A world-class onboarding experience can turn average sales hires into above-average salespeople.

When you are scaling a sales team, the onboarding experience determines how quickly your new hires ramp to hitting 100% of full quota.

Better onboarding experiences also lead to longer-tenure for salespeople. 

You can hire the best salespeople for your company, but they will struggle to ramp if you have a poor onboarding experience.

And if they struggle to ramp, they won’t stay around for very long.

We hired and onboarded over 100 salespeople and sales leaders in my time as CRO at Levelset.

In the early days, we made every mistake you could make.

Like most early-stage companies, we relied on the resourcefulness of each salesperson to figure out how to be successful.

We leaned on our tenured salespeople  to “show them the ropes”.

Lots of shadowing and listening to demos.

This is no way to learn how to be a successful member of a sales org.

Over the years we developed an onboarding structure that:

• Reduced our ramp-time from 7 months to 4 months.
• Increased average quota attainment for full-ramped reps
• Increased average sales rep tenure

The benefits of a strong onboarding program are obvious. 

I love this article by Tomasz Tunguz from 2016 The Other Payback Period That Matters in SaaS.

The article shows the math of how long it takes to reach “break-even” for a new sales hire.

Shorter ramp times lead to better cash flow for the business. 

So how do you design a sales onboarding experience that makes such a positive impact on sales performance?

Let’s dig into how to create a world-class onboarding experience for your sales team.

Turn average salespeople into high-performers

In the last few weeks, I’ve talked with over a dozen founders who are hiring and ramping new salespeople.

They all have the same thing on their mind: “how do I find the right salespeople for my team?”

This is the wrong question to ask.

We should be asking “how do I build an onboarding experience that turns any capable salesperson into a high-performer?”

Of course no one wants to hire average salespeople. Everyone says they only hire the absolute best salespeople.

This can’t be true.

By definition, not every salesperson can be exceptional.

But we pour effort into the hiring process to find the perfect candidates.

There’s a ton of pressure to get the right people on the team.

We scour the market for the best candidates with the right characteristics.

We back-channel references to make sure we are bringing on the right candidate.

We agonize over the compensation plan to make sure the salesperson is motivated but not overpaid.

And finally we make the hire and bring that new salesperson onto a sales team for their first day.

Then we hope that the salesperson learns fast enough and starts hitting them full quota.

The first week usually looks like this:

The salesperson spends the first day setting up their computer and attending a few meetings with HR about the company and culture.

The rest of the week is a mix of lectures and time spent reading or watching onboarding material. Most companies call on their experienced reps to let the new hires “shadow” them for phone calls and demos.

The salesperson may not even meet a customer or a prospect for weeks after they start!

A poor onboarding experience puts the salesperson fully in charge of their own learning. They are required to be resourceful and “figure it out”.

It’s fine to have this expectation for your salespeople. They should be resourceful. That’s part of why you hired them.

The best reps are going to figure out how to be successful regardless of the onboarding experience. These reps are an exception to the rule.

It’s OK to have high expectations for new hires, but you must insulate yourself from the inevitable fact that not all reps are exceptional.

You manage to the average, not the exception.

Your sales team will be an unstoppable force when you can turn any capable salesperson into a high-performer.

Create attachment to the org

Starting a new sales job is stressful. 

Humans are herd animals. We fear separation from the herd.

Think about the last time you started a new job. You don’t know the product. You don’t know the customers. Tenured sales reps are sticking their elbows out because you pose a threat. 

That’s why it’s so important to create attachment to the sales organization as quickly as possible.

Attachment comes in many forms.

Most companies will host a happy-hour or get-to-know you session with new hires.

Others will introduce a buddy-system or mentor-syle approach to cultural onboarding, relying on peers to help the new salespeople attach to the org.

These things are good and helpful, but they aren’t the main thing.

If you want a new salesperson to ramp quickly, show them exactly what they need to do to be successful.

Salespeople want to win. They want to close customers and bring in revenue. They want to earn commissions. They want the admiration of their peers and supervisors.

Even more fundamental, people want to do things that they are good at doing. So show them how to be good at selling your product to your customer, and they will want to do more of that thing.

Time to first sale leads to faster ramp time

Over the many salespeople we hired at Levelset, we learned that sales reps ramped faster when they had a shorter time to first sale.

So we leaned into this. We created an environment that showed a rep exactly where to go and what to say in order to land their first customer within the first 30 days. 

Closing your first sale should be so straightforward that anyone who passes the interview process and joins the team should be able to get a new customer in the first 30 days.

If a new sales hire isn’t able to close a customer in the first 30 days, it is a warning-sign that the new rep may struggle to perform in your sales org.

This isn’t a black-and-white rule. It could be that the rep took just a bit longer to get that first customer. But it’s directionally correct.

In the same way, a rep that closes a customer in the first 30 days doesn’t guarantee that they will ramp quickly and become a high-performer. But it’s directionally correct.

So make it a point to get them a sale as quickly as possible. Give them the blueprint for success.

Make it color by numbers. Even if you have to feed them a sales-ready opportunity.

Creating a win will create attachment to the org.

Make it a Moment

When your new sales hire finally closes their first customer, make it a moment that they will remember.

There’s a tradition in aviation for new pilots who complete their first solo flight.

The student-pilot’s shirttail is removed or cut when they reach the ground and get out of the plane. 

Even experienced pilots remember and celebrate this moment. It’s seared in their brain as a right-of-passage in their journey as a pilot.

This is the power of moments. You can use this to your advantage in your own sales onboarding.

When your new salesperson closes their first team, make it a big deal.

You don’t have to rip their shirt, but you can do something that signals how important that moment is.

Make an announcement to the entire company by email.

Talk about it in the weekly sales team meeting.

Send a handwritten card to their house congratulating them on their first closed customer. Include a gift card for “dinner for two”.

Get them a physical memento that they can put on their desk to remember the moment. A coin. A model car. A trophy. Doesn’t matter much what it is, just something that they can point to as a signal of their success.

When you make it a moment, people remember.

This kind of effort makes the salesperson feel successful, it pulls them closer to the organization and makes them feel part of the team.

And when the salesperson feels closer to the team, they will be more motivated to work on the things that make them successful.

That’s how you accelerate your ramp time for new sales hires.

The 4 aspects of a successful sales onboarding

There are four main categories of learning for new sales hires:

Drink the Kool-Aid

We talked about this in the section above. Get the sales hires bought into the culture. Give them the history of the company. Who are the founders? How did you get your first customers? What values does the company stand for and why are you in business?

It’s been said before “people don’t buy what you do, they buy why you do it”. This goes for new team members.

You have to bring them into the culture and make them feel part of something bigger than themselves.

‍Learn the industry

Every salesperson needs to have a basic understanding of the industry they sell into. What are the common problems that plague the companies in the industry? Where do the industry folks hang out? Are there major publications they read? Who are the major players and solutions available to the industry.

All of these aspects combined give a salesperson the right context to understand the customer and how they can deliver value to the market.

‍Learn the product and packaging

Every salesperson must become an expert on the product and the packaging. They need to understand the key value proposition. The key features that customers care about. They need to understand the common objections that lead to lost deals. They must be able to clearly explain how the product is priced and how that relates to the value that the product delivers.

It’s more than listing out features and benefits. The salesperson needs to understand the product at a user-level. They should be able to demo the product without the help of a sales engineer. This level of detailed understanding produces the pocket stories and engaging anecdotes and create trust in customer conversations.

‍Learn the sale process and sales tools

Finally, the salesperson needs to learn how to sell products for your company. Learn the stages of the sales process. Entry and exit criteria for each stage. How to run your sales playbook. And how to use the tools and enablement that you have bought or created for the sales team.

This effort may require that the salesperson unlearn habits and processes from their prior sales experience.

It’s better to have your salespeople running your sales process and playbook than to have them using whatever they decide to remember from their previous roles.

Design your onboarding to appeal to all types of learning

Each person learns in their own way. When you are building your onboarding schedule, it’s important to pay respect to the different styles of learning.

A well-designed onboarding appeals to every learning style. There should be a mix of in-person, lecture, video, written content, live coaching, shadowing, etc.

It’ not that every person is going to consume every style of onboarding 100%. But having the entire spectrum of learning styles ensures that every rep will be able to consume enough of the right material across a mix of mediums.