Sales Onboarding: How To Bring New Reps Up To Speed Fast

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Written by
David Levy

Read this guide to optimize your onboarding process and reduce rep ramp times!

Does your organization belong to the 62% of businesses with underperforming onboarding processes? If you’re seeing the following roadblocks when hiring new reps, you might be facing:

  • High sales rep turnover
  • Slow ramp-up times
  • Lack of inside sales effectiveness from an individual and organizational level

On the other hand, effective sales onboarding can help new hires become productive 3.4 months sooner than the sluggish average of 6-9 months!

I put together this guide to offer practical solutions.

You’ll get a sales onboarding checklist, best practices, and tips for onboarding sales managers (crucial players in the rep training process).

Table of contents:

An Overview of Sales Onboarding

Sales onboarding is hard. Your reps are likely learning a new industry, new buyer personas, new competitors, new products/features, new partners, etc.

Meanwhile, buyers expect more when they engage with your sales team, and the competition is ready to deliver if you’re not.

How do you get reps confident from day 1 that they can add value during their customer 

conversations and help guide the buyer to a purchasing decision?

This is the role of sales onboarding.

With the right enablement tools, your new hires can build the knowledge and confidence they need to start adding value during customer conversations much more quickly than they would without the right program and processes in place.

But only 37% of companies have onboarding programs that exceed one month, according to Aberdeen Research — that’s just not enough time to yield results. 

A 90-day model (AKA 30-60-90) is a better approach to helping reps absorb sales material and best practices long term. For example, new reps could receive training broken down in the following 30-day increments: 

  • Days 1-30: Learn the company’s mission, structure, executives, cross-functional partners, and expectations
  • Days 31-60: Ramp up the workload to apply the first 30 days of learning; sit in on live calls
  • Days 61-90: Focus on skill mastery and collaboration  

The timeframe isn’t the only important factor contributing to effective onboarding. The materials you use are extremely important, too. So make sure your onboarding system follows these criteria:

  • Contains digestible sales content. (Create a sales playbook that reps can reference and use before, during, and after sales calls)
  • Integrates these materials in a sales rep’s workflow
  • Ensures that the content is being used consistently 

Why Sales Onboarding is Critical

Sales onboarding matters more today than ever. Here are 4 reasons why.

1. Sales rep retention 

Sales onboarding creates a positive domino effect.

Here’s what I mean:

Elite-level onboarding gives new hires a better grasp of the product, the persona you’re selling to, sales processes, tools, competitors, etc., boosting their confidence and chances of meeting or exceeding quotas. 

Also, reps that hit or exceed quota will have increased morale, which will reduce turnover — and in turn — costs of training new reps to replace burnt-out ones.

2. Improve sales effectiveness

New sales hires are expected to make mistakes on their journey to reach their full potential. However, experienced company sales reps can also fall victim to poor habits ingrained over time. For example, they may resort to outdated messaging, stale competitive intel, and/or not staying on top of the company roadmap, thinking they have all the answers.  

Your sales onboarding process creates a repeatable system for new and experienced reps alike to fall back on when they’re straying away from proven systems and best practices. At a time when competitors seemingly have more reps, resources, and partners, the onboarding and enablement of your team are critical to maximizing sales effectiveness.

3. Attract better sales talent

Providing a great sales onboarding experience encourages reps to recommend your company to peers. In addition to the financial aspect of hitting or exceeding quota from a more thoughtful onboarding, reps also care about personal development. When reps see a company investing in them, they become advocates for your company when talking to their peers.

On the other hand, a negative or insufficient onboarding process can quickly lead to unhappy sellers if they are not hitting their numbers. This has a trickle-down effect, where reps may leave negative remarks on job review platforms like Glassdoor. 

You need to create an onboarding process that gives an exemplary first impression of your company culture and maximizes sales effectiveness to attract future sales talent.

4. Provides a consistent customer experience

Say you were to pull 10 reps aside:

Would their approaches to selling for your company be uniform?

Is their messaging consistent?

Would they handle competitive objections based on what's on the battlecards?

The sales onboarding big picture is to galvanize reps to keep the customer experience consistent and identify gaps getting in the way of sales effectiveness.

4 Signs That Your Sales Onboarding Process Needs an Overhaul

62% of businesses believe their onboarding process is ineffective.

If you aren’t sure your problem stems from onboarding, look for the following signs: 

1. Long ramp times

The average ramp time is about 6-9 months.

That time frame is simply too long if you want to see a fast ROI from reps, especially in today’s competitive market. 

If your organization is seeing a slow or average ramp-up time, it’s time to implement a sales onboarding overhaul. 

Review your sales enablement if your reps aren’t being brought up to speed fast enough. Compliment traditional enablement training by implementing software like Aircover, which helps bring reps up to speed with in-meeting battlecards and notes that’ll help them smash through objections and be more effective.

2. New reps missing quotas

If most of your new reps are missing quota, your onboarding process may be the culprit.

To confirm, compare new hire and seasoned rep numbers. If new reps are disproportionately missing quota, revisit how you onboard them.  

3. Struggling to scale your sales team

A high turnover rate may be evidence of organizational weaknesses, such as:

  • Poorly defined and repeatable sales processes that win deals
  • Few or ineffective enablement tools 

Eliminate these issues before they start by implementing an onboarding plan that arms new hires with the knowledge they need to reach their numbers.

4. No concrete and measurable sales onboarding plan

Quickly learning the rules of a game is important, but executing a proven strategy puts you on a winning streak. 

Your sales onboarding process is a vital part of your overall business strategy, but if you neglect to treat it that way, you’ll miss out on easy wins. 

As you onboard reps, maintain a timeline and track key milestones you want the reps to reach (more on this later).

How to Build a Playbook for Onboarding Success: 9 Must-have Sections

If you are in need of an onboarding overhaul, your sales playbook likely needs to be revamped to help reps learn and repeatedly reach sales success in your organization.

Here are the most critical components to include in your sales playbook, and why you can’t afford to leave them out. 

1. Product Information

Product details help new hires get acquainted with its features and value, so they can identify angles to pitch at different leads. 

Here’s what your product section should include:

  • A summary of your product 
  • Its value proposition
  • Pricing
  • Use-cases
  • Technical features
  • How your product solves pain
  • Customer stories & ROI messaging

Train reps on areas of your product that offer value to a specific customer segment. With a dynamic product and market, complement your traditional enablement sessions with real-time, in-meeting enablement to help reinforce all of the product training in your playbook.

Your enterprise customers will care about things like SSO, role-based access, and global data centers, while mid-market clients will prioritize price.

When your hires can segment their talking points and battlecards based on these different client types, they’ll be able to personalize the customer experience and win more deals.

2. Your Sales Process Stages

The sales process covers the customer journey, and new hires need to know the key actions that need to be executed to move a deal forward.

Create an outline of your company’s sales process and how your reps should approach the customer based on each stage. 

Provide common hypothetical sales scenarios in your playbook and break down each customer journey stage. Then, annotate these scenarios with insights into why and how deals were won or lost. 

When available, use tools and workflows that integrate your sales process directly into your reps' day-to-day selling activities.

3. Sales enablement tools

76% of organizations using sales enablement tools see their sales numbers increase between 6%-20%.

The more sales enablement tools you offer your reps, the more value they have at their fingertips for their customer conversations and the more confident they will be during their calls.

Now, this doesn’t mean overwhelming them with 1000s of pages of material. 

In fact, sales enablement is better when it’s digestible and clear. 

You can create effective sales enablement programs by incorporating:

  • Battlecards (competitor, industry, and product analysis)
  • CRM data (customer trends, revenue metrics such as ASP, sales cycle time, win rates, etc.)
  • Objection handling
  • Discovery and probing questions
  • Customer wins

Take your sales enablement to the next level by implementing Aircover’s real-time AI sales assistant. Your reps get quick, actionable insights during calls to help them be more confident on customer calls, and your organization gets the benefit of happier customers and a more effective sales team.

4. Buyer Personas & Market Pain Points

Your buyer personas are a foundational tool for effective selling.

Earlier, I touched on the importance of segmenting your product’s value proposition based on certain customer types. 

Buyer personas allow new sales reps to align the information they know about your product to those different segments. 

Don’t try and create 100 buyer personas to capture every possible customer. Typically, just 3-4 personas contribute to 90% of a company’s sales. So isolate your top ideal buyers and train your reps to become experts on those profiles. 

Buyer personas should include:

  • Firmographic and technographic data (helping pinpoint who your customers are, what’s important to them, and what technologies they use )
  • Job title
  • Age
  • Gender 
  • Industry
  • Pain points
  • Buying habits
  • Motivations

If you’re wondering how to gather this information, you’ve got plenty of options:

  • Industry groups (e.g., if you sell to Marketing Operations, check LinkedIn for MOPS groups)  
  • Social media (following influencers in the industry you are selling to. They will convey trends and what people care about more broadly in their space)
  • Customer inquiries
  • Surveys
  • Company and competitor reviews. 
  • Historical CRM data

When it comes to your CRM, one of the most accurate places to find your buyer persona is your closed-won sales opportunities — here, you can find data about who your champion, influencer, and decision-makers are.

Finding commonalities between these deals can create an accurate picture of who your reps should be speaking to and how to handle interacting with them.

5. Sales Messaging

Sales scripts and sales decks help reps understand your brand’s messaging, the value proposition, and the broader ecosystem that you operate in. Sales messaging gives reps the takeaways they can integrate directly into sales calls and have a productive conversation.

Your sales messaging should appear in multiple resources:

Well-crafted sales messaging accomplishes 5 crucial things:

  • Helps customers feel heard
  • Brings customers value
  • Establishes trust
  • Builds credibility for your reps
  • Establishes a consistent brand 

It can be difficult for your reps to internalize so much information, and so whatever tools and content you can integrate into a seller's workflow will help them unblock their deals and/or move them further down the funnel.

6. Sales Methodology

Sales methodologies are frameworks for winning deals in a predictable way. 

They are foundational to help guide reps through the sales process, and provide managers a way to analyze a deal and offer recommendations to move it forward.

Sales managers should focus a lot of time and energy on ensuring their onboarding covers what sales methodology they use, as well as applying to deals they’ve recently closed.

Here are some of the most common sales methodologies to consider: 

  1. SPIN (Situation, Problem, Implication, Need-Payoff
  2. MEDDIC (Metrics, Economic buyer, Decision criteria, Decision process, Identify pain, and Champion)
  3. SNAP (keep it Simple, be iNvaluable, Always align, raise Priorities)
  4. Gap selling
  5. NEAT (Need, Economic impact, Access to authority, Timeline)
  6. BANT (Budget, Authority, Need, Timeline)
  7. Challenger selling
  8. Value selling 

Implementing a sales methodology can be easy, but ensuring it's used in practice is challenging. 

Some immediate recommendations would be to set up fields in your CRM that tie to the methodology (deal role, metrics, pain, etc), and use tools that can help enforce good sales hygiene (i.e. auto-sync contacts and deal roles to CRM; auto-track action items; remind reps of thoughtful discovery questions they can ask to expand the opportunity and value you can provide, etc).

7. Sales Plays

Sometimes sales methodologies may miss industry or company-specific sales situations. Sales plays fill this gap by covering company-designed protocols for sales situations. 

In other words, sales plays help new reps make smarter decisions around their calls to increase the odds of success. 

Here are some examples of sales plays:

  • Call a new lead within 5 minutes after they enter the pipeline (there’s a 21x higher chance of qualifying leads with a quick response than waiting 30+ minutes)
  • Use a 12-touchpoint cadence across email, phone, and social over 20 days when trying to engage a new prospect
  • Non-selling touchpoints by offering value to your prospects vs. just trying to set up that next meeting. Figure out what keeps them up at night and offer them resources to help them accomplish their goals or mitigate risks

Successful sales plays are:

  • Outcome-based - They’re designed with the end goal in mind. 
  • Time-bound - They rely on deadlines and timeframes to add urgency to the objective. 
  • Executable - They include specific actions reps can take. 

8. KPI goals

Metrics motivate people to play their best. Sellers are inherently competitive, so benchmarking and showcasing the top performers drive people to peak performance.  

KPI goals set the tone for productivity and effectiveness. In fact, 79% of sales executives said that pushing reps to hit new targets is a leading driver of productivity.

Both individual and company-wide KPIs create energy around your business’ goals and motivate new hires to hit those numbers while keeping the entire organization on track. 

Here are KPIs that show up in an array of industries your sales managers may want to motivate reps to pursue:

  • Average Selling Price
  • Sales cycle length 
  • Upsell & cross-sell rates
  • Conversion rate 
  • Sales pipeline coverage 
  • Sales activity metrics
  • Competitive win rates

9. Sales organizational design

Reps need to see your organization’s structure clearly, so make sure you include a diagram outlining the sales team hierarchy. 

Understanding the sales organization design will help your reps identify who to go to for what and when. For instance, your reps need to know if there are outbound SDRs that prospect and inbound SDRs that qualify new leads, or if your AE’s happen to be paired one-to-one with an SDR and an SE.

Here are 4 common sales organization structures to consider:

  1. Customer Size - You’ve likely heard phrases such as velocity, mid-market, enterprise, global, strategics, etc. These are customer segments broken down by customer size, which can be based on employee count, company revenue, expected revenue to your company or some combination of these. All of these require different sales motions and different skill-sets from your reps. By segmenting by customer size, you can provide a better customer experience (i.e. not trying to close Home Depot the same way you would close a 10 person startup) and provide your sellers with a promotion track (senior reps working larger accounts)
  2. Product Line - Segmenting your sales team by product will help create specialists that can master skills around customer storytelling, discovery and probing questions, and pricing for a particular product. Issues may surface if the prospect is not best suited for the product they are selling and the rep doesn’t have the foundational knowledge to know one of your other products may actually be a perfect fit. 
  3. Geographic Territories - Segmenting your sales team by geography provides the added benefit of physical proximity to the customer for onsite visits, in-person events, and overlapping time zones. The trick will be creating a sales compensation plan for your reps that are commensurate with the overall territory opportunity. For example, the Bay Area region will likely have a higher quota attainment than the Southeast territory. 
  4. Industry or Vertical Focused - Segmenting your sales team by industry is the most expensive way to structure your team as you need to hire and train your reps to become specialists in one particular vertical. You’ll obviously want to perform an analysis to ensure you have the lead flow and opportunities to warrant this type of specialization. You’ll also likely want to have marketing and product teams that are segmented in a similar manner, as your banking customers will have very different requirements from your retail customers.

These are all productive ways to organize your team, and in fact, the largest B2B sales organizations in the world have some combination of all of these. For example, they will have an overall account manager (relationship manager/owner) that is focused on a specific industry within a certain geographic region, and a supporting cast to assist: sales executives for a specific product, subject matter experts (SMEs) who act as product specialists, SDRs to qualify new leads, etc. 

Your Sales Onboarding Checklist For Onboarding New Reps

If your sales playbook is squared away and updated, it’s time to implement these 9 actionable steps to onboard reps successfully.

1. Outline your sales onboarding

Your first step is to break your sales onboarding into a 30-60-90 day plan. 

This is a clear-cut outline of what your new hire will be doing, along with what expectations, priorities, goals, and “milestones” you want them to work toward. Be sure to evaluate the major onboarding events that make a rep successful and put those events in a linear order. 

Each 30-day window should have distinct goals, metrics, and takeaways. Not sure what to put within each window? Use a pre-made template to get started or find inspiration. In step 7 we’ll give you a specific example of what this should look like.

2. Review your Sales Enablement ensuring it’s up-to-date

All sales enablement materials should be up to date, so you’ll need to work closely with those who contributed to the playbook last.


The truth is, a lot can happen in your industry in just a 3-month window:

  • New competitors might emerge. 
  • Existing competitors may release new features. 
  • New partnerships with your organization may now fill an old gap. 

But your updated enablement tools are only as valuable as your reps consistently use them. 

Make sure the following are up-to-date and as relevant as possible to your current target customers:

  • Buyer personas
  • Case studies
  • Customer stories
  • Testimonials
  • Battlecards for the most common objections
  • Email templates and sequences for leads at different stages
  • Discovery questions and templates
  • Demo recordings
  • CRM data
  • Sales scripts

If your team uses Aircover, you can integrate sales enablement content during customer meetings, so reps get relevant, personalized intelligence based on their real-time conversations.  

3. Have your new reps acquainted with the company

This is the time to get them up to speed with the company's vision, direction, traditions, and values. 

Provide sales enablement resources and your sales playbook for new reps to study the history and mission of your company. Consistently stress your company values in team meetings to keep reps onboard.

This experience generates excitement about their role and the company’s direction. That’s the excitement and buy-in you want to flow into their calls and daily sales activity. 

4. Set clear expectations

Here are some reflection questions that can help you outline expectations for your reps:

  • What does sales success mean to your company?
  • What notable KPIs should be reached and at what time frame?
  • What kind of support can reps expect from your organization?
  • What sales tools do you expect reps to use and when?

It’s a good practice to reiterate expectations on multiple occasions and in different formats. For example, saying things live, in writing, and on video messaging can go a long way.

5. Walk new reps through your sales playbook

A sales manager should guide all new hires through the following practices around your sales playbook: 

  • The sections of the playbook
  • Its value (connecting it to recent customer wins)
  • How and where to access it (is it in Google Drive? Notion?)
  • Which sections should be applied in which situations and sales stages and why

The sales playbook walkthrough is important since a strong majority of a sales rep's results will come from the playbook’s contents.

Sales leaders should explicitly and thoroughly walk through the playbook to set the expectation that the rep will do the same. 

6. Get them acquainted with team members

Team members can help new AEs learn the ropes, find a support system, and identify mentors.  

Introduce new hires to their cross-functional teammates in marketing, product, and engineering. These departments can present what they do at the company and how they work in tandem with the sales team.

7. Follow your established sales onboarding plan 

It’s now time to execute your sales onboarding plan.

I’ll give you an example of a detailed outline using the 30-60-90 days approach:

First 1-30 days:

Don’t rush the initial training, so new hires can retain the information by reviewing it multiple times.  

Here’s what month 1 should include: 

  • An introduction about the company, the culture, the product, and the industry
  • Times for new hires to meet with team members and build relationships 
  • Exposure to important documents and sales enablement resources (scripts, templates, CRM how-to’s, ICPs in the playbook)
  • Training on their tech stack
  • Practice role-playing sales calls and some live sales calls. 
  • Sales shadowing
  • Quizzes and certifications that demonstrate understanding  

Outcome expectations: Reps acquire an understanding of the product, sales process, sales enablement foundations, and sales call best practices.

Days 31-60:

  • Implement feedback from managers
  • Aim for KPIs
  • Establish repeatable sales habits that get results 
  • Continue sales shadowing 
  • Use enablement consistently and in the right situations 
  • Apply sales plays in real situations 
  • More check-ins from leadership to track progress and guide reps 

Outcome expectations: Reps apply feedback well, meet adequate KPI numbers, and grow sales play knowledge. 

Days 61-90:

  • Improvement based on monthly KPIs should be adequate
  • Sales enablement use should be second-nature
  • Expectations that were set at the beginning should also be adequately followed (i.e., performance standards, compliance guidelines, etc.
  • Reverse shadowing
  • Improved pipeline management
  • Continued Check-ins 

Outcome expectations: Reps close their first deal, make better sales decisions, demonstrate strong knowledge of expectations, need less micromanaging. 

To help accelerate milestones that would otherwise be found in Day 61-90 (i.e., closing your first deal), tools like Aircover can help accelerate new rep onboarding by providing them the information they need to move a deal forward, live on the call with the customer.

8. Have routine check-ins 

Use frequent check-ins during your onboarding process to give feedback and answer questions. 

Check-ins provide a structured time to review sales calls, analyze results, give coaching ideas, and offer critiques. Inviting your new reps to ask as many questions as possible will encourage autonomous and continuous improvement as a habit. 

9. Continuously improve onboarding & sales effectiveness

Training isn’t over at the 90-day mark. 

As a matter of fact, reps are just scratching the surface by the end of their 3rd month. 

Conditions like market changes, competitor improvements, and product upgrades require your reps (both new and experienced) to learn new things. 

Here’s the bottom line: sales onboarding and enablement should be continually refined. 

Sales leaders can compare how reps perform with the new onboarding strategy with the old process to identify new strengths, isolate old weaknesses, and address potential vulnerabilities. 

How to Onboard a Sales Manager In 6 Steps

Your next sales manager plays a critical role in the success of your reps, company, and customer experience. 

In fact, Adam Rapp, professor of marketing at Ohio University, reported that top-performing managers achieve 39% more of their target than less-performing managers.

In the same study, Rapp found that the top 25% of sales managers had 65% of their reps reaching quota.

With that said, here are 6 important steps to onboarding a great sales manager:

1. Identify the experiences, traits, and skill sets you want to see in your managers 

Create criteria that outline the skills, traits, and experiences you want your sales managers to bring to the table. 

Should they be successful reps with lots of experience within your company?

Is past sales managerial experience important to you?

Collaborate with stakeholders and higher-ups to create a specific set of criteria. This might include:

  • Strong coaching ability when it comes to a team of x number of reps
  • Active listening skills 
  • Strong communication skills 
  • 10+ years of sales experience
  • Knowledge of specific industry verticals
  • Sales technology know-how
  • Detailed and big picture thinker 

2.  Initially, onboard managers the same way as reps 

Training a new manager as if they were a new sales rep gives them first-hand experience with the process they’ll eventually bring their reps through. This prepares managers to answer rep questions and anticipate sticking points.

Onboarding managers this way helps them understand the company, enablement, potential sales mistakes, and how to deliver sales feedback.

3. Set clear goals and expectations 

Goals are just as important for managers as they are for reps.

Let new managers know your performance expectations for them, reps, and the team as a whole each quarter. 

Remember, metrics motivate productivity and boost the likelihood that managers will direct their teams toward high ROI activities.

4. Create a sales coaching plan 

Implementing a blueprint is a fantastic way to keep coaching quality consistent. 

Your company's coaching approach should cover protocols for one-on-one and group training. Here are some specifics your blueprint can cover:

  • How to coach underperforming reps 
  • How to deliver feedback
  • How to connect with reps 
  • How to encourage self-evaluation 
  • How to hold reps accountable
  • How to motivate the team
  • How to use sales enablement to coach reps

5. Coach managers on maximizing key areas in their role

Sales managers have a lot on their plates, so it’s not uncommon for their energy to be split in 50 different directions. 

Help your managers identify the actions that move the needle most and outline the skills you want them to continuously improve, like hiring, coaching, onboarding, software utilization, and sales analysis. 

Have them shadow another manager across a 30-60-90 day span to provide more value to their learning experience.

6. Continued enablement 

Enabling your new manager never ends. 

Audit your managers, ask them about their approach to sales coaching, and talk to them about which sales enablement resources are working and why.

If you want to see your business scale, make ongoing enablement across your organization a priority. 

A Final Review on Better Sales Onboarding

Establish your sales onboarding approach before your next hire to get the most out of the process. 

You can be especially effective by incorporating a sales playbook into all sales training, including onboarding. 

Reps are more likely to flourish in the company when they’re given the tools and processes that set them up for success from day one. 

Accelerate your sales onboarding and improve new hire ramp time by 50% by complimenting the enablement you’re doing with real-time, in-meeting insights and tools provided by Aircover.

Get early access to Aircover’s solution to increase sales effectiveness and help your reps be confident on calls from day 1.