Should sellers discount to close deals?

Stevie Case · Jan 25, 2023

Discounting to close deals is legitimate and can be powerful, but it is a bad sign if discounting is your only lever for creating urgency

A 15% discount on a newly bundled package with no prior price closed a Fortune 500 airline deal at 4pm on December 31 — essentially free money — but terms, pricing, and the risk/attention of not getting it done are other urgency levers

Scope: especially defensible when discounting a newly created bundle that had no prior price

38:56 20Sales: Why You Should Not Do PLG and Enterprise Sales at the Same Time | How To Move Into Enterprise Sales Gradually | How To Make a Comp Plan For Sales Teams | Why Discounting is Good and Can Be Used with Stevie Case, CRO @ Vanta

Matt Rosenberg · Oct 4, 2023

Discounting is sometimes unavoidable and defensible, but it must be done with principles, guideposts and a clear reason communicated to the customer

A company's tradition of end-of-quarter discounting sets the market's expectation; without fence posts, discounting gets out of control

Scope: a perfect process means some percentage of deals need no discount; calls it a personal decision for the sales management team

32:40 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Matt Rosenberg · Oct 4, 2023

Discounts should be capped around 10%, as 10–15% or more is a problem and starts a slippery slope to 30% and 50%

A discount is a concession, and you shouldn't need to discount if you're solving customer issues and pricing appropriately

34:13 20Sales: Why the Founder Should Not Be the One to Create the Sales Playbook, Why You Should Hire a Sales Leader Before Sales Reps & Why You Should Not Hire Sales Leaders From Big Companies with Matt Rosenberg, CRO @ Grammarly

Larry Shurtz · May 10, 2024

Discounting is a normal part of enterprise selling and appropriate discount levels scale with deal size, but a rep asking for a discount without an articulated value proposition and business case means the team hasn't done its job

Industry practice shows a linear correlation between investment size and discount, and buyers are now very sophisticated — they benchmark, compare and get Gartner pricing advice; so the only unacceptable discount is one substituting for value work you failed to do

Scope: a small unproven vendor selling into a large enterprise like Chase will pay a price to win the business because the buyer is taking a flyer

40:10 20Sales: How to Build Vertical Sales Teams, Why No Customer Success is BS and Everyone Needs it, How to Hire, Train and Retain the First Reps and Lessons Scaling to $2.1BN Revenue and 1,300 People with Larry Schurtz, CRO @ Genesys

Matt Plank · Dec 20, 2024

Price variation across customers is fine as long as you have a consistent, firm discount policy reps can't override and can defend to customers

Customers do compare invoices, but if you can walk them through the policy — deal length, product count, timeline — the differences are justifiable; without policy it becomes a Wild West that spirals

Scope: requires reps cannot invent their own prices

26:37 20Sales: Rippling's CRO on Why Founders Should Not Create Sales Playbooks | Why Discounting is BS and How to Create Urgency in Deals | The Biggest Lessons on Pricing and How to Win the Pricing Game with Matt Plank

Lori Jimenez · Aug 2, 2023

A discount should never be given for free — it should always be traded for value back, especially in the early stages: references, customer stories, and referral introductions.

Trading for something preserves the value of the product and, early on, references and referrals extend reach the founder couldn't get alone.

Scope: especially in early stages

34:22 20Sales: Why The Founder Has To Be The One To Create The Sales Playbook, When To Hire Your First Rep, Why Junior is Better Than Senior, How to Manage Sales Rep Compensation, How To Onboard New Sales Reps and more with Lori Jimenez, CRO @ WorkRamp

Sean Murray · Jan 24, 2024

Price concessions should be reframed as flexibility and traded for something in return — references, conference speaking slots, social posts — rather than given as a straight discount

It's not a discount, it's a trade: you get something of value back for the lower price

38:16 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Sean Murray · Jan 24, 2024

Winning hard deals creatively is about 'give and get' — trading things like customer advisory board seats, co-promotion, or new product usage — rather than discounting

There are ways to create value on both sides that make the deal a no-brainer instead of just cutting price

Scope: for must-win strategic accounts

64:04 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Chad Peets · Aug 23, 2024

Early-stage companies should be willing to do negative-margin deals to win referenceable accounts

The reference value is worth the loss and can be made up later

Scope: early stage only; discounting policy varies by company stage

56:31 20Sales: How Snowflake Built a Sales Machine | Why You Have to Hire a CRO Pre-Product | Why Most Sales Reps Do Not Perform | Why Hiring Panels are BS in Interviews | Why Remote Sales Reps Do Not Care About Their Development with Chad Peets

Doug Adamic · Sep 8, 2023

Discounting is a bad lever for creating urgency because it sets a bad precedent and demeans the value you established in discovery

If you did the discovery work and established value, the price is fair, and reps should stand up for it rather than play games; discounting undermines deal size, cycle time and conversion

Scope: conditional on the organization actually delivering on its promise

23:07 20Sales: Why Everyone is Responsible for Demand Generation, How to do Great Sales Discovery, How to Reduce Sales Cycles and Create Urgency and Deal Reviews; Good and Bad Reasons to Lose a Deal with Doug Adamic, CRO @ Brex

Dave Kellogg · Jan 31, 2024

The best discounting strategy is to avoid the discount conversation altogether and, failing that, to come armed with the quantified value of the system

Value selling lets you respond to a last-day $100K discount request by pointing out the buyer already agreed the system saves them $5M a quarter

42:04 20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K

Jeetu Mahtani · Sep 27, 2024

Leading with discounting is a disservice to the customer, the company and the rep and should not be prominent in a sales process

Scope: there is a place for discounting once need is established and only to close a genuine budget gap; structure it so the discount falls away in year two; acknowledges other sales leaders believe in discounting

47:09 20Sales: Scaling Hubspot from $3M to $1BN in ARR | How to Hire and Ramp Sales Teams | How to Scale Customer Success Successfully | How and When to Go International and Crush It with Jeetu Mahtani

Steve Goldberg · Dec 13, 2023

Discounting should never be a flat no, but what matters more than the price is what's in the contract

For a workflow platform the customer needs consulting, support and services built into the deal so they can become self-sustaining and truly integrate the product into their workflow

Scope: framed for workflow platforms requiring consulting and services

35:31 20Sales: How to Close Sales When Selling to CFOs, How to Guarantee You Win Every Renewal, Core Questions All CFOs Ask Today When Buying, Why Revenue Operations is the Most Important Role in a Company with Steve Goldberg, CRO @ Salesloft

Ben Fiechtner · Aug 2, 2024

Good deal construction means understanding the client's constraints (OpEx, CapEx, cash flow) and your own internal levers, then threading the needle to a win-win — not just quoting a price and a discount percentage

Most sellers stop at 'here's my pricing, here's my discount, do you want to buy?' whereas real budget constraints often sit with a finance person the seller never talks to

Scope: client constraints are often hard to uncover because the buyer or procurement may not hold them

7:23 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Ben Fiechtner · Aug 2, 2024

Rather than dictating user counts, sellers should map the client's deployment schedule and work backwards, then openly state their own levers and ask where the client has flexibility

Discovering the deployment model together and then marrying both sides' levers is what produces the deal

Scope: approach differs between named-user and consumption models

8:35 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Ben Fiechtner · Aug 2, 2024

The 'pricing expires at the end of this month or quarter' tactic is dead — buyers call bullshit on it every time

It reads as used-car-salesman pressure; nobody believes the deal turns into a pumpkin on a date

48:13 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Julian Teixeira · Mar 7, 2025

The end-of-month expiring discount tactic is dead and will keep declining in importance

Buyers and procurement teams have wised up and now deliberately wait until the last day of the month to make desperate salespeople give more away; it's a bad behavior to train buyers on

Scope: there was a time and place for it in the past

47:22 20Sales: Everything You Know About Sales Playbooks is Wrong | How to Hire and Train Your First Sales Hires | How to Crush Pipeline and Deal Reviews as a Team | How to Structure Sales Teams and Sales Comp Plans with Julian Teixeira, CRO @ 1Password

Becca Lindquist · May 2, 2026

End-of-quarter discounting is a poor way to create urgency; real urgency comes from the buyer's own pain and the metric owner who needs the software now.

Buyers know the same discount will be available on the first day of the next quarter — 'is my money not green on April 1st?' — and as a buyer herself she moves fast because she needs the tool, not because of the rep's timeline; if the metric owner doesn't care, the rep skipped a step.

49:23 20VC: Inside Clay's Sales Playbook Scaling to $100M ARR | How to Set Sales Comp Plans | How to Read Sales Talent Linkedin Profiles | What Profiles to Hire & Fire | How to Increase Performance and Speed in Sales Teams with Becca Lindquist

Kevin Egan · Jul 12, 2023

Startups selling through procurement face more discount pressure because procurement knows they need the revenue, but procurement is actually looking for the startup to hold the line and show conviction in its product's value

Procurement agents test for conviction and understanding of the business value and ROI

Scope: applies to procurement-led deals, not PLG/credit-card motions

29:11 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Dave Kellogg · Jan 31, 2024

Great salespeople do not instantly cave to a competitor's lower price, because caving signals to the buyer that further discounts are available

Conceding immediately invites the buyer to keep asking for more — like squeezing a wet rag, they keep going as long as water comes out, and even then give one more twist

42:27 20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K

Harry Stebbings · Jan 31, 2024 · hedged

The right approach to discounting depends on the macro environment

41:33 20VC: The Metrics That Matter in SaaS Today; Why CaC Payback is Flawed & CAC Ratio is Better, Why You Need to Hire Three Sales Reps at a Time, How to Forecast in 2024 & Biggest Mistakes Made Forecasting & How to Make Customer Success Sell More with Dave K

Ben Fiechtner · Aug 2, 2024

In today's macro environment with SaaS in the tank, sellers must be focused on adoption and long-term customer success more than ever, which justifies unusual deal structures like heavy ramps

If you know the client's constraints and they're willing to share them, you can always find a structure that works long-term

10:18 20Sales: 12-Week Step-by-Step Framework to Crush Every Sales Quarter | Moving from SMB to Enterprise: How and When | Verticalised Sales Teams: Why They are a Gamechanger and How to Build Them with Ben Fiechtner, CRO @ Clari

Kim Graves · Jun 27, 2025

Reps should treat the discount/negotiation conversation as just another customer conversation rather than a tense one, state the value and price and then pause in silence.

The customer feels the rep's energy — if the rep is scared of the price, that transmits; staying neutral keeps the conversation collaborative.

7:30 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

Harry Stebbings · Jun 27, 2025

Reps who fill the silence after quoting a price by volunteering concessions instantly signal desperation.

Interjecting with 'I'm sure there's something we could do' comes across as too direct and desperate.

8:46 20Sales: How to Layer Enterprise Sales on PLG | How to Sell AI Tools To Enterprises That Are Scared | Should Reps Own Their Own Pipeline | Mistakes All Founders Make When Moving From Founder-Led to Rep-Led Sales with Kim Graves

John McMahon · Nov 28, 2025

You should not discount to drive urgency; discounting at quarter end is only for timing a deal you were going to win anyway.

The only question a quarter-end discount answers is whether you need the deal in this quarter or not.

16:44 Discount only times a deal already won

Sam Blond · Apr 12, 2024

Startups should discount deliberately to accelerate deal cycles, while positioning as the premium-priced product; the mistake is defaulting to discounting

Sales is psychology and the feeling of getting a good deal drives buyer behavior; time kills all deals, so a discount that speeds the cycle, keeps buyers away from competitors and frees the rep for the next opportunity is worth it — but it should come very late in a deal with a clear trade-off for urgency

64:42 Discount deliberately to accelerate the cycle

Matt Plank · Dec 20, 2024

Discounting is a made-up concept — only net price matters, since discount percentages are relative to an arbitrary list price

List price is a fake number nobody cares about; a 50% or 25% discount is meaningless except relative to whatever list price you set

24:56 Only net price matters list price is fictional

Ron Gabrisko · Aug 4, 2025 · hedged

Rather than heavily discounting to land logos, shrink the scope of the deal to fit a champion's signing authority and rely on a value-based pricing model to expand

A director typically has up to $100K of authority, so a scoped pilot with one team gets you inside and the pricing model scales from there

18:00 Shrink deal scope to fit champions authority instead of discounting

Carlos Delatorre · Jan 24, 2025

Discounting cannot manufacture a deal that wasn't otherwise going to happen in a considered purchase; either a champion is willing to advocate to the economic buyer or they aren't, and price doesn't change that.

Champion advocacy against everything else on the economic buyer's plate is binary — $250k versus $200k doesn't flip it.

50:00 Price cannot create a deal champion advocacy decides

Kevin Egan · Jul 12, 2023

Discounting should originate from the office of the CFO, with a discount matrix cascading approval authority from rep to manager to sales VP and exceptions escalating to the CFO

The CFO knows the margins and what the company can afford to give away at what volumes; if discounting is disconnected from the CFO's office you go in circles and have problems

28:29 Cfo owned discount matrix governs approvals

Ben Fiechtner · Aug 2, 2024

Service start date is a major pricing lever because SaaS companies can't recognize revenue until users activate, which makes early-quarter deals worth materially more than deals activating later

If activation is six months out, the revenue doesn't land until Q4, so a Q2-activating deal is worth a lot more

9:33 Service start date timing is a hidden pricing lever due to revenue recognition

Ben Fiechtner · Aug 2, 2024

Deferring payment terms for a long period because a customer is cash-strapped usually ends poorly and should be treaded on lightly

He has made those bets out of sympathy for strapped customers and they tend to go badly, so they must be made very intelligently

13:08 Deferred payment terms for cash strapped customers usually backfire

Dave Kellogg · Jan 31, 2024

Customer references are important but should not be used as a negotiating chip

A satisfied customer receiving real value will give a reference anyway, and a reference extracted under duress won't be a good reference

45:05 References should not be a discount negotiating chip except as last resort

Dan Fougere · Nov 22, 2024

Discount authority should be held as high up as possible — at the CRO/CPO level — rather than delegated to reps.

Salespeople left to their own devices peg at the maximum discount 100% of the time, which destroys unit price and valuation; in consumption businesses customers who get the deepest discount at small spend will demand even more as they 10x; and centralizing it keeps the discount data comparable across deals.

46:35 Discount authority centralized at the cro

Dan Fougere · Nov 22, 2024

Discount approval should stay deliberately high-friction and un-automated — better that reps spend their energy resisting discounts with the customer than efficiently extracting them from the CRO.

Protecting unit price at scale is worth an extra day of latency, because reps talk to each other and customers talk to each other, so any discount granted propagates.

50:10 Keep approval friction high deliberately

Mark Goldberger · Apr 19, 2023 · hedged

Discounting is an expectation baked into procurement teams and modern selling, but the more pain you uncover and the better your solution matches it, the less you need to discount.

Some organizations lean heavily on discounting while others sell the value and hold the line; pain-fit is what determines which you can do.

20:00 Pain fit determines discount need

Harry Stebbings · May 2, 2026

The speaker dislikes discounting, while acknowledging it is an effective way to create urgency and stop deals slipping into the next quarter

49:10 Avoid discounting even though it does drive urgency

Rich Liu · Jun 7, 2023

Discounting policy should follow from the go-to-market model: a crowded knife-fight market argues for the lowest sustainable margin price to capture share then raise prices, while a genuinely best product argues for holding a premium

Every approach has trade-offs, and the premium you can charge depends on how well you tell the story, quantify the value and prove delivered results

36:27 Price position follows competitive market model

Rich Liu · Jun 7, 2023

Discounting aggressively to break into a new space or market is justified, but only if you know you are effectively eating CAC by doing it

The discount is a knowing trade-off against customer acquisition cost

37:19 Discount as deliberate cac spend