May 11, 2014
Rep Onboarding: The First 30 Days

You just hired a new sales rep. Now it’s time to dig into Chapter II of your playbook and focus on getting them up to speed quickly.

In the next three posts, we’ll cover the game plan for 30, 60 and 90 days after starting. The average inside sales rep takes 4.2 months to ramp (for SaaS companies), but here we’re on an ambitious path to beat the average.  Each stage will have specific tactics to execute on as well as homework to keep you and your rep on track.

Time is short, so let’s jump in.

Day 1-30


Your new rep just started. The first 30 days will set the course for success (or not), and is all about getting them immersed. There is a lot to take in when you start a new job – the product, the customers, the people, the processes – so make it easier by giving him or her just two things to focus on.

First, get intimately familiar with the pain that your company solves. Learn about the customer’s business, what problems they have and why. Focus on the customer’s business, not yours.

Second, become an expert in solving that problem. Some of this will dig you into your product, but be careful to avoid focusing on each and every feature. Instead, think holistically about this pain point and how your customers solve it. When you get introduced to a new part of the product, ask “Why does this matter to my customers? How does it solve their pain?”


Have your rep join a minimum of 5 calls per day. These should be a mix of sales activities that they will be doing once ramped: prospecting calls, demos, trials, closing calls, etc. Add calls with other teams within your company as well. Join a few of the weekly marketing team meetings. Sit in on tech support calls for a full day. Join the Account Managers with existing accounts meetings. Getting to know the customer’s pain involves interacting with customers in more than just a sales context.

Next, have daily one-on-one meetings with your new rep. Yes, daily. You need to spend a lot of time together in the early days to prevent bad habits from forming. Five calls per day is asking the new rep to spend a lot of time with their colleagues and you need to ensure the inmates aren’t running the asylum. In these one-on-ones, dig in on the specifics of what they are hearing on each call. As an added bonus, you may even learn where current reps are falling short of expectations. Ask questions about the calls they joined, do some light role plays (“how would you have answered this question”), and give your new rep a chance to ask open ended questions to you.


To make sure your new rep is staying focused on these calls, ask them to send you an email summary at the end of each day with a few sentences about each call. At first, it can be a simple recap of the call. Next ask them to focus on the prospecting and qualifying questions that were asked (and those that weren’t). Then have the rep highlight the questions the customer asked and the answers their colleague gave. Change the focal area to keep them engaged and learning new things.

Each of your one-on-ones should end in some homework as well. Give an assignment that leads up to tomorrow’s meeting, or follows up on what you covered today. Just like it did back in school, these assignments should bring the lectures together. Don’t overthink it here, as the homework can be very simple. If you’re talking about how the CRM is setup, have them create a test lead and opportunity and log some activity. Then in your meeting, check to make sure they have followed all the right steps, correcting course as needed.

Finally, give your new rep some outside reading. This could be an industry blog, or a book on your solution category. For example, if you sell to marketers have them read Inbound Marketing by the HubSpot team. For those focused on customer success, perhaps Delivering Happiness is the better route. When I sold to sales people, my team would read numerous sales texts like Sandler and Challenger Sale. Your goal is to help make the pain real, and begin to create an industry expert. Cap it off by having them present a summary of what they learned to the rest of sales team. Not only does this get your newly hired rep to do the homework well, but also has the added benefit of providing a refresher course for your existing team.

Jim Schuchart is the VP of Sales at Privy.  You can find this blog post, as well as additional content on his blog located here.  You can also follow Jim on Twitter (@JimSchuchart) by clicking here.