How should new sales hires be onboarded and how soon should they face customers?

Jeanne DeWitt Grosser · Mar 9, 2022

New sales hires should be put in front of customers almost immediately rather than waiting until they know the product deeply

A savvy salesperson can run a call knowing little about the product because what great salespeople do is ask good questions and admit when they don't know an answer

Scope: harder at very early-stage companies; requires pairing with tenured reps or solution architects and heavy shadowing

16:26 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

Mark Goldberger · Apr 19, 2023

Sales onboarding should mix structured and asynchronous learning with call shadowing and daily/weekly 1:1 coaching, and the training wheels should come off quickly rather than giving reps a cushy ramp period

You learn a lot in the first few weeks about whether a rep can run at pace and synthesize information when they have to drink from the fire hose

Scope: acknowledges larger companies tend to extend ramp periods

37:38 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

Larry Shurtz · May 10, 2024

Being new in front of customers is a valuable learning position, so long as the new rep goes with their manager and has done real preparation and brings something to the table

You only get a limited window to be 'new' and ask basic questions; he still uses it himself after a year at Genesys, but the discipline and preparation of the meeting is non-negotiable

Scope: never send a new AE alone into a big account; preparation and homework still required

24:09 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

Ashley Kelly · Jun 7, 2024

New SDRs should be on the phone and given their account books by week two, rather than held in a separate training track for a month

Models like the old Yelp approach delay production until month three; reps can only learn to scrub accounts, identify contacts and run sequences on their actual books

Scope: week one is company/product/competitor onboarding; not expected to perform at full scale in weeks two or three

31:02 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

New reps should be on customer calls within the first couple of days of onboarding, before formal boot camp.

A pre-built messaging framework with value prop, sample questions and proof points lets reps be credible on the phone immediately.

Scope: requires an existing messaging framework reps can absorb before starting

41:33 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

Julian Teixeira · Mar 7, 2025

New reps should be talking to customers almost immediately, well before being given a book of business or leads

They can join calls, listen in and interject, taking the training wheels off gradually — but they have to get out there

Scope: including in enterprise sales

18:44 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

Ishan Mukherjee · Apr 4, 2025

Onboarding should be AI-enabled and put reps in front of live deals and customers rather than running two to three months of traditional training

Classroom-style training information is stale by the time it's delivered; it's the difference between school and learning from YouTube

26:55 20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

Carles Reina · Feb 14, 2026

New reps should be put on live customer calls within days: drill the product for 24 hours, pitch the leader, then co-sell with the leader taking a backseat

It gets them fully up and running within a week; it was riskier but they had nothing to lose and had to move fast in a crowded market

Scope: riskier approach; justified by early-stage urgency and a crowded market

49:52 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

Shaunt Voskanian · Mar 21, 2026

Enterprise reps should be thrown into one or two real accounts immediately, before formal product and sales-skills onboarding

There's already a lot of work to be done on those accounts, and getting them building relationships and learning the customer's business early is more valuable than starting with training

Scope: applies to enterprise/strategic reps who bring some sales skill with them; formal onboarding follows a couple of weeks later

37:55 20Sales: Inside Figma's $1BN ARR Revenue Machine | Why We Do Not Have Customer Success or SDRs | Why I Do Not Believe in Sales Quotas with Shaunt Voskanian, CRO @ Figma

Lauren Schwartz · Oct 19, 2022

The most important thing in onboarding a new sales rep is early exposure to customers — recorded calls, shadowing the founder or manager, and taking lower-stakes calls

At-bats accelerate ramp, and in enterprise the real opportunities are few and far between so each one is high leverage and too risky for an unramped hire

Scope: especially for enterprise reps; she did this at Segment

25:40 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Unknown · Nov 16, 2022 · hedged

Roughly two months is a reasonable onboarding period before an early-stage rep is truly ready, though they can start talking to customers within about three weeks

They need time to acquire knowledge and a great demo, but early low-stakes customer conversations build reps

Scope: early stage; talking to customers early is easier for PLG or open-source companies with inbound flow or a community

Unknown · Nov 16, 2022

A new rep should listen to as many recorded sales calls as possible but must not stay in listening mode — they should practice fast on a pool of discarded or off-ICP leads to work out the kinks before real opportunities arrive.

Practicing discovery and pitch on low-stakes leads means you look really good when a good opportunity lands in your pipeline.

Scope: practice pool = discarded/SMB leads the company doesn't bother selling to

Unknown · Nov 16, 2022

In enterprise, new hires should be given deliberately low-risk at-bats rather than real opportunities, because opportunities are few and far between and each one in a long sales cycle is high leverage.

You don't want a new hire taking the call with a major account like First Republic.

Scope: enterprise sales specifically

Mark Goldberger · Apr 19, 2023

Sales leaders should deliberately create space for junior reps to fail when the stakes are low so they can succeed when the stakes are high, rather than either doing the deal for them or letting them run free.

A leader can't be in every deal and call at once, so reps need the tools to succeed unsupervised; and no matter how often you say the stove is hot, people still need to touch it — the leader's job is keeping the burner on simmer so the wound isn't catastrophic.

30:54 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

Julian Teixeira · Mar 7, 2025

AEs should cold-outbound to ICP-fit companies themselves and learn to personalize based on real research about the prospect, before being handed any marketing-generated leads

Failing outreach builds the muscle of figuring out what a specific prospect cares about; otherwise they blunder expensive paid-for leads

19:16 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

Jordan Van Horn · Aug 17, 2022

Onboarding should match the stage and maturity of the company: unstructured 'here's the info, go figure it out' plus heavy feedback for the first sales hires, and rigorous competency-based programs once you're hiring in tens and twenties

At five employees a new hire is walking into a disaster that won't end after 30 days, so structure would be false; at scale you need to define what people must know, by when, and how it's demonstrated

Scope: applies to first couple of sales hires vs. hiring at scale

38:48 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

Unknown · Nov 16, 2022

Early-stage companies should use their fundraising deck as the market-education material for new sales hires because a sales deck usually doesn't exist yet

At Asana with $10M in revenue driven by self-serve there was no sales deck, and that is very common

Scope: early stage

Unknown · Nov 16, 2022

Onboarding should match the stage and maturity of the company: unstructured and feedback-heavy for the first few hires, rigorously structured once hiring in tens and twenties

Early hires are walking into a disaster that will continue, so they need to figure it out; at scale you need defined competencies, timelines and demonstration of mastery

Chad Peets · Aug 23, 2024

At scale, onboarding must be programmatic and properly resourced, with classes and on-site time over months, and companies should not expect revenue from a rep before enablement is complete

Getting greedy and shortcutting enablement puts reps in positions they aren't ready for

Scope: ad hoc onboarding is fine at early stage

55:41 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

Kim Graves · Jun 27, 2025

How fast to put reps in front of customers depends on company stage: at the earliest stage throw them into customer calls almost immediately, while at scale gate them behind checkpoints and manager-approved mock scenarios

Early on you just need adaptable people talking to customers; at scale you can practice discovery and pitch with a manager or onboarding cohort before risking a real customer

Scope: stage-dependent

32:51 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

Lauren Schwartz · Oct 19, 2022

A library of recorded sales calls plus captured win/loss postmortems from deal reviews is the most valuable onboarding material for new reps

Captured learnings can be amplified when new people join the organization

26:51 20 Sales: How To Structure The Interview Process for All Sales Reps, The Must-Ask Questions When Identifying Potential Sales Talent & The 3 Biggest Mistakes Founders Make When Hiring Their First Reps with Lauren Schwartz, VP of Enterprise Sales @ Fivetran

Unknown · Nov 16, 2022

Companies should build a library of recorded sales calls and capture postmortems from wins and losses through deal reviews, so those learnings can be amplified for new joiners.

Captured learnings from deal reviews are what you replay to people as they ramp.

Brendon Cassidy · Mar 8, 2024

The best way to onboard a new sales rep at a startup is osmosis — shadowing the founder on every sales call and listening to a bank of recorded calls, rather than formal sales training

In a startup, osmosis is the best way to learn; call recording tools make it easy to analyze and synthesize the data, and companies generally aren't spending on sales training right now

Scope: startup with a founder-led sales motion; first couple of weeks with low expectations on the rep; limited to call recordings relevant to the sales cycles they'll run

23:45 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

Becca Lindquist · May 2, 2026

Early-stage founders should train their first reps by letting them ride along on founder-run calls and sending them every recorded sales call

The recordings let reps hear how the founder talks about the product, which is the key to transferring what's in the founder's brain into the rep's brain, and reps will also give feedback on how to sell

Scope: formal boot camps are a later-stage thing

19:05 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

Unknown · Nov 16, 2022

Onboarding should culminate in a high-stakes demo and role play in front of the founder, a PM and other customer-facing teammates, functioning as a certification

It's the equivalent of a PhD defending a thesis and acts as a forcing function to consolidate everything learned; if you can't present to your own team you certainly can't present to customers

Unknown · Nov 16, 2022

When a new enterprise rep is put in front of customers should be governed by how quickly they ramp through structured onboarding, not by a fixed calendar date

Onboarding is structured around learning the company, the pitch, the customers and value drivers, and reps progress at different speeds through that certification-style process

Scope: enterprise sales context; assumes a structured onboarding plan exists, e.g. a 90-day plan

Kyle Norton · May 30, 2025

New reps should be certified on craft and on operations, then have managers on all their early calls, being given progressively more rope as they show competence

The manager can take over when the rep freezes, which is why many first-weeks deals are manager-closed

42:03 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

Jeanne DeWitt Grosser · Mar 9, 2022

Throwing new hires into customer support queues in their first week is a great onboarding mechanism because it teaches users-first orientation, gives hands-on customer experience, and forces them to find answers in imperfect materials

At a startup you won't have a perfect playbook, so learning to work from whatever exists and find answers beyond it mirrors the actual job

14:55 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

Carles Reina · Feb 14, 2026

The best early-stage rep training is joining calls immediately as a silent observer, answering support tickets, and going deep with engineers on the product

They learn by seeing how others do it and by getting product depth from support and engineering

Scope: early stage only

50:49 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 · May 10, 2024

You should not put brand-new reps in front of large customers on day one, because they don't yet know the sales cycle, contracting steps or how deals close

A customer paying large sums doesn't want a rep who can't explain the process or next steps

Scope: large enterprise customers, e.g. $500k contracts; day-one / untrained reps

23:47 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

Kyle Norton · May 30, 2025

New AEs should be held back from live calls longer (day 11-12 rather than day 5) to be better trained first

A deal doesn't matter unless it launches; an undertrained rep says slightly inaccurate things, the customer discovers it at launch, trust breaks and they pull out since contracts are month to month

Scope: month-to-month contract model

40:30 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

John McMahon · Nov 28, 2025

A new rep failing the onboarding test is as much a problem with their hiring manager as with the rep, and a repeat failure means the leader has a big problem with that manager

The manager hired them and knew they would be tested, so failure shows the manager didn't ensure preparation; the rep's failure shows they didn't take the time despite claiming enthusiasm

32:21 Hiring manager shares accountability for onboarding failure

Frank Fillmann · Mar 22, 2023

A sales leader should be willing to invest a few quarters to a year going on calls and doing the work alongside a new rep until they're ready to operate alone

Backing someone fully creates the safety they need to perform, and the right potential justifies the effort

10:58 Leader invests a year going on calls with a high potential rep

Frank Fillmann · Mar 22, 2023

Telling a high-potential rep 'you've got this' and sending them into a big meeting alone is a mistake; a more experienced leader should prep, role-play and physically attend the first meetings before handing over the wheel.

The rep has never had, say, a CEO meeting; the customer may run the meeting and blow up the plan, so the senior person can tee up softball questions or step in if it goes off the rails, and only after a few at-bats has the rep demonstrated the experience.

20:47 Leader preps role plays and attends first big meetings before handoff

Frank Fillmann · Mar 22, 2023

There is no substitute for on-the-ground handholding in enterprise sales; leaders should keep two to three hours a day unplanned so they can drop everything and join a rep's account work.

Personally getting in the trenches is the only way to teach reps and you never let them out on their own until they're ready.

22:46 Leader keeps daily unplanned time for hands on account support

Frank Fillmann · Mar 22, 2023

A new rep should not be given a big account with a one-to-two-year buying cycle on the expectation of landing it in year one; either give them the account in year two or not at all.

Cyclical buying patterns mean a new rep effectively faces an eighteen-to-twenty-four-month cycle, so expecting a first-year close is setting them up for failure.

23:53 No cyclical long buying account in rookie year one

Stevie Case · Jan 25, 2023

The first sales hire must be glued at the hip with the founder — joining every call, including investor and partner conversations — until they can speak like a cofounder

No human can recreate a founder's storytelling and passion by reading a document; the only way to transfer it is to model it so the rep absorbs the whole story and can speak to the why and vision with enthusiasm

21:07 First sales hire must shadow founder on every call until they embody the story

Larry Shurtz · May 10, 2024

Sales onboarding will never fully return to the pre-pandemic in-person, multi-week, curriculum-based model

COVID shut down what everyone considered normal onboarding and the remote/in-person balance has permanently shifted

22:04 Post pandemic onboarding permanently shifted away from in person multi week model

Harry Stebbings · May 10, 2024

Having new sales hires listen to customer support calls is the most effective onboarding tactic and the closest way to train empathy

You hear the actual pains of customers

23:21 Listening to support calls is the best empathy training

Larry Shurtz · May 10, 2024

New reps should be paired via a buddy and mentorship system during ramp

You rarely get the chance to be new, so the window should be used well

23:34 Buddy mentorship system during ramp

Carlos Delatorre · Jan 24, 2025

Enablement should be designed backwards from a hypothetical fully-ramped rep: decompose every skill into competencies learnable in three hours or less, group them by ideal learning modality, and sequence them so reps can land a new logo as early as possible.

Breaking the ideal rep into learnable units and sequencing them lets you build a structured learning journey rather than ad hoc training.

39:22 Reverse engineer onboarding from the fully ramped rep

Kyle Norton · May 30, 2025

Call libraries are most useful as short methodology-matched snippets for specific skills, not whole recorded calls

Clips can show exactly how to open a call, ask discovery questions two to three levels deeper, deliver value prop and ask for the sale; AI tooling surfaces the parts of calls that best match their methodology

17:30 Short methodology matched clips beat whole call recordings

Kyle Norton · May 30, 2025

Scripting the basics of a sales call to the word does not make reps replaceable; it frees their cognitive load for higher-order work like tailoring the demo to discovery findings

If you're spending mental energy deciding where to take the call next, you can't think strategically; like a sports team, you can only execute sophisticated tactics once the basics are drilled

18:15 Scripting the basics frees cognitive load for higher order work not replaceability

Kyle Norton · May 30, 2025

A structured learning management system with modules and embedded examples does work for sales onboarding, rather than dumping reps into a call library

The content is interesting, reps are moved fast through a lot of material, there are consistent check-ins, and they know week two is practical application so they must be ready

19:14 Structured lms modules with embedded examples beat raw call library dumps

Kyle Norton · May 30, 2025

A large lead universe doesn't justify putting reps on calls early, even in high-volume SMB

Every opportunity was paid for and a more seasoned rep could have closed it; there's reputational risk, and throwing reps in too early can stunt their growth

41:22 Large lead volume does not justify rushing reps to calls early

Ashley Kelly · Jun 7, 2024

Hiring SDRs into an inbound role first and moving them to outbound after about six months is a better ramp than starting cold

Inbound gives warmer conversations where they learn more before having to pitch cold

45:14 Start on inbound then graduate to outbound

Patrick Forquer · May 11, 2026

Because Legora hires both lawyers and technologists, onboarding must cross-train each group in the other's domain — tech literacy for lawyers, legal subject-matter expertise for technologists

The two hiring pools arrive with opposite gaps

37:30 Cross train domain experts and technologists in each others domain