The Twenty Minute VCRich Liu: Sales in 2023; How to Onboard, Manage and Scale Reps; PLG vs Enterprise Growth | E1023
CHAPTERS
- 0:00 – 0:21
Cold open: the most common founder mistakes in sales
The episode opens mid-conversation with Harry pressing Rich on the biggest mistakes founders make in sales leadership. It sets a blunt tone and tees up the later discussion on founder-led sales, hiring, and scaling go-to-market correctly.
- •Teaser question on “biggest fuck-ups” founders make
- •Frames the episode around practical, operator-level sales lessons
- •Signals upcoming focus on scaling founder-led sales into a repeatable motion
- 0:21 – 3:21
Rich Liu’s path from engineering to sales (and early SDR grind)
Rich explains how he moved from a biomedical engineering background into sales, largely by studying what top executives had in common. He recounts his first role doing cold outbound at Fisher Investments and how that shaped his sales foundation.
- •Engineering upbringing and early career expectations
- •Decision to pursue sales after noticing many CEOs had sales roots
- •First job as an SDR with low base salary and heavy outbound
- •Direct-to-consumer growth tactics: mailers, cold calls, early digital
- 3:21 – 8:32
Meta lesson: speed beats perfection (and how to build urgency)
Rich shares his biggest takeaway from Meta: move fast, run more experiments, and accept that most “glass ball” decisions are rarer than teams think. From there, the conversation pivots into how sellers can create urgency even as sales cycles slow.
- •“Move fast and break things” as a scaling advantage
- •Use more shots on goal vs waiting for perfect data
- •Why sales cycles are slowing and default buyer stance is ‘no’
- •Urgency comes from quantifiable value tied to top executive fears
- 8:32 – 12:27
Selling in 2023: CFO/procurement gatekeeping and the value narrative
In a tighter market, Rich argues that shiny-product demos no longer break through—clear ROI does. He explains how to reframe product capabilities into strategic business levers that resonate with economic buyers and unlock approvals.
- •Buying power centralizes to CFOs and execs in downturns
- •Map product to measurable outcomes: efficiency, productivity, margin
- •Case example: expanding a law firm deal by reframing value
- •Need crisp talk tracks, proof points, and a buyer-aligned story
- 12:27 – 14:16
New GTM operating envelope: productivity metrics and investment trade-offs
Rich describes what he’s hearing from CRO/COO peers and boards: the shift from growth-at-all-costs to productive growth. He outlines how to normalize GTM performance per head and compare channels to decide where to invest.
- •Boards pushing for “productive growth” and tighter operating envelopes
- •Measure productivity per rep/seat: bookings per rep, ROI per channel
- •Compare pipeline and efficiency across SDR, marketing, AE outbound
- •Make explicit trade-offs rather than relying on instinct
- 14:16 – 17:36
Renewals get harder: re-selling value post-sale and aligning CS with sales
Renewals are pressured by SaaS rationalization and budget scrutiny, forcing teams to prove value continuously. Rich explains why CS and sales must be tightly connected and how teams can rebuild the business case even after an initially tactical land.
- •Post-sale mirrors pre-sale: customers demand justification and ROI
- •Risk when initial deal lacked exec buy-in or centralization rationale
- •CS needs playbooks for mapping org, adoption, and expansion signals
- •Sometimes you must “redo the sale” correctly to protect renewal
- 17:36 – 23:58
Who owns the sales playbook: founder-led discovery vs scalable execution
Rich breaks down when founders must stay deeply involved in sales and when they can start stepping back. The key is whether the company has nailed a repeatable ICP, message, and motion—and whether learnings feed back into product/customer fit.
- •Conflicting investor advice: hire CRO early vs founder must own sales
- •Founder involvement is critical until repeatable ICP/message exists
- •Early reps must be close enough to feed learnings back to product
- •Transition timing depends on conviction in repeatability
- 23:58 – 26:50
Founder-led sales transition: biggest mistakes and why to hire reps in pairs
Rich details the most common failure modes when founders try to scale beyond themselves—either staying too involved too long or outsourcing too early to the wrong profile. He also argues for hiring reps in cohorts of two to increase signal and speed learning.
- •Mistake: founder has too many reps reporting directly (no leverage)
- •Mistake: hiring a large-scale leader who can’t do early-stage work
- •Early-stage leaders must build comp plans and processes from scratch
- •Hiring two reps creates better ramping, accountability, and diagnosis
- 26:50 – 33:25
PLG vs enterprise: why doing both early is so hard (and how to sequence)
Harry challenges teams trying to run PLG and enterprise simultaneously; Rich agrees it’s difficult because product DNA, marketing motion, and org design diverge. They discuss when to start small and move upmarket—and when that strategy flips by category.
- •Operational definitions: self-serve PLG vs long-cycle enterprise
- •Product design and GTM muscles differ dramatically across motions
- •Common failure: claiming a motion without resourcing it properly
- •Rich’s view: generally easier to start small and move upmarket
- 33:25 – 45:22
How to hire your first sales team: structured interviews, exercises, references
Rich lays out a rigorous hiring approach inspired by MuleSoft: define outcomes, map to skills, then design interviews and exercises that actually test those skills. He emphasizes calibration, coachability signals, and using references/backchannels thoughtfully.
- •Start with “job outcomes,” not titles or resumes
- •Use structured questions (STAR) and consistent interviewers
- •Coachability signals: humility, learning loops, seeking help effectively
- •Add realistic exercises: cold call, prospecting email, mock meeting
- •References: ask what they do well/need coaching on; ensure fit
- 45:22 – 48:59
Comp packages: avoid title/offer inflation and hire for the next 12–18 months
Rich warns founders not to get anchored by competing offers or inflated titles from the prior market. He recommends aligning role scope to near-term goals, pricing the role to the real job, and being explicit about the trade-offs of over-leveling.
- •Benchmarks exist—bigger issue is role/level fit for your stage
- •Title inflation can block future upgrades and org design flexibility
- •Define what you need: downmarket/upmarket, global, mainstream shift
- •Hire for the next 12–18 months, not an imagined 3-year future
- 48:59 – 59:10
Art of the sale: discounting strategy, deal reviews, why deals fail, and forecasting
Rich explains when discounting is appropriate and how to do it intentionally based on the business model and market entry strategy. He then outlines how to run effective deal reviews using a framework (e.g., MEDDPICC), the most common deal-killers, early rep red flags, and how to forecast more accurately in 2023.
- •Discounting depends on strategy: share capture vs premium positioning
- •Weekly deal reviews with rep + manager + exec; use a consistent framework
- •Deals fail from weak initial buy-in and lack of economic buyer access
- •Early rep red flags: no pipeline generation and slow product/message grasp
- •Forecasting: inspect mid-stage reality—EB access, business case, close plan
- 59:10 – 1:05:32
Quick-fire: timeless tactics, what’s dying, and a standout sales strategy example
In rapid Q&A, Rich highlights what hasn’t changed in selling—deep pain-based discovery tied to quantifiable value—and what’s no longer effective, like overly polished “personalization” emails. He closes with a creative enterprise freemium-style contract example that drove expansion even during the pandemic.
- •Timeless: force management/challenger-style value discovery
- •Dying: perfectly crafted emails and shallow personalization gimmicks
- •Modern outbound: multi-touch across channels (text, video, LinkedIn, etc.)
- •Advice to new sales leaders: align fast with CEO on top metrics
- •Example: contract-based “try it free” to earn expansion commitment
