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Rich Liu: Sales in 2023; How to Onboard, Manage and Scale Reps; PLG vs Enterprise Growth | E1023

Rich Liu is the CRO @ Everlaw and a unicorn GTM exec having scaled five multi-billion dollar tech unicorns across two IPOs, a successful acquisition, and numerous funding rounds. Prior to Everlaw, Rich architected the GTM motions for companies like Navan (TripActions), MuleSoft, and Meta (Facebook). As a result of his incredible success, Rich has been recognized as a 2021 Top 100 Global Sales Leader. ----------------------------------------- Timestamps: 0:00 - Rich Liu’s Journey from Meta to Everlaw 8:32 - How Sales Has Changed in 2023 17:35 - Creating The Sales Playbook 23:58 - Biggest Mistakes Founders Make 26:48 - PLG vs Enterprise 33:23 - How to Hire for Sales 45:23 - Comp Packages for Sales Members 48:47 - Art of the Sale: Discounting 52:30 - Why Deals Fail 59:06 - Quick-Fire Round ----------------------------------------- In Today’s Episode with Rich Liu We Discuss: 1. Entry into the World of Sales: How Rich made his way from biochemistry into the world of sales? What is 1 takeaway from his time at Navan, Meta and Mulesoft that has shaped how he thinks about sales today? What does Rich know now that he wishes he had known when he entered the world of sales? 2. Sales Today: What is Happening? What are the biggest sales leaders saying today about price sensitivity and deal cycles? What has changed in the way companies buy software with the macro downturn? What do companies need to do to get deals over the line today? How do startups need to change the way they message to enterprises in order to sell today? How has the renewals process changed? What does this mean for customer success teams today? 3. PLG vs Enterprise: When and How? Is it possible to do both PLG and enterprise at the same time? Is it easier to start with enterprise and move to PLG or visa versa? How does the type of sales leader you need change dependent on the motion? When is the right time to move from founder-led sales to sales team? How does one know whether to hire a junior jack of all trades or a senior sales leader? 4. How To Hire The Best in Sales: How does Rich structure the hiring process for all new reps today? Does he use case studies to determine their depth and ability? Is the case study of the company they are interviewing at or a fresh company? What questions does Rich ask every candidate for a new role? What are some of the biggest red and green flags in how candidates talk in interviews? ----------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Rich Liu on Twitter: https://twitter.com/richiliu Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------- #RichLiu #Everlaw #HarryStebbings

Harry StebbingshostRich Liuguest
Jun 6, 20231h 5mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Rich Liu on scaling modern sales: urgency, hiring, PLG vs enterprise

  1. Rich Liu, a veteran CRO/COO, breaks down how sales has shifted in a capital-efficient, CFO‑driven market and what founders and sales leaders must change in their approach. He stresses moving from “cool product” pitches to quantifiable business value, with direct access to true economic buyers. Liu dives into how to design founder-led sales playbooks, when and whom to hire, and how to run disciplined hiring, comp, and forecasting processes. He also explores the tradeoffs between PLG and top‑down enterprise motions, emphasizing the difficulty of doing both too early.

IDEAS WORTH REMEMBERING

5 ideas

Tie your pitch directly to the CFO’s top fears and metrics.

In a budget-constrained world, default answer is “no” unless you show quantifiable impact on efficiency, productivity, margins, or turning cost centers into profit centers—and you do it directly with the economic buyer.

Founders must own the early sales playbook before hiring senior sales leaders.

If you haven’t nailed “what problem, for whom, and how we sell it,” outsourcing that learning to a head of sales is dangerous; you need enough early proof and clarity before you scale headcount and leadership.

Hire two early reps in a cohort and test for pipeline generation.

Cohorting gives comparative signal on whether poor performance is the rep or the motion; a key early red flag is any AE who won’t or can’t generate their own opportunities (e.g., at least ~one new opp per week).

Use structured, skills-based hiring and realistic exercises, not gut feel interviews.

Define jobs-to-be-done, break them into skills (e.g., track record, coachability, execution), use consistent question sets, and run mock calls/meetings so you see how candidates actually sell, not just how they talk about selling.

Don’t attempt full PLG and full enterprise motions simultaneously without deep resourcing.

Self-serve PLG and long-cycle enterprise sales require different product DNA, marketing, and org design; most startups under-resource one and end up doing both poorly—commit to one path first, then layer the other later.

WORDS WORTH SAVING

5 quotes

Unless you can speak in a quantifiable way to the thing the CFO is most afraid of right now, you’re getting nothing done.

Rich Liu

If you don’t know the problem, who you sell it to and how you sell it to them, you shouldn’t be doing this company.

Harry Stebbings

The transition away from founder-led sales is the hardest thing in startups.

Rich Liu

If you don’t see AEs generating their own pipeline early, they’re not going to work here.

Rich Liu

I’m a huge believer you’ve got to commit to at least one motion, and it’s okay to evolve to the other—but don’t try and do two too early.

Rich Liu

Creating urgency and selling in a CFO-dominated, budget-tight environmentFounder-led sales, building the first sales playbook, and timing leadership hiresHiring, interviewing, and compensating early sales reps and sales leadersRenewals, customer success, and value realization in a downturnPLG vs enterprise sales motions and when to pursue eachDeal reviews, forecasting discipline, and common causes of slipped dealsRed flags and failure patterns in early sales teams and leadership

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