Jun 7, 2023 · 1h 5m · news
Rich Liu: Sales in 2023; How to Onboard, Manage and Scale Reps; PLG vs Enterprise Growth | E1023 · 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 insightful interview, tech sales executive Rich Liu joins Harry Stebbings to discuss modern enterprise sales tactics, founder-led sales playbooks, rigorous GTM hiring structures, and strategies for navigating slowing enterprise sales cycles.
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 12.6% of the talking time here. How this is scored →
Harry as informed peer 3.9 Guest teaching 5.0 Guest disagreement 1.5 Harry pushing back 3.3
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 27:30 Rich rejects binary framing of PLG vs Enterprise
Rich explicitly pushes back against Harry's assertion that mixing PLG and enterprise is a mistake, insisting that sales motions exist on a spectrum rather than a binary choice.
Hardest push from Harry ▶ 9:46 Harry refuses the CFO-centric enterprise framingHarry cuts in to call out Rich for assuming early startups have CFOs, forcing him to adapt his advice to pre-CFO stage founders.
Biggest teaching moment ▶ 37:01 Rich's detailed interrogation technique for candidate coachabilityRich systematically educates Harry on how to bypass superficial sales answers by digging into deal failure reactions and humility signals.
Harry holds his own ▶ 44:53 Harry shares an advanced reference-checking question frameworkHarry demonstrates strong practical talent knowledge by explaining how to uncover candidate weaknesses by asking references what skills adjacent hires should possess.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Lessons from Meta: Moving Fast and Breaking Things | 2 | 4 | 1 | 1 | Harry opens with a quickfire icebreaker about Meta. Rich shares operating lessons on moving fast and prioritizing speed over perfection without any friction or pushback. | |
| Creating Urgency and Value in a Slowing Sales Cycle | 3 | 5 | 1 | 2 | Harry asks how to drive sales urgency amidst slowing sales cycles. Rich explains how sellers must shift from feature selling to solving quantifiable executive fears. | |
| Selling to CFOs and the 'Jobs to Be Done' Model | 4 | 5 | 2 | 6 | Harry challenges Rich's premise about selling to CFOs, pointing out that early-stage startups operate pre-CFO. Rich accepts the nuance and adapts his advice for early founders. | |
| GTM Trends: Productive Growth and Renewals | 5 | 5 | 1 | 3 | Harry demonstrates industry knowledge by referencing Henry Schuck's approach at ZoomInfo regarding renewal org restructuring. Rich expands on post-sale ROI justification. | |
| Who Should Create the Sales Playbook? | 5 | 4 | 2 | 5 | Harry forcefully asserts that founders who do not know their buyer or problem should not be running a company. Rich agrees and outlines when to transition playbook ownership. | |
| The First Sales Hires and Transitioning from Founder-Led Sales | 4 | 5 | 1 | 3 | Harry references Jason Lemkin's benchmark on hiring two reps at once. Rich reinforces the logic with an engineering perspective on cohort testing and signal isolation. | |
| PLG vs Enterprise: Choosing and Executing a Growth Strategy | 5 | 6 | 3 | 6 | Harry asserts that combining PLG and enterprise simultaneously is a major mistake. Rich rejects the binary view, breaking down how companies like Facebook and Slack navigate the spectrum. | |
| Structuring a Rigorous Sales Hiring Process | 3 | 6 | 1 | 2 | Harry prompts Rich for actionable hiring frameworks. Rich delivers a masterclass on structured interviewing, dissecting candidate coachability and past performance metrics. | |
| Vetting Candidates: Red Flags, Mock Exercises, and References | 6 | 5 | 1 | 2 | Harry shares an insightful back-door referencing trick regarding complementary skill questions. Rich details mock exercises, candidate red flags, and reference ring-fencing. | |
| Offers, Titling, and Compensation Packages | 3 | 5 | 1 | 2 | Harry asks about sales compensation and title inflation. Rich warns founders against over-titling and throwing away equity to compete with inflated market offers. | |
| The Art of Sales: Discounting and Structured Deal Reviews | 5 | 5 | 2 | 6 | Harry interrupts a nuanced answer on pricing to press Rich directly on whether he personally discounts deals. Rich admits he does and explains the deal review cadence. | |
| Managing Rep Performance, Leaders, and Forecasting | 3 | 6 | 1 | 2 | Harry asks for rep red flags and forecasting advice in tough markets. Rich highlights lack of self-generated pipeline as the immediate early warning indicator for new hires. | |
| Quickfire Round: Sales Truths, Diversity, and Great Strategies | 3 | 4 | 2 | 3 | Rich reflects on sales demographics and stereotypes. Harry playfully banter-pushes back on the stereotype description before concluding a collaborative interview. |
Statements from this episode (26)
Liu: Execution speed carries a 10x premium in fast-changing markets
“Move fast and break things. Like the idea that you don't have to be perfect, but sometimes, especially in a fast changing market, speed is at a 10 X premium.”
Liu: Far fewer operational decisions are irreversible than leaders assume
“How many things are actually that, that if we screw it up, if we fuck it up, we can't go back and try to fix it? It's actually fewer than we think.”
Liu: Product-led sales models fail in a tight economic market
“That early adopter, that product lets sale does not work in a tight market.”
Liu: Startups should not base strategic decisions purely on cost control
“For most startups, you don't want to just make your investment decisions based off of, like, pure economic and cost control.”
Liu: Software sales must connect product value to CFO efficiency priorities
“I need to be able to make sure I can map back my narrative of what my product does and To that big thing. And unless I can do that, I'm not going to get in the room.”
Liu: SaaS renewals require explicit agreement on quantifiable value to avoid churn
“Without trying, tying clearly to value quantifiable value and agreement of what that value is that relationship is going to be at risk right now.”
Liu: Hiring a VP of sales before defining customer fit is dangerous
“If you're trying to go bring in a head of sales to outsource that for you at that stage, that's pretty dangerous, right?”
Liu: Navan co-founder Ariel Cohen personally closed early sales deals
“Ariel at Navon was really involved with a lot of the earliest deals and knew the product, knew the people really well.”
Liu: Founders must demonstrate a working GTM MVP to attract senior leaders
“I don't want to go work with that founder unless they, we've actually done a little bit of legwork to show there's some MVP of a go to market of a something that works there.”
Liu: Startup founders should never have five or more direct sales reports
“Biggest fuck-ups would be, one is staying too close, right? I speak sometimes with founders who have, like, 10 sales reps reporting directly to them. That is, like, that makes no sense. Five sales reps reporting directly, makes no sense. It completely impedes”
Liu: Early-stage startups should always hire sales reps two at a time
“But the two point is just so valuable because cohorting in terms of ramping, the supporting each other, the ramping, the competitive elements of it, it's really hard to know, is my product market fit fundamentally wrong? Is the way I'm telling the story fundam…”
Stebbings: Pursuing PLG and enterprise sales simultaneously is a massive mistake
“I see as a massive mistake people doing PLG and enterprise at the same time. They're almost too nervous to do one and commit and burn the boats on PLG or just be a top-down enterprise org. For me, I think that's a big mistake.”
Liu: It is easier for startups to start small and move upmarket
“If you're going to ask me personally what I think is easier, personally, I think it's easier to start small and go up.”
Stebbings: Adding enterprise sales to PLG is easier than vice versa
“I also think it's because it's the product and growth mindset that's inherent within a PLG-led org where it's product first. And it's so difficult to imbue that in an enterprise org. Oh. And actually tacking on enterprise sales into a PLG motion, not as hard a…”
Liu: Standard job interviews are ineffective at predicting actual employee performance
“Interviews, by the way, are like the most, if you think about it, they're actually a pretty ineffective way to understand if someone's going to be good at something, right? Whoever interviews well gets the job, but that doesn't mean they're a great engineer an…”
Liu: Multiple consecutive one-to-two-year job stints are a major red flag
“And frankly, when people talk about, for example, you know, job changes, a lot of job changing, huge red flag for me. At some point, everybody's got a good reason, but if you, say, do one or two year stints for, like, several in a row, that's a huge red flag.”
Liu: Top sales reps always know their exact historical performance numbers
“Great sales reps know exactly how they did every year. Like, I can tell you, okay, and this year, in 2007, I did this, and I made this amount of money. . I was number one on the sales board. I was number two on the sales board note three. John Holbrook beat me…”
Liu: Rely on VC compensation benchmarks over candidate counteroffers
“There are some good benchmarks out there for any role, AE, CSM, marketer, you know, partnerships person, ops person, strategy person. So, so, so trust that any, all the VCs, all the talent folks and recruiter will give you that.”
Liu: Inflating titles to land candidates blocks future executive hiring
“But don't get caught into the, like, I gotta do this title of this offer just because somewhere else, and if you do, do so knowingly. I'm trading off that I'm giving this higher title to someone, to some person that I might need to up level later, because now …”
Liu: PLG startups should avoid discounting; enterprise sales should discount selectively
“If I'm running a PLG, like, don't waste your time getting into these cycles of, like, discounting and not, but if I'm running, like, an enterprise sale, I like to hold a high list and then figure out how I need to discount to still protect the premium and get …”
Liu: Deal reviews drive maximum value on early-stage pipeline opportunities
“Doing that for all the key deals that are not necessarily just going to close in a quarter, but that you need to go evolve from whether it's 10 or 25% stage to the 50, 90% stage. That's actually where the impact is driven. Like, when we're looking at the deals…”
Liu: Failing to reach economic buyers is killing enterprise deals
“Second one is not getting to the economic buyer and actually selling to them. Right now the, oh, I got, you know, I got the EB back behind the scenes. That's not a true champion. You don't have a deal. Those are probably the things that are hurting deals the m…”
Liu: Enterprise AEs should independently generate one outbound deal per week
“A good rule of thumb is like an AE in my book should be generating at least a new op a week. By themselves, without SDRs, without marketing, helping them in an enterprise software sale, outbound sale.”
Liu: Pain-based discovery remains the most essential, unchanging sales tactic
“Doing that level of pain-based discovery has not changed. And actually getting to that true, I don't know, standard call like level three pain of like, what is the true business pain and figuring out how to map what you do, your service, your platform, really …”
Liu: Personalized two-paragraph cold outbound emails no longer work
“Having that perfectly crafted email of like, hey, I did a great UI now, it's two paragraphs, I've done a lot of research, or I've done the cheap thing where it's like, hey, you went to Yale, you were the captain of the volleyball team, what do you think about …”
Shorts cut from this episode
▶ Rich Liu: From Biomedical Engineer to Sales Guru 🧑🏻🔬 · 2 (@1:05)
▶ When should a salesperson offer a discount? -Everlaw CRO Ric (@50:11)
▶ The Biggest Mistake a Sales Team Can Make When Hiring · 20VC (@1:01:24)
▶ How To Get a Job Today 🤔 · 20VC with Harry Stebbings (@1:00:20)
▶ Everlaw CRO Rich Liu's biggest lesson at Meta 😲 · 20VC with (@3:55)
▶ What every great salesperson can tell you 🗣️ · 20VC with Ha (@41:09)