The Best Cadence for Training a New Closing Rep

As your company and your sales revenue grows, you will inevitably need to grow your closing team…and that’s a good thing! After all, you only need more closing reps if you have more opportunities to close right?

The question then, is how do you quickly train a new closing rep and ramp them up to full quota-carrying status swiftly? The sooner they can get rid of their training wheels, the sooner they can start bringing in sales dollars.

So what exactly is the right cadence when training a new closing sales rep?

It’s all about meetings

Sales reps go to a lot of meetings – they are a necessary evil that complements and enhances the actual selling that these reps want to do. You want your new closing reps to be a part of each of these meetings as soon as possible. If you’re promoting from within, as soon as the decision has been made, get those in-house reps in these meetings right away. Even if they have not received a quota, you want them to feel confident in getting their training wheels off soon.

Here at InsightSquared, our reps have a typical weekly meeting cadence that looks something like that:

  • Pipeline review meeting – 1 hour, first thing every Monday morning. This is an opportunity-by-opportunity review of all the key accounts that each rep is working on this week. Be sure to distinguish between early-stage and late-stage opps, while looking for sales coaching moments with individual reps.

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  • Individual rep coaching session – 1 hour each week. Co-sign and co-create a plan with each rep, identifying the individual skill to work on. Role-playing is also effective here.

  • Team coaching session – 1 hour each week. The whole team meets to discuss across-the-board issues and skills that everyone needs improvement on. This is a good time to introduce new positioning statements through more role-play scenarios, for example.

  • Team film review – 1 hour each week. Play back a call – either successful or not – and have the whole team dissect it. Look for the turning point of where the deal was won…or lost.

  • Forecasting meeting – 1 hour each week, for the whole team. This meeting is all about gauging the overall health of your sales pipeline, from an input/output perspective.

Give a man to fish, and you feed him for a day…

But show him how to fish? Now, you’re feeding him for a whole lifetime. That famous adage is a good driving force behind how we want to ramp-up new closing reps: “We’ll hold your hand, but not for long, so you better learn how to swim quickly.”

This doesn’t mean throwing the new rep in the deep end (other than the aforementioned meetings), dumping a quota on him and wishing him good luck. No, first you must teach him to fish, so that he can fend for himself out there. Along with the aforementioned meeting cadence, new closing reps need more focused attention from you too. This includes:

  • Getting on calls as a silent observer – These calls should be early-stage ones – after all, you don’t want a new rep still learning the ropes to screw up a potentially valuable deal. Observe the rep in action and take note of both good and bad practices to review later. As you sit in on more calls as a silent observer and you find yourself getting bored, that’s a good thing! It means the new rep is starting to get it.

  • Getting on calls as an active participant – When you’re an active participant, make sure to first let the prospect know that both of you will be on the call – “Hey [Prospect], I also have another rep Joe here on the line with me. Together we’ll be able to answer any of your questions.” This is like swinging on the trapeze while wearing a harness. Even if your new closing rep makes a mistake, you’re there to catch them.

  • Record calls for film review – This is your chance to really get tactical and nit-picky. The little things matter – sometimes a lot – on sales calls. The benefit of a film review is that you can really go in-depth in your dissection, while also giving the rep a chance to role-play with the just-learned lessons.

  • Bring in third-party experts – Your existing closing reps are no doubt good at what they do, but sometimes bringing in a third-party for training can be really helpful to new closing reps (not to mention the rest of your team that can also benefit from this expertise).

  • Cultivate an environment of open dialogue – This is perhaps the most important thing you can do to quickly ramp-up new reps. You want these reps to know that they don’t have to be afraid of asking ‘stupid questions’ because there really are none. Make it known that even your

There’s an added benefit to teaching someone else how to fish (or sell too); you reinforce your own knowledge and skills in selling. Explaining concepts is one of the best ways to prove that you know what you’re talking about. A good exercise here is to have on of your relatively new reps run some of these sales coaching sessions for the brand-new reps.


Training and ramping up a new closing rep is challenging. It requires a careful balance of independent discovery with a comprehensive sales coaching program, a steady learning curve with an urgency to ramp-up quickly, hand-holding and knowing when to let go. Immerse them in meetings right away, but don’t forget to give them the individual and focused attention they need.

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