The Complete Expert-Led Guide to Sales Onboarding

Introduction

Sales onboarding is one of those areas of sales enablement where many organisations place a lot of their focus.

Often, the urgency in building a sales enablement function actually stems from the need to develop a more structured process to onboard, engage, and upskill new reps.

It’s well-known that improving time to ramp and seller retention can significantly enhance the reps’ revenue-to-cost ratio and the growth and profitability of an organisation. Conversely, if these metrics worsen, it can quickly lead to disastrous outcomes.

For instance, I recently read an article from the Revenue Enablement Institute discussing the growing talent crisis in sales.

The article highlighted that a mere five percent increase in sales rep attrition can raise selling costs by 4-6% and reduce total revenue attainment by 2-3%.

For companies with low growth and low margins, a ten-point increase in sales force attrition can derail revenue plans and margins if no one compensates for the loss.

The gap between a 5% attrition rate and a 25% rate can lead to over a 50% increase in selling costs and a 20% drop in revenues.

This is why improving the economics of field selling is crucial, and effective onboarding alongside strategic sales hiring plays a significant role in achieving that.

Building an onboarding programme was my sole focus during my first role in enablement as a Training & Performance Specialist.

In that role, I was fortunate to have full ownership of the onboarding process in a hypergrowth context, onboarding nearly 200 sellers across various roles within a year.

I learned a great deal in the process, and as I progressed to a leadership position, I continued to refine my approach to building effective onboarding plans. To date, I have onboarded more than 350 sellers across different organisations.

In this article, we’ll explore the fundamentals of sales onboarding, highlighting its benefits and addressing the common pitfalls of traditional methods. We’ll describe a modern approach to sales onboarding, structured into three key phases.

Additionally, I will detail how to create a structured onboarding plan, and, to round out the guide, look at how to measure success in sales onboarding.

By the end, you’ll have a comprehensive understanding of how to build a successful sales onboarding (or shall I say “everboarding”) programme, significantly improving both time to ramp and retention rates for your sales team.

Understanding sales onboarding

As touched upon above, early in my sales enablement career, I was tasked with building an onboarding programme from scratch for a fast-growing organisation.

The goal was to ensure consistency in the proficiency level of the sales force across key areas of competency.

The solution we sold was somewhat transactional, so my initial onboarding programme focused on the first two weeks.

The programme was structured as a bootcamp, with all sellers in the “classroom” all day, and conducted in person.

I remember the first two days covered a high-level overview of the company, our industry position, and a deep dive into our core offerings.

Starting from day three, we focused on sales fundamentals that were company-agnostic before moving into specifics like the sales pitch, value proposition, call scripts, and objection handling.

The second week was more operational, involving laptop setup and sales tool training.

Role plays began based on the sales content distributed in week one.

At the start of week three, reps moved on to their sales managers and teams.

At the time, I believed this setup was quite effective, but now I realise there was much I didn’t know.

Despite many new sellers telling me it was the best onboarding they had experienced, I now see the significant limitations of traditional onboarding programmes, which we will explore next.

The problem with traditional sales onboarding methods

Reflecting on my early days, it’s clear that traditional sales onboarding methods, like the bootcamps I initially championed, are fundamentally flawed.

While these concentrated programmes aim to quickly familiarise new hires with their roles, they often fail to truly engage and accelerate them towards mastery.

The intensity and volume of information presented in a short period can overwhelm new hires, leading to cognitive overload rather than practical knowledge retention.

Many organisations, including my own in the past, overload new hires’ brains with an avalanche of information, much of which is not immediately applicable to their selling scenarios.

This approach often results in new hires struggling to recall crucial details when needed most.

Additionally, another common mistake is overly focusing on company details, products, and features, rather than delving as quickly as possible into understanding the target markets, industries, customer needs, buyer personas, sales processes, selling techniques, and other sales playbook items.

Sales onboarding success is not about the sheer quantity of material covered; it’s about the quality and relevance of the training provided.

The greatest success is found when new salespeople can apply what they’ve learnt, make mistakes, ask questions, receive feedback, and try again until they get it right. This iterative learning process establishes a deeper understanding and retention, ultimately leading to more competent and confident sales professionals.

As we explore modern onboarding methods, we will see how a more phased and hands-on approach – powered by new sales enablement technologies – can significantly enhance the onboarding experience and outcomes.

The benefits of sales onboarding when done right

When done right, effective sales onboarding offers a wealth of benefits, both measurable and experiential, transforming the way your sales department and the entire GTM organisation operate.

In this brief section, I will list out a few deeply interconnected quantitative and qualitative benefits you can expect.

Quantitative benefits

1. Reduced time-to-ramp: A robust sales onboarding slashes the time it takes for new reps to become fully productive. Consequently, they start driving revenue sooner, boosting overall sales performance.

2. Higher retention rates: Well-structured onboarding decreases employee turnover by equipping new hires with the knowledge, skills, tools, and resources they need to thrive. As a result, this not only cuts down on the costs of rehiring and retraining but also builds a more stable and seasoned sales force.

3. Increased revenue: Competent and confident sales reps, thanks to effective onboarding, tend to close more deals and hit their targets consistently. This leads to better revenue-to-cost ratios and accelerates business growth.

4. Enhanced efficiency: With clear processes and comprehensive training, sales reps spend less time figuring things out and more time selling. Consequently, this operational efficiency translates to better resource utilisation and higher profitability.

Qualitative benefits

1. Improved morale and engagement: When new hires feel supported and valued from day one, their job satisfaction soars. An engaging onboarding experience fosters a positive work environment and encourages long-term loyalty.

2. Stronger team cohesion: Onboarding that includes team-building and cross-departmental interactions helps new hires integrate seamlessly into the company culture. This leads to better communication and collaboration within the team.

3. Better customer relationships: Sales reps who deeply understand their customers’ needs and the industry landscape, thanks to a robust onboarding, are more effective in building strong, lasting relationships. This customer-centric approach can enhance brand reputation and drive repeat business.

4. Continuous improvement: A modern onboarding plan and process instils a culture of ongoing learning and development. Under these conditions, sales reps are more likely to stay up-to-date with industry trends, market changes, value propositions, and sales techniques, keeping them competitive and innovative.

5. Alignment with company goals: Effective onboarding ensures new hires grasp the company’s mission, values, and strategic objectives. This alignment fosters a unified direction and purpose across the sales team.

The modern approach to sales onboarding

Having explored the key flaws of outdated training methods and highlighted the benefits of effective sales onboarding, it’s now time to introduce and break down a more modern sales onboarding approach.

First and foremost, before proceeding, I recommend reviewing my piece on sales training best practices.

In that article, I delve into concepts like adult learning principles and blended learning approaches, which are fundamental to effective sales onboarding, even though I won’t go as deeply into them here.

I’d also recommend checking out our collaborative sales onboarding best practices article, where enablement leaders from some of the world’s biggest companies shared how they do onboarding the modern way.

Finally, in my sales training statistics article, you will find plenty of information on how onboarding is done, what salespeople expect from it, and where companies often go wrong.

I strongly believe that the era of predominantly in-person, bootcamp-style sales onboarding should come to an end.

Typically, in such scenarios, new hires are put through an identical onboarding process regardless of their specific sales role or level of experience.

While this approach may seem simpler, it incurs significant hidden costs in the long run.

The ideal approach should involve tailored onboarding tracks that vary based on the sales role and experience level of the new hires. Specifically, organising new hires into cohorts according to their role and experience can be highly effective.

This method promotes better peer learning and focuses on shared goals relevant to their specific roles.

Subjecting veteran salespeople to basic sales training quickly diminishes their initial enthusiasm and momentum.

Conversely, placing junior hires in advanced sessions more suited for sales leaders may pique their interest academically, but they will struggle to grasp practical knowledge that they can later apply.

With the rise of hybrid and fully remote working models in sales and GTM teams, coupled with advancements in learning and enablement technologies, sales onboarding can now be conducted in a more phased and controlled manner, allowing for higher levels of customisation and scalability from anywhere.

A blended learning approach, which combines traditional face-to-face or virtual-led instruction with online learning, can help develop more targeted and personalised onboarding tracks while also providing a higher degree of learning autonomy.

In-person activities still play a crucial role in building a sense of belonging and connection among new hires, as well as sparking valuable discussions and knowledge sharing.

However, a truly effective onboarding programme should be phased and focused on the right things at the right time, which is best achieved through digital means.

Digital learning in combination with in-person activities ensures new hires receive continuous support and development, enabling their growth and success in the long term.

As we introduce the three key phases of sales onboarding using a more modern method, keep in mind the importance of the aforementioned. Each organisation is unique, with varying levels of enablement and technology maturity.

While it may not be possible to achieve fully personalised paths right from the start, it’s important to strive for an ideal scenario that can bring significant returns to the organisation.

The three phases of sales onboarding

As I alluded to in previous paragraphs, it’s very easy and tempting for organisations to bombard new hires with a lot of information during their onboarding journey, expecting it to stick and be effective.

What’s truly challenging is getting a cohort of new hires to join your organisation, hit quota in their first two quarters, and then have subsequent cohorts do the same.

Achieving this requires much more than merely “transferring” a large amount of knowledge; it necessitates having frameworks and systems in place.

This is exactly what we are doing here. The sales onboarding approach I propose is structured in three phases:

Let’s now break down each phase in a practical, actionable way.

Once you’ve thoroughly grasped the three phases explained below, I recommend downloading my sales onboarding checklist – which summarises the steps from this guide in a concise, checklist format – and my sales onboarding plan template – which provides you with a useful framework to effectively organise your onboarding curriculum and list of activities.

Prepare: pre-start to first prospect-facing activity

The Prepare phase begins once the offer letter is accepted and continues until the first prospect-facing activity is performed. There is a lot that happens during this phase, so let’s take it step-by-step.

Pre-start

Considering the moment the letter is accepted as the starting point of onboarding can greatly enhance the new hire’s experience because there are actually numerous actions you can take to make this period impactful.

For instance, you could send a welcome pack with company-specific items and some warm messages. Additionally, having team members who will work closely with the new hire send welcome messages on LinkedIn can be very impactful.

I still remember joining one of my previous companies and receiving many warm LinkedIn messages from future colleagues a month before my start date. This made me feel like part of the “family” even before I joined and significantly boosted my excitement for the new role.

Speaking of excitement, the period after accepting the offer is when the new hire is likely to be most enthusiastic about the role.

For this reason, it’s important to harness this enthusiasm to engage and prepare them early.

This period is ideal for sending pre-onboarding materials along with some associated “homework.” The materials might include information about the company’s market position, key value propositions (perhaps illustrated with customer stories), a high-level pitch of the company’s products, and general industry knowledge.

The homework could involve asking the new hire to reflect on what they have learned and email their thoughts. Providing this initial context will help them make the most of the upcoming onboarding process, build momentum, and, therefore, reduce overall ramp-up time.

To streamline the process further and save time, you also want to make sure that all HR paperwork is completed before the first day. Dealing with administrative tasks during the first days can kill momentum and enthusiasm.

The same goes for the IT setup – ensure it is smooth and as error-free as possible to minimise the burden on the new hire and reduce any back-and-forth required. This is essential to allow for a positive onboarding experience and enable the new hire to focus on their role from the outset.

The first few days – ensuring clarity in role expectations

Once the new hire has joined the organisation, it’s important to complete an initial “orientation.”

This should include:

• Clarifying the job and activities the seller will perform.

• Outlining the path to success for the salesperson.

• Communicating where resources are available and how to get help when needed.

In my experience, I tackle these items by using checklists of the most important activities to complete week-by-week and clearly outlining the key expectations for KPIs to reach month-by-month as they ramp up. Providing this level of clarity helps the rep channel their energy and efforts in the right direction.

Equally important is setting the expectation that there will be challenges and failures along the way.

It’s crucial to make it clear from the outset that failure is expected as they learn.

In fact, the prepare phase should create opportunities for new hires to try, fail, and learn as quickly as possible.

Additionally, part of the orientation should include sessions to introduce the new hire to the company culture and values.

When explaining the prepare phase to peers or colleagues, I am often asked, “How do I define the most important learning focus areas during this phase?”

This is an important point and something we can transition to next.

The first few weeks – focusing on the right learning areas

When a new sales rep joins the organisation, the amount of information they could potentially learn is vast.

However, given the constraints on time and retention capacity, it’s crucial to prioritise the learning areas that will fast-track their ability to do their job effectively, and, most importantly, execute their initial prospect-facing interactions (as far as the Prepare phase is concerned).

Unfortunately, many organisations inundate salespeople with initially unimportant items, such as:

• Extensive product training

• Detailed explanations of every custom field and integration in the CRM

• User training for every tool in the sales tech stack

• Responses to every conceivable objection

• Demo decks for every scenario

• Administrative tutorials, like proposal creation and document signing

• And much more…

The truth is, if something isn’t required for the first conversation with a prospect, it should be deprioritised until later.

Instead of the above, you should consider focusing on the following during the initial prepare phase (assuming a full-cycle sales rep or AE role):

• Understanding the target market and industry landscape: This includes the attributes of the ideal customer profile (ICP), the types of companies that should be disqualified from the start, and where the company is positioned in the overall industry or industries it belongs to.

• Familiarity with the key buyer personas: Learn how these typical buyers operate, their reporting structure, key drivers and motivations, important metrics, and main pain points.

• General pitch and value-based language: Develop a general pitch for your product or service, including a couple of compelling customer stories for social proof.

• Sales qualification framework: Understand the general sales qualification framework applied by the organisation.

• Functional CRM training: Gain the necessary competence in the CRM for the first few weeks.

• Navigating the sales playbook: Learn how to find and use resources in the sales playbook as needed.

• Basic prospecting methodology: Understand and apply the basic methodology for prospecting new accounts, including cold calling scripts, objection handling frameworks, multi-channel approaches, and operationalising the account list. Consider supporting reps by having them shadow or listen to their colleagues’ prospecting calls and letting them perform practice calls.

• Developing discovery questions: Create pain-based and value-based discovery questions for conversations with prospects. Consider supporting reps by having them shadow or listen to their colleagues’ prospecting discovery calls and letting them perform practice calls. (Make sure to check out my guide on sales discovery training!)

These guidelines provide a generalised foundation; however, if you wish to identify the most important learning areas for the Prepare phase specifically for your organisation, one effective method is to first define the “jobs-to-be-done.”

The “jobs-to-be-done” (JTBD) theory, popularised by Harvard Business School Professor Clayton Christensen, is an insightful framework that originated from his work in “The Innovator’s Solution” and was further detailed in “Competing Against Luck.”

The core idea of JTBD is that customers “hire” products and services to accomplish specific jobs or tasks in their lives. These jobs represent the fundamental problems that customers need to solve, and understanding them can lead to more effective and innovative solutions.

The interesting thing is that you can take this framework and apply it to the onboarding context.

First, identify the key jobs that the new hire needs to accomplish.

For an AE, these might include things like account-based prospecting, qualifying leads, delivering pitches, handling objections, conducting discovery, running demos, and closing deals. Here you’d want to get as granular as possible (you can check out my AE sales competency framework).

Next, define and prioritise the learning areas and activities that directly support these jobs.

For example, understanding the target market and ideal customer profile (ICP) as well as getting familiar with buyer personas is essential for prospecting and qualifying leads.

Thus, initial training should cover detailed information on the ICP – including the characteristics of qualified and disqualified leads – and buyer personas profiles, accompanied by role-playing exercises to practice prospecting and lead qualification conversations.

For delivering pitches, new hires need to master the general pitch and key value propositions of the product or service.

Training activities could include developing pitch scripts, conducting mock presentations, and using customer stories to provide real-world examples and social proof.

Handling objections is another critical job.

Training should focus on objection-handling techniques and frameworks, providing guidelines on the most common objections (prioritising earlier stages vs later stages) and effective responses.

Role-playing sessions can be extremely beneficial here (particularly leveraging emerging AI role-playing software), allowing new hires to practice in a safe and controlled environment.

Asking discovery questions is also a vital job for an AE.

Training should cover how to develop pain-based and value-based discovery questions that elicit meaningful responses from prospects. This can involve learning the theory behind effective questioning, practising with sample questions, and participating in role-playing exercises to refine this skill.

By the end of this process, you should have a clear definition of the most important “jobs-to-be-done” and the associated learning activities. The table below offers a basic example summary.

Some tips on learning content and live sessions

When creating learning paths that tackle any of the above areas or other identified essentials, it’s critical that all content presented during live sessions, e-learning, or follow-up materials is designed to build competency around a specific job-to-be-done.

If it doesn’t, it shouldn’t be included.

Too many organisations overwhelm new hires with content they “should know,” only to realise later it wasn’t retained.

Furthermore, it’s important to consider how to run instructor-led sessions effectively.

These sessions are excellent for engaging new hires, enabling discussions, Q&A, role-playing, and more.

However, their effectiveness in promoting learning and retention depends heavily on their structure and execution. Therefore, I recommend leveraging a training session checklist to ensure adherence to sound learning principles and a uniform quality standard across all sessions.

Below, I provide a basic example that you can adopt and enrich as you see fit.

The absence of some clear standards often results in a variety of scenarios, including the typical “death by PowerPoint” or the fact that learners are engaged and having a good time but they aren’t learning anything that can be applied, measured, and retained – you might receive high satisfaction score from those sessions but in truth, salespeople didn’t get what they needed to be successful.

In summary

We’ve reached the conclusion of the first phase of sales onboarding, covering the crucial steps from the acceptance of the offer to the initial prospect-facing activities.

Key areas discussed include:

• Early engagement and welcome strategies to foster a sense of belonging and excitement.

• Preliminary onboarding tasks to prepare the new hire for a smooth start.

• A structured orientation to clarify role expectations and resources.

• A focus on targeted learning areas crucial for early success in the role.

• The application of the “jobs-to-be-done” framework to define and prioritise essential training tasks.

By following these steps and advice, you’ll be in a good position to ensure new hires are well-prepared, confident, and equipped to tackle their role effectively.

I’d like to stress that the focus of this first phase is on selecting and appropriately sizing learning activities to maximise retention and impact.

It’s best to concentrate initially on the earlier sales activities of the sales cycle and the most standard scenarios, avoiding the complexity of numerous nuances which can be introduced later in the onboarding process.

Finally, don’t ever forget that each onboarding cohort offers a valuable opportunity for continuous improvement of the programme.

Based on feedback and reflections on session effectiveness, adjustments may include altering the sequence of topic introductions, modifying the depth of topic coverage, or enhancing the reinforcement mechanisms for certain concepts.

We are now ready to progress to the second phase of the sales onboarding process: Perform.

Perform: first prospect-facing activity to first deal

The Perform phase starts with the initial significant interaction with a prospect and extends until the new hire successfully closes their first full-cycle deal.

This phase should be seen as the period of time during which a new hire develops the skills necessary to meet their objectives and shows early signs of success.

Key milestones

As new hires progress toward sealing their first deal, it’s important to monitor and guide them through specific milestones:

• Initial engagement at each sales stage: Track the first activity they perform at each step of the sales cycle, from prospecting to closing.

• Learning and certification: Ensure they undergo training and achieve certification in the crucial tasks they will execute throughout the sales process.

• Review of lost deals: Analyse lost deals to understand the reasons behind them and discuss potential alternative strategies that might have changed the outcome.

Now, we know that the ultimate milestone is closing that first deal, yet there is an important premise.

This deal should be a new hire’s first deal that they independently managed from start to finish, within their designated market, utilising the same resources that will be employed in subsequent deals. Types of first deals that should be disregarded include:

• Unique case: Deals with customers whose needs are exceptionally rare or not reflective of typical future transactions.

• Guided close: Deals where the sales manager or another senior significantly intervenes, leading the deal to closure while the representative mainly observes.

• Given deal: Deals either handed to the representative midway through the sales cycle that were already close to closing, or inherited from another salesperson where most of the groundwork had been completed.

• Simple win: Deals that close remarkably easily, often due to flash sales, promotional conditions, or because the prospect has a prior relationship with the salesperson, which may not necessarily reflect the rep’s ability to negotiate and close under normal conditions.

• Low-hanging fruit: Deals where the prospect already showed a high intent to purchase or the circumstances required minimal effort from the salesperson, offering little challenge or requirement for full engagement in the sales process.

The purpose of evaluating the first deal is to ensure that the rep can see tangible outcomes from their efforts, setting the stage for accelerated performance and quota attainment over subsequent quarters.

Certifications

As mentioned in the above key milestones, certifications are a typical aspect of the Perform phase.

In this context, you shouldn’t think about certifications as conventional classroom learning or rigorous academic exams.

Instead, certifications must be tailored to develop and hone skills directly applicable to the immediate tasks a new hire will face (jobs-to-be-done), ensuring they contribute effectively to tangible business outcomes.

When considering certifications, it’s beneficial to think of them in terms of progressive levels. A practical approach is to envision these as four levels of competence development, aligning certifications accordingly:

1. Understand the basics (“Know it”): At this foundational level, the emphasis is on grasping core concepts, methods, and structures related to specific sales activities, such as discovery. The learning process involves interactive e-learning modules, reading materials, instructor-led sessions, and workshops designed to build a solid theoretical understanding. The goal is for new hires to demonstrate a clear and comprehensive grasp of the material, ensuring they can articulate what they have learned accurately.

2. Apply your knowledge (“Do it”): Once foundational knowledge is established, the next step is application within controlled, low-stakes environments. This stage incorporates role-playing scenarios, simulated sales calls, and other structured activities. These settings are safe and allow new hires to experiment and apply their skills without the risk of real-world consequences, focusing on building confidence and practical understanding.

3. Master the craft (“Do it well”): Transitioning from basic application to skill refinement, this stage still operates within controlled environments but introduces elements that are closer to real-world interactions. Sales representatives engage in more complex and challenging scenarios, such as advanced role-playing and participation in live calls, albeit still under supervision or with immediate coaching feedback. The complexity and the stakes are gradually increased to prepare reps for real-world pressures without fully exposing them to those pressures yet.

4. Excel under stress (“Do it well under pressure”): The final stage marks a significant shift to actual real-world application, where the safety nets are removed, and the stakes become genuine. Here, sales reps are immersed in typical real-world sales scenarios and face genuine sales challenges that require them to use all the skills they have honed. The focus is on performance under realistic and more demanding conditions, testing their ability to remain effective, persuasive, and calm when it truly counts. This stage is critical for assessing whether a rep can not only perform but excel when faced with the typical pressures of a sales environment.

This table should provide you with a simple high-level example of what the four competence levels would have to demonstrate for specific sales activities:

For these four levels, you might consider structuring the certifications as follows: basic certification for Level 1, intermediate for Level 2, advanced for Level 3, and expert for Level 4.

Alternatively, if you want to simplify things, you might have a basic certification that encompasses levels 1 and 2, and an advanced one including levels 3 and 4.

A real example

Now, let’s take a look at a practical example of defining criteria for various certification levels tied to a specific sales activity.

When I say “criteria”, I am essentially breaking down the high-level description of the competency (as per the above table) into actual, tangible milestones that should be accomplished to reach a specific level of competence.

I will focus on the discovery phase – one of the key sales activities highlighted in the previous table.

For this demonstration, I’ve outlined two certification levels: Basic and Advanced.

Basic certification (combining “know it” and “do it” levels):

• Successfully articulate what the key components of an effective discovery meeting are.

• Demonstrate comprehensive research skills by presenting at least 4 detailed prospect account profiles that include business insights, key decision-makers, industry context, and potential challenges.

• Show basic proficiency in building rapport and engaging in small talk in at least 3 role-play scenarios.

• Successfully set an agenda and upfront contract for 3 practice meetings, demonstrating an understanding of the meeting’s structure and purpose. 

• Perform basic objection handling and set clear next steps at the end of each session in 3 practice meetings, demonstrating initial problem-solving and guided selling.

• Identify the prospect’s challenges by asking open-ended and probing questions during 3 practice meetings.

Advanced certification (combining “do it well” and “do it well under pressure” levels):

• Conduct eight simulated discovery sessions with progressively challenging scenarios, focusing on detailed needs analysis and solution mapping. During those simulations, achieve the minimum evaluation score by setting an agenda and upfront contract, using effective discovery questions, managing advanced objections, creating urgency, and defining clear next steps.

• Execute five real discovery meetings with minimal to no supervision, effectively aligning discussions with prospects’ needs and handling unexpected challenges using appropriate discovery questions.

• Achieve a discovery conversion rate of at least 50% across the considered discovery meetings.

Keeping this example in mind, it’s also important to acknowledge that certifications can’t encompass every scenario; they are most effective in addressing common ones.

We should always remember that much learning occurs through experience and continuous feedback – making mistakes, reflecting, and improving for next time.

This also underscores the importance of sales coaching in this second phase of onboarding and beyond, as reps begin to apply what they learned during the Prepare phase and continue to learn and apply these skills in real-life situations during the Perform phase.

For a deeper exploration of sales coaching, I recommend reviewing my guide on sales coaching and my articles on advanced sales coaching techniques and sales training vs sales coaching.

The value of scorecards

Among the above criteria, you may have noticed that under the advanced certification, I mentioned “During those simulations achieve the minimum evaluation score…”. That wasn’t random.

A comprehensive certification should cover the main sales activities in a sales cycle, such as prospecting, discovery, demo, business case, and negotiation.

If we consider the area of cold calling for example, we know there are several sub-competencies that need to be performed with a certain standard (e.g., using an effective opener, demonstrating personalisation and relevancy, effective questioning).

These should be observed, evaluated, and given feedback through a rigorous and standardised approach. The evaluation of whether a rep has reached a minimum score can be aided by the use of scorecards.

A scorecard is essentially a tool to evaluate the effectiveness and quality of specific sales activities. It typically includes a set of criteria and metrics (often framed as questions) that assess various aspects of the call.

To give you an idea, here’s an example of a scorecard tailored for a cold call.

Something similar could be built for a discovery call, demo call, and so forth.

It’s important to mention that the scorecard should be closely aligned with the training that has been provided and the resulting playbooks.

For example, the above scorecard is fully aligned with a phone prospecting guide I created so that reps can be evaluated and given feedback in a way that reinforces the concepts, structures, and techniques learned during training.

A scorecard can help provide more objectivity in qualitative evaluation.

The more a scorecard reflects the principles put forward in your training programme, the more powerful it becomes in supporting effective feedback and driving improvement in a specific skill area.

Additionally, with the emergence of AI coaching, a precise scorecard could allow AI to evaluate all reps’ calls at scale and provide relevant feedback that aligns with the learning.

Hopefully, this demonstrates, in a practical manner, how scorecards can be an important component of a certification.

A caveat and some final thoughts

As I wrote this Prepare section, I recognised that, no matter how much I tried to make it practical, what I put forward is still partly theoretical; I understand that real life can often be very different.

Firstly, what has been described follows a linear path, but in reality, things tend to be more iterative, often messy, and include overlaps between phases.

Secondly, creating an onboarding programme that covers all core areas of the sales process with a rigorous certification is no easy feat and can be very resource-intensive.

The extent and speed at which you achieve this depend greatly on the maturity and size of your enablement function.

What is discussed here represents the ideal scenario, but everything should be contextualised.

Remember, it’s a journey, and by being patient and diligent, you can use this guide as a compass to develop the best sales onboarding plan possible over time.

Beyond this caveat, there are a few final thoughts I’d like to share:

• To better connect the Prepare phase with the Perform phase, remember that during the Perform phase, you want to consolidate what has been learned in the Prepare phase with a basic certification and progress towards a more advanced one. Additionally, you should add training on new areas that may not have been a priority during the initial weeks of onboarding (e.g., negotiation), as they become more important later in the learning process. For these areas, again, aim for both a basic and an advanced certification, thinking of it as a phased and continuous learning process. Ideally, those areas will also be linked by a common thread represented by one of the many sales methodologies you can find out there.

• To eliminate any certification anxiety among new hires, especially those who aren’t good at taking “tests,” it’s crucial to design the certifications to emphasise practical application and incorporate varied learning styles. Following the principles outlined above should help alleviate this concern.

• A common question regarding certification is: “What if people fail?” Well, failure is not inherently bad as long as it is used to tweak the approach and improve for next time. If a rep fails a certification, providing clear feedback on what is needed to succeed should enable them to meet the required standard. If failure persists after 2-3 attempts, consider whether, given the individual’s current performance and potential, it is worthwhile to invest the necessary energy and resources to help them meet the required standards. If it is, then proceed with the support. If not, begin planning to transition them out of the role (or the company) and review the talent identification process to identify any shortcomings. Certifications can thus serve as an early indicator of potential issues with specific individuals, ultimately saving time, resources, and money.

• Another important aspect to mention is the importance of clearly defining what enablement is doing and what the frontline sales managers are doing. Often, there’s a disconnect where enablement is teaching one thing, while sales managers are saying, “we don’t do it that way” or “you don’t need to know that.”
  To prevent confusion and contradictions for new hires, both teams must be aligned on what’s being taught and when. This collaboration ensures the onboarding process is seamless and effective for the learners. To a large extent also sales management owns onboarding.

With these final thoughts in mind, let’s now move on to phase three of this sales onboarding process.

Perfect: first deal to repeat quota attainment

When a new sales rep closes their first full-cycle deal, it’s just a small step towards mastering their role.

While the Perform phase is focused on achieving that first deal, the Perfect phase aims to enable repeat quota attainment over consecutive quarters, generating consistent, on-target performance.

During this phase, we become much more KPI-driven, with the balance of learning and development shifting more towards sales coaching rather than sales training.

By this point, the new rep should have completed many of their certifications, with perhaps a few still in progress.

They will have learned a lot, put it into practice repeatedly, and received feedback.

Therefore, at this stage, it is crucial for enablement and sales management to work closely with the rep, providing consistent and specific feedback to reinforce and course-correct the appropriate sales behaviours that are most likely to lead to the best results.

Key milestones

In this sub-section, I’ll examine the various milestones on the path to mastering and perfecting the new rep’s sales approach.

Some of the details of these – particularly the criteria checklists you will see – are taken from the book “Hiring, Onboarding, and Ramping Salespeople” by Cory Bray and Hilmon Sorey, which I’ve found very intuitive to apply in the real world.

Let’s dive in.

Full pipeline coverage

The first milestone in this phase is achieving full pipeline coverage. This means that if the new rep closes every deal in their pipeline, they will meet their quota.

Consider these three criteria when validating full pipeline coverage:

• All opportunities align with the salesperson’s target market and Ideal Customer Profile (ICP).

• Exit criteria for each opportunity are met before moving them to the next stage.

• A certain percentage of opportunities (minimum defined standard) have a next step agreed upon by the prospect, with a meeting scheduled.

These criteria help indicate whether the salesperson is effectively applying what they have learned in the previous phases.

Starting with inspecting pipeline coverage is crucial because if a rep doesn’t have enough deals in the pipeline, reaching their quota will be impossible.

The below table represents an example of what a full pipeline coverage could look like for someone with a $200k quarterly quota.

Full quota coverage

Once full pipeline coverage is achieved, the next goal is to reach full quota coverage, where the pipeline’s expected value matches the sales quota.

To determine the expected value of the pipeline, each stage of the sales process should have an estimated conversion rate. These conversion rates need to be reviewed and adjusted quarterly or annually based on actual performance data.

If you lack this data, consider sourcing aggregated benchmark data from similar companies, which may be available publicly.

The table below illustrates how you can calculate the total expected value for each stage of the sales process.

In this case, the “Total Value ($)” refers to the entire potential revenue that could be generated from all deals currently at each stage of the sales process. This figure represents the cumulative worth of all prospective transactions that the seller is working on at a given stage.

The “Conversion Rate (%)” is an estimate of the percentage of deals that are expected to progress from one stage of the pipeline to the next. This rate is essential for forecasting future sales and understanding how effectively deals are being moved through the pipeline.

The “Expected Value ($)” at each stage is calculated by multiplying the Total Value by the Conversion Rate. This calculation provides an estimate of the revenue that is likely to be realised from the deals at each stage of the pipeline, offering a more precise projection of future sales based on the current pipeline status.

When looking at full quota coverage, consider these criteria for validation:

• All opportunities align with the salesperson’s target market and Ideal Customer Profile (ICP).

• Exit criteria for each opportunity are met before moving it to the next stage.

• A certain percentage of opportunities (minimum defined standard) have a next step agreed upon by the prospect, with a meeting scheduled.

• Deal sizes are realistic based on historical data and market conditions.

• Closed dates are realistic and align with the prospect’s timeline.

This checklist introduces the two latter elements compared to the one associated with full pipeline coverage; this is to ensure more critical thinking about how opportunities are assessed, thereby reducing the likelihood of unrealistic expectations and inaccuracies

25% quota attainment

Reaching 25% quota attainment signifies that the sales rep has started to effectively engage with their pipeline and is closing initial deals, or that at least they can close a large deal. This milestone demonstrates their ability to generate early revenue and gain momentum in their sales activities.

At 25% quota attainment, a suggested criteria list (building upon previous ones) would include:

• All opportunities align with the salesperson’s target market and Ideal Customer Profile (ICP).

• Exit criteria for each opportunity are met before moving it to the next stage.

• A certain percentage of opportunities (minimum defined standard) have a next step agreed upon by the prospect, with a meeting scheduled.

• Deal sizes are realistic based on historical data and market conditions.

• Closed dates are realistic and align with the prospect’s timeline.

• Each lost deal has a documented reason, and coaching has been provided for any deals that could have been saved.

The main addition here revolves around lost deals.

This is about ensuring that salespeople understand why they are losing deals, and, more specifically, whether the losses are due to factors beyond their control (e.g., product or use case issues) or if there are aspects they can improve on for future similar deals.

50% quota attainment

Achieving 50% quota attainment indicates a certain level of repeatability in deal closure by the rep.

The criteria for validation you’d consider at this stage (building upon previous ones) include:

• All opportunities align with the salesperson’s target market and Ideal Customer Profile (ICP).

• Exit criteria for each opportunity are met before moving it to the next stage.

• A certain percentage of opportunities (minimum defined standard) have a next step agreed upon by the prospect, with a meeting scheduled.

• Deal sizes are realistic based on historical data and market conditions.

• Closed dates are realistic and align with the prospect’s timeline.

• Each lost deal has a documented reason, and coaching has been provided for any deals that could have been saved.

• The length of the sales cycle for each closed-won deal is in line with expectations.

Now, I’ve introduced the sales cycle metric. This is because if a salesperson takes longer than expected to close deals, enablement and sales management need to step in with coaching support to identify possible causes and develop an action plan to try and stay on track.

80% quota attainment

Reaching 80% quota attainment shows that the rep is nearing full quota, consistently closing deals and proceeding with a strong level of performance.

Criteria at this stage would include:

• All opportunities align with the salesperson’s target market and Ideal Customer Profile (ICP).

• Exit criteria for each opportunity are met before moving it to the next stage.

• A certain percentage of opportunities (minimum defined standard) have a next step agreed upon by the prospect, with a meeting scheduled.

• Deal sizes are realistic based on historical data and market conditions.

• Closed dates are realistic and align with the prospect’s timeline.

• Each lost deal has a documented reason, and coaching has been provided for any deals that could have been saved.

• The length of the sales cycle for each closed-won deal is in line with expectations.

• Win rates are aligned with expectations.

At this stage, there will be sufficient data to evaluate the win rate as a crucial metric and compare it to the expected performance.

If the win rate is below expectations, it might indicate that the rep is either missing potential revenue opportunities or focusing on deals that do not align with ideal use cases.

If this is addressed early on, it can fast-track learning and save time and money.

Full quota attainment

Achieving full quota attainment is a critical milestone that demonstrates the rep has full capability to drive revenue.

Criteria at this stage would include:

• All opportunities align with the salesperson’s target market and Ideal Customer Profile (ICP).

• Exit criteria for each opportunity are met before moving it to the next stage.

• A certain percentage of opportunities (minimum defined standard) have a next step agreed upon by the prospect, with a meeting scheduled.

• Deal sizes are realistic based on historical data and market conditions.

• Closed dates are realistic and align with the prospect’s timeline.

• Each lost deal has a documented reason, and coaching has been provided for any deals that could have been saved.

• The length of the sales cycle for each closed-won deal is in line with expectations.

• Win rates are aligned with expectations.

• Time to full quota attainment is in line with expectations

The new metric introduced is the time to full quota attainment.

This measures whether the salesperson reached their quota within the first or second quarter (or the relevant reference period based on your organisation’s sales cycle).

If it took longer and there were repeated misses, the key question is whether the salesperson can achieve sustained production that justifies their continued role. If not, it’s important to assess their willingness and capability to reach this milestone in the future.

Back-to-back quota attainment

With enough attempts, anyone can achieve a difficult task like making a three-pointer, bowling a strike, or hitting a bullseye. However, the number of people who can do it consistently is much lower, and these individuals have demonstrated mastery in their field.

While there’s always room for improvement, a salesperson who has met their quota for two consecutive quarters and satisfied all the checklists in this chapter is well-positioned for long-term success.

As a salesperson strives to meet their quota for the second consecutive quarter, it’s important to continue monitoring the milestones that were crucial in achieving their initial success.

If they are reaching these milestones more quickly than before, it’s a positive sign. If their progress has slowed, identify coaching opportunities to help them address any gaps and maintain their momentum.

As you may have noticed, the training and development focus during the Perfect stage shifts significantly towards coaching and feedback compared to the earlier onboarding phases.

This transition represents the natural progression of learning towards mastery. The more structured and timely the coaching and associated feedback, the higher the chances of continuous success for the new rep.

Creating a structured onboarding plan

When it comes to putting together a structured and effective sales onboarding plan, I’ve often come across the concept of the 30-60-90 day plan.

While this traditional approach provides a clear timeline for new hires to achieve specific goals within the first three months, I think it can fall short in several areas.

The rigidity of a fixed timeline may not account for the individual learning pace and unique challenges that each new hire faces, and this is where a milestone-based approach offers significant advantages.

A milestone-based onboarding plan emphasises flexibility and personalisation, allowing each new hire to progress at their own pace while ensuring that they achieve key competencies within an expected time range.

Unlike the 30-60-90 day plan, which can sometimes lead to a checkbox mentality, a milestone-based approach focuses on mastering necessary skills and achieving meaningful outcomes.

This ensures that new hires are genuinely prepared for their roles before moving to the next stage.

Moreover, a milestone-based approach is inherently adaptable to changing market conditions and role expectations. As unforeseen challenges arise, the onboarding process can be adjusted to ensure new hires meet the necessary milestones, maintaining relevance and effectiveness.

While milestones are linked to time, the focus remains on achieving specific competencies rather than adhering to a strict schedule.

Weekly checklists and goals can still be used within a milestone-based framework to ensure continuous progress.

Also, by monitoring the time taken to achieve each milestone, organisations can identify areas where new hires may need additional support, allowing for timely adjustments and optimisations to the onboarding process.

This perspective aligns well with the three phases of sales onboarding we discussed earlier.

The onboarding plan should be designed to enable new reps to achieve the milestones that characterise each phase as efficiently as possible.

At the same time, it should allow for the flexibility and personalisation needed to cater to individual learning paces and unique challenges.

Here are the three phases summarised:

1. Prepare – Pre-start to first prospect-facing activity: The initial phase begins once the offer letter is accepted. During this period, early engagement is essential to boost the new hire’s excitement and prepare them for their role. Key steps include sending a welcome pack, engaging with future colleagues, and completing administrative tasks beforehand. Early training materials should focus on understanding the company’s market position, key value propositions, basic industry knowledge, basic selling techniques for the early stages of the sales process, and any other relevant areas that would help achieve the initial milestones.

2. Perform: first prospect-facing activity to first deal: The Perform phase spans from the initial significant interaction with a prospect to the successful closing of the first deal. During this time, it’s essential to track key milestones such as the first activity performed at each sales stage, completion of relevant training and certifications, and analysis of lost deals to refine strategies. The goal is to ensure that the new hire can independently manage a full sales cycle within their designated market.

3. Perfect: First deal to consistent quota attainment: Once the first deal is closed, the focus shifts to achieving consistent quota attainment over consecutive quarters. This phase emphasises a more KPI-driven approach with a strong focus on coaching and feedback. Milestones during this phase include full pipeline coverage, full quota coverage, and incremental quota attainment (25%, 50%, 80%, and 100%).

Measuring success in sales onboarding

As we get towards the end of this article, one last area that must be addressed is the aspect of measuring sales onboarding success.

I am sure this question has been lingering in your mind: how do we measure the success of our sales onboarding programme?

In one of the initial paragraphs, I discussed the benefits of sales onboarding when done right, hinting at various success indicators.

In this final section, I will dig deeper into some tangible sales onboarding metrics that should be considered and tracked to evaluate the ongoing success of sales onboarding and ensure continuous improvement in relation to those metrics.

Time to productivity (time to ramp)

This metric is one of the most commonly measured ones when it comes to sales onboarding.

It’s the time it takes for new hires to become fully productive and start contributing to revenue. A well-structured onboarding programme should reduce this time, allowing new reps to reach full productivity faster.

This metric can be measured by tracking the duration from the start date to the point where the rep consistently meets or exceeds their sales targets.

For specificity, we can define this endpoint as:

• First quota achievement: The initial milestone could be when the rep hits their sales quota for the first time. This indicates they can meet the set expectations.

• Consistent quota achievement: To ensure sustained performance, the rep should hit their quota for at least two consecutive quarters. This demonstrates their ability to maintain productivity over a sustained period.

This duration can then be compared to previous cohorts who might have gone through an older version of the onboarding process.

Sales performance metrics

To comprehensively evaluate the effectiveness of your sales onboarding programme, it’s also important to focus on specific performance metrics that indicate how well new hires are adapting and succeeding in their roles.

These metrics provide insights into their ability to meet targets, manage their pipeline, and progress through the sales cycle efficiently.

• Quota attainment: Track the percentage of new reps who meet or exceed their sales quota within a specified timeframe (e.g., first quarter, first half-year).

• Pipeline coverage: Measure the extent to which new hires build a pipeline that aligns with their quota, indicating their ability to prospect and qualify leads effectively.

• Conversion rates: Evaluate the percentage of leads that move through each stage of the sales funnel, reflecting the new hire’s proficiency in advancing deals.

• Average deal value: Track the average revenue generated per deal closed by new hires, which helps in understanding their ability to close deals that have a monetary value that falls into the expected range.

• Sales cycle length: Measure the average duration of the sales cycle for new hires. A decrease in the sales cycle length can indicate that new hires are effectively applying their training to move deals through the pipeline faster.

These metrics can then be compared to previous cohorts who have gone through an older version of the onboarding programme or those who have not undergone a structured onboarding process at all.

Additionally, comparing these metrics to the existing averages for more experienced sales reps can provide a broader perspective.

Improved metrics over time from cohort to cohort, or better metrics compared to existing reps, can indicate the effectiveness of the onboarding process in enabling new hires to contribute to the sustainment and growth of the organisation.

Retention rates

A robust sales onboarding process should lead to higher retention rates among new hires. This can be measured by comparing the turnover rates of new hires who went through the updated onboarding programme with those who underwent previous versions.

As mentioned earlier in this article, even a slight increase of five per cent in sales rep attrition can raise selling costs by 4-6% and reduce total revenue attainment by 2-3%.

Therefore, monitoring and improving retention rates is crucial.

This metric not only reflects the effectiveness of the sales onboarding process but also significantly impacts the overall health and profitability of the sales organisation.

Tightly connected to retention rates are also employee satisfaction and engagement. Conducting regular surveys to gauge new hires’ satisfaction with the onboarding process is essential. Metrics such as Net Promoter Score (NPS) or Employee Engagement Scores can provide insights into how supported and valued new hires feel, which is crucial for long-term retention.

Training effectiveness

You can assess the effectiveness of your training sessions within the sales onboarding plan by evaluating knowledge retention and application. This can be done through:

• Quizzes and assessments: Conduct periodic quizzes and assessments to ensure that new hires retain key information. Metrics to track include:

  • Minimum score achievement: Set a benchmark score that new hires must achieve to pass.

  • Score improvement over time: Track the progress of scores from initial to subsequent quizzes to measure knowledge retention and improvement.

  • Pass rate: The percentage of new hires who meet or exceed the minimum score.

• Role-playing and simulations: Observe new hires in simulated sales scenarios to assess their ability to apply what they’ve learnt. Metrics to track include:

  • Performance scores using scorecards: Evaluate role-playing sessions using standardised scorecards to assess various competencies, such as cold calling, handling objections, pitching, and discovery.

  • Improvement in simulation scores: Measure the progress in scores across multiple simulation sessions to gauge skill development.

  • Feedback utilisation: Track how well new hires incorporate feedback from previous role-plays into subsequent simulations.

• Certifications: If you have implemented a structured certification process that aligns with the key competencies required for the sales role, you can also consider the following metrics to gauge training effectiveness:

  • Certification completion rate: The percentage of new hires who successfully complete the certification process. A high completion rate indicates that the training is accessible and comprehensible.

  • Time to certification: The average time it takes for new hires to achieve certification. Shorter times may indicate effective training methods and materials that facilitate quicker learning.

  • Certification scores: Analyse the scores achieved on certification assessments. Consistently high scores suggest that the training is effectively imparting the necessary knowledge and skills.

It is essential to emphasise that quizzes, assessments, role plays, simulations, and certifications should not be conducted merely as formalities.

Instead, they should be meticulously designed to directly correlate with the specific outputs and performance standards that sellers are expected to achieve.

Ultimately, it should all translate to tangible sales performance metrics improvement and business impact.

Revenue impact

Ultimately, the goal of sales onboarding is to drive revenue. Track the revenue generated by new hires within their first year and compare it to the cost of the onboarding programme. This comparison will help you calculate the return on investment (ROI) of your onboarding efforts.

Another effective way to demonstrate revenue impact is to compare the revenue produced within a specific time frame (e.g., one year) by reps who have undergone a structured onboarding programme versus those who have not.

Customer feedback

This is often neglected, but collecting feedback from customers who interacted with new hires can help you understand the impact of onboarding on customer experiences.

Positive feedback and higher customer satisfaction scores can reflect the effectiveness of the onboarding programme.

Continuous improvement

Regularly review these metrics to identify areas for improvement in your onboarding process.

Set up periodic check-ins with new hires to gather qualitative feedback, and be prepared to make iterative changes to the programme based on this feedback and the quantitative data collected.

By continuously refining your onboarding approach, you can ensure that it remains effective and aligned with your organisational goals.

The sales onboarding maturity journey

When it comes to implementing a comprehensive sales onboarding programme, like we’ve described in this piece, it’s important to recognise that reaching the full maturity of such a programme is a journey.

Organisations often underestimate the time and resources required to establish a robust onboarding process that genuinely impacts performance.

As I already briefly touched upon in previous paragraphs, creating an effective onboarding programme that covers in-depth all three phases discussed above is not an overnight task – it’s a strategic endeavour that evolves over time.

Drawing from my experience so far, I’ve seen that successful onboarding initiatives typically progress through several phases of maturity. Each phase builds on the previous one, allowing the organisation to gradually develop a more sophisticated and effective programme.

Let’s break down the maturity journey into three key stages, with realistic timelines and priorities for each stage.

As I dig deeper, remember that timelines can still vary greatly depending on your resource levels and technology maturity; what’s being covered below only represents a high-level guide.

Stage 1: foundation building (0-6 months)

At this initial stage, the key focus areas include:

• Needs analysis and stakeholder alignment: The first step in building a strong onboarding programme is understanding the needs of the organisation and aligning with key stakeholders. This involves conducting a thorough needs analysis to identify the process, skills and knowledge gaps that the onboarding programme should address.
• Early engagement initiatives: Implement all of the early engagement strategies we learned, such as sending welcome packs, pre-onboarding tasks, completing HR paperwork ahead of the new hires’ start date, and ensuring the IT setup is as efficient as possible.
• Basic onboarding framework: Establish a foundational onboarding framework that includes pre-start engagement, a clear orientation process, and initial training materials. At this stage, focus on creating content that covers the essentials: company overview including values and culture, market positioning, key value propositions, buyer personas, ideal customer profiles (ICPs), and basic selling techniques relevant to the early stages of the sales process. In other words, focus on creating what’s included in the Prepare phase.
• Initial milestones and metrics: Define simple, clear milestones for the first 30-60 days, focusing on key activities like understanding and identifying the ICP, prospecting, and conducting initial discovery calls. Start tracking basic performance metrics to gauge early success.

By the end of this stage, the organisation should have a basic but functional onboarding process that ensures new hires are prepared to begin their roles.

The focus should be on creating momentum and building a foundation for more advanced training.

It’s perfectly fine if much of the curriculum isn’t fully developed yet; most reps will still be able to learn and adapt by absorbing information from their peers and managers in more informal, unstructured ways.

Stage 2: programme expansion (6-12 months)

At this intermediate stage, the key focus areas include:

• Curriculum development and content creation: As the programme matures, expand the onboarding curriculum to include more in-depth content on product knowledge, qualification frameworks, advanced selling techniques that include further stages into the sales process, objection handling, and CRM training. Begin developing role-playing scenarios and case studies that simulate real-world sales situations.
• Introduction of certifications: Implement basic certifications that assess new hires on foundational competencies. Certifications should focus on the “Know it” and “Do it” levels, ensuring that new hires understand the core concepts and can apply them in controlled environments.
• Sales manager enablement: Begin integrating sales managers into the onboarding process. Provide them with the tools and training needed to support their reps effectively. Alignment between enablement and sales management is crucial at this stage to avoid mixed messages and ensure a united front.
• Feedback loops and continuous improvement: Establish regular feedback loops to gather insights from new hires and managers. Use this feedback to refine and improve the onboarding content and process. Start introducing mechanisms for continuous improvement, such as periodic reviews and adjustments to the curriculum.
• More developed milestones and metrics: During this phase, the focus on metrics should evolve to include more complex indicators of success. Start including the basic certifications completion as learning milestones, and move beyond the basics with regards to performance metrics. Include indicators like time to full pipeline and quota coverage, opportunity conversion rates, and the speed at which new hires close their first deals. These metrics will help gauge how effectively new hires are applying their training in real-world scenarios and progressing towards full competency as well as how the onboarding may be impacting overall performance.

By the end of this stage, the onboarding programme should be more comprehensive, with structured content that covers a broader range of sales activities.

New hires should be equipped to handle more complex sales scenarios, and the organisation should start seeing improvements in time to ramp and early-stage quota attainment.

Stage 3: full maturity (12-24 months)

At this final stage, the key focus areas include:

• Advanced certifications and mastery levels: At this stage, introduce advanced certifications that cover the “Do it well” and “Do it well under pressure” levels. These certifications should focus on refining skills in high-stakes scenarios and ensuring reps can perform consistently under pressure.
• Integration with sales methodologies: Incorporate advanced sales methodologies (e.g., MEDDPICC) into the onboarding programme. Ensure that all training content, certifications, and role-playing exercises are aligned with these methodologies, providing a cohesive learning experience.
• Enhanced sales coaching: Shift the focus towards a more coaching-driven approach, particularly as new hires transition from closing their first deal to achieving consistent quota attainment. Implement structured coaching processes, frameworks and tools (e.g., scorecards, 1:1 coaching templates) to provide targeted feedback and support continuous improvement. Double down on sales manager enablement to enhance their capacity to develop the capabilities of the new hires on a daily basis.
• Advanced milestones, metrics, and reporting: Introduce advanced certifications completion and all performance indicators included in the Perfect phase (e.g., 25% quota attainment) as additional milestones. Additionally, start enabling more sophisticated tracking of performance metrics, such as conversion rates from stage to stage, average contract value, win rates, sales cycle length, and time to quota attainment. Use these analytics to identify patterns, optimise the onboarding process, and tailor coaching to individual needs.
• Cross-functional integration: By this stage, the onboarding programme should be fully integrated with other functions, such as marketing, product, and customer success. This means that new hires not only learn about their own role but also gain insights into how marketing drives lead generation, how product teams prioritise features and updates, and how customer success manages ongoing customer relationships.

By the end of this stage, the organisation should have a fully mature onboarding programme that not only accelerates time to ramp but also drives long-term success and retention.

New hires should consistently achieve and exceed their quotas, and the programme should be a key contributor to the organisation’s overall growth and profitability.

Conclusion

Writing this piece has been an interesting process.

It has allowed me to reflect on my past practices and recognise how much they have evolved to meet current demands. Additionally, the research I had to conduct to draft this guide in the most comprehensive way possible has helped me identify new areas for improvement in my current approach.

I hope this guide will prompt you to evaluate your current sales onboarding practices. Perhaps you will identify areas where your planning and execution could be strengthened to drive greater business impact.

Noticeably absent from this discussion was a detailed focus on technology (e.g., sales onboarding software).

This omission was intentional.

While technology can undoubtedly supercharge your onboarding process, it should not be the starting point.

A clear, effective process and approach must come first.

Only then can tools serve as amplifiers to an already solid practice.

I aimed to provide a robust foundation for a successful sales onboarding programme, ensuring new hires are well-prepared, confident, and capable of contributing significantly to your organisation’s success.

Implement these practices, and you’re well on your way to building a world-class sales team.

Thank you for reading, and I look forward to seeing how these insights help shape your sales onboarding best practices and strategies.