My Ultimate 4-Week Sales Onboarding Program

I hate 90 day sales onboarding programs.

Sellers learn by doing and won't actually gain any real learnings until their first contact with a customer. By keeping them on the bench, you're slowing them down from building a pipeline to hit their early quotas AND slowing your company's revenue goals.

As a VP of Sales, I mandated a "4-Weeks-To-Field" onboarding program. Get your reps in the game, safely, and through learning from the best people at your organization.

We'll start with some core principles, then break it down week-by-week.

Keys to a Great Sales Onboarding Program

Before we jump into the week-by-week schedule, let's talk about what should go into an onboarding program.

What To Cover

I like to teach industry, product, and sales training, in that order:

1. Industry Training: What is the prospect's day-in-the-life and the problem with it?
2. Product Training. How do we solve those problems?
3. Sales Training. How do we attach problems to solutions in a sales conversation?

How Deep You Should Go

There are 3 levels to a sales onboarding topic. My goal is to get everyone to level 1, foreshadow level 2, and then coach to level 3 over time. Using discovery as an example:

1. Level 1 (Basics). You can set an agenda, find a problem, set next steps.
2. Level 2 (Style). You can artfully ask those questions in a way that feels "smooth."
3. Level 3 (Control). You can challenge prospects as if you were an industry peer.

The Types of Training

The 3 different training styles for sales onboarding include:

1. Training (Morning). Try to keep this to the morning while they're fresh.
2. Doing (Afternoon). Apply the concepts in roleplays, field tests, or self-practice.
3. Homework (Evening). Give them primer materials for the next day.

Ready for week 1? Grab your backpack and that iced coffee, let's do it...

Week #1: Minimum Viable Sales Rep

Week 1 is focused on teaching reps about giving them minimum viable industry, product, and sales training so that they can start to generate pipeline.

As you can see in the example training schedule above:

• Day 1: They're usually stuck with HR doing company onboarding.
• Day 2: I try to get their minimum-viable industry training done.
• Day 3: Now that they know the personas, we can do basic product training.
• Day 4: Now that they know the problem we solve, they can start prospecting.
• Day 5: And now we can finally start getting ready to take discovery calls.

In the following week, we'll dive much, much deeper into the sales process. But again, the key is to build minimum-viable competence so they can start DOING THINGS!!!

Also notice the morning trainings, afternoon field tests, and evening homework.

✅ Your exit criteria at the end of this week: They should have their accounts in hand and know enough about the industry, product, and prospecting process to be able to initially tier their accounts.

Week #2: Death By Roleplay

Again, Week 1 was MINIMUM VIABLE training so that week 2 can focus on doing: Working their territories, doing mock roleplays, and coaching them on all the above.

You'll notice a few things above throughout the week:

• The morning "trainings" proceed to level 2. We start to get into more advanced concepts like asking more artful questions or getting access to power.
• The afternoon "doing" includes a *lot* of mocks: The afternoons should be reserved for prospecting and discovery call roleplays.

On the mocks, you want your reps doing a minimum of 2-3 mocks per day (yeah) and they should be the ones setting them up. Give them a list of people to reach out to on the team and make sure that your team is carving out the time to support the new hires.

If you do a certification, it should happen at the end of this week.

✅ My exit criteria for this week was level 1 discovery proficiency. It ain't gonna be pretty, but by their final mock with me or their manager, they need to be able to have a basic agenda, find 1 problem, and set next steps.

Week #3: Live (SMB) Action!

Not only are we getting out of the classroom even more in week 3 (80/20 split), but we're into live action! Key Callouts here:

• The training is all about how to get smart: Now that reps are trained on how to prospect, teach them how to become an efficient machine. Now that they have the basic talk tracks down, we can teach them the fancier level 2 industry lingo.
• The doing is real on low-risk SMB and DQ demo requests. Have these supervised by a rep or manager. They have to get into the field to learn the job.

✅ That means the week 3 exit criteria is surviving SMB and DQ demos. If you do this, you're ready to get access to your full book of business and take demos in-territory.

Week 4: Live (Supervised) Action!

Say goodbye to the classroom in week 4! Because now it's all about coaching.

The reps are taking legit discovery and demo calls with prospects, and pretty much all of these should be supervised by their manager or a seasoned rep.

If you're starting new hires in cohorts, I really recommend you do tape reviews at least once per week to spread the learnings across your team. We had a smaller org, so we always did a team-wide tape review every week.

✅ The final exit criteria is to be "level-one-proficient" on real disco calls. Again, it might not be pretty, but if they can set an agenda, get to a problem, and set a next step, they're on the right path.