How should sales leaders motivate their teams?

Matt Rosenberg · Oct 4, 2023

In an early sales team, momentum should be built from small process milestones (first call, second meeting, feedback relayed to product) rather than from closed wins

The eventual win is a byproduct of many small steps, so each step is itself a win worth studying and celebrating

Scope: applies to the earliest days of a sales team

7:16 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

Harry Stebbings · Oct 4, 2023

Leaders should deliberately manufacture hype around new hires' small wins, celebrating them beyond their actual size, to build the hire's confidence

Amplifying small early wins gives new hires confidence

Scope: about new hires

8:09 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

Sean Murray · Jan 24, 2024

Morale after missed goals is maintained through goal visualization and celebrating small daily wins, plus reminding the team of the mission and its market impact

You have to go deeper than quota because not everyone is motivated by money

64:47 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

Ashley Kelly · Jun 7, 2024

The way to rebuild SDR morale is to get very close to the team, refocus on basic inputs, and celebrate small daily wins like dials and connects

Morale is one of the hardest holes to dig out of, so improvement has to be built day in and day out through compounding small wins

Scope: hardest thing to overcome

37:22 20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Carlos Delatorre · Jan 24, 2025

A Friday all-team wrap-up telling stories of PG wins and pipeline created from prior weeks' PG builds belief and reinforces the habit

PG is important and powerful but hard, so it needs enthusiasm and reinforcement

Scope: run by the CRO/sales leader themselves

32:09 20Sales: Why Every Sales Rep Should Do Pipeline Generation & How to Teach Them | Verticalised Sales Playbooks: When and How | How the Best Sales Reps and Leaders Structure Their Time with Carlos Delatorre, CRO @ Harness

Maggie Hott · Dec 14, 2022

A new sales leader should diagnose each rep's individual motivation — money, pride, or a path to management

Knowing a person's why tells you exactly how to coach and motivate them

59:47 20 Sales: Webflow's Maggie Hott on When to Start and How to Scale the Best Outbound Sales Team, Why Founders Should Not Hire a Head of Sales First, The Must Ask Questions When Hiring Sales Reps and How To Structure the Process

John McMahon · Nov 28, 2025

Money motivation in salespeople is fine, but leaders make a mistake assuming all reps are money-motivated; you have to learn each person's individual motivation

Understanding where someone came from and what they want makes it easier to train, coach and motivate them

Scope: requires unstructured one-on-one time such as 'windshield time' driving to accounts

46:07 20Sales: John McMahon on How to Hire, Train & Retain the Best Sales Reps | How Sales Changes in a World of AI | Sales Lessons from Snowflake and MongoDB | How to Create and Drive a Sales Process with Urgency

Chris Degnan · Nov 10, 2023

Sales reps should not feel safe; they need pressure and a sense of urgency.

He never feels safe himself, and laid-back reps without urgency drive him crazy.

38:33 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

Carles Reina · Feb 14, 2026

A sales leader should always be anxious about hitting the quarter, because the certainty of hitting the number leads to relaxing

The worry is a signal that you are pushing really hard; if you know you'll get there you stop pushing

69:24 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

Harry Stebbings · Nov 15, 2023

Competition is psychologically useful as a common enemy to fuel and rally your team.

71:05 20VC: How to Survive and Thrive in a World of OpenAI, Are LLMs Being Commoditised, Where Does the Value Lie; Infrastructure or Application Layer, How Apple Could Win in a World of AI, How Amazon Could Threaten OpenAI and Why Google Struggle with Des Trayn

Harry Stebbings · Oct 28, 2024

Companies need to create a common enemy to motivate teams

57:18 20VC: Why SaaS is Dead | Why AI First Companies Will Win | We are in the Middle of a Cold War for AI Talent | Why Europe is F******* and We Need to Stop Whining with Daniel Khachab, Co-Founder @ Choco

Daniel Khachab · Oct 28, 2024

Intrinsic mission-based motivation must come first and extrinsic motivation like a common enemy or competition a distant second

Teams should focus on achieving the mission as fast as possible rather than on beating competitors — lions don't lose sleep over sheep

Scope: accepts that a common enemy does work to some extent

57:21 20VC: Why SaaS is Dead | Why AI First Companies Will Win | We are in the Middle of a Cold War for AI Talent | Why Europe is F******* and We Need to Stop Whining with Daniel Khachab, Co-Founder @ Choco

Kyle Norton · May 30, 2025

Mission and customer success stories are a stronger motivator for a sales team than beating named competitors

It's easy to get excited about helping a struggling restaurant owner take home meaningfully more money; competitor talk is just joking around, not the driving motivation

Scope: they still pay some attention to competitors

67:36 20Sales: From $2M ARR to $40M ARR: The Playbook | How to Use AI To Supercharge Your Sales Team | Why Pipeline Reviews are BS | The Sales Call Script that Closes 99% of Prospects and How to Hire the Best Sales Reps with Kyle Norton, CRO @ Owner

Doug Adamic · Sep 8, 2023

The way to motivate a sales team at the start of a quarter is to tie personal goals and aspirations to professional advancement and to the rarity of the current company moment, not chest-banging Wolf of Wall Street energy

Most people don't believe they can achieve greatness because they've never had an environment that invites personal aspiration into the professional process; a deeper motivation compounds and is what builds an infinite, sustainable organization

Scope: Doug says he still likes Wolf of Wall Street, but considers it shallower

29:54 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

Julian Teixeira · Mar 7, 2025

Connecting with people on a personal level and understanding what motivates them is the key to motivating them and keeping them engaged through the hard changes of building and scaling a company.

Building and scaling companies takes people through really hard changes, so personal connection is what sustains engagement.

Scope: drawn from a decade at Lightspeed

4:34 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

Stevie Case · Jan 25, 2023

When reps are missing the top-line number, the better tactic is to go further back in the funnel and spiff or gamify the underlying activities rather than spiffing revenue itself

Nobody loves outbounding and hounding them doesn't work; incentivizing the first activities that lead to revenue gives reps an early win

32:37 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

Ashley Kelly · Jun 7, 2024

Spiffs and competitions should always be tailored to the specific end goal you want, such as fast-start incentives that get reps halfway to quota in week one

Like any incentive, it should be designed around the outcome you want; and making the job fun matters because reps get told no all day

38:35 20Sales: How Rippling Built Their Sales Machine: How to Hire, Train and Manage the Best SDRs, What is the Right Comp Package for Sales Teams & The Playbook to Start and Scale Your SDR Team

Ishan Mukherjee · Apr 4, 2025

Morale in a sales org is maintained by continuing to work relentlessly, truth-seeking about gaps and wins early with extreme ownership, and doubling down on the top performers

A power law applies: 10-15% are true believers who will be there long term, and the middle 40-50% sways toward either the top or bottom, so the only way to manage the middle is to double down on the outliers

63:55 Double down on top performers to pull the middle

Carles Reina · Apr 11, 2026

Public leaderboards don't demoralize salespeople because sales self-selects for outspoken, extroverted people willing to take harsh feedback

You don't go into sales in the first place if you can't handle losing in public

44:11 Public leaderboards fit sales self selection

John McMahon · Nov 28, 2025

Complacency in a winning sales team is prevented by driving discipline and constantly retraining reps, because the product, competition, market and customer sophistication change continuously

Software now ships releases daily rather than every six months, competitors and markets shift, and customers ask more educated questions, so training never stops

45:28 Constant retraining and discipline prevent complacency

Chad Peets · Aug 23, 2024

Expecting sales reps to love their day job is unrealistic; they should love working for you and their CRO, but nobody enjoys pipeline generation

Cold calling and pipeline generation are a grind nobody likes; what reps can love is a CRO who invests in and develops them and makes them win

36:56 Loyalty to the leader not love of the work

Daniel Khachab · Oct 28, 2024

Competition is the simplest motivational tool, and goal-setting becomes unclear once you are number one

When you're second the goal is simply to get just above number one; once you're first, 'stay number one' is defensive and you have to redefine winning as dominating

56:50 Competition is the simplest motivator but goal setting becomes unclear once number one

Harry Stebbings · Mar 22, 2023

In sales, psychological safety should be paired with a lot of healthy competition and quarter-end urgency, so that safety comes with a little fear of not hitting targets.

Quarter ends drive efficiency and urgency in sales specifically

11:27 Psychological safety paired with competitive quarter end urgency

Frank Fillmann · Mar 22, 2023

If you hire naturally competitive people, their own internal drive exceeds any pressure a manager could apply, so you don't need to apply external pressure

Like athletes on the field, the right people bring energy and competitiveness intrinsically

11:51 Hire naturally competitive people so external pressure is unnecessary

Stevie Case · Jan 25, 2023

Spiffs work best when tied to something other than revenue — a behaviour the business needs that isn't already covered by the comp plan

The quota in the compensation plan already addresses revenue

34:52 Spiff only behaviors not already covered by the comp plan

Stevie Case · Jan 25, 2023

Cash is the best default spiff, but recognition-based rewards like dinner with the CEO or special access also work because of the leaderboard competition they create

People want to come out on top and you want the program to be fun; a gamified points-based pipeline week at Twilio worked well

35:19 Cash is the default spiff but recognition based rewards also drive leaderboard competition

Carlos Delatorre · Jan 24, 2025

When a team is in a morale funk, the right move is to stop, get everyone in a room, talk about how they're feeling, and diagnose the root driver — whether it's lack of buy-in or a skills/training gap — rather than pushing harder.

The fix differs depending on whether reps don't believe the motion works or don't believe they can do it, so you have to get to the underlying driver.

45:11 Diagnose belief versus skill gap before pushing harder

Dave Kellogg · Jan 31, 2024

Managing by always keeping the carrot in front of the donkey — never being satisfied, always asking for a bit more — is a terrible way to manage people

Under that style the person is constantly failing; and with forecasting specifically there is no way to win because the number can never be right

30:14 Never satisfied carrot and stick management is counterproductive

Kyle Norton · May 30, 2025

Instilling a stoic mindset focused on inputs and the daily grind effectively inoculates sales teams against inevitable down periods

If people already accept challenge and failure as the journey, they are mentally prepared when results dip

73:36 Instilling a stoic input focused mindset inoculates reps against down periods

Mike Hudack · Sep 13, 2024

To turn around bad morale in a product team you need two things: give people a win they can be proud of, and give them a reason to believe by connecting their daily work to a good thing in the world

Meaning can be reframed — ads become helping people discover products and helping small businesses and entrepreneurs grow, Facebook sharing becomes maintaining loose ties with people you'd otherwise lose, Monzo becomes helping people pay rent and avoid debt; pair that with shipping momentum where you see impact and morale flips quickly

51:15 Combine a visible win with reconnecting daily work to larger meaning

Dan Fougere · Nov 22, 2024

Building a great sales culture starts with articulating an explicit vision of greatness — that the team will make life-changing money, be best in class, have fun, learn more than anywhere else, and carry the halo of that success for the rest of their careers — plus stating concrete revenue and IPO targets from day one.

The vision that 'we will be great' is the foundation; he delivered it to the whole team in his first week.

42:36 Explicit vision of greatness from day one

Harry Stebbings · Nov 10, 2023

If you don't celebrate the good times, people will leave.

45:38 Celebrating wins is a retention lever

Ashley Kelly · Jun 7, 2024

Motivation approaches must adapt to local culture — imposing American playbooks on international teams will never work, so leaders should go see the ground level themselves

Building trust requires understanding cultural differences firsthand

44:40 Motivation must be localized to culture