5 Tips to Build a World-Class Rep Onboarding Experience

By Bryan Naas

When it comes to your sales onboarding program, are you rolling out the red carpet for new hires and welcoming them in an engaging way that sets them up for long-term success?  A quality onboarding experience can mean the difference between hitting or missing company goals. In fact, a high-quality onboarding program can lead to higher productivity, quicker results, and happier employees. 


Even though it’s such an important part of enablement, onboarding doesn’t just magically happen. It takes planning and hard work to build a program that matches the needs of your business and sales reps. That’s why optimizing onboarding should be a top priority for any team that’s hiring new team members. 

An onboarding program is like an iceberg. Everything you see above the water line is the rep’s onboarding experience and everything below is the planning, building, and execution that falls on leaders’ shoulders. Each is exceptionally important and needs to be treated with care to reach your goals as an enablement team and business.


Focusing on five C’s can help you develop onboarding experience that will lead to unmatched success. This includes evaluating: 

Culture:Help integrate new reps to the team

Consistency:Help them understand what’s happening and when

Clarity:Help reps understand what is expected of them

Calibration: Help them understand where improvement is needed

Coaching:Help them understand how to get better

Think about this process like you’re evaluating a diamond for purchase. Gemologists actually evaluate diamonds on four C’s: Cut, Color, Clarity, and Carat. Each of these criteria plays a bigger part in the value of the diamond. A large carat diamond with poor color or clarity will result in a lower value than a smaller diamond with perfect color and clarity. Each evaluation point works in conjunction to create a high-quality buying experience. The five C’s of onboarding work the same way to create an onboarding experience for our reps that build knowledge and confidence (oh no—is this a sixth C?) through their journey. 

Let’s dig into each one and see how they work together to create an onboarding experience your reps will rave about. 


Integrating new reps into the team starts with the hiring process by ensuring they are a good culture fit from both a company and a team standpoint. Assuming these qualities are met, the goal of onboarding is to provide growth opportunities with their peers so new reps enjoy coming to work each and every day. There are many ways this can be accomplished, but let’s focus on two specific ways: Cross-departmental interactions and a mentor program. 

Cross-Departmental Interactions

On the surface, cross-departmental interactions seem straightforward and simple. But, too often this is missed because we’re so focused on the day-to-day and functional job knowledge. We forget to pull out of the weeds and create a solid support structure. To overcome this issue, we like to structure our cross-departmental interactions both formally and informally. 

For formal interactions, schedule meeting times for teams to present who they are, what they do, and how they will interact with the rep. This provides a couple of benefits. First, the rep learns about the support structure and how they can leverage the larger team during the selling process. It also gives the support team the opportunity to set expectations for interactions and clarify processes. Be sure meetings to set clear expectations for both the support team presenter and your new rep so each interaction builds on the experience of your onboarding program. 

For informal interactions, focus more heavily on personal connections. While the end goal is the same as formal interactions, the setting is different. It builds a more emotional connection and is best executed over coffee and lunch meetings where the expectations are less formal. These types of environments foster a more meaningful, natural, and emotional connection which is beneficial for everyone.

Peer Mentor Programs

Mentor programs are certainly nothing new but they play an important role in helping a new rep become part of the team. I could write a book on the value of these programs and the best ways to execute them, but for now, I’ll cover some basics. We choose to keep our peer mentor program informal and allow them to grow organically. Every new rep is paired with a “buddy” on day one that becomes their peer mentor. Just like our cross-departmental interactions, we set clear expectations for both the mentor and mentee so they understand how they should interact. This includes basic “get to know you” coffees and lunches and continues with ride-along meetings. The program gives new reps a go-to resource and lifeline when they simply need a peer to give them the lowdown. 


A great onboarding experience also helps reps clearly understand what they need to do and when they need to do it. Our goal, especially in the first couple of weeks, is to remove as much ambiguity as possible so reps can focus on learning and development instead of simple administrative tasks. We primarily accomplish this with a detailed onboarding guide that breaks the program into five phases.


Each phase is progressively less detailed to promote ownership of responsibilities throughout the onboarding journey and provides clear learning goals and milestones. We start with a two-week immersive experience where every hour of a rep’s day is scheduled. The day includes meetings with other departments and time they need to access on-demand learning materials that promote the practice of newly learned skills.  

Phases two, three, and four build on phase one, but continually add additional responsibilities as reps become more knowledgeable and comfortable. Each phase is flanked with a clear set of milestones and a capstone evaluation point that allows the rep to show their progress. 

Phase five functions as a maintenance phase of the onboarding journey. At this point, reps should have all the knowledge they need and show competence in the skills they need to perform. We primarily focus on coaching and making tweaks to ensure they are progressing to plan.



We all work better when we clearly understand what’s expected of us. This starts with consistency and continues with clarity. On each rep’s first day, we establish a clear set of ramp goals for each phase of onboarding. We use these ramp goals at every check-point of their journey to ensure every rep understands how they are progressing against their goals.


Ramp goals should clearly align with what success looks like. That’s why we break our ramp goals into two sets of metrics. The first set, which aligns to our first four phases of onboarding, is activity centric. Essentially, we want to measure if they are doing the right things so we look at training engagement and completion, training assessments, role activity metrics, and leading performance indicators. Once we move into the fifth phase, we review performance measures. This allows each rep to clearly track their performance and receive coaching for improvement.



As reps progress through onboarding, it’s important to guide them to fill their knowledge and skill gaps.

This coaching comes from three pillars: Their manager, their mentor, and the enablement team, which is delivered in both formal and informal settings. 

To support informal coaching, we train managers and mentors on how to provide good feedback and coaching through observation and interactions. A major part of this process is live/recorded meeting coaching. When observing or reviewing a meeting, managers and mentors focus on key coaching criteria based on where each rep is in their onboarding journey. For example, if a rep is just starting, coaching will center around good discovery and conversations, while conversations with more seasoned new hires will focus on negotiation and closing. 

Formal coaching is structured around our phases and onboarding checkpoints. At each checkpoint, the rep is presented with a scorecard that matches the ramp goals that were established at the beginning of onboarding. Onboarding checkpoints are pinpointed during collaboration with the enablement team and the sales management team. During the meeting, the rep gains a clear understanding of their progress toward their goals and receive coaching on how to progress in gap areas. Each meeting ends with clear action items that the rep needs to complete before the next checkpoint meeting.



The final C in our onboarding experience focuses on calibration and makes sure that onboarding meets each rep’s individual needs. Since every rep is unique and enters our team with unique skills and experiences, calibration gives us the flexibility to ensure we are providing each rep with the best opportunities to develop and achieve their goals. This may mean some reps have extra work to develop in one area or another or extra practice to ensure they are meeting development goals. 

Each onboarding checkpoint meeting creates a natural calibration point, but this isn’t the only time we make changes. This is an important part of every onboarding program and must be co-owned across the entire team. 

Building a world-class onboarding experience for your sales reps takes planning and hard work. Focusing on these five C’s will help ensure you develop an experience that prioritizes rep success. Just like every development opportunity, iteration is key to the success of your program. The best thing you can do is start and iterate as you progress through the program. Start with one rep or cohort as quickly as you can to learn what works and what needs modification. As you develop and grow, continue to iterate and you’ll reap the benefits of a world-class program.

Author, Bryan Naas is Director, Sales Enablement at Lessonly 

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