How to onboard a sales team in 4 weeks

by Ramin Assemi

Nick Persico is a co-founder at Smart Host (Techstars Austin ‘14), where he runs sales. Before Smart Host, Nick worked at Close.io as the first person to ever sell the product when it first launched. You can follow him on Twitter and read his personal blog here.

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So you’ve just hired your first group of salespeople. Their first day is coming up, and you need to turn them into selling machines as soon as possible.

It’s typical for large and established companies to put new hires into long and exhaustive training programs. New hires can spend weeks or months going over the product, shadowing other employees, and attempting to learn through mock training exercises.

I experienced this myself. I was hired by Sysco, the largest foodservice distributor in North America, to be an outside sales rep at 21 years old. My first day was in the beginning of February, and they had me in a training program until the middle of May. That’s right, three months went by before I actually got to speak to my first prospect.

The beauty of being a startup is that you get to skip all of that nonsense. Forget long training sessions filled with hypothetical bullshit.

Let’s turn people with little or no experience into selling machines in just four weeks.

Onboard new reps faster with the free 4-week sales team onboarding schedule.

Before their first day

The first step to onboarding a sales team in four weeks is preparation. You need to have every day of each week mapped out. Not only do you need a schedule, but you need to have benchmarks at different points throughout the four weeks. To help you put this together, download the exact schedule we used when we onboarded our first sales hires at Smart Host a few months back.

At the end of two weeks, what milestones should each new hire have under their belt? Should they already have a pipeline? Closed a deal already? That’s up to you, but set a benchmark and make it clear that everyone should be on pace to hit the milestones.

Your sales team’s first day should always be on a Saturday. I’ve written about this in the past, and I believe it’s the most effective way to onboard anyone joining a company.

By coming in on Saturday, they get to meet the team without the distraction of the work day. They get a test run in finding your office. You can equip them with the tools they need and focus 100% of your attention on putting them in a position to be successful.

Most importantly, they know what’s expected of them when they come in Monday morning.

Week 1: They are making calls to prospects by noon on their first day

If calls are happening before noon on the first day, you’re off to a great start. The great thing about this goal is that it most likely requires them to have a script and access to all of the software your team uses internally. It also means they are learning how to do the job in a real way.

Stop fucking around with training sessions and put them in front of prospects as soon as possible. Let them learn the hard and fast way like you did.

Use the first week to let them learn the ropes on their own. Schedule a stand up at the end of each day where they can ask you questions. A daily stand up is very important for a number of reasons:

  • The team asks questions about direct feedback they are hearing out in the market. You can help them get better at managing objections or improve their pitch.
  • You’ll be able to figure out if the leads they’re calling are any good. Look at daily reach rates to see if you can add or improve on the lead list overnight.
  • They are part of the improvement process. The discussion is there to help everyone improve, as well as improve the sales process.

You didn’t learn how to ride a bike from your parents telling you about every aspect of how the bike worked. You just got on the bike, fell a bunch of times, and eventually figured it out. Treat new sales hires like they are learning to ride a bike. They’ll appreciate the process.

Week 2: Train them on the sales process as they move deals forward

The biggest mistake people make when training salespeople is overloading them with processes. You should not be spending time training the group on how to send a proposal or create a new user account.

No one sends a proposal or creates a user account until they earn it.

I always train new hires on the sales process as they are moving their deals forward. The most common and basic SaaS sales process is four weeks long. If they start their first week calling people trying to schedule product demos, they may be conducting those demos and creating opportunities in the second week. Tell them what they need to know as they move the deal forward.

New hires will reach certain parts of the sales process at different times. Train each person individually on each part of the process as they move forward. It will give you the opportunity to work with them 1-on-1 and continue to evaluate if they are a good fit.

Week 3: Focus on small individual improvements

By the third week, the good salespeople will start to separate themselves from the pack. They’re hustling every day, and getting better at pitching your product. Now it’s time to help each person work on their weaknesses.

One person may be weak at organizing their day. Another may be using the wrong terminology to describe something. Identify those weaknesses and communicate them, and have each person focus on improving on that single aspect of their sales game.

Use the single focus to see if they are capable of prioritizing things. Did they improve on that metric or trait? Did they take the feedback?

If so, you’re starting to build a great sales team.

Week 4: They can manage themselves

The fourth week is all about taking off the training wheels. Ask yourself: Are they realizing their mistakes and self-correcting? Are they working together to improve by sharing feedback? Are they following the schedule laid out in the first three weeks?

By the fourth week, your team should have a clear understanding of what’s expected of them, from their quota to their goals. Even if the goal is team-oriented for now, they should be aware and focusing on making it happen.

Bonus: 4-week sales team onboarding schedule

A few months back, we onboarded our first sales hires at Smart Host. To help other founders onboard their first sales hires, we're giving away our 4-week sales team onboarding schedule for free.

4-week sales team onboarding schedule

Recommended reading:

Training a new sales team? 5 ways to set them up for success
Enjoyed this article? Nick has written about onboarding new sales teams before and shares 5 great tips on training a new sales team to be their best.

The sales rep onboarding hack
Want to accelerate your sales ramp up, train new reps in less time? Here's a scalable strategy for onboarding new sales hires in a single day.

The ultimate sales hiring guide for B2B startup founders!
When to hire sales people, who to hire and how to manage them at every stage of your sales process. If you haven't read this post yet and are a startup founder hiring sales reps... this is a must-read!

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