A series of essays about sales, startups, & general banter by Nick Persico

Training a New Sales Team? 5 Ways to Set Them Up for Success


This post was originally posted on CloserIQ's blog.

CloserIQ is a sales career platform connecting top sales talent to startups. If you're looking to grow your sales team, I highly recommend using CloserIQ to get great candidates in your pipeline.

If you run an early-stage startup, your first sales hires—and how you train and introduce them to your company—will set the tone for the next stage of your startup’s growth. After all, it’s likely that this will be the first time your product will be sold by someone other than you or your cofounders. It’s the first time that people without the context of your company’s history will represent you.

And these early team members are especially critical because they’ll become leaders for the next batch of salespeople that follow them; their habits, skills, and experience will rub off on new team members to come. So think of your first salespeople as founders of the sales team.

And as a founder, it’s your job to put your new salespeople in a position to be successful. (After all, poor sales management leads to high sales churn.) They need to feel inspired and involved. Here’s what you can do to make that happen:

1. Always hire more than one salesperson at a time.

Any time you’re hiring salespeople, hire more than one. In your company’s early days, you won’t have data to help measure a sale hire’s progress. You won’t know what, exactly, “good” or “bad” performance means. Hiring two or three people can help you figure this out, create competition among them, and also protect you if someone quits or needs to be let go.

Hiring a batch of salespeople will also benefit your new hires. Being the lone first salesperson at a new company is hard: there are no precedents in place, no examples of success. So make sure your first sales team is a pair or a group of peers who can experience the job together.

2. Schedule their first day for a Saturday.

First impressions are everything. The chaos of a Monday morning should not be the way your new team members interact with you for the first time. (This works in your favor, too; you know that running a startup is a constant battle against time, so why waste a precious weekday on training?) Instead, plan to have your new sales team start on a Saturday when you can really focus on teaching them the basics and introducing them to the rest of the company.

Here’s how a Saturday spent onboarding your new sales team might go:

  • 9:00 a.m.: Have breakfast, make introductions, and fill out legal paperwork.
  • 9:30 a.m.: Give a fun presentation on your company’s history and how you got to this point. Don’t forget to take questions!
  • 10:30 a.m.: Tell your new team about your industry. Who are they selling to? Who are the players? Why are we doing this?
  • 11:00 a.m.: Go over your email and phone scripts and what they’ll be expected to accomplish by the end of their first week.
  • 12:00 p.m.: Have lunch.
  • 1:00 p.m.: Train them on basic CRM and sales tools, like how to contact people and use lead lists.
  • 2:00 p.m.: Review the scripts and make mock calls so your team can start making calls and sending emails Monday morning.
  • 3:00 p.m.: Get drinks as a team, and invite investors and even customers, if possible. Now when your new sales team comes back in on Monday, they’ll already know what they have to do to be successful in their new jobs.

3. Don’t overload your new sales team with information.

All your new sales hires need to know at this point is how to be successful in their first week. If their first task is to schedule product demos by making cold calls and sending cold emails, train them only for that. This early on, there’s no need to show them every aspect of your sales process, how to send an invoice, or even how to conduct a demo (and even if you do teach this information right away, it likely won’t be retained).

Instead, cross each bridge when your salespeople actually reach these points with real prospects. Practice scripts with them so they get better at scheduling demos; once they’ve nailed that, then they can conduct demos themselves. Essentially, learning the next step in the sales process should be a reward for mastering the previous one.

(You can see this tactic at work in the movie Boiler Room. Each new hire is only allowed to cold call prospects. Once they qualify a prospect, they have to watch a senior salesperson take the deal from there. After they master that first step in the sales process, they earn the right to close their own deals.)

4. Document everything (and we mean everything).

Starting as a salesperson at a new company is like drinking through a fire hose. Retaining the amount of information necessary to do the job is impossible. So help them out by carefully documenting every part of your sales process, including scripts, frequently asked questions, CRM processes and definitions, and even trivial things like proper email signature structure.

Give your salespeople the ability to look up anything on their own. When they ask you a question, refer them to the materials. (It may seem mean-spirited, but it’s the best way to establish that they are expected to follow directions.) Plus, it’ll save you from having to answer the same questions over and over again.

Encourage your sales team to contribute to the documentation too. As they learn new tips and tricks on how to sell your product, they should be sharing it with everyone.

As a real-life example, here’s what the sales onboarding documentation at my company, Smart Host, looks like:


Yes, we’re thorough. Over-communication is key. If you want your sales team to operate with a certain level of professionalism, give them a step-by-step guide of how to operate at that level.

5. As the old adage goes, lead by example.

Organization and attention to detail will rub off on your team and create a culture of excellence. If you lead by example, and follow the above steps, your new sales team will practically onboard themselves.

Profile of Nick Persico

Nick Persico

Director of Sales at Close.com. Previous: Co-Founder of Smart Host (acquired), VP of Ops at Krossover (acquired), and sales at Sysco. Travel nerd, Baltimore Orioles and Ravens fan, and GIF enthusiast.