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Eleanor Dorfman: How We Scaled Retool to $50M ARR; Red Flags for Sales Hires | 20VC #925

Eleanor Dorfman is a Sales Leader @ Retool, the company that allows you to build internal tools, remarkably fast. Prior to Retool, Eleanor joined Retool when there were only three account executives and has scaled the sales org sales to over 30 AEs, many SEs, and an entire SDR team. Before Retool, Eleanor was at Segment, where she built out the company’s customer success operations team before pivoting to creating an expansion sales team, renewals team, and a new business sales team. Finally, before Segment, Eleanor made her way into startups, starting as an unpaid intern at Clever, just four years later, Eleanor was Head of Customer Success and Solutions Engineering. ------------------------------------- Timestamps: 00:00 - Intro 00:30 - How do you get into the world of tech? 02:50 - Customer success to Sales 04:37 - What did you learn from team at Segment? 06:20 - What does “Sales Leader” mean? 07:04 - Who creates the sales playbook? 08:25 - When do you hire your first salesperson? 09:42 - What gives you confidence at Retool? 11:30 - PLG vs Enterprise Sales 13:30 - Challenges of serving both PLG and Enterprise 15:10 - How do you sell a product with no buyer or use case? 16:30 - How do you do product marketing? 17:20 - Blending PLG with traditional sales-led model 18:27 - How do you think about pricing? 20:28 - Why don’t you like to hire from incumbents? 22:56 - The process of hiring a sales member 24:15 - How do you test for technical aptitude? 25:52 - Analyzing past performance 27:01 - Red flags in hiring 27:31 - Case studies - pitch us Retool 29:18 - How does the market change hiring? 30:17 - Sales comp plans 31:10 - How do quota targets change in cold and hot markets? 33:08 - How to prevent reps from being demotivated 35:25 - Discounting to get deals done 36:20 - Advice for Account Executives 37:30 - How to onboard new sales reps 39:35 - Redflags you’ve made the wrong hire 40:45 - What relationship should founder have with sales leader? 42:12 - How do you structure a sales review? 43:37 - The hardest thing about scaling into a sales leader? 44:30 - What sales tactics have and have not died? 45:11 - How to do Webinars 47:03 - What company’s sales strategy have you been most impressed by? ------------------------------------- In Today’s Episode with Eleanor Dorfman We Discuss: 1.) Entry into Sales from Working with the US Education Department: How did Eleanor get her first role as an unpaid intern at Clever? What are 1-2 of her biggest takeaways from her time at Segment? What are the biggest advantages of sales reps having experience in customer success? 2.) The Sales Playbook: How does Eleanor define, “a sales playbook”? When does it need to be created? Does it need to be the founder who creates it or can it be a Head of Sales? Is it possible to run a PLG and enterprise motion from Day 1? How does this change your sales playbook? How does Eleanor advise founders on when is the right time to layer on an enterprise motion, on top of a PLG motion? 3.) Who, What and When: Building the Sales Team Should founders hire a Head of Sales first or sales reps first? If sales reps, should founders always hire sales reps in two’s? How does Eleanor structure the hiring process for all new sales team recruits? What are the clearest signals of 10x sales hires? What are red flags in the interview process? How does Eleanor use demo’s and case studies to determine technical ability? 4.) The First 30, 60 and 90 Days: The Onboarding: What is the right structure for all new sales hires to be onboarded? Why does Eleanor believe you will always hire your Head of Sales Enablement too late? What are the signs that now is the right time to hire your Head of Sales Enablement? What tools, materials and resources can founders provide to shorten the ramp time for new AEs? What are the single biggest mistakes founders make in the onboarding of new sales reps? ------------------------------------- #Sales #Retool #EleanorDorfman #Salesleader #Salesmanager #HarryStebbings #20VC #20SALES

Harry StebbingshostEleanor Dorfmanguest
Sep 13, 202248mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Scaling Retool’s Sales: Hiring Street Fighters, Blending PLG, Hitting $50M

  1. Eleanor Dorfman, sales leader at Retool, explains how her customer-success roots and experience at Segment shaped her philosophy of building sales as a company-wide function, not a standalone department.
  2. She details when and how founders should hire their first sales reps, why early sales must be founder-led, and how to blend product-led growth with traditional enterprise sales up to roughly $100M ARR.
  3. A major focus is on hiring: why she avoids incumbents early, what profiles and interview processes she uses, and the red flags that indicate a mis-hire or weak culture fit.
  4. Dorfman also covers compensation, quota-setting in changing markets, onboarding, enablement, discounting, and how to maintain accountability and morale in tougher macro conditions.

IDEAS WORTH REMEMBERING

5 ideas

Founder-led selling is required to generate inputs for a real sales playbook.

Founders don’t need to codify the full process, but they must talk to many customers, learn how buyers actually want to purchase, and validate product-market fit, retention, and some reliable inbound before hiring sales to “accelerate the machine.”

Early-stage sales hires should be ‘street fighters,’ not incumbents.

When playbooks, enablement, and ICP are still fuzzy, you need adaptable, scrappy reps who thrive without a safety net—people who can self-onboard, experiment, and help *build* the motion instead of expecting a polished machine like Salesforce or Stripe.

Always start with the problem you’re solving—products, org structure, or GTM.

Dorfman repeatedly returns to the question, “What problem are we trying to solve?” Whether designing hiring profiles, choosing PLG vs. enterprise, or changing pricing, clarity on the underlying problem prevents copy-paste strategies and mis-scaling.

PLG and enterprise sales can coexist—until scale forces a primary motion.

Up to roughly $100M ARR, it’s viable (and useful) to run both motions and learn from each deal. Beyond that, buyer, product, and market maturity usually force you to pick a primary lane, though the other motion can still support it.

Design hiring and interviews around what you must ‘buy,’ not what you can ‘build.’

She screens heavily for IQ, EQ, character, drive, curiosity, customer centricity, technical comfort, and ownership—traits she can’t train—then uses deep deal debriefs, technical walk-throughs, and a Retool pitch to test for real competence vs. surface résumé.

WORDS WORTH SAVING

5 quotes

Sales is there to accelerate a healthy machine, but it can't fix a broken one.

— Eleanor Dorfman

I don't see myself as a sales team builder; I see myself as a company builder.

— Eleanor Dorfman

You have to know what problem you're solving before you build anything.

— Eleanor Dorfman

It's a lot easier to sell a Ferrari when someone knows what a car is.

— Friend’s father, quoted by Eleanor Dorfman

You can't hire enablement or rev ops once you already need them. You have to hire them before.

— Eleanor Dorfman

Founder-led sales and defining the early sales playbookBlending PLG and enterprise motions in category-creating productsHiring profiles, interview process, and red flags for sales talentBuilding and scaling sales orgs: enablement, rev ops, onboardingComp plans, quotas, and performance management in hot vs. cold marketsCreating urgency, handling discounts, and deal/win-loss reviewsCulture, leadership, and psychological safety in high-growth sales teams

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