The Twenty Minute VC

Fivetran's Lauren Schwartz: Must-Ask Questions to Identify Potential Sales Talent | 20VC #939

Lauren Schwartz is Vice President of Enterprise Sales at Fivetran, the leading platform for modern data movement. She has helped scale Fivetran’s enterprise business from its infancy to a team of nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth. Lauren earned an MBA from Stanford Graduate School of Business after 6 years at Google where her enterprise sales career began. ---------------------------------- Timestamps: 0:00 Intro 1:15 Journey into Sales 3:10 Biggest takeaways from working at Google 4:45 What to tell a first day sales rep 6:40 Does outbound sales still work today? 8:03 When do partnerships become viable? 9:30 How to turn sales insights into marketing 11:00 How to think about the sales playbook 13:06 PLG or enterprise, do startups need to choose? 14:25 How important is “multi-threading” 16:10 How to instill urgency in sales 20:10 Hire sales rep or head of sales first? 21:55 Do you play reps off each other? 23:00 How do you hire sales reps? 25:25 How do you define attribution in sales? 28:49 Do you do case studies when interviewing? 30:48 Biggest mistakes you’ve made in hiring 32:11 How do you do onboarding? 35:45 Indicators that a new sales rep isn’t performing well 38:03 Deal reviews 41:49 How do you create an environment of safety? 44:40 What deal are you most proud of? 45:25 How have sales tactics changed over the last 5 years? 46:04 Advice for new sales leader starting today 46:15 How to increase diversity in sales leadership 46:55 Hardest part of role with Fivetran today 47:53 Secret to a successful comp plan 49:29 What makes the best sales teams? ---------------------------------- In Today’s Episode with Lauren Schwartz: 1.) How Being Rejected as an Eighth Grader Can Lead to World Class Sales Leader: How Lauren made her way into the world of enterprise sales with Google? Why, for a while, Lauren wanted to get away from the label of a salesperson? Why “salesperson” does not do the job of sales justice? Why does Lauren believe that one of the core traits the best salespeople have is being able to cope with rejection? How has Lauren been rejected? How did she respond? What changed their mind? 2.) The Sales Playbook: What, Who, When: How does Lauren define the term “sales playbook”? What are the nuances? Does Lauren believe the founder should always be the first sales rep? What are the core signs that a founder is now ready to bring in their first sales hires? What are the 3 biggest mistakes founders make when they hire their first sales reps? What are the core traits that the best early sales reps have? 3.) The Hiring Process: Building the Best Sales Team: How does Lauren structure the hiring process? What are the most unconventional but useful questions Lauren uses to determine the depth and quality of potential sales hires? What are glaring red flags that Lauren looks for in this interview process? How does Lauren use case studies and deal reviews in the interview process to determine the quality of a candidate? 4.) Scaling the Machine: The Onboarding Process: What are the single biggest mistakes founders make when onboarding sales reps? How should sales team onboarding be structured? What materials should the founder have in place for the sales team to learn from on Day 1? How can sales leaders ensure new sales team members engage across functions? ---------------------------------- Subscribe to the podcast: https://www.thetwentyminutevc.com/lauren-schwartz/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings ---------------------------------- #Fivetran #LaurenSchwartz #salesleader #Saleswoman #Saleswomen #HarryStebbings #salesadvice #20SALES

Harry StebbingshostLauren Schwartzguest

Oct 18, 202250mWatch on YouTube ↗

WHAT IT’S REALLY ABOUT

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.

IDEAS WORTH REMEMBERING

5 ideas

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.

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.

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.

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.

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.

WORDS WORTH SAVING

5 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

Lauren’s career path from Google to Segment to Fivetran and early sales lessonsEffective discovery, qualification, and creating genuine urgency in enterprise dealsDesigning early-stage sales motions: outbound vs partnerships, PLG vs sales-ledHow to hire first sales reps: interview structure, questions, and common mistakesOnboarding and ramping reps: at-bats, recorded calls, and early performance indicatorsRunning high-quality deal reviews and learning from wins and lossesSales leadership: culture, psychological safety, comp plan design, and diversity

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.