How should a startup codify its sales approach, and who owns that codification?

Jordan Van Horn · Aug 17, 2022

The founder is 100% accountable for v0 of the sales playbook, which should document only three things: what problem you solve and for whom (including who you are not for), the wins/losses/points of resonance with customers, and the two or three reasons customers want to solve the problem right now

Defining who you're not for focuses the sales team you hire; the founder should know the points of resonance better than the sales team

Scope: doesn't have to be pretty, precise or formal

7:41 20 Sales: Three Reasons Why Sales People Fail | The Two Things That Matter When Hiring Sales Leaders | Why Revenue, Discounting and Price Do Not Matter in the Early Days with Jordan Van Horn, Revenue Leader @ Monte Carlo

Lori Jimenez · Aug 2, 2023

Founders, not the head of sales, are the right people to create the initial sales playbook

They have the most passion, can best articulate the story, and know the why and what deeply enough to anticipate the problem being solved, pivot the playbook on customer feedback, and route that feedback back to product

Scope: can carry through as the company grows, with the founder adjusting the playbook from feedback even when less close to it

9:25 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

Harry Stebbings · Oct 4, 2023 · hedged

The speaker feels strongly that the founder, rather than the first sales hire, should build the sales playbook

Scope: stated as a strong feeling

12:16 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

The founder must define the playbook first, because without clarity on motion, channels, messaging, positioning and ICP you cannot know what type of sales leader to hire

Sales leaders vary enormously by motion (PLG vs heavy enterprise), so without a playbook you risk hiring completely the wrong profile

14:11 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 · Dec 13, 2023

In a startup, the founder — not the sales leader — should create the first sales playbook, including messaging, ICP, sales motion and pricing.

Scope: applies to the first playbook at a startup; Harry notes many others disagree

28:34 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

Harry Stebbings · Jan 24, 2024

The founder should build the first go-to-market playbook themselves, because without knowing the buyer, ACV, channels and message they cannot know which type of sales leader to hire

If the founder doesn't know the buyer, the ACV, the channel and the message, they can't know which of the many types of sales leader to hire

61:24 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

Harry Stebbings · Apr 12, 2024 · hedged

The founder must create the sales playbook and be the one selling before hiring sales reps

Scope: states others tell him he's wrong

14:00 20Sales: The Biggest Sales Lessons Scaling Brex to $400M ARR, Why Startups are Doing Outbound Wrong and How to Fix It & Why Demand Gen is the Bottleneck for all Startups and How to Solve it with Sam Blond, Former CRO @ Brex

Ashley Kelly · Jun 7, 2024

The founder should build the first sales playbook and be the main seller and storyteller of the company

The playbook content comes from the vision — what problem is being solved and what's being built — translated into something that works for prospects

Scope: if not the founder, someone senior in marketing or sales; depends on company size

15:08 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

Jeetu Mahtani · Sep 27, 2024

Founders should actively co-create the sales playbook and be on every sales call until roughly 100 customers

Prospects buying from a no-brand company respond to hearing the founder's vision, and live calls create the feedback loop founders need since they don't get the product right on day one

Scope: until about 100 customers; early stage with only two or three reps

31:24 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

Julian Teixeira · Mar 7, 2025

The founder, not an early head of sales, should create the first sales playbook.

Firsthand front-line exposure to how customers react gives the founder the leverage to call bullshit on whoever they later trust sales to.

Scope: strongly believed but admits exceptions exist; a capable go-to-market first hire can do it

7:24 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

Kyle Norton · May 30, 2025

The founder must build the basics of the sales playbook themselves — the framework of what customers want, where they get it, how to message them and what a sales cycle looks like — and cannot outsource it to an incoming VP of sales.

A founder who outsources it won't understand the customer in enough depth, and without understanding what persuades a customer you can't build the rest of the organization.

Scope: a sales leader can come in and build everything beyond the basics; acknowledges there's a range of opinions on this

8:38 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

Stevie Case · Jan 25, 2023

The founder must build the story portion of the sales playbook and be the first salesperson, while the mechanical step-by-step playbook should come later and not be authored by the founder too early

Early customers need to believe in the vision and buy in with the founder, so trust and storytelling can only come from them; but writing down mechanics before product-market fit and a validated ICP locks you into something you can't iterate on

Scope: mechanical playbook comes once product-market fit exists

18:22 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

Kevin Egan · Jul 12, 2023

The founder/CEO's job is to provide the inspiration and high-level talking points about how the product solves business problems; it is the sales VP's job to pull from that, codify it in writing, and turn it into sales motions.

7:20 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

Matt Rosenberg · Oct 4, 2023

Founders should not be the ones to build the sales playbook; a sales leader should build it

Building a playbook requires a layer of abstraction founders lack — they speak the language of investors and pilot customers, and sales is fundamentally translating what the company does into the buyer's language and back again

Scope: founder should still be in the meeting and lead positioning because they understand the product deeply

12:33 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

Steve Goldberg · Dec 13, 2023 · hedged

Founder passion can carry a product company to early revenue but most founders lack the go-to-market experience to build an enterprise sales process.

Founders can convince one person their product is best, but multi-stakeholder enterprise selling requires process, RevOps, enablement and infrastructure, which most founders have never built.

Scope: founders may be strong on product or marketing side; Salesloft had ~$50M revenue on passion alone before adding process

28:59 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

Brendon Cassidy · Mar 8, 2024

Founders should sketch a loose first playbook of principles and plays that work, but the playbook written in ink should come from the VP of sales

Early plays are provisional and shouldn't be locked in; the VP of sales, having seen them in action, is the right person to formalize it

13:55 20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy

Chad Peets · Aug 23, 2024

The conventional advice that the founder should build the sales playbook first and then hire a sales leader is backwards — a salesperson should create the sales playbook

A VP of engineering has no expertise in creating a sales playbook

Scope: framed as 'backwards' rather than BS

13:56 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

Dan Fougere · Nov 22, 2024

Founders do not build the real sales playbook — the sales leader does; founders may build a lightweight early motion but it will not scale to billions in revenue

He has never seen a founder do it; at Datadog Amit's early version was a marketing-to-self-serve-demo-to-credit-card motion, which is a great start but not the documented multi-stage process needed at scale

Scope: based on his own experience at every company he has been at

31:54 20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

Harry Stebbings · Dec 20, 2024

Founders are not the ones who should create the sales playbook

52:38 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

Matt Plank · Dec 20, 2024

Founders should not create the sales playbook; they should set direction and pressure-test it while a revenue leader authors it

A founder like Parker is unmatched at articulating why the product matters and at sniffing out go-to-market bullshit, but he doesn't think like the buyer and can't convert that thinking into a consistent, repeatable sales playbook

Scope: Founder should still be involved in go-to-market direction and give hard feedback

53:04 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

Kevin Egan · Jul 12, 2023

'Sales playbook' is the wrong framing; the right term is 'sales motions' — understanding buyer, user persona, industry, business problems, and how the product uniquely solves them.

'Playbook' implies a simple one-two-three set of steps that closes a deal, and selling is more than that.

6:27 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

Lori Jimenez · Aug 2, 2023

A sales playbook should be a GPS-style guide to the successful motion at each stage of the cycle, not a minute-by-minute script

It should draw on experience and success from previous sales engagements while leaving enough creativity and flexibility to account for each salesperson's style

8:29 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

AJ Tennant · Oct 23, 2024

The concept of a sales playbook is overrated — it is just a fancy word for strategy, messaging and plan, and elevating it beyond that complicates a simple business

Sales is simple: a target ICP, messaging, a good product and content, then outbound to create interest, convert interest to opportunities, and work them through a funnel; he prefers measuring net new meetings, conversion to opportunities and funnel progression

Scope: self-described as controversial

5:27 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

Doug Adamic · Sep 8, 2023

A sales playbook is a defined sequence of steps, each with checklist criteria that must be fulfilled before advancing to the next step

If a step or checklist item is skipped, the gap reveals itself at the end of the deal and the promised partnership can't be delivered

Scope: framed as the highest-level definition; specifics vary by segment

27:12 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

Dan Fougere · Nov 22, 2024

A real sales playbook is a fully documented, chronological process — personas, cold-call scripts, objection handling, discovery format, demo content, and explicit exit criteria for each stage — such that an outside hire can be trained into it

It gives a generally repeatable framework so each stage has defined desired outcomes and criteria for advancing to the next

29:52 20Sales: What I Learned Scaling Datadog from $60M to $1BN in ARR | How to do Outbound in 2024 | Why Discounting is Dangerous and Contract Sizes are Misleading with Dan Fougere

Ron Gabrisko · Aug 4, 2025

A sales playbook should be literally codified: customer profile, buyer personas, the discovery questions to ask, first-pitch positioning, and the POC/pilot process

Everyone gets trained on it so you can rinse and repeat as fast as possible and gather customers

28:18 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

Chris Degnan · Nov 10, 2023

The sales playbook is simply: go on eight sales calls a week and be a student of what you sell — do that with a good product and you will succeed, with a bad product you will not

He had to interview the founders to understand the value proposition himself; the method has stayed identical from first hire to today's new-hire training

Scope: success is conditional on having a good product

9:25 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

Fabien Pinckaers · Feb 12, 2025

The sales leader should be a promoted internal trainer-type rather than an external hire, and sales scaling comes from massive product demo practice — two demos a day until reps become good

Sales scaling for them is all about the product, and reps become good after doing two demos a day for a few weeks

47:16 20VC: The $5BN Company Built from the Belgian Countryside | The Story of Odoo: The Company with No Plans to Sell, IPO & Their Billionaire Founder Who Does Not Care About Money with Fabien Pinckaers, Founder & CEO @ Odoo

Larry Shurtz · May 10, 2024

Playbooks should be built outcome-first and worked backwards, kept simple, and paired with measurement and cadence

Teams get playbook-happy and end up with conflicting playbooks; starting from the desired outcome lets you derive what must be true, by when, and who does it, and cadence tells you whether you're on track and when to pivot

10:33 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

Larry Shurtz · May 10, 2024

Founders building a vertical sales playbook should pick a single vertical to focus on and build the playbook by working backward from customer outcomes.

51:05 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

Lauren Schwartz · Oct 19, 2022

The word 'playbook' is too prescriptive for a super early-stage startup; the first sales hires' job is to collect market information and customer feedback that informs the product roadmap.

There is nothing to codify yet — the founder is the first seller, and early reps work off the founder's vision and story of the business outcomes the product solves.

10:22 Too early for a playbook first hires job is collecting market information

Frank Fillmann · Mar 22, 2023

A sales playbook should be defined as 'repeatable and relevant', with client relevance coming first — built around the client's metrics and firm, not your product or org

Clients don't care about you, your gear, your product or your org; they care about themselves, and relevance also lets a new rep ramp far faster than the typical six to twelve months

5:54 Playbook defined as repeatable and client relevant not product centric

Frank Fillmann · Mar 22, 2023

Translating your technology into industry use cases and specific personas actually compresses the sales cycle rather than lengthening it, and ramps reps in weeks instead of months or quarters

An insurance claims adjuster doesn't want a technology demo — they want to know how you get them to the accident scene faster, detect fraud, speed up payment; that relevance engages the client faster and lets the rep focus on whether there's a problem they can solve, so you find the dollars in April–June rather than September–October

8:18 Translating tech into industry personas compresses sales cycle and ramp

Frank Fillmann · Mar 22, 2023

Sales teams should build lightweight industry playbooks so reps can go straight into calls instead of each preparing their own materials, driving repeatability.

New reps shouldn't have to rebuild all the product, industry and customer material their peers already built; a template drives repeatability and makes them immediately relevant to the client.

24:50 Prebuilt industry playbooks replace individual rep prep

Matt Plank · Dec 20, 2024

A sales leader should hand off ownership of pitch decks, scripts and competitive positioning to segment VPs far earlier than most do, rather than remaining the org's single expert

Once the company has 5, 10 or 20 segments the central leader is no longer the expert on any of them; the segment teams do it all day and are better at it, and centralised authorship makes people defer instead of calling out material that is stale or broken

44:34 Decentralize messaging ownership to segment leaders

Ron Gabrisko · Aug 4, 2025

Once you have product-market fit and references, the job shifts to the scale function: building a real playbook and training more salespeople

You've now seen how and why customers buy, so the motion can be codified and repeated

27:56 Pmf and references trigger the shift to building a codified playbook and training

Jordan Van Horn · Aug 17, 2022

A sales playbook is the discrete steps to help the customer understand what you do, evaluate whether you drive a critical business outcome, gain consensus among decision makers, formalize the relationship, and — most importantly — create a blueprint for the customer's success

The playbook must let you make good on the promises made during the sales cycle

7:03 Playbook must cover buyer understanding evaluation consensus and success blueprint

David Schneider · Sep 11, 2024

Sales teams become effective through a repeatable system: define the ICP, learn the issues from existing customers, turn those into stories and playbooks covering what to say, to whom, and how to handle objections.

All of that is trainable and onboardable, so performance is a management output rather than luck.

10:52 Define icp then convert customer issues into trainable playbooks