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The Twenty Minute VC

Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241

Matt Plank is Rippling's Chief Revenue Officer where he oversees all Sales and Account Management functions in the US and Internationally.

Matt PlankguestHarry Stebbingshost

Dec 20, 20241h 10mWatch on YouTube

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CHAPTERS

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Chapter summaries

Cold open: Founders shouldn’t write the sales playbook (and why pricing friction matters)
A quick teaser from later in the conversation: Matt argues founders often wait too long to hire go-to-market leadership and shouldn’t be the ones authoring the sales playbook. He also flags a common scaling mistake—failing to raise prices until you feel real customer “friction.”
- •Founders shouldn’t create the repeatable sales playbook
- •Founders commonly delay GTM hiring due to perceived lack of traction
- •Pricing should be increased gradually until you hit resistance
- •Lack of price friction often signals underpricing and missed revenue
Matt’s origin story in sales: competition, rejection, and learnable skills
Matt shares how he got hooked on sales early (from school fundraisers to commission jobs) and what he believes makes someone successful. The discussion frames sales as a game of resilience—winning matters, but rejection is constant.
- •Early exposure to sales through school competitions and commission roles
- •Salespeople need competitiveness plus emotional recovery from losses
- •Even top reps lose most of the time due to low win rates
- •Core skills can be taught once the “ingredients” are there
Why win rates are so low: indecision, ghosting, and the “circle-back” pipeline
Matt explains that many deals aren’t lost to competitors—they die from indecision or going dark. He outlines a practical tactic: treating “no” with kindness to build future pipeline when prospects re-emerge ready to buy.
- •Primary loss reason is often indecision vs. competitor selection
- •Large portion of closed-lost is unresponsive/ghosting after early calls
- •Decisioned win rates are higher than overall win rates including ghosts
- •‘Kill them with kindness’ creates a long-term circle-back pipeline
Replacement vs net-new: why ripping-and-replacing is easier to sell
Matt contrasts selling a replacement product with creating an entirely new budget line item. He argues replacement deals are more predictable because a decision is more likely—buyers will choose someone rather than keep doing nothing.
- •Replacing an existing system is easier than creating net-new budget
- •Net-new can collapse late when buyers revert to old workflows
- •Rippling often displaces an incumbent, making competition clearer
- •Replacement sales focus on winning vs. peers, not inventing urgency
Outbound isn’t dead: scaling limits of inbound and why Rippling had to build outbound fast
Matt pushes back hard on the claim that outbound is dead, calling it a sign of inexperience at scale. He shares Rippling’s lesson: inbound can be extraordinary, but it eventually caps—forcing a rapid buildout of outbound.
- •‘Outbound is dead’ is engagement bait or lack of scaling experience
- •Inbound eventually can’t grow at the rate required by the business plan
- •Rippling had to stand up outbound quickly after hitting inbound limits
- •Outbound still works: significant volume booked via phone
How to build outbound that works: tight marketing partnership, intent, and execution discipline
Matt details the mechanics of effective outbound at scale. The core is a no-credit, high-trust partnership with marketing that supplies intent signals and messaging, while SDR teams execute ruthlessly against daily KPIs.
- •Outbound success requires deep sales–marketing partnership
- •Marketing contributes intent signals (site/reviews/job changes) and sequencing
- •Sales/SDR org owns consistent execution and KPI rigor
- •Culture prevents blame games; marketing is measured on pipeline outcomes
Planning and segmentation at scale: from CEO growth targets to 50 sub-segments
Matt explains how Rippling turns an ambitious top-line target into an operational capacity plan across dozens of segments. He describes the CRO role evolving into planning/ops: staffing, demo volume, quotas, and gap-closing levers.
- •CEO sets an outlier growth target; teams build bottoms-up capacity plans
- •Rippling models ~50 sub-segments across size, channels, and product suites
- •CRO work shifts from closing to operational planning as revenue scales
- •Planning focuses on demos, rep capacity, quotas, and explicit growth levers
Close rates, funnel stages, and the ACV threshold for outbound
The conversation quantifies win rates by segment and explains why measurement definitions matter (e.g., Stage 2 vs Stage 3). Matt also gives a concrete ACV example for when outbound economics make sense for Rippling.
- •SMB win rates can be ~50–60%; mid-market ~20%; enterprise ~15%
- •Win rates vary depending on where you start measuring in the funnel
- •Rippling outbound focuses on 50–250+ employee segments, not tiny SMB
- •Mid-market economics: ~45K average deal size supports outbound investment
Customer success vs account management: why multi-product companies must choose
Matt argues that for multi-product businesses, classic CSM and quota-carrying expansion roles can’t be the same job. Rippling split responsibilities into new logo reps, account managers (commercial ownership), and technical account managers (adoption).
- •Multi-product companies struggle to combine ‘success’ and ‘selling’ in one role
- •High-velocity new logo reps shouldn’t handle small add-ons months later
- •Rippling created account managers for renewals/expansion and TAMs for adoption
- •CSMs generally can’t be converted into quota-carrying sellers
Discounting and pricing strategy: list vs net price, consistent policies, and finding price friction
Matt reframes discounting as largely arbitrary—only net price matters. He emphasizes disciplined, consistent pricing rules to avoid chaos, and advises founders to raise prices gradually until buyers push back (healthy friction).
- •Discounting is relative to list price; net price is what matters
- •Maintain a firm discount policy to avoid “wild west” pricing differences
- •Explain price differences by deal structure (term, timeline, product count)
- •Raise prices gradually until you encounter meaningful buyer resistance
Creating urgency and managing deal slippage: parallel paths, real timelines, and “push vs poof”
Matt explains why time-based discounts rarely create true urgency and can backfire without trust and qualification. He then lays out how Rippling runs pipeline reviews and what constitutes an unacceptable reason for deals slipping—especially avoidable legal-process delays.
- •Don’t offer time-based discounts before confirming the buyer can move fast
- •Qualify the buyer’s “ideal timeline” early and get explicit buy-in
- •Weekly pipeline reviews focus on poking holes in rep optimism
- •Deal slip ‘red flag’: legal review delays often indicate poor parallel-tracking
Leading through volatility: morale, ownership, and building a culture of accountability
Matt shares lessons on staying constructive when deals disappear and budgets freeze. He stresses controlling emotional reactions, owning misses as a leader, and avoiding blame-shifting—your job is to make the team execute, not prove you know the answers.
- •Stay gracious after losses to preserve future re-engagement opportunities
- •Leaders must own misses upward and downward—no finger-pointing
- •Competitive people must avoid emotional reactions that damage relationships
- •Sales leadership is about enabling execution, not showcasing personal skill
What’s weakest in the GTM org: weaving outbound into a historically inbound sales culture
Matt reflects on Rippling’s evolution from purely inbound selling to scaling outbound in many segments. He argues SDR teams outperform AEs at consistent prospecting funnels and explains why he prefers delaying AE-owned prospecting as long as possible.
- •Rippling sales historically relied on inbound; outbound became necessary later
- •AEs at Rippling have no prospecting targets; SDRs own outbound quota
- •Outbound is a measurable funnel—something is always fixable to increase demos
- •SDR management system differs from AE management; structure matters
Playbooks, hiring for slope, and who scales: founders’ role, promotions, and losing the locker room
Matt argues founders shouldn’t author the sales playbook but should hire GTM leadership earlier than conventional wisdom. He shares what he looks for in early sales leaders (rapid internal promotions), why “all-star VPs” rarely join tiny startups, and how to spot leaders who stop scaling.
- •Founders provide product vision; revenue leaders turn it into repeatable playbooks
- •Hire GTM earlier; trusted revenue leaders help sequence what to build
- •Hire for slope: rapid multi-promotion at one company is a strong signal
- •Non-scaling leaders ‘lead from the back,’ stop modeling the work, and lose the locker room
Quick-fire: competitors, hustle, in-office culture, CEO intensity, and specialization by product
In the closing quick-fire, Matt discusses which competitors he respects, the enduring advantage of effort, and his preference for in-person culture. He also highlights a key GTM strategy shift at Rippling: splitting product specialists from core new-logo reps to compete in focused vertical battles.
- •Respect for legacy competitors’ GTM ability even when product is weaker
- •Hard work/hustle remains a durable differentiator post-COVID
- •Belief that in-person culture is valuable (with hybrid realities)
- •Scaling sales motion by creating product AEs alongside core new-logo reps

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