Sep 14, 2022 · 48m · news
Eleanor Dorfman: How We Scaled Retool to $50M ARR; Red Flags for Sales Hires | 20VC #925 · 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 of the 20VC podcast, host Harry Stebbings interviews Eleanor Dorfman, sales leader at Retool, to explore how she transitioned into tech sales, built high-performing sales teams, and established robust playbooks for horizontal platforms. The conversation offers highly tactical advice on recruiting "street fighter" talent, conducting deep interviews, and scaling sales enablement while navigating challenging economic environments.
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 23.6% of the talking time here. How this is scored →
Harry as informed peer 2.4 Guest teaching 4.4 Guest disagreement 0.9 Harry pushing back 1.8
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 11:44 Rejecting the PLG vs Enterprise Binary
Eleanor explicitly rejects Harry's framing that companies must strictly choose between PLG and top-down enterprise motions, labeling it a false dichotomy for early-stage companies.
Hardest push from Harry ▶ 18:27 Challenging Pricing StrategyHarry directly challenges standard startup advice around custom pricing by aggressively arguing for copying established market models.
Biggest teaching moment ▶ 26:13 Probing 19 Levels Deep on Candidate ResumesEleanor explains the psychological flaw in evaluating salespeople by their surface metrics and details how to probe 19 levels deeper to evaluate true individual contribution.
Harry holds his own ▶ 25:49 Calling Out Resume Inflation from Macro TailwindsHarry demonstrates keen industry insight by pointing out how landing major accounts at hypergrowth companies like early Twilio can mask mediocre individual sales performance.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Eleanor Dorfman's Journey into Tech | 1 | 2 | 0 | 0 | Harry welcomes Eleanor warmly and asks an open-ended introductory question about her path into tech and sales leadership. Eleanor shares her non-linear journey from public education to Clever, explaining how she taught herself scripting and took an intern role before scaling to head of CS. | |
| Lessons from Early Career: Customer Success & Segment | 2 | 4 | 0 | 1 | Harry references suggestions from mutual contacts to prompt Eleanor on her Customer Success background and learnings from Segment. Eleanor educates Harry on company-building mindsets and uses the analogy of needing to educate buyers on what a car is before selling a Ferrari. | |
| Foundational Sales Strategy: Playbooks, First Hires, and PLG vs. Enterprise | 3 | 5 | 1 | 2 | Harry asks sharp questions about founder playbooks, sales hiring thresholds, and whether companies must choose between PLG and enterprise models. Eleanor gently pushes back on the binary PLG vs. enterprise framing, calling it a false dichotomy for companies under $100M ARR. | |
| Selling a Horizontal Platform: The Retool Playbook | 3 | 5 | 2 | 2 | Harry relays a provocative question from Jordan asking how Retool sells a product with no defined buyer or use case. Eleanor reframes the premise, explaining that there is a buyer, just no single clear owner out of the gate, and details horizontal platform positioning. | |
| Pricing, Urgency, and the 'Street Fighter' Hiring Philosophy | 3 | 5 | 2 | 3 | Harry offers a counter-perspective on pricing, flippantly suggesting founders copy established models rather than reinventing the wheel, and questions why Eleanor avoids incumbent hires. Eleanor pushes back on the pricing stance by emphasizing value-metric alignment and explains her 'street fighter' candidate philosophy. | |
| The Structured Sales Interview: Testing, Red Flags, and Comp Plans | 3 | 5 | 1 | 2 | Harry plays devil's advocate, prompting Eleanor to break down her sales interview framework step-by-step and citing how macro tailwinds can inflate rep resumes. Eleanor provides a masterclass on probing deal mechanics 19 levels deep to uncover candidate traits. | |
| Navigating Cold Markets: Quotas, Morale, and CEO Education | 3 | 5 | 1 | 2 | Harry asks how sales leaders can manage target setting and educate CEOs when market conditions soften. Eleanor outlines her quota methodology aiming for an 80 percent rep attainment rate and counsels against giving into market whiplash. | |
| Tactics for Sales Performance: Discounting and Creative AE Strategies | 2 | 4 | 1 | 2 | Harry asks how to drive sales performance in a cold market and challenges her on discounting. Eleanor dispels rigid views on discounting, reframing it around value exchange, and highlights creative AE tactics like sponsoring customer hackathons. | |
| Onboarding, Enablement, and Scaling as a Sales Leader | 2 | 5 | 0 | 2 | Harry presses on onboarding expectations and early red flags for mishires, suggesting performance outputs should be visible within 30 to 60 days. Eleanor shares detailed enablement structures, identifies empty calendars and lack of questions as core red flags, and candidly discusses hypergrowth leadership demands. |
Statements from this episode (20)
Dorfman: Never build processes or teams before defining the problem
“Do not ever build a process or a structure or a team or anything until you know what problem you're trying to solve.”
Dorfman: Selling new software categories requires driving behavior change
“Selling into a new category is really challenging. It's a different type of challenge retools, a new category segment was a new category. You're not just selling a point solution. You're not just selling a product. You have to create budgets. You have to creat…”
Founders should generate sales playbook inputs, not write the playbooks themselves
“That's not their job, I believe, to create the sales playbook, but it is their job to generate the inputs That go into that playbook.”
Dorfman: Sales accelerates healthy systems, cannot fix broken ones
“Sales is there to accelerate a healthy machine, but it can't fix a broken one.”
Startups must choose between PLG and enterprise sales at $100M ARR
“I think that works from zero to a hundred million roughly. And I think once you hit around a hundred million, You need to start to pick a lane a little bit more because by that stage, your buyer has likely changed.”
Retool's value proposition shifted from speed to efficiency during the market downturn
“What's been interesting actually about the market shift over the last Few months, it feels like years is, is the value property tool has shifted a little bit. It was acceleration. It was time to value. It was enabling people to grow really quickly and move at …”
Founders adding sales to PLG should scale reps incrementally, not rapidly
“It's a risk because you create complexity when you create both and you have to do it for a reason. So you, it comes back to what's the problem you're trying to solve. What's the hypothesis you're testing. Don't go out and just hire 10 or 15 reps. Hire one, hir…”
Dorfman: Startups should not reinvent software pricing models
“They, you know, there are no models going out and creating a new pricing model is why, like, do not reinvent the wheel when it comes to pricing.”
Early-stage startups should hire adaptable 'street fighters' over incumbent sales reps
“So I think in the beginning, you have no idea what you're doing. You have some ideas, you know, what hypotheses you're testing, but you don't have sales enablement. You don't really have the playbook for the deals yet. Do you have your ICP? Do you know if your…”
Dorfman: Customer-first mindset cannot be taught and must be bought when hiring
“A customer first mindset is also something you can't teach. You can't build it. You have to buy it.”
Dorfman: Interviewers must probe deeply because sales candidates excel at selling themselves
“Salespeople are good at selling. That is their job. And when they're interviewing, they're selling their favorite subject themselves. And the key is to go 19 levels deeper until you reach the real point.”
Tech sales candidates are prioritizing cash over equity to de-risk careers
“And so I think now folks are optimizing for cash a little bit more than equity. Still both though. But they're more focused on de-risking versus finding the moonshot.”
Sales leaders should design compensation plans where 80% of reps hit quota
“And how can you take that and map it into a comp plan where, you know, hopefully I think the logic I've always used is that you should design a comp structure where at least 80% of your reps are hitting.”
Dorfman: Discounting in sales is a red herring without clear ROI
“There's a time and a place. But I think discounting is Sort of a false hearing. It's just, do you understand the value you're providing? Do you understand how important that is to them and what problems you're solving? Do you understand their alternative to us…”
Retool AEs host customer hackathons and dinners to close deals
“We've got two folks down at a customer onsite right now, running a hackathon with the team. They're retool sponsoring a hackathon and they're building applications together. And so they're meeting all these new teams. They're embedding themselves in the busine…”
Dorfman: Retool hired sales enablement too late, creating process debt
“I think that one of my biggest lessons was you hire for sales enablement too late and I think we hired too late. I think we have a lot of Process debt as a result.”
Dorfman: Startups hire RevOps and sales enablement too late
“I always think people hire rev ops too late and sales enablement too late because you can't hire it once you need it. You got to hire it before you need it.”
An empty calendar and lack of questions are early sales mis-hire indicators
“I would say an empty calendar is a red flag to your point. They're not outbounding. They're not booking any meetings. They're not meeting with their SDR. They're not meeting with their sales engineer. They're not meeting with their CSMs. So I think an empty ca…”
Dorfman: Spray-and-pray outbound sales cold calling is dead
“Lack of personalization, like spray and pray outbound, hold calling without knowing who you're talking to. I think buyers now today expect a level of personalization that they historically have not.”
Dorfman: Monte Carlo defined its category via heavy content and event marketing
“Monte Carlo has invested in fields and content in a way that I have found very impressive. I think they've created a category through Just sheer market education in a way. They somehow seem to be at every conference producing new content every week and have cr…”