Sales Onboarding Best Practices – 16 Leaders Share Their Secrets 

Disclaimer: The views and opinions expressed in this article are those of the individual contributors and do not reflect the official policy or position of their current or previous employers. This content is for informational purposes only.

Introduction

A few months ago, when we tackled sales enablement best practices, Ashton Williams, the Director of Strategic Programs (Enablement) at a company whose product you probably used today, had the following to say: 

“Onboarding is a program that often gets neglected once built, but having a solid onboarding ensures you are not running enablement debt every time you launch initiatives because you know your reps are ramped and at the same level of learning on most things.

So many of the reactive programs enablement gets asked for are a symptom of missing skill, operational excellence, or product mastery in the first 90 days.”

In a few sentences, she perfectly illustrated the importance of a good onboarding programme, as well as the negative consequences of not having one. 

Moreover, onboarding is among the most common responsibilities of enablement teams, as we found out when we consulted a wealth of quantitative research and wrote our sales enablement statistics article to get a better sense of enablement teams’ focus areas around the world. 

That is also why I recently decided to publish my complete guide to sales onboarding alongside my sales onboarding checklist, sales onboarding plan template, and sales onboarding metrics guide.

However, I didn’t want to leave it at that.

I wanted, as is the tradition here at The Enablement Insight, to tap into the collective knowledge of my peers, more precisely, the enablement professionals who’ve dedicated much time, energy, and focus to onboarding new sales hires and enabling them to be as productive as quickly as possible. 

Therefore, I reached out to the community and was lucky enough to have sixteen enablement leaders share their best practices on sales onboarding:

Alex Bedford – GTM Enablement Lead

Alexander Stefansson – Head of Global Sales Excellence

Arup Chakravarti – Director of Sales Excellence

Chad Trabucco – Senior Director of Sales Enablement

Devon McDermott – Head of Enablement

Estefania Rodriguez Merino – Senior Revenue Enablement Manager

Fiona NicChoiligh – Director, International Revenue Enablement

Gail Behun – Senior Director of Revenue Enablement

Jenelle Knight – Senior Sales Enablement Manager

Karolina Janus – Global Sales Onboarding Lead

Kieran Smith – Senior Director of Enablement

Milko George – Global Director of Sales Enablement

Nelson Frech – Sales Enablement Senior Manager, Sales GTM Onboarding

René Ngadi – Sales Enablement & Onboarding Manager

Ronnie Rodriguez – Senior Manager of Sales Onboarding

Ryan Kolofsky – Senior Director of Sales Training & Enablement

Once again, our contributors exceeded my already high expectations, sharing a veritable treasure for anyone even remotely associated with onboarding salespeople of various seniorities, regardless of the industry, the product, the size of the company, or any other differentiating factor you can think of.

As I organised their contributions, I noticed a few themes and decided to categorise their responses according to the following:

Build a structured onboarding programme

Given that most of our contributors were at the Director level, their recommendations leaned heavily towards a strategic approach to sales onboarding.

They emphasised the importance of developing an intentional, structured onboarding programme that goes beyond merely “going through the motions” to become a fundamental part of building strong go-to-market teams.

Kieran Smith, the Senior Director of Enablement at a B2B media company that delivers marketing and data for 600+ technology companies, highlighted the need for intentionality in the sales onboarding process. 

“Onboarding is often seen as a necessary evil,” he noted, but he stressed that a well-designed programme can transform this perception:

“Having intentionality behind your entire onboarding program is fundamental to having it be an enjoyable and educational experience for new starters.” 

Kieran believes that when onboarding is approached with clear purpose and structure, it not only shortens the learning curve but also boosts the overall morale of new hires.

Kieran also elaborated on structuring the onboarding process. He recommended a logical progression starting with understanding the company and market, then moving to product training, role-specific skills development, and finally, the day-to-day processes:

“This is a natural flow of knowledge, skills, and then putting it into action before learning day-to-day processes that you will do from day one in the role”. 

This approach helps new hires build a solid foundation before diving into the specifics of their roles.

Nelson Frech, the Sales Enablement Senior Manager (Sales GTM Onboarding) at the world’s leading data intelligence platform which serves more than 50% of the Fortune 500, also offered practical advice on organising the onboarding curriculum. He suggested dividing it into core pillars: 

• Foundations

• What We Sell

• How We Sell

• Do Your Job

This structured approach ensures that new reps quickly become proficient in the necessary skills, processes, and tools. 

Nelson also advocates for a multi-modal learning strategy that includes e-learning for foundational knowledge, followed by virtual or in-person Instructor-Led Training (ILT) for hands-on practice. He reminded us that onboarding is not just about training:

“Your sales onboarding program is vital to building company culture – be an ambassador!”

Fiona NicChoiligh, Director of International Revenue Enablement at the leading conversational and revenue intelligence tool, advised focusing on three key activities in the first month: 

• Understanding personas

• Knowing the outcomes that matter to customers

• Learning how to prospect effectively

“Less is best,” as she put it, also noting that by concentrating on these areas, new hires can build a strong foundation without feeling overwhelmed.

Gail Behun, Senior Director of Revenue Enablement at the global leader in financial information, analytics, and market insights, underscored the importance of clarity towards the sales personnel in the onboarding process:

“Make sure that you give your learners a very clear pathway of what they will be learning when and what’s in it for them.”

Gail warned that without understanding the benefits of each part of the training, new hires may be tempted to skim through content without fully engaging. A well-defined pathway helps ensure that they stay focused and motivated.

Chad Trabucco, Senior Director of Sales Enablement at the world’s learning & development content company, shared a key insight that transformed his approach to onboarding.

He realised that structuring onboarding around the company’s actual sales stages, rather than abstract themes like competitive landscape or product knowledge, provided new hires with a clear roadmap:

“When the content is structured around your company’s actual sales stages and the exit criteria required to advance to the next stage, new hires more readily have a roadmap to what they need to do (and when) to close their first deal.”

This approach also helps embed the critical sales stages and exit criteria early on, giving reps a clearer understanding of their goals.

Alexander Stefansson, the Head of Global Sales Excellence at a leading employee performance management software company, emphasised the importance of focusing on customers rather than overwhelming new hires with product knowledge or shadowing top performers. 

He advised spending the first week delving deeply into buyer personas and ideal customer profiles (ICPs). “You need to spend more time getting to know your best customers,” he says.

Alexander suggests exploring questions such as:

“What do our best customers have in common?

What are their main challenges, problems, fears, and aspirations?

What would motivate them to change?” 

His rationale is that by starting with an in-depth understanding of the potential buyers and customer, sales reps are better equipped to connect with them and address their needs. 

Estefania Rodriguez Merino, a Fractional Sales Enablement Partner with many years of enablement experience at very successful European SaaS companies, stressed the importance of organisation and project management in onboarding:

“Be a real orchestrator, not only during the building phase but also when executing the onboarding process.“

Estefania suggested using a single calendar to organise onboarding meetings, ensuring clear visibility for both the onboarding team and sales managers and easier syncing between the two. 

Milko George, the Global Director of Sales Enablement at a global commerce media company, also shared his vision of the structured sales onboarding process.

He suggested using a flipped classroom approach in the first 4-6 weeks, where new hires start with self-paced learning through modules and videos that cover essential topics such as product knowledge, sales techniques, and CRM systems.

This phase allows new employees to build a foundational understanding at their own pace.

Following this, the onboarding transitions into a more interactive, classroom-based period lasting 2-3 weeks.

During this stage, the focus shifts to the practical application of the theoretical knowledge gained earlier.

New hires engage in role-playing scenarios, which help them simulate real-life sales situations and refine their skills.

Milko notes that subject matter experts are available during this time for open office hours, providing new hires with opportunities to ask questions and deepen their understanding of sales processes.

The final part of the onboarding programme underlines the importance of applying what has been learned. New hires practice key skills such as pitching, addressing customer needs, and effectively applying their knowledge to solve real customer business problems. 

A few of our contributors also pointed out how important it is for the onboarding programmes to adopt an iterative approach and be truly agile. 

Ryan Kolofsky, the Senior Director of Sales Training & Enablement at a company that specialises in software for the commercial construction industry, suggested gathering feedback to ensure the programme evolves and gets better with each iteration.

Karolina Janus, the Global Sales Onboarding Lead at THE global ride-hailing and transportation platform, elaborated more on this subject:

“Constantly checking on the employee experience and re-evaluating and adjusting the sales onboarding program is extremely important. 

What worked six months ago might not be relevant anymore in an ever-changing environment. 

Sales enablement teams need to stay updated on all changes that might affect new hire ramps and adjust training programs, content and modalities accordingly.

This could include updating assignments, replacing 1:1 engagements with group sessions, extending support beyond 90 days, accelerating bootcamp dates, and much more. 

Constant innovation and creativity are paramount for onboarding programs to remain effective and relevant.”

Estefania Rodriguez Merino suggested taking this iterative approach a step further and introducing the concept of impermanence for every onboarding programme:

“Embrace the fact that your Sales Onboarding won’t be perfect from the start.

It needs to iterate to become best-in-class!”

Alex Bedford, the GTM Enablement Lead at a leading enterprise micro-segmentation cybersecurity company,  added another layer to the discussion, focusing on the challenges of managing ongoing programmes within an organisation.

He highlighted the importance of aligning onboarding activities with the ramping journey of the rep, cautioning against overwhelming new hires with too much information at once:

“This means [the many interested parties within the organisation] may have to settle for a short video introduction or online Q&A session rather than an hour ‘chalk and talk’ at the physical event.”

Customise your onboarding

Another common thread that started appearing as I went over the best practices our contributors shared is the importance of making onboarding programmes as customised as possible (in the context of your enablement maturity), never forgetting who you are onboarding and what their specific needs are. 

Milko George clearly championed the personalised approach while acknowledging it may be time-intensive:

“In my practice, I’ve focused on developing close-to-personalised learning paths tailored to different sales positions, segments, or geographies. This requires a significant investment of time upfront to understand the necessary pieces of knowledge and prioritise them to ensure the most cost-effective and time-efficient benefits for new hires.” 

Milko emphasises the importance of customisation by geography in particular, reflecting product segmentation and relevance to different types of customers in those regions.

Estefania Rodriguez Merino reinforced the need for structured onboarding by suggesting a programme that considers the different roles within the sales team:

“Build your Onboarding program by considering the different roles within the Sales team. This approach allows you to create common paths and diverge when addressing role-specific needs.” 

She also highlighted the importance of scalability while adapting to different learners (as everyone integrates knowledge and skills differently).

Understanding the new hire profile is crucial, as Nelson Frech pointed out. He advised:

“Meet with your talent team (and GTM leaders) to understand the ideal new hire profile—where they are coming from, and expected skills. A great onboarding program can fail if your audience assumptions are incorrect.”

Nelson stressed the importance of considering nuances in sales roles (e.g., velocity versus strategic), and finding ways to specialise the onboarding experience for different audiences.

René Ngadi, a Sales Enablement & Onboarding Manager at the company behind leading PR software, also advocated fiercely for role-specific training. He explained:

“Starting on Day 2, we provide specialised training and role-playing exercises tailored specifically for the Account Executive role. By customising the training for each position, we ensure new hires are well-prepared to begin effectively and make a significant impact.” 

This approach helps AEs practice pitching regularly and develop a prospecting strategy that they can implement immediately after onboarding, building their confidence and proficiency as they progress.

Empathy for the end user (the salesperson being onboarded) is another critical perspective.

Chad Trabucco warned against the tendency to overload onboarding programmes with unnecessary information.

He painted a vivid picture:

“It’s easy for onboarding to become the proverbial kitchen sink.

New product feature?

Throw it in.

Pricing change for one region?

Throw it in.

Whitepaper that’s 30 pages long?

Throw it in.

But I’ve found that some simple organisation and empathy for what a new hire needs to know now to ramp vs. what they need to close a deal in six months makes a world of difference for increasing early confidence and decreasing time to ramp.”

Making onboarding fun is also essential, especially in hybrid or remote environments. Fiona NicChoiligh suggested:

“Engaging onboarding programs help new hires connect and support each other, which is especially important in hybrid or remote environments. Use daily stand-ups, end-of-week quizzes, games, and competitions to keep the process fun and engaging.”

By following these best practices, onboarding can become more effective and also an enjoyable experience that fosters connection among new sales representatives.

Gail Behun addressed the importance of balancing generic and specific content in onboarding. She advised:

“At least 60% of the onboarding content should cover foundational information that applies to all roles within the revenue organization, such as details about the company, buyers, pricing, products, and competitive intelligence. The remaining 40% should then dive deeper into role-specific training.” 

Gail also stressed the importance of pacing the onboarding process to avoid information overload, ensuring that tools and technologies are introduced when they are needed, with just-in-time learning to reinforce knowledge application.

Promote company vision, values, and culture

While, for the most part, our contributors focused on the nitty-gritty, customer-focused aspects of sales onboarding, it was great to learn that many of them still included company vision, values, and culture as some of the key factors to consider for successful onboarding. 

René Ngadi, for instance, stressed the effect of a strong first impression:

“There is no second chance to make a good first impression. We focus on immersing our new hires in our company vision, values, and culture. This sets a solid foundation, ensuring everyone aligns with our mission from the get-go.”

By deeply embedding new sales professionals into the company’s core values, they are more likely to develop a sense of belonging and purpose, which is very important for long-term engagement and success.

Karolina Janus underscored the need for a comprehensive introduction to company culture during the onboarding phase. She pointed out that “…it’s essential for new hires to understand and absorb the company’s values, winning behaviors, and rules of engagement early in the process.”

A thorough induction, especially one led by sales enablement, can help new employees adapt more quickly to their new environment, even if they come from a similar industry. 

Arup Chakravarti, the Director of Sales Excellence at one of the leading global data, analytics, and technology companies, offered practical advice for integrating senior leadership into the onboarding process, especially given their limited availability.

He suggested using video recordings to capture their welcoming messages, ensuring these can be used regularly without overburdening leaders:

“Senior leadership capacity is a very scarce resource. Use video recordings where you need their welcoming voice on a regular basis, engage them early, and ensure they have nominated a delegate if you need them in person.”

For remote employees, Arup recommended capturing a video walkthrough of the office:

“This gives everyone a chance to see (and feel) the office location, culture, and where everyone sits!”

This approach helps remote workers connect with the company’s physical space and culture, reinforcing a sense of inclusion even from a distance.

Tap into peer expertise and enable sales managers

The proverb, “It takes a village to raise a child”, translates surprisingly well to sales onboarding.

Successful onboarding should never be carried out solely by one person, and it is important to involve peers, subject matter experts, and especially sales managers in the process.

This is something many of our contributors also pointed out.

For instance, Karolina Janus highlighted the critical role of a structured buddy or mentorship system during the first 90 days of onboarding, “Buddies/mentors are invaluable partners for new joiners,” helping them navigate various aspects of their new role, from shadowing and targeted coaching to tool setups and prioritising daily tasks. 

Janus explained that at her company, comprehensive guides are provided to mentors and new hires, outlining specific tasks to complete each week. These guides serve as a roadmap for new sales reps, helping them integrate smoothly into the business environment.

Ronnie Rodrguez, the GTM Enablement Leader at the world’s leading data intelligence platform, also emphasised how experienced mentors offer personalised guidance, and peer support groups enhance learning and relationship-building.

Estefania Rodriguez Merino highlighted the importance of involving stakeholders, managers, and top performers in the onboarding process. She advised:

“Rely on stakeholders to build the onboarding program, choosing the most experienced individuals for each topic to ensure credibility.”

By engaging these individuals in mentorship, role-play sessions, and progress tracking, the onboarding programme becomes more robust and aligned with the company’s goals.

The role of sales managers in co-building and supporting onboarding programmes was identified as a key success factor by many of the contributors.

Chad Trabucco shared his experience co-building onboarding programmes with managers.

He found that involving managers in the development of the curriculum encouraged them to take ownership, which in turn gave them more time to coach their teams.

Trabucco recounted a success story:

“After taking this approach, a manager reached out to me to say that it normally took them 10 weeks to feel confident putting a new hire in front of a customer – but after taking the approach above, it only took 3 weeks.”

Kieran Smith also advocated for close collaboration with managers when designing onboarding programmes. He believes that by working together to define the “must-have,” “need-to-have,” and “good-to-have” skills and knowledge for new hires, the onboarding process becomes more effective:

“I also believe that by building/refreshing your onboarding with managers/leaders leads to a stronger buy-in from them and, in turn, will help the success of onboarding”.

Fiona NicChoiligh was another contributor who stressed the importance of managers being involved from the start.

She suggested that managers should create checklists, participate in new hire Slack channels, and be involved in skill validations.

She wrapped this up by saying:

“This shared responsibility enhances the onboarding experience and speeds up ramp time.”

Gail Behun focused on the clear delineation of what enablement is doing and what the frontline sales managers are doing:

“Very often enablement is teaching something and sales managers are saying, “Oh, we don’t do it that way” or “You don’t need to know that”; it is essential that both parties are on the same page about what is being taught and when to avoid confusing or contradicting the new hires.

This united front ensures that the onboarding process is efficient and effective for the learners.” 

Move from theoretical to practical

One area where most of our contributors saw great potential for better onboarding is the rapid and timely practical application of theoretical knowledge. 

As Fiona NicChoiligh put it:

“People Learn by Doing, Not Listening – Avoid back-to-back sessions with experts presenting. Incorporate interactive practice sessions like teach-backs, role plays, peer brainstorming, and competitions. This hands-on approach accelerates learning.”

Milko George described this transition from theory to practice in great detail:

“The last part of the onboarding process involves applying the theoretical knowledge that new hires have acquired through practicing key skills in real-life situations.

This phase is based on two principles. 

First, we try to emulate customer calls or meetings and involve a larger group of people to minimize subjectivity in evaluating the performance of new reps.

In practice, this involves two types of evaluations.

First, a manager-based evaluation using a pre-recorded sales pitch to a defined customer, which could be a business case or an existing customer.

The second type involves a panel usually composed of individuals from sales, go-to-market, sales enablement, and product enablement. 

This evaluation is typically conducted via a virtual Zoom call where participants simulate a real meeting with a customer, discovering and uncovering specific business needs and then presenting a business case involving the products they are supposed to sell.”

Alexander Stefansson highlighted the indispensable role of practice in the sales onboarding process:

“Practice, Practice, Practice. Doing anything new takes practice and dedication.

Practice alone, practice with colleagues, practice with a coach, practice with AI.

Mock call, live demos, exercises, talk tracks, memorisation, group work.” 

Alexander also points out the importance of adapting to various learning styles, saying:

“We all learn in different ways, cater for the broader audience, but leave room for individual best practice learning styles.”

Estefania Rodriguez Merino stressed the significance of interactivity in the onboarding process, even if the learners are engaging with it autonomously:

“Mixing theoretical and practical activities, along with asynchronous actions and live interactions, breaks the routine and ensures that knowledge is acquired and skills are ready to be put into action!“

Trust is a crucial element in this process, as Estefania noted:

“Before allowing learners to proceed autonomously, ensure that trust is established: you are responsible for the newcomer’s engagement, which is directly related to the success of the onboarding process.”

Measure as much as possible

As expected, a number of our contributors made sure to cover the metrics, the KPIs, and other measurements that help them evaluate their onboarding programmes, demonstrate the results to the organisation, and improve them over time. 

Nelson Frech stressed the need to define ramp success metrics and align them with the onboarding timeline:

“Your organization likely has a target ‘ramp period’ of 60 days, 90 days, or longer. Enablement should align the timeline with ramp metrics in order to measure the success of your program and new hires.”

Nelson advised that, if the ramp expectation is 90 days, the programme should adhere to this goal, with specific “hustle” metrics such as pipeline generation and number of customer meetings being tracked.

He also highlighted the importance of communicating these objectives with stakeholders, noting that it’s essential to “receive support on the objectives.”

Karolina Janus also advocated for a comprehensive, data-driven approach to identifying gaps in the onboarding process early. She explained:

“We track multiple data points in the first six months and beyond for each new hire to get a comprehensive view of their progress.”

She added that along with tracking sales activities and pipeline creation, her team collects and analyses feedback from new hires, their peers, and managers, which helps to quickly identify and address knowledge or skill gaps. Karolina also emphasised the value of certifications and tests – “excellent indicators of existing knowledge gaps that need attention.”

Estefania Rodriguez Merino underscored the importance of monitoring onboarding activities and measuring their impact on new hires’ progress.

She explained:

“Tracking results (both quantitatively and qualitatively) is important for two reasons: ensuring that your onboarding program iterates effectively each month and proving the program’s success, which is directly related to the success of the Sales reps during their ramp-up period.”

Estefania suggested using specific KPIs, such as: 

• Time to “Operational”: The exact date when the newcomer starts effectively working.

• Time to “First Success”: The exact date when the newcomer generates the first business opportunity, closes the first deal, or retains the first client.

• Time to “Maturity”: The month when the newcomer hits the standard target set for their role, no longer being in ramp-up time.

Devon McDermott, Head of Enablement at a digital platform for dentists, highlighted the importance of tracking the impact and effectiveness of the onboarding process from the very beginning. She advised:

“Align with leaders on ramp metrics and ramping quota to define clear milestones. By tracking impact and continuously improving, you’re not just onboarding – you’re building a sales team ready to crush their goals.” 

Devon recommends practical steps such as launching surveys at regular intervals to monitor programme impact and mapping progress against a standard rep scorecard to obtain a data-driven view of development. This approach, she asserts, “turns your onboarding program into a key driver of sales success.

Alex Bedford, shared insights on the importance of metrics and baseline agreements in the onboarding process. He emphasised:

“The goal of any sales onboarding should be to minimise the time it takes a new seller to “get up to speed” …but what does that mean?  

Actual time depends on the industry and complexity of the sale, but you need to know the appropriate amount of pipeline (2x/3x/4x etc) that needs to be built and then closed out to retire their quota.  

Knowing that your onboarding process is designed with these metrics allows us to remove some of the risk of adding new sellers into the organisation.”  

He also recounted a success story where at a certain organisation they were able to demonstrate that sellers who completed (the 12-week) onboarding program built 40% more pipeline and closed $300k more than those who did not attempt or complete the program. 

This case offers a perfect example of the tangible impact that a successful sales onboarding process can have. 

To summarise it all, as Ryan Kolofsky shared with me:

“Track onboarding from Day One.”

Use certifications and milestones

One of the ways to track how salespeople are being onboarded and progressing in their learning journeys is to introduce a system of milestones and certifications that clearly demonstrate an individual sales rep or any other member of the GTM team has reached a certain level of required competencies.

Alexander Stefansson talked about the importance of incorporating both written and verbal certifications into the onboarding process.

He described a robust certification process where the written exam, “…consisted of 60 open-ended questions about ICP, buyer persona, pains, problems, challenges, desired outcomes, product, sales process, ways of operating, tech stack, and basic sales training.”

The verbal certification includes a 45-minute live call going through a successful 1st call, testing various aspects such as preparation, mindset, discovery, demo, and next steps.

This rigorous process ensures that new hires are fully prepared before they move forward.

Kieran Smith shared a similar perspective, underscoring the long-term benefits of role-based certifications:

“I have a strong belief that role-based certifications should be part of onboarding pass out and, if designed correctly, they can be fantastic indicators of long-term success for reps.”

This approach validates the skills of new hires and sets them on a path to sustained success within the company.

Ryan Kolofsky offered practical advice on how to effectively integrate certifications into the onboarding process. He suggested tying milestones to specific courses and weekly progress to ensure continuous development.

Ryan also recommended implementing capstone exams that go beyond simple multiple-choice knowledge checks and incorporating tasks like recording pitches or delivering live presentations to sales leadership as part of the certification requirement. 

He concluded:

“The certification process adds value for both management and reps, offering something tangible, like an award or certificate.”

Don’t separate hiring from onboarding

Separating hiring from onboarding is at best myopic and at worst irresponsible. 

If you do not hire the right profile of people for specific roles, it is more than likely that even the best-designed and best-performed onboarding programmes will have underwhelming results. 

Even VPs of sales and CROs talked about the importance of proper hiring when I talked to them about sales leadership best practices.

Milko George highlighted the high cost of hiring (and its infamous inefficiency), as well as the subsequent effects this has on onboarding. He explained:

“One of the main challenges we face is the significant investment in hiring, which makes an efficient onboarding process crucial to ensure quick ramp-up times and on-time productivity.”

Milko advocates adopting Gartner’s “Fail Fast” approach as part of the onboarding process.

He believes it’s crucial to “quickly filter out candidates who are not suitable for their roles,” as keeping ineffective candidates can be costly, leading to missed productivity opportunities, and wasting valuable training resources.

Milko added, “Poorly trained new hires can harm the company’s reputation and brand equity,” underlining the importance of ensuring that only the right candidates make it through the onboarding process.

Devon McDermott reinforced the importance of hiring the right people as a foundational element of successful onboarding. She emphatically stated:

“Hire the right reps! This probably goes without saying, but this is a game changer.”

Devon explained that when the ideal candidate profile is identified and matched with the right onboarding strategy, time to productivity gets a lot faster.

She added, “We can be confident that new hires have the correct skills and knowledge to be successful,” which not only accelerates their ramp-up time but also ensures that they contribute positively to the team and the company’s goals from the outset.

Pre-board and ever-board

A number of our contributors made sure to point out that sales onboarding should never be seen as a one-off event that lasts a set number of days.

They see successful onboarding as starting on the day the salesperson accepts an offer and lasting throughout their tenure at the company. 

Devon McDermott put it like this:

“Treat onboarding as part of the employee journey, not a one-off moment”

She advises designing it as a sustained programme that supports new reps at key moments during their first 90 days. She added:

“Emphasize building efficient, yet meaningful velocity to productivity in the role. For all you enablement pros, this means finding the right balance of the following:

• Sparking cultural alignment and quickly plugging new hires into your company’s DNA

• Boosting hands-on skills, like pairing up new folks with experts for rapid real-world upskilling

• Unpacking strategy to ensure your new reps grasp your positioning and goals

• Crafting engaging ways for reps to own your offerings and master product expertise”

Echoing the sentiment of an extended onboarding journey, Arup Chakravarti noted that “The onboarding journey starts way before the new hire’s first day at work.”

He advocates for early engagement, ensuring that the onboarding process is already in motion before the new hire even steps through the door.

Jenelle Knight, a Senior Sales Enablement Manager at a company behind a widely-used API platform for data delivery, also supports the concept of “preboarding,” emphasising the excitement people feel once they accept a new role:

“The onboarding process begins as soon as a candidate signs their offer letter (when they’re level of excitement is highest!), not on day 1 of the role like many people think.”

Jenelle makes the most of this high-energy period by sharing a resource PDF with new hires shortly after their offer is accepted.

This document includes information about the company, the team, and the culture, along with details on what they can expect during onboarding.

Additionally, she sends out emails introducing them to different colleagues and sharing company videos on their products, all aimed at helping them feel more prepared and connected by day one.

Leverage technology 

On one level, I was relatively surprised that only two of our contributors mentioned technology as part of their onboarding best practices.

Then, as I thought more about it, I realised that it is probably mostly because top-level enablement and onboarding people hold a holistic view of onboarding as a process and understand that technology is only an additional layer that can only be truly effective when standing on a solid foundation.

Karolina Janus, for instance, pointed out the technology’s potential to accelerate new hires’ ramp-up:

“We are fortunate to have a large stack of tools within our company that can be leveraged to enhance peer learning and improve the overall onboarding experience.

We are continuously testing the new solutions that the technology offers for a contemporary learner and adjusting our onboarding programs to accommodate these advancements.”

Fiona NicChoiligh suggested using conversational intelligence tools as an aid in:

“Creating a robust library of resources that follow the customer journey can be transformative. Use call snippets, spotlights, and “ask me anything” sessions to build out these libraries and help new hires ramp up faster.”

Conclusion

Once again, our contributors have outdone themselves and provided us with an inexhaustible source of inspiration for building and running successful onboarding programmes.

Considering their experience and the number of salespeople they have collectively onboarded throughout their careers, this should come as no surprise. 

Still, the sheer breadth of their tips on sales onboarding best practices doesn’t stop to amaze me, after weeks of re-reading their contributions. 

I am sure you will agree and find a lot to take from these incredible insights ] from exceptional sales enablement and onboarding professionals. 

A huge thanks to Alex, Alexander, Arup, Chad, Devon, Estefania, Fiona, Gail, Jenelle, Karolina, Kieran, Milko, Nelson, Rene, Ronnie, and Ryan!

In case you enjoyed getting the perspective of different voices from the field, make sure to check out my articles on sales kick-off best practices and sales leadership best practices.