise sales leader with Fivetran?
Yeah. Um, well, I discovered sales at the age of seven when I became a Brownie Scout, and th- that's when I fell in love with the art of cookie sales. So, thinking back to that time in my life, absolutely-
Can I- can I ask, what did y- what did you love about sales then? What was it?
Oh. Well, we were selling cookies, and there was an opportunity to create repeat purchasing, uh, by evangelizing the- the freezer lifespan of a cookie. So, for me, it was really about the opportunity to compete with other Brownie troops, uh-
(laughs)
... but also to spread the love that I personally have for cookies.
(laughs) And so you're-
Um-
... seven, you realize the love of sales through selling cookies, which I'm sure you won this competition with other brownie providers.
No. (laughs)
Um, w- take- take me forward a little bit. What happened then?
So, then, um ... no, I mean, as I, as I moved into my, my career after college, I, I started things at Google. Um, I spent six years in sales at Google, uh, where I learned a ton from the machine that is Google and really, it's- it's a great place to grow up and learn from adults. Uh, which is, you know, different from working in a startup. So, uh, learned a lot there, and that's ... I landed at Google, um, I'm born and raised in the Bay Area, in San Francisco, um, and I landed at Google because I knew it would be a great place to learn from really smart people. Um, and that, to me, was what got me excited about sales, uh, learning from the best. After about six years at Google, uh, I decided I had learned enough about sales (laughs) and I went to business school, uh, where I wanted to learn a little bit more about just how to run a business. And, um, I actually spent a lot of time at Stanford trying to distance myself from being labeled as a salesperson.
(laughs)
I think it's ... you know, the associations people make with sales professionals are rarely positive, um, even just the word selling. You know? No- nobody-
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