The Twenty Minute VCFivetran's Lauren Schwartz: Must-Ask Questions to Identify Potential Sales Talent | 20VC #939
CHAPTERS
- 0:00 – 3:08
From cookie sales to Google: how Lauren found sales (and fought the label)
Lauren traces her earliest love of sales back to Brownie cookie selling, then fast-forwards to six formative years at Google. She also unpacks the stigma around “sales” and why the job is often misunderstood as persuasion rather than customer education.
- •Early motivation: competition, repeat purchases, and product evangelism (cookies)
- •Six-year foundation in sales at Google as a “learn from adults” environment
- •Business school as a way to broaden beyond sales into running a company
- •The negative connotations of “selling” and why buyers resist it
- •Reframing sales as helping customers find the best solution
- 3:08 – 4:44
Core lessons from Google: curiosity and asking forgiveness, not permission
Lauren shares the two most enduring takeaways from her Google years: relentless curiosity about what’s possible and a willingness to bend “rules” in service of customer outcomes. She explains how sellers must guide buyers through uncomfortable truths about their current pain—then help them envision a better future.
- •Insatiable curiosity as the most important sales skill
- •“Forgiveness over permission” as creative problem solving within guidelines
- •Sales requires bringing customers into uncomfortable current-state reality
- •Responsibility to “catch them” by mapping a path to a better future
- •Balancing challenge with support to build trust
- 4:44 – 6:39
First-day selling advice: discovery questions that surface pain and outcomes
Harry asks Lauren to coach a brand-new rep on how to run discovery without relying on yes/no questions. Lauren lays out an outside-in approach: current state → consequences of doing nothing → future state → business outcomes tied to value drivers like revenue, cost, risk, and speed.
- •Use open-ended prompts: “Tell me about…” “Describe for me…”
- •Define current state and the negative consequences of staying there
- •Elicit future state and what it would unlock for the business
- •Translate technical benefits into business value (so what? then what?)
- •Common value drivers: revenue, cost savings, risk mitigation, time-to-market
- 6:39 – 8:02
Does outbound still work? Reframing outbound through partners and ecosystem selling
Lauren argues “outbound” has a bad reputation because it’s often done without relevance. At Fivetran, the most effective path is co-selling with ecosystem partners (e.g., Snowflake, Databricks, AWS/GCP), because data movement is purchased as part of a broader stack, not in isolation.
- •Outbound works when it meets buyers where they are with relevant context
- •Partnership-led co-selling can be the best form of modern outbound
- •Fivetran’s product is naturally ecosystem-dependent (sources + destinations)
- •Partnerships aren’t just “lunch and learns” when done well
- •Modern data stack motions benefit from coordinated GTM with partners
- 8:02 – 9:19
When partnerships become viable: use warm paths from day one
Harry challenges how early startups can partner without big-brand leverage. Lauren’s view: it’s never too early—founders should pursue the warmest route via investors, accelerators, and community introductions rather than defaulting to cold outreach.
- •“Path of least resistance”: prefer warm calls over cold calls
- •Founders already have networks: investors, cohorts, communities
- •Start partnership development early, even pre-scale
- •Borrow distribution through credible introducers and ecosystems
- •Treat partnerships as a core GTM lever, not a late-stage add-on
- 9:19 – 10:56
Turning sales conversations into company learning: CRM + storytelling rituals
Lauren frames early-stage sales as equal parts selling and R&D. She describes how to operationalize customer insight sharing through CRM hygiene and recurring storytelling mechanisms like deal reviews, fireside chats, and postmortems—so learnings spread across sales, marketing, product, and CS.
- •Sales is also research: uncovering market needs and message fit
- •Capture learnings systematically in CRM (e.g., Salesforce)
- •Use deal reviews, firesides, and postmortems to spread insight
- •Storytelling as both knowledge transfer and data collection
- •Share across functions to influence roadmap and positioning
- 10:56 – 12:50
What a “sales playbook” really is (early stage): at-bats, pattern recognition, and iteration
Lauren cautions that “playbook” is too prescriptive at the earliest stages; the first sellers are primarily collecting market signal. She shares why high-velocity at-bats (like her SMB AE stint at Segment) accelerate learning and allow a repeatable motion to emerge.
- •Early-stage sellers should collect market feedback, not follow rigid scripts
- •Founder story/vision is the initial “playbook seed”
- •High at-bat volume builds fast learning loops and confidence
- •Segment experience: SMB velocity helped ramp into more complex selling
- •A playbook is earned through patterns, not written upfront
- 12:50 – 14:21
PLG vs enterprise: combining bottom-up adoption with top-down recognition
Lauren argues startups often wait too long to add real sales capability because they over-trust “the product sells itself.” In enterprise, a narrow land doesn’t create broad organizational momentum; the best outcomes come from pairing product-led adoption with top-down enterprise sales to drive wall-to-wall awareness.
- •Many startups over-rely on PLG and underestimate selling as a skill
- •Enterprise deals often start as narrow lands that require expansion work
- •Enterprise sales teams create market recognition across the org
- •Best motion can be PLG + enterprise, not either/or
- •Top-down + bottom-up together builds durable momentum
- 14:21 – 16:10
Multi-threading in enterprise: mapping champions, competitors, and the economic buyer
Lauren explains multi-threading as essential in complex enterprise buying. She describes systematically gathering current/future state input across roles, identifying “champions” (including the champion for doing nothing), and packaging those insights for the economic buyer as synthesized internal research.
- •Multi-threading is critical as complexity and company size grow
- •Identify: your champion, competitor’s champion, and “do nothing” champion
- •Repeat discovery across stakeholders and iterate the narrative
- •Bring cross-functional inputs to the economic buyer as validated evidence
- •Outcome: buyer feels helped, not sold—“participate in their own rescue”
- 16:10 – 20:07
Diagnosing ‘no urgency’ and creating timelines without discounting
Lauren introduces Fivetran’s deal test: “Why do anything? Why now? Why Fivetran?” If you can’t answer “why now,” the deal was never real for the quarter. To build urgency ethically, she recommends backward planning from the customer’s desired outcome date to reveal the true signing deadline.
- •Framework: Why anything / Why now / Why us
- •If “why now” is missing, a slip is just poor qualification
- •Avoid discounting and relationship pressure as urgency hacks
- •Use reverse mutual action plans: walk backward from the value deadline
- •Urgency comes from time-to-value realism, not price manipulation
- 20:07 – 22:45
First sales hire vs head of sales: scrappy process-builders and hiring in pairs
Lauren advises early startups to prioritize sellers who can operate in ambiguity while still running process—so the company can learn through pattern recognition. She supports hiring multiple reps early (not as a competition gimmick) to separate product/message signal from individual performance noise.
- •Early stage needs door-kickers who gather market truth, not process-heavy leaders
- •First reps must combine fearlessness with repeatable process discipline
- •Avoid “artist-only” reps if you can’t learn what worked and why
- •Hire multiple sellers to distill signal vs noise from individual variance
- •Goal is learning velocity and comparability, not internal competition
- 22:45 – 28:47
Interviewing sales talent: drilling into metrics, attribution, and unprepared reality
Lauren’s hiring approach centers on specificity: attainment by year, deal mechanics, and who contributed what—so candidates can’t hide behind stories. She recommends forcing “live thinking” by asking for the second-proudest deal, probing losses for accountability, and validating customer experience directly.
- •Don’t allow open-ended storytelling—test for metrics and repeatability
- •Ask attainment over multiple years and how results were achieved
- •“Second-proudest deal” reveals real behavior beyond rehearsed anecdotes
- •Loss analysis shows internal vs external locus of control
- •Reference via customers they sold to, not hand-picked friends
- 28:47 – 31:55
Case studies vs role plays: simulating procurement and real objections
Lauren is skeptical of traditional pitch panels because interviewers often aren’t credible buyers and candidates can be unfairly penalized. Instead, she prefers unprepared role plays based on real scenarios (e.g., procurement negotiation) to test listening, adaptability, and value anchoring under pressure.
- •Pitch-your-product panels can become unrealistic monologues
- •Pitch-our-product can unfairly stump candidates on company-specific nuance
- •Unprepared role play better mirrors real selling dynamics
- •Use real scenarios: procurement, late-stage friction, objection handling
- •Assess ability to pivot back to business outcomes in real time
- 31:55 – 38:02
Onboarding and early performance signals: call libraries, postmortems, and leading indicators
Lauren argues new reps ramp fastest through customer exposure: listening to recorded calls, joining live conversations, and studying win/loss postmortems. Because enterprise cycles are long, she emphasizes leading indicators in the first 30 days—deal progression, disciplined resource use (e.g., trials), and cross-functional collaboration.
- •Onboarding priority: customer exposure (recorded calls + ride-alongs)
- •Create libraries of calls and capture win/loss postmortems
- •Enterprise at-bats are high-leverage; protect marquee customer moments
- •Leading indicators: progression, follow-ups, and trial discipline
- •You can gauge likely success within ~30 days via curiosity and organization
- 38:02 – 44:34
Deal reviews and psychological safety: weekly cadence, qualification clarity, and transparent leadership
Lauren outlines deal reviews as frequent, structured learning systems—ranging from company-wide storytelling to weekly deep dives with cross-functional teams. She links great deal inspection to psychological safety: leaders must model accountability, explain the “why,” and create an environment where mistakes become shared learning rather than blame.
- •Run deal reviews frequently; weekly deep dives for active deals
- •Rep leads with SE/partner/teams present to surface all angles
- •Company-wide win stories must include learnings and “do differently”
- •Common loss root cause: poor qualification and misaligned problem selection
- •Safety comes from leader transparency, shared agendas, and modeling mistakes
- 44:34 – 50:40
Rapid-fire leadership principles: curiosity, value-aligned pricing, diversity, focus, and comp design
In the closing rapid-fire, Lauren doubles down on curiosity as the enduring sales advantage and calls out outdated models like value-misaligned pricing and shelfware licensing. She highlights goals for the profession—more diverse leadership—and shares practical operating challenges: keeping the sales org focused and aligning comp to consumption and customer outcomes.
- •Timeless skill: deep curiosity driving discovery and qualification
- •Dying tactics: shelfware/subscription black boxes and misaligned pricing
- •Advice to new leaders: listen to customers above all
- •Diversity in sales leadership requires community, pipeline, and promotion pathways
- •Comp plans should align incentives with adoption/consumption, not just bookings
