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

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

The Twenty Minute VCJun 7, 20231h 5m

Harry Stebbings (host), Rich Liu (guest), Narrator, Narrator

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

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.

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.

Key Takeaways

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.

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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.

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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. ...

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

Define jobs-to-be-done, break them into skills (e. ...

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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.

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Quantifiable value and executive alignment are now mandatory for renewals.

Post-sale teams must effectively ‘re-do’ the sale: define ROI metrics with customers, get CFO/CIO buy-in on what success looks like, and arm CSMs with commercial awareness, or renewal and expansion are at risk.

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Set realistic, aligned targets with the CEO to avoid destructive stretch.

Misalignment between a founder’s aspirational targets (e. ...

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Notable 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

Questions Answered in This Episode

How can an early-stage founder practically translate their product’s features into a hard-numbers business case a CFO will care about?

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. ...

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At what specific revenue or repeatability milestones should a founder start to pull back from direct selling and bring in a true head of sales?

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If you’ve already half-committed to both PLG and enterprise, how do you rationalize and reset without blowing up your current team and roadmap?

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What concrete metrics and leading indicators should founders track in the first 90 days of a new sales hire to decide whether to keep or part ways?

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How can a startup redesign its renewal and CS motion to build executive-level value stories when most customers were originally closed on ‘cool product’ rather than quantified ROI?

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Transcript Preview

Harry Stebbings

What are the biggest fuck-ups that you see people make?

Rich Liu

Ah, ah, ah. Biggest fuck-ups would be... (instrumental music)

Harry Stebbings

Rich, my man, I have heard so many great things. I've been so looking forward to this. Some of the references gave me things that we could talk about in the show, some we've just bonded about instead. But thank you so much for joining me today.

Rich Liu

Happy to be here, Harry, thanks so much for having me.

Harry Stebbings

Not at all, the pleasure is mine. But I wanna start with a little bit on you, 'cause you've worked at some of the most incredible orgs in, in the last kind of 10 years of business building really. And so I wanna start with, how did you make your way into the world of tech and sales first?

Rich Liu

Yeah, yeah, it's a great question. Fir- first of all, it's, uh, it's, uh, there's a lot of luck involved. I think it's a lot easier to see things going back than looking forward. Um, but I, I started my career as a, as an engineer, biomedical engineer. My parents are both engineers, we're immigrants, and so that idea of get a technical degree, get a technical background, and then, you know, you'll always have work to do was a little bit of what I grew up with. But after finishing, I realized, oh, wow, I watch the movies, I, I see TV, and I really wanted to be some kind of a business executive someday. I didn't really know what that meant. Uh, and I thought, well, okay, this was during the, uh, dot-com bubble burst, so there weren't a lot of jobs out there. And I was reading and doing my research and going, huh, you know, it looks like a lot of these, uh, these, uh, business leaders, these CEOs, they, they seem to have this, like, sales background. That's interesting. Maybe I should try that. And, uh, and, you know, if I, if it, if I don't, can't do it well, if I suck at it, you know, I'll go back and take one of these engineering offers I, uh, that, that I had walked away from. And so my first job was, I always think the base salary was, like, $20,000. And so it was like, well, if I can't make a good commission, I won't pay my rent anyway, so why don't we give this thing a shot for a year? And that was really it, right? I went into an investment company called Fisher Investments that was really transformational at the time, really trying to get people from all money management being distributed through your financial advisor or brokerage house to, oh, we're gonna build this direct-to-consumer money management shop through what was junk mail, cold calling, and later, you know, internet advertising, search advertising, and, uh, to sell high-net-worth asset management into institutions. And so it sounded, like, kooky, right?

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