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

ℹ️ EPISODE INFO

Released

June 7, 2023

Duration

1h 5m

Channel

The Twenty Minute VC

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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?

1. 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?

1. 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?

1. 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

🎤 SPEAKERS

• Harry Stebbings

  host

• Rich Liu

  guest

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Twenty Minute VC, featuring Harry Stebbings and Rich Liu, Rich Liu: Sales in 2023; How to Onboard, Manage and Scale Reps; PLG vs Enterprise Growth | E1023 explores rich Liu on scaling modern sales: urgency, hiring, PLG vs enterprise 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.

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