Top Sales Onboarding Program Challenges in 2018


The last quarter of the year is always an interesting time.

Sales and marketing are getting ready to close up the quarter. Everyone is busy, and sometimes a little on edge (if they’re not hitting quota).

It’s also a great time to start reflecting over the year and start planning for the next year.

I recently had the opportunity to connect with many sales enablement and operations practitioners at Experience Sales Enablement 2017 in Dallas and Dreamforce 2017 in San Fran, where we had many conversations about sales-related challenges in 2018.

One theme kept coming up: their sales onboarding program.

It makes sense that it’s top of mind, knowing that Q1 is fast approaching and there will be many new hires starting their respective sales onboarding program.


Through various conversations and workshops, here are some of the top challenges that enablement practitioners mentioned:

  • Reducing ramp of new hires
  • The difficulty of a sales onboarding program when you run a dispersed sales model
  • Understanding and defining when someone is officially ramped
  • Lack of accountability of the hiree for completing a sales onboarding program
  • Facilitating the flow and sequencing of content and information
  • Managers actually coaching, and not just managing
  • Keeping reps engaged during a sales onboarding program
  • Running a sales onboarding program for global teams/remote workers
  • Measuring behaviour change while someone is ramping

I can see why a few of the people I chatted with were exasperated and a bit stressed out that there are only a few weeks left in 2017. Those are some big challenges, and not so easy to solve!


What’re you doing to solve your sales onboarding program challenges

As I was listening to the conversations, and thinking about the challenges that were mentioned, I started asking how they’ll be tackling these next year.

And I received some really interesting answers.

One of the questions I frequently asked was “If I were a new rep starting at your company today, how would you onboard me?” Most people replied with an eye roll, then sighed, and said

“Well….. You’d go through boot camp. Then there’s a spreadsheet with stuff you can read…”

And that’s it.

Then reps are off to the races. Expected to be able to sell. On Monday.

Here’s the problem: Many companies treat onboarding like it’s an orientation. Some of you might be saying “Dan, what do you mean - those are synonyms.”

They’re really not.


Orientation is an event. It’s a checklist of the basic stuff you need to know to work at your organization.

Onboarding is a period of time that requires mentorship and training for a rep to be productive.

 Orientation is a part of onboarding, but not onboarding as a whole. And when you speak with some practitioners and ask what they’re doing for onboarding, they’re really describing orientation.

There’s a bit of a disconnect between the way they’re executing a sales onboarding program for new sales reps and the reality of what’s required during onboarding, which is creating the challenges and gaps they brought up during our conversations.

These challenges are not going to be solved in boot camp. These challenges are not going to be solved in spreadsheets.

If you’re reading this and thinking “Yup… that’s us,” then there’s a big opportunity for reimagining sales onboarding at your company in 2018.

You’re not alone

It’s been proven time and again that organizations with a well-thought-out sales onboarding program are much more effective at getting their reps productive.

Organizations with a standard sales onboarding program experience 54% greater new hire productivity. On top of that, employees of companies that have the longest onboarding programs gain full proficiency 34% faster than those in the shortest programs.

However, only 37% of organizations extend their onboarding programs beyond the first month.

I was surprised at how many practitioners I spoke to measured onboarding success with a checklist, and not actual metrics and milestones! There’s research that supports this too.

77% of new hires who hit their first performance milestone had formal onboarding training. Of those who do not hit initial performance milestones, almost half had no formal onboarding training. Even worse, 60% of companies fail to set milestones or goals for new hires!

I think as enablers, we can do better than that. 

What will you do to close the sales onboarding gap?

Imagine you could accelerate sales onboarding and reduce ramp at your company. Imagine you could automatically track the progress of your new reps, as they’re going through onboarding, and measure the financial impact of their progression. Imagine you could deploy your onboarding program globally, across teams, all within your CRM.

Wouldn’t that be great?

But you’re tasked with figuring all of this out by using spreadsheets and checklists. It’s tough, I get it.

 So what can you do?

Keep your sales onboarding program simple.

Orientation (1)

Make your sales onboarding program interactive

Great onboarding programs don’t need to be overcomplicated, but they need to be engaging.

Salesforce   Enterprise Edition (1)

People learn in different ways: Reading, watching, listening, and practicing. When you’re designing your onboarding programs, make sure that the exercises you’re prescribing are interactive, engaging, and valuable for your reps.

 Consider adding these interactive exercises to your sales onboarding program to make it more engaging:

  • Watching videos of peers delivering a pitch or conducting a product demo
  • Reading product marketing documentation and case studies
  • Listening to discovery calls. One of our favourite tools at LevelJump is You can automate call intelligence across your team to understand what the top reps are doing differently and listen to call recordings.
  • Attend a kickoff with senior executives
  • Do a peer review of your pitch or demo to get feedback and coaching from more experienced reps
  • Set-up a buddy program, where coaching sessions happen with mentors

And don’t forget to track milestones and metrics while reps are onboarding

Salesforce   Enterprise Edition (2)

  • First confirmed discovery call
  • First 200 activities logged in Salesforce
  • Time to first identified opportunity
  • First 5 qualified opportunities
  • Time to first deal
  • Time to second and third deals

Here’s an example of a simple onboarding program you could run with new BDR


Simplify the delivery of your sales onboarding program

The point is, onboarding is not the same as orientation. You need to provide mentorship, training, and the right content in a prescriptive manner to keep reps engaged. It's a lot. Fortunately, we're here to help:

Having interactive activities and leveraging technology like this will make reps want to complete their onboarding, so you don’t have to be worried about any accountability.

But there’s a lot more we need to do as enablers to solve the onboarding challenges you mentioned to me during our conversations.

Wrap up

Building and running a great sales onboarding program is hard work. As we saw, there’s a lot of challenges still to overcome, including formalizing the onboarding program, ramping new hires faster, keeps teams accountable and getting reps engaged with the program all the way to the end. And just as clearly, the traditional model of boot camp and then nothing isn’t working very effectively. 

But just a clearly, there’s a pretty clear solution. If you can marry your sales enablement program to the revenue metrics that matter, you can achieve better sales outcomes, faster. Metrics like calls, activities, opportunities, deals, and quotas hit.

All in all, the future’s looking good for sales enablement!