Essential Guide to Modern Sales Onboarding

A New Look at Sales Onboarding

Sales organizations onboard new employees differently now than they did just five years ago. This transition to modern learning practices reflects exciting new opportunities for today’s professionals in Sales Enablement and Training as well as Learning and Development to transform onboarding into an organizational capability that drives growth.

We’ve helped over a hundred organizations build out successful modern onboarding programs and gained perspective on themes that consistently emerge among top performers. We’ll illustrate these throughout this guide while giving you tactical recommendations for driving better and faster onboarding today.

Well-architected onboarding programs speed time-to-productivity for new reps, improve production levels during ramp-up compared to previous performance benchmarks, and lower T&E expense by empowering teams to train and learn remotely. In stark contrast, traditional sales onboarding methods rarely produce business results or move the needle on key metrics.

Today, many companies still:

  • Neglect to take full advantage of modern learning practices or the available technology efficiencies
  • Struggle to find ways to make onboarding more efficient (shorter ramp time) and more effective (improve results both during ramp-up as well as after onboarding)

But this doesn’t mean you should abandon traditional training methods. Like any practical innovation, modern onboarding doesn’t completely do away with the past. It builds on it. Modern onboarding takes what we’ve learned about training and combines new systems and technology to make a leap forward.

The results speak for themselves:

  • Decreased ramp-up times by: 23%, 34%, 47%, 52%, and 55% (3-18 months)
  • At 120 days, new reps outperformed a control group of 5-year reps by 21% (6 months)
  • 21% increase in average contract value (12 months)
  • $398mm YoY revenue increase, $9.96mm net profit increase, and a 400% ROI (12 months)
  • Increased sales/rep in the 90 days after training by 2.3/month – avg. increase of $183k/class or $36.6mm/year (9 months)
  • Improved average profitability/new reps by 11% (4 months)
  • Improved new rep win-rate by 16% (6 months)
  • Saved $4.1MM annually in training cost (18 months)


We’ve distilled everything we’ve learned from organizations practicing modern learning into five key principles:

Strong instructional design and a performance consulting approach to onboarding infused with modern learning practices produces compelling and measurable business results.

Five Principles of Modern Sales Onboarding

1. Content is easy to create, absorb and access

THE FIRST PRINCIPLE of modern onboarding owes its existence to three technologies pushing the boundaries of what organizations can offer learners. First is the mobile device. The devices we use during every waking hour make it easy for organizations to meet reps where they live and work. The second key technology is video. The brain processes visuals faster than text so reps absorb video content more easily. The third is peer-topeer networking. New reps, managers, support staff and leaders’ ability to create and share video content from their mobile device opens new collaboration points throughout a sales organization.

Subject matter experts, senior leaders, managers and top-producing reps across industries use these technologies to contribute to the learning content creation effort. They capture ideas and new thinking on video, while learning software stores and surfaces the most effective ones an ongoing basis. Trainers and Enablement professionals search these videos by topic and repurpose them into learning modules by adding quiz questions, prompts, and other interactivity. This becomes a supplement to their formal course authoring efforts. This secondary source of fresh content gives Sales Enablement and Training professionals new agility to supply the field with learning content on a continual basis that reflects the latest goings on in their market.

Selecting your training topics

No one can prescribe exact topics to cover for onboarding content because too many variables exist for a cookie-cutter approach to be useful. Even with evergreen topics such as researching prospects, call planning, prioritizing accounts, contacts, and calls, and building rapport, you should tailor the content to reflect your top producers’ practices, the current market, verticals, ICP (ideal customer profile), and business situation.

However, sales enablement professionals can use the following approach to look within their business and determine the right content:

Knowledge. New hires need to learn a lot of things quickly. Whether it’s products or services, buyer personas, sales process, sales methodology (the knowledge of the methods which is the precursor to developing skill), pricing, competitors, industry outlook or more, your content repertoire needs to communicate everything they’ll need for success.

Start by determining which topics matter most for your sales reps and then back into the content required to ingrain them. Whenever possible, sales onboarding and sales training content should originate from a top-producer analysis (always best) or known best practices. Don’t be shy about enlisting the rest of your organization to create learning content. Encourage (or incentivize) top sales reps, subject matter experts and senior leaders to record video of themselves on their smartphone explaining recent wins or losses, discussing good ideas and demonstrating useful talk tracks and selling strategies. Then repurpose those into supplementary learning content with quiz questions and prompts and place them in your onboarding courses.

Pit a good performer against a bad process, and the process wins almost every time.

Geary Rummler

Skills. These are your sales competencies – the skills and behaviors that lead to success as a sales rep in your organization. Again, your selected competencies should be fueled by top-producer analysis or known best practices that produce results. Take care not to overlook soft skills such as communication, collaboration, creativity, and critical thinking.

Documented processes. This includes your sales process of course, but also other processes. A sale can be quickly derailed by a lack of internal process competency. Adequate time should be taken to teach things like lead follow-up, finding and using your buyer engagement content (sales collateral), proposing/ quoting, legal review, digital signing, customer onboarding, and related items. Organizations with defined processes outperform those without them. Sales reps who follow your well-defined processes will outperform those who don’t.

Content buckets. Below are some content buckets to consider as you decide what you will train on during onboarding.


Sequencing with performance milestones

Setting performance milestones for new hires and building out your onboarding content and programs to move reps through them is an opportunity to maximize efficiency often missed by Sales Enablement professionals.

After you’ve established your content buckets, set a series of measurable performance milestones. Then determine the activities the rep needs to do to achieve each milestone. From there, determine what the rep needs to know and do to conduct the activities successfully and maniacally focus on building your content accordingly.

Those become the performance and/or learning objectives for this piece of the onboarding curriculum, and thus drive the decisions about which learning content pieces are needed.

Some performance milestones might include:

  • Making their first sale (could be further sliced by product, service or dollar amount, assisted vs. unassisted)
  • Having a specific number of qualified opportunities in their pipeline
  • Having the appropriate multiple of their quarterly target in qualified opportunities in their pipeline (such as 2X, 4X, or whatever’s right for either your business or the individual’s skill level)
  • Achieving their first quarter at quota (or whatever time period is right for your business) or finishing at the expected percent-to-quota

The objective for any sales onboarding program is to get new reps productive as quickly as possible to increase annual revenue. Therefore, identifying the most critical skills necessary to achieve early success is key. Many sales enablers list these skills in a format of 30, 60, and 90 day goal documents.

As the saying goes: content is king. But it’s not the only consideration. Next we’ll discuss the second key principle of modern onboarding: make it personalized.


Example of a performance milestone with corresponding activities

Performance milestone: Generate their first active, qualified opportunity with a dollar amount assigned.

Activities that support the milestone:

Researching accounts and contacts

Sales call planning

Preparing and executing a personalized, omnichannel prospecting approach

Generating interest and setting an appointment

Conducting discovery and qualifying the opportunity

Securing commitment to pursue a solution

2. Modern Sales Onboarding is “Just for Me”

ORGANIZATIONS NOW USE systems and software to assess each learner’sstrengths and weaknesses and then deliver “just for me” learning to them. Modern learning systems and technology empower organizations to act on leading indicators like sales stage competency levels and subject mastery so they don’t have to waste opportunities waiting for lagging indicators — like win rate and average contract value — which only surface once deals are won or lost.

Competency assessments with personalized learning paths

Sales competencies should be the foundation of your sales selection (hiring) process, your sales onboarding program, and your ongoing training and development efforts in order to raise the overall effectiveness of your sales force.

One way to make skill development an ongoing part of your culture is through competency assessments. This includes both knowledge assessments (surveys) and skill assessments (role plays, simulations and field observation).

Assessing seller competency might go something like this:

  • Sales reps self-assess with a survey on each competency using a rating scale (a Likert scale).
  • Sales managers rate their reps in the same way.
  • The resulting 180-degree ratings will uncover areas of good manager-rep alignment around ratings that match as well as any perceptual gaps that might exist where ratings do not. This creates a great opportunity for an alignment discussion or even role play and field observation to validate the current state of the rep’s skill. Much of the training intervention can now be conducted remotely using video practice and coaching software.
  • Based on areas where the rep and manager determine development is required, a personalized learning plan can be created and delivered.

If done on a recurring basis (such as every six months), and accompanied with both training and coaching to first close competency gaps and then increase mastery levels over time, this method will keep you focused on doing the right things well. This will allow you to raise the competency levels of your sales force and – assuming you’ve ensured the competencies you’re focusing on actually correlate to performance levels – will help you improve sales results.

During onboarding, a number of ways exist for managers to use this approach.


Finally, keep in mind that learning which feels like it’s “just for me” doesn’t always need to actually have been created just for me. Modern learning solutions automate the process of serving up tailored content and programs to new reps joining your organization based on things like which onboarding cohort they fall within, where they sit in the reporting chain, which organization they belong to or even which team they’re on. The right learning paths and content show up for each individual automatically.

Then as they get out in the field, they receive content recommendations for each individual opportunity that guide them through the sales process with best practices and procedures based on the current sales stage, industry, competitor, product and more.

It’s critical organizations appreciate the value of learning that happens on a continuous basis throughout a sales rep’s tenure. This brings us to the third principle of modern onboarding: learning should be continuous and bite-sized.


Make sure to evaluate solutions which support automated creation and updating of user groups. Without this, Sales Enablement professionals can get bogged down having to manually update groups every time a rep gets promoted, switches teams, leaves the organization, etc.

3. Learning Should be Continuous and Bite-sized

SPREADING THE LEARNING over time and breaking it up into small chunks wherever possible reduces cognitive load and can actually ease the perceived burden of learning. Studies show that this gives people a sense of empowerment when it comes to learning and thus produces better training outcomes.

People learn more naturally when training is spaced over time — when they take breaks between “breakfast, lunch and dinner.” However, this doesn’t mean you should abandon the in-person boot camp model. Design the overall sales onboarding program to support the achievement of milestones throughout and take every opportunity to break up learning content and space the delivery over time.


Pre-boarding prepares new sales hires for assimilation into your organization’s culture before live training boot camp begins. Preboarding programs also give new hires a baseline of knowledge to build upon so they can jump right into more substantive learning when live training begins.

Now, you might wonder why we’re talking about basic new-hire orientation activities in a guide about making sales onboarding more effective. Well, when pre-boarding is neglected or bungled, new hires often fail to engage. They develop bad habits, waste time figuring things out on their own when somebody else could have shown them, and often experience confusion and frustration – all of which leads to negative perceptions of the training (or company), potential for disengagement or regret, and increased attrition. Several studies show that cost associated with replacing a sales rep exceeds $100,000, so it’s worth paying attention to your pre-boarding experience.


Have new employees sign an NDA as part of the acceptance of their offer letter. Otherwise executive stakeholders may only be comfortable with a pre-boarding track of publicly available information about your business.

Pre-boarding includes introductory activities, paperwork, meetings, and training that introduce the employee to the company, policies, culture, local facility (as applicable), and key personnel with whom they’ll be working. The goal is to prepare them as quickly and comfortably as possible to begin their job-related sales onboarding. If  you assign a mentor, coach, or onboarding buddy, this is the time to do it.

Pre-boarding also includes pre-start logistics to ensure the employee moves as quickly as possible through the pre-boarding into their sales onboarding.

Sharing high-impact content. The best pre-boarding programs use high impact, diverse content in the form of bite-sized videos, checklists, toolkits, and other short-form documents, as well as during in-person orientation meetings and one-on-ones. Pre-boarding content should focus on getting the new hire excited about the organization and conveying organizational culture first and foremost, in addition to communicating best practices and key ideas a new rep should start internalizing. Once your content plan is designed, enlist the entire organization’s help with creating pre-boarding content to build out a deep library quickly. Equip your subject matter experts, senior leaders, and top reps with the means to capture great stories, their latest thinking, best practices or hard-won wisdom on video and repurpose that  into learning content for new hires.

Acculturation is key for driving engagement and overall onboarding success so many companies introduce new hires to established employees by way of either bringing them together in-person or exposing new hires to the organization’s video platforms. New reps get access to peer videos from various learning exercises as well as highlights from videos getting shared around the organization throughout the course of day-to-day knowledge sharing. That way they can start putting faces to names and get acclimated with the departments and people with whom they’ll interact before they ever arrive for boot camp.

Job aids, checklists, and other performance support (online and/or printed documentation) can be used to help new hires avoid feeling overwhelmed and find what they need when they need it.

Preboarding content should focus on getting the new hire excited about the organization.

Teeing up personalized learning. If using sales competency assessments to personalize learning paths for sales onboarding, assign and complete them during pre-boarding to speed the process as well as give yourself a basis for personalizing the onboarding training where possible.

Also, every rep is different and possesses varying degrees of experience and expertise. So exposing them to some early one-on-one coaching and interaction with their managers gets them engaged right from the start. Organizations now use video coaching software to facilitate these early manager-rep interactions that take place before live training.

Sharing high-level overviews (macro before micro).  In addition to acculturation and orientation topics,  pre-boarding is an excellent time to put things in  context for new employees and provide a big-picture view of the organization. From an instructional design standpoint, providing high-level (macro) overviews  is especially helpful before diving into the detailed (micro) content.

Consider an overview for things like:

  • The rep’s upcoming sales onboarding experience
  • The markets, verticals, and buyers you commonly serve
  • Your customer lifecycle, including a common buyer’s journey
  • How your solutions provide value to customers (preferably with customer success stories)
  • Your sales process, which supports your buyer’s journey

Live training (virtual and classroom)

Like we said earlier, modern onboarding doesn’t do away with the past. Traditional boot camp using virtual instructor-led training (vILT) and classroom-based instructor-led training (ILT) provides an excellent baseline for imparting knowledge and skills.

With a well-trained and experienced virtual facilitator, vILT is excellent for answering questions, providing skill demonstrations, and fostering engaging discussions. Combined with software for conducting role plays and skill practice (in Fishbowl role plays where everyone observes those who are role playing, or in virtual breakout rooms) it packs a punch.

But in many cases, for commencing the learning journey with deep skill practice and feedback loops, classroom ILT still reigns supreme. Many still find discussion and debrief more natural in classroom settings, and the level of focused time dedicated to exercises, activities, role plays and feedback is much more intense, personalized and valuable to foster skill adoption and behavior change quickly. For this reason, we still encourage classroom ILT, but specifically encourage “flipped classrooms,” where modern learning solutions establish a foundation of knowledge, skills, and acculturation during pre-boarding (and reinforcement with just-in-time learning support afterward) while vILT answers questions and supports preparation for the classroom. All of this culminates in a very active learning environment in the classroom. Sales training is highly skills focused, so the flipped classroom approach offers sales teams an opportunity to engage in extra practice and role play before boot camp begins so they walk in prepared to go deep.

Pre-boarding is an excellent time to put things in context for new employees and provide a big-picture view of the organization.

Capture the in-class experience. Record relevant class sessions, role plays, and video workshops to evaluate baseline competencies and tailor follow-up reinforcement after the event. Managers can review their new sales reps’ role play performance and provide personalized coaching. Personalized learning techniques have seen a substantial increase in adoption due in part to rapid advances in technology, as well as the added ability to monitor individual students on a large scale and subsequently assign learning tasks based on competencies.

As you can see, the most effective forms of live sales training are starkly different than the traditional model. Modern onboarding incorporates a variety of techniques to maximize training time and deliver the best possible results by seamlessly blending videos, eLearning, assessment, spaced repetition, virtual instruction, and flipped classrooms.

When teaching reps the skills to do their job during live boot camp training, sequence topics by business process or sales process. It’s always best to teach reps exactly what they need to do when they return to their desk after training. The live classroom training environment should simulate reality as much as possible.

Sales certification and validation

One of the advantages of modern sales onboarding is that organizations can now easily verify whether each trainee acquired a given proficiency. Sales certifications can be synced with the performance milestones discussed earlier and become excellent tools to  validate rep readiness and assess the effectiveness  of live, virtual or asynchronous training.

Picking your team of sales certifiers. Since a new rep’s sales manager is typically their mentor, it’s usually best to have each rep’s respective sales manager score and give feedback on sales certification submissions when using video for sales certification. When doing in-person sales certifications during boot camp and sales managers aren’t present, then Sales Enablement pros and trainers should select team members with deep knowledge of the business to do scoring and feedback.

Sales certification timing. During the onboarding process, the first round of sales certifications should happen either on a nightly basis during boot camp, or within two to three weeks following. Have reps practice key messages on video each night after boot camp ends for the day, then submit their final sales certification video for each major subject area. For some companies, that means one for each major product category, one for key sales tools, and one for large account management best practices – but each organization is different so you should weight the importance of key subject areas and conduct validation on those. Certifications should be refreshed as needed during the onboarding period, perhaps again in three months and then six months, to ensure key knowledge and skills are retained.

How should it be done? The possibilities are endless, see one example below.

A note on the importance of mobile

Modern learning reflects the engagement patterns of today’s workforce when they interact with the pervasive consumer technology available to them. A sound mobile learning strategy is necessary to reach learners where they live and work in order to make learning a continuous process rather than an event.

According to Statista, in 2017, 68.4 percent of the U.S. population used a smartphone. The more pertinent question, though, is this – is there a single salesperson at your company who doesn’t use one?

At the time this guide was published, an Internet search for “mobile learning” produced 956,000,000 results in less than half a second. In today’s business environment — and especially in sales — a mobile-friendly approach is mandatory but a mobile-first approach is best. This mindset should be pervade onboarding and beyond.

Here are just a few more things to consider when planning and administering pre-boarding and live training:

  • Design your training to be delivered in bite-sized chunks. If reps have time, they can always continue to take lessons successively.
  • Use a system with “memory” that allows reps to pick-up where they left off, in case they get interrupted.
  • Rather than creating bite-sized content (or microlearning) with a rigid timeframe in mind (e.g., “This content we’ll create must be five minutes or less”), consider thinking about it in terms of the learning objective instead. The lesson should last the length of time required to achieve the learning objective (which ultimately, should be a performance-based learning objective).
  • Make every possible part of your training mobile-friendly. This includes the initial pre-boarding content, the courses they take, the reinforcement options such as question/answer and spaced repetition practice, the skills practice through virtual coaching, the two-way role play practice using mobile video systems, mobile access for video libraries of best practice examples, and mobile performance support.

Wherever they are, whatever device they’re using, your sales reps need easy access to learning and performance support in order for you to drive continuous and bite-sized learning. The next section discusses another key facet of any modern onboarding program that all-too-many enablement professionals miss: ongoing reinforcement.

4. The Program Incorporates Reinforcement Mechanisms

RESEARCH SHOWS that people forget 80% of what they learn within a month of training. Modern onboarding programs make use of technology that utilizes machine learning and other advanced technologies to push automated, daily reinforcement exercises to each rep’s mobile device using spaced repetition — a method of spacing learning over time for maximal retention.

Another oft-overlooked form of sales training reinforcement is ongoing skills coaching and sales practice. Design your onboarding program to make use of these key performance drivers.

Automated spaced repetition and reinforcement

The forgetting curve is real. How can you get new hires to retain the information learned when studies show it inevitably disappears over time? Ensure reps “use it” so they don’t “lose it.” Ongoing reinforcement exercises with spaced repetition is the key.

If sales competencies are the backbone of sales onboarding, reinforcement is the skin that holds everything together. Here are two of the most effective ways to boost retention.

Periodic assessments. As trainers proceed through lesson plans, it makes sense to insert systematic refreshers and knowledge checks into the training. Traditional reviews should occur either after a specific subject and/or at the end of multiple related subjects. Lead off with questions that will be answered as the lesson proceeds.

Ongoing adaptive microlearning. Spaced repetition gives trainers a way to reinforce a body of facts a little at a time without overloading reps with work. You can provide reps with a fun, easy way to absorb and retain what they learn on an ongoing basis so they consistently apply it in customer conversations. Quiz them for a few minutes each day after onboarding ends to eliminate the forgetting curve and drive better knowledge retention. Look for ways to personalize the order and frequency of the quizzes, based on gaps in each rep’s knowledge. Modern learning solutions use machine learning and other advanced technology to automate this process.

Practice and role play scenarios with feedback loops

In a modern onboarding program, you can provide deliberate practice opportunities in vILT or classroom ILT, as well as on an ongoing basis after boot camp through virtual coaching systems, web conferencing video, or in-the-field coaching sessions with managers.

While regular practice might include mindless repetitions, deliberate practice requires focused attention and is conducted with the specific goal of improving performance.

James Clear

Done well, role play is one of the best methods to train, coach, and improve skill levels. Here are some examples of popular role play and practice scenarios.

  • One-on-One/Paired Role Play: One-on-One or Paired Role Plays can be done with a trainer, peer, manager or other sales coach. It’s excellent for demonstrations and understanding checks.
  • Triad Role Play: This is a common role play used in sales training courses, with three roles: Salesperson, Customer, and Observer/Coach. Usually, each person gets to play each role (three role plays per Triad).
  • Fishbowl Role Play: A Fishbowl is when a role play occurs in front of a group of people, usually in a classroom.
  • Role Play: A Round-Robin Role Play is a form of the Fishbowl where the Sales role rotates among participants. Often the instructor or sales manager plays the Customer role, for consistency.
  • Single Skill Practice: As the name indicates, a Single Skill Practice Role Play is an opportunity to practice a single skill, such as “make an empathy statement.” They are often done in round robins or pairs.
  • Case Study/Scenario Role Play: These are often used in Triads, but may be used in any role play. This technique is designed to create as real a simulation as possible for the role play practice.
  • Process Simulations: A Process Simulation is an advanced form of a Case Study/Scenario Role Play that spans beyond one interaction to include a series of key prospect/client interactions, over time.

Recorded role plays. Using modern learning software to record role plays for both learning and skill validation/certification can be very valuable, especially for the sales rep. This makes it easier to accurately benchmark their evolving skills as they finish onboarding and get out into the field, helping them chart their progress  three months, six months or 12 months later.

Teams record practice product demos or sales presentations during onboarding training for feedback and scoring and reps get access to objective audio-visual benchmarks of skill levels over time. The same applies with recording live meetings to review, analyze, learn from, and coach (following any applicable laws and company policies).

Formal vs. informal role plays. Formal role plays are designed to meet specific learning objectives, such as the Single Skill or Scenario Based role play. Informal role plays take place on-the-spot or on-the-fly and are usually conducted by sales managers or sales coaches to address a specific skill or performance gap. Using video role play technology empowers managers to do this much more often than they’d be able to relying solely on face-to-face role play.

Providing feedback. In all cases, the quality of feedback is critical. At a minimum, feedback should be:

  • Behavioral (what you observed the rep doing or saying)
  • Specific to that particular activity (rather than generalizations about recurring habits or tendencies)
  • Clear as to why the behavior was exemplary or needing improvement
  • Given right at the moment the behavior occurred without delay

Done well, role play is one of the best methods to train, coach, and improve skill levels.

Ongoing coaching to mastery

The frontline manager plays a pivotal role in developing employees, managing results, and leading change no matter the organization or function. Coaching is integral to those efforts and nowhere is this truer than in a sales organization. To maximize the success of your sales onboarding program, partner closely with your frontline sales managers.

Specifically, managers should:

  • Know and buy-in to the content you teach in onboarding, especially the sales competencies and your sales methodology
  • Know “what good looks like” (the expected or standard levels of competency for sales readiness or certification) as well as what true sales mastery looks like
  • Be able to diagnose gaps in performance and tie them to gaps in sales competencies
  • Be able to ascertain whether their rep needs training and reinforcement (e.g. the rep doesn’t know or remember what to do, why to do it, or how to do it), or practice and coaching (they know it but need to get better at doing it)
  • Deliver the field training reinforcement or sales coaching that is needed to close the performance gap and improve both their skills

While the details of enabling your sales managers is out of scope for this guide, you may find this eBook on Sales Coaching Excellence to be helpful.

Ongoing simulation exercises. Coaching and simulations are useful for developing skill mastery and should continue past your boot camp, and even past onboarding. Ongoing one-to-one sessions allow trainers (or sales managers) to provide insights into why a particular technique or approach may or may not work under various circumstances, as well as how to shift  the approach to achieve the desired goal.

Set agreements with managers to stay on a cadence after onboarding ends to follow up and coach each rep a minimum number of times per month. Effective sales coaching can increase win rates by up to 25%. Companies with reps who receive less than 30 minutes of coaching a week have a win rate of 43 percent. But companies where reps are coached more than 2 hours a week have a win rate of 56 percent. Newly hired reps should receive 2-3 hours per week of coaching from their manager for the first 6-9 months of their tenure. Then managers can move the rep into their standard management operating rhythm, based on their individual needs.

Mentoring. Isaac Newton credited his success to the fact that he “stood of the shoulders of giants.”  Mentoring programs give new reps an advantage like this by empowering them to learn directly from successful salespeople. This speeds ramp time by creating an open line of communication for new hires to get answers and advice quickly. Hence, instituting a mentorship program is a best practice for sales onboarding.

When building a mentorship program, make sure you:

  • Determine a budget for mentorship advocacy
  • Define goals of the mentors, mentees, and program
  • Create guidelines for mentors and mentees
  • Establish a group of overseeing members along with a code of ethics

Ongoing coaching and mentorship gives new reps the boost they need to quickly break through barriers throughout the sales process when they get out in  the field. But coaches and mentors can’t be there every time the rep runs into a roadblock. The next principle  of modern onboarding exists to remedy this.

5. Modern Sales Onboarding Establishes Ongoing, Informal Learning

TODAY, MANY ORGANIZATIONS DEVOTE most (if not all) of their training resources to structured, formal learning despite the fact that the majority of learning happens informally. Much of the time, the learning is self-directed where the rep finds answers at the exact times and places they need to turn around and use them. The rest of the time, the rep is learning hard-won best practices directly from their peers as well as trusted home office experts.

Onboarding training is key for acquiring new knowledge.  But since your sales reps will spend the majority of their learning time out on their own, it’s critical you make learning resources and performance support accessible in a format they’ll engage with.

Transfer and Application to the Job with Just-in-time Learning and Performance Support

The onboarding process doesn’t end when reps arrive at the application phase. Learning is ongoing and field application with performance support and measurement is key.

In fact, you can shorten the initial bootcamp portion  of your onboarding by spreading learning over time,  just-in-time, by segmenting it into small, “snackable chunks” and making it available to reps on the fly during informal learning (instead of cramming it in boot camp “just in case”).

This is the reason for setting performances milestones, building your curriculum around them, and teaching just the need-to-know content to reach each milestone.

Case in point: if reps in boot camp haven’t even started prospecting to fill their pipeline yet, teaching them your digital signature software during boot camp doesn’t make sense. Teaching them closer to when they need it, and providing just-in-time learning resources and performance support is far better. Things like video libraries filled with best practice demonstrations by peers and SMEs accessible on mobile, digital job aids,  downloadable PDF checklists, or in-app guidance and training software support learning on the fly.

You can use this concept of performance support freely. In some cases, you may find it even replaces the need for formal training. You can create:

  • Videos
  • Playbooks
  • Checklists
  • Manager toolkits or “meetings in a box” – These are mini-training guides that managers use to reinforce a topic that reps learned in training, help their reps use the available job aids, and prepare reps to apply what they learned during onboarding when they get in front of real customers
  • Other workflow performance support (digital or otherwise) to help your reps do their work –and apply what they learned during onboarding –in real-time, on-the-job, within their workflow

Provide just-in-time access to best practices. Create best practice libraries filled with short videos featuring top sales reps, SMEs or respected company leaders demonstrating or providing commentary on a variety of key topics that reps can access on the fly. Show reps how to use it, and make it searchable and intelligently keyworded and tagged so when they’re perusing the system during informal learning they stumble upon content that actually helps them win deals. This works equally well for skill or competency demonstrations of things like effective call planning, videos of how to open a meeting, top reps managing objections, and more.

Modern learning solutions let you take this just-in-time content and serve it up at the right moments throughout the sales cycle on an automated basis from right within your CRM based on the current circumstances of each specific deal.

Content agility powers your informal learning engine. Instead of relying solely on centrally produced just-in-time content and performance support assets, modern learning solutions “democratize” the creation process by making it easier for SMEs, managers, senior leaders or peers to create just-in-time learning content. People capture their ideas, updates or new thinking by recording video of themselves talking it through while it’s fresh in their mind, and then share it either directly to the field or first to the enablement team for batching of communications in order to prevent overload. Most top-performing sales enablement teams are taking control of sales communication, to become the single channel for funneling communications to the sales force.

Sales enablement professionals use modern learning solutions to surface the best of this content so they can repurpose it into interactive just-in-time learning and performance support assets for best practice libraries, on-demand channels or playbooks. Reps get something close to “face time” with key people at their company when those moments arise (like we described earlier) where they need to break through a barrier in the sales process but their coach or mentor can’t be there. The content continually stays fresh and the messages are coming straight from the horse’s mouth, so it’s more relevant and well-received. Reps are actually interested in perusing the learning content available to them during informal learning cycles.

Bringing It All Together

Curriculum Design: Organizing Content by Milestone

THIS IS WHERE the previous concepts of content buckets, performance milestones, and modern learning converge into curriculum design.

Here’s how it comes together:

  • Determine the staged performance milestones you need new sales hires to meet.
  • Determine the activities that will lead them to achieving those milestones.
  • Determine the bare minimum new reps need to know and do to conduct the activities successfully and hit each milestone.
  • Organize learning content from the content buckets and teach just what reps need to know and do to achieve the first performance milestone.
  • As each rep hits the first milestone, validate the knowledge and skills gained.
  • Ensure the reps apply what they’ve learned leading up to the first milestone in the real world.
  • Measure effectiveness to ensure reps meet the learning and performance goals at each milestone.
  • Repeat for each of the other milestones until onboarding ends.

If you do all that well, the last bullet should read, “Celebrate success.”

Rather than teach the bucketed content abstractly, you can now pull it into the activities for reaching each milestone where it fits best. Teaching reps only what they’ll be expected to do on the job based on what will help them achieve each milestone (one at a time) is a far better way to drive performance.

Measuring Effectiveness

TWO COMMON SAYINGS about measurement still ring true. You can’t manage what you don’t measure, and what gets measured gets done.

To properly calculate ROI for sales onboarding, you’ll first need to define the measurement and capture benchmarks for the beginning of the onboarding. Attempting to do so retroactively can create headaches you don’t need since measuring training ROI is difficult in the first place.

Calculate Value. It’s vital to understand the total (or expected value) of the sales reps going through onboarding. You should compare the revenue you expect them to furnish annually to the cost of training. Then you can put a number to the sales efficiency of the training. As time progresses and you make adjustments to the onboarding program, you can calculate value for isolated changes and double down where performance levers exist.

Establish Baseline Metrics. Never enter onboarding “metrics blind.” Just keep it simple and use the numbers to generate expected outcomes. Determine a reasonable number of reps you’ll expect to complete training (a drop-out percentage should be anticipated) and take a tally of skill validations or certifications given and compare these the against real world ROI figures the training generates.


Consider measuring both lead and lag indicators for both learning performance and sales performance. Measurements for learning performance might include (not exhaustive):


Measurements for sales performance might include (not exhaustive):


If you have a business analyst or data scientist on your team, track and benchmark as much data as you can and look for correlations — especially between the lead and lag indicators within each category — and then between learning performance and sales performance. If you don’t have dedicated staff or the capability to do this sort of statistical analysis, start by focusing on measuring the key performance indicators that you or your senior leaders want to improve.

To evaluate your program’s effectiveness, you will want to benchmark the metrics that matter most and work to continuously improve them. This should certainly be the case with:

  • Time to achieve the performance milestones you set
  • Time to sales readiness validation or certification (considered “readied”)
  • Time to first sale
  • Time to acceptable sales production (considered “ramped”)

Some other ways to measure the effective of onboarding include:

  • Simulation Effectiveness – Measurement of trainees during individual, group, and one-on-one mentoring sessions involving sales simulations. This data will correlate to real world figures (and where it does not, it may serve as a check and balance – revealing bias on part of the grader).
  • Sales Activity – Measuring conversion rates and their velocities throughout the sales process for each rep is an obvious data collection point. Still, insightful collectors will find ways to find trends in this data to improve sales rep outcomes.
  • Revenue Yield – Calculation of revenue milestones and year-end quotas for sales reps is more than just a ROI check. This data can alert the business to valuable information when compared to other data such as market share, onboarding history, and forecasting.

For a deeper dive on measuring the impact of onboarding, click here.

Start by focusing on measuring the key performance indicators that you or your senior leaders want to improve.


We hope you’ve found this guide thought-provoking and helpful. These concepts and ideas power successful onboarding across numerous organizations in a wide array of industries. Our intention is to give you some building blocks to work with as you construct or enhance your own program.

At the same time, no guide can prescribe exactly what’s best for your company. Context is critically important and every situation features some degree of nuance.

If you need help or want to explore how you can begin to transform your sales onboarding program to capitalize on the ideas shared in this guide, reach out to us at We’re here to help.

Thank you.

About The Authors

Allego’s sales learning and coaching platform elevates sales performance by combining training, practice, coaching and knowledge sharing into one app.  With Allego, sales teams onboard faster, confidently deliver the right messaging, rapidly adopt best practices, coach and practice more frequently, and collaborate better with peers and the home office.

Mike Kunkle

Transforming Sales Results, LLC

Mike Kunkle is the founder and sales transformation architect for Transforming Sales Results, LLC. He’s a respected sales transformation leader and an internationally-recognized sales training and sales enablement expert.

Mike has spent over 30 years in the sales profession and 24 years as a corporate leader or consultant, helping companies drive dramatic revenue growth through best-in-class learning strategies and his proven-effective sales transformation methodologies. He consults, advises, writes, speaks, leads webinars, designs sales learning systems that get results, and guides clients through all aspects of their  sales transformation.


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