How should CEOs and sales leaders set and respond to revenue plans?

Jason Lemkin · Jan 13, 2023

Founders should base their plan on their trailing three-to-four-month average growth and burn rates rather than aspirational numbers, scaling up only gradually, and should build sensitivities into their models because missing the growth plan even slightly can dramatically increase burn.

There is still widespread delusion about the odds of raising later rounds across all markets; the only real evidence is a term sheet or a trusted investor committing to specific milestones.

Scope: evidence = a term sheet or explicit milestone commitment

17:13 20VC: WTF is Going On in VC? Are VCs Still Investing? How Has What VCs Want in Investments Changed? Are LPs Investing in New Funds? Why VCs That Invest in Public Markets Are Losers? Dec 2023; Will It Be Better Or Worse with Jason Lemkin

Stevie Case · Jan 25, 2023

Annual plans should be built for the worse macro outcome while staying prepared for a better one

The recession could be mild or very significant and no one knows, so the plan has to accommodate either

Scope: framed under uncertainty about recession severity

43:51 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

Chad Peets · Aug 23, 2024

Setting a forecast backwards from a desired fundraising valuation is tail wagging dog; the business should dictate the forecast

Arbitrary jumps like moving rep productivity from $750k to $950k have no underlying justification beyond the round the CEO wants to raise

53:53 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

Harry Stebbings · May 23, 2026 · hedged

The gamification of scaling — setting revenue targets to unlock the next fundraising valuation — is a bad way to run a company

Scope: framed as possibly being 'old'

38:32 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Chad Peets · May 23, 2026

A forecast must be something you can hit with a level of certainty from headcount and productivity math, not a lucky number reverse-engineered from a target valuation

He looks at the number of salespeople and the productivity plan; if the number isn't realistic, forecasts become hope, and he has threatened to leave companies that do this

39:12 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Jeanne DeWitt Grosser · Mar 9, 2022

The CEO and head of sales must explicitly tie out on the operating plan and agree on how achievable the targets actually are, rather than assuming a shared reading of a stretch plan

At Dialpad she signed up for a stretchy plan assuming a Google-style OKR norm where 70% attainment is good delivery, and she and the CEO were never aligned on how audacious the underlying assumptions were

28:10 20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St

Rich Liu · Jun 7, 2023

Founders and sales leaders must close the gap between what each believes is achievable before setting targets, rather than letting the founder impose an unnegotiated stretch number

If the sales leader lacks confidence to push back, the team runs itself ragged, and even hitting 90% of a wild target feels like failure to the board while 4x on a 5x goal might actually be amazing; worse, the company invests cost structure against a growth rate it won't hit

Scope: especially important in the current environment where investment levels follow the target

41:24 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Harry Stebbings · Aug 23, 2024

CEOs often set revenue goals well above what the CRO believes achievable, setting everyone up for failure

53:43 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

Carles Reina · Feb 14, 2026

The biggest mistake CEOs make with sales leaders is imposing a number on them and expecting delivery without understanding the implications of that target

68:42 20Sales: Inside ElevenLabs $330M ARR Sales Machine | The 20x Sales Comp Plan Reps Must Hit | How to Land and Expand in a World of AI | Why Product-Market-Fit is BS, Reps Should Not Be in the Office and Outbound is King with Carles Reina

Doug Adamic · Sep 8, 2023

After a missed quarter, morale is best maintained by doing a deep dive on what went wrong while pointing to leading indicators trending up and reinforcing adherence to the system and playbook

Positive leading indicators signal success is around the corner, so leaning on process rather than getting rattled pays off long term

Scope: assumes leading indicators are in fact trending positively; the miss must not become a pattern

49:50 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

Chris Degnan · Nov 10, 2023

After a missed quarter you protect morale by being honest and measured rather than emotional — showing the team the market data and separating sales, product and macro causes.

Looking at the metrics reveals what actually changed, such as CFOs cutting back and buying behaviour shifting.

46:07 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Julian Teixeira · Mar 7, 2025

When results are bad, leaders should call out what is genuinely going well while being brutally honest about what isn't, attacking the problem rather than the person

Selling is an emotional sport — deflated salespeople can't get customers excited if they don't believe in themselves

38:46 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

Steve Goldberg · Dec 13, 2023

A disciplined weekly forecast call that walks every single opportunity in every category and digs hard into any gap minimizes end-of-quarter surprises

Because nobody could show up unprepared, the rigor cascaded down through every layer of the team

Scope: Based on ten years working under Dave Vernitsky's Friday 10am forecast call

15:04 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

Julian Teixeira · Mar 7, 2025

Pipeline inspection should be weekly regardless of segment, with daily attention to SMB pacing and account-level focus for larger deals

Pipeline is not something you review once a month or quarter — you live in it daily; even enterprise deals that take two quarters need weekly objectives about what must be true to win and what progress was made

Scope: the larger the deal, the more focus is at the account/deal level rather than segment totals

32:47 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

Weekly forecast calls should interrogate the pain, the metric attached to it, and whether you're talking to the person who cares about that metric — and deals should be moved back a stage when steps were skipped.

Those questions reveal whether the rep actually has control of the deal and whether it's in the right stage, rather than discovering a broken deal at the end.

Scope: how the call is run (team or 1:1) doesn't matter, that it happens does

45:10 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

Matt Plank · Dec 20, 2024

The right way to plan is to build the capacity plan bottoms-up while ignoring the CEO's target number, then explicitly identify the levers to close the gap between attainable and desired

The outlier growth number the CEO sets is never easy by definition, so you need a detailed segment-by-segment capacity build to know what's actually attainable before working the gap

Scope: Rippling runs ~50 segment capacity plans

13:36 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

Chad Peets · May 23, 2026

Sales plans must be built bottoms-up from capacity; you cannot start from the number you need to hit and work backwards

He tells companies the bottoms-up model determines what they can do, and top-down target-setting simply doesn't work

38:43 20Sales: The $100M CRO Bubble: Why Anthropic Are Causing a Comp Crisis | Why You Should Never Hire From Salesforce or Service Now | How to Hire, Train and Forecase in a World of AI with Chad Peets and Chris Degnan

Julian Teixeira · Mar 7, 2025

Setting a goal 20-30% higher than what you think is achievable produces better results than a realistic goal, even when the stretch goal is missed

In his experience teams still end up doing ~10% more than the initially realistic goal; there is a mental element that pushes people to think creatively

Scope: based on his own repeated experience

12:29 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

Ron Gabrisko · Aug 4, 2025

Ali Ghodsi's approach is to set sales targets as high as possible

Scope: Ron's counterweight was making sure reps could still earn

35:09 20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko

Mark Goldberger · Apr 19, 2023

When goals are missed, the root cause is inevitably pipeline coverage, and pipeline coverage is everyone's responsibility

46:42 20Sales: Why You Should Never Hire a VP Sales First, How To Create Urgency in a Sales Process, How to Do Traditional Outbound 10x Better, Why Revenue Doesn't Matter with Your First Customers | Mark Goldberger, Head of Enterprise Sales @ Ramp

Kevin Egan · Jul 12, 2023

The best reps generate enough pipeline throughout the year that they hit quarterly numbers without doing anything unnatural — pipeline covers all sins

With ample pipeline, if one deal falls out another comes in, so you never have to jam deals at quarter end

Scope: not always possible every quarter; early-stage companies that absolutely need a deal may need executive support to push

26:54 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

Jeanne DeWitt Grosser · Mar 9, 2022

When a startup is missing its numbers, the right response is an honest conversation about the burn-rate consequences plus a sales-run root cause analysis, not just re-motivating the team

Burn rate doesn't change, so missing revenue shortens the runway to the next fundraise; the diagnostic usually uncovers both untuned sales process and legitimate product gaps

30:05 20 Sales: The Stripe Sales Playbook; Who Should Create It, When Should it Be Done, Where Do Many Go Wrong | How To Identify 10x Sales Hires and How To Structure the Hiring Process in Sales with Jeanne DeWitt Grosser, Head of Americas Revenue & Growth @ St

Chris Degnan · Nov 10, 2023

After a bad quarter you must honestly diagnose whether the cause was the macro environment or your own sales team.

Bad quarters will happen, and external factors like COVID or inflation must be separated from execution failures.

45:19 20Sales: Five Lessons Scaling Snowflake to $1BN ARR, Why Customer Success is BS and Should Be Removed, Why All Sales Reps Should Do Eight Calls Per Week & Why You Should Hire a Head of Sales Sooner Than You Think with Chris Degnan, CRO @ Snowflake

Chad Peets · Aug 23, 2024

Not enough CROs push back on unrealistic forecasts or headcount plans, because they want to keep their jobs

They can see in the data that the plan (e.g. doubling from 100 to 200 reps) isn't supportable, but say they'll do everything they can anyway

55:21 Cro must push back even at personal risk

Lori Jimenez · Aug 2, 2023

Forecast inspection must happen with the same rigor in strong quarters as in weak ones

If you only inspect when you're down, decisions are made from a fear-based, stressed mindset; consistent rigor is what builds accountability and must be taught to leaders

45:40 Inspect with equal rigor in good and bad quarters

Chad Peets · May 23, 2026

CEOs should set quotas erring on the low side, because overpaying for a year is survivable while quotas set too high destroy the sales org

Too-low quotas mean overpaying but blowing through the forecast; too-high quotas mean nobody makes money, morale collapses, A players quit, and you can't replace A players with A players — the remaining A players learn not to join

12:09 Err low on quota overpaying beats breaking the org

Chris Degnan · May 23, 2026

When a segment misses its number, diagnose by layer — check whether every rep and every manager missed — because the root cause is usually a second line manager, and then take action

People get apathetic and lazy; you have to find where the failure actually sits

19:04 Diagnose misses layer by layer down to the second line

Chad Peets · May 23, 2026

Forecasting should leave flexibility between the data-driven productivity plan and the CEO's astronomical target, and land somewhere in the middle

Reps can likely do more than the productivity model says, so a rigid data-driven number understates what's achievable

59:06 Land between the capacity model and the ceo stretch number

Ben Fiechtner · Aug 2, 2024

The best sales leaders push their teams for more but do not believe the stories they are told, staying honest about the real state of the business

Every AE presents a slide showing themselves finishing at 120% of plan, yet 100% of AEs never finish at 120%, so realism requires a structured thirteen-week process to find the holes

18:11 Push for more while staying skeptical of reps self reported forecasts

Dan Fougere · Nov 22, 2024

A leader should publicly stake out audacious targets they genuinely believe in, because the public commitment functions as burning the ships and forces you to deliver.

Like telling people you'll run a marathon — once you've said it, you have to do it; putting a stake in the ground commits everything to making it happen.

43:42 Public audacious commitment forces delivery

Becca Lindquist · May 2, 2026

The biggest forecasting mistake frontline sales leaders make is not being in the details of the deals alongside the rep.

A manager who is actually in the deal can give a perspective and immediate next step without checking notes; anyone can read the Salesforce update, so the manager's value is their own view of the deal.

46:14 Managers must be inside the deal not reading the crm

Emil Michael · Oct 24, 2022

Founders should set and hit modest numbers rather than promise aggressive ones, because the dry powder sitting on the sidelines will go to CEOs who hit their goals

In the prior era missing projections didn't matter because there was enough money that up was up; now investors who haven't deployed for a year will back CEOs who proved growth levers and transformed their business to meet the environment

25:42 Hit modest realistic numbers rather than aggressive promises wins scarce capital

Patrick Forquer · May 11, 2026

Legora's quota setting last year was poorly calibrated, since average attainment came in at 280%

Attainment that far above target means the targets were set too low

48:00 Extreme over attainment proves the quota was mis set