How to Onboard New Sales Hires

You’ve hired a couple of snazzy new sales reps. They’ve impressed you with their natural hustle, competitive spirit, and initiative. Dollar signs light up as you imagine all the new bookings and revenue these new reps will bring to your business.

Surprise! Until your salespeople reach full activation, they cost you money. A SaaS company's average new sales rep takes 5.3 months to reach full productivity. That’s almost half a year when your business has been losing money per rep.

Proper onboarding is the most powerful way to close this gap and get your sales reps quickly up to speed. It allows you to build a scalable sales process that will accelerate the growth of your business and blaze past the competition.

2 Ways to Screw up Onboarding

But most startups foul up the onboarding process by going to two extremes. They either push new sales reps into the deep end and get them started calling prospects way too quickly, or they do the opposite and bombard new reps with training materials, documentation, and tests that drag out the process.

Both approaches will damage the efficiency of your sales team and undermine the potential growth your new sales hires could unlock for your company.

"Traditionally, sales organizations have invested a lot of time, effort, energy, and money in hiring the best players. They want ‘A players’. They agonize about their hiring process. Then they bring them on board and they have a terrible onboarding process."Trish Bertuzzi, President & Chief Strategist, The Bridge Group, Inc

When you onboard new sales reps, you need to provide practical, real world scenarios that teach them about the contact sport of sales—within controlled parameters, where you can coach them and empower their success. Give them the tools they need to succeed and then stick them out there.

Let’s dive into the four stages of onboarding successful sales reps.

1. Give Homework

Start your sales onboarding process by assigning homework, which provides guidelines for how you do business. You want to help new hires develop a process and framework that will allow them to navigate the highly complex sales process.

Create a training manual that’s part sales script and part objection management document. Provide your reps with battle cards and other sales enablement materials. Your sales training manual allows you to build a more scalable strategy for onboarding new sales hires by getting everyone to speak the same language from day one. It pools together the collective wisdom and resources of your team.

Here's how to start creating your training manual:

  • Write out 10–15 of the most common questions your customers ask
  • Write out 10–15 of the most common objections you hear from customers
  • Write concise responses (no longer than 3 sentences) for each

Have your new reps study the manual and then test them.

Call them at night, and say: “I don’t have time.” They should respond without skipping a beat: “I get that you might not have time. But I know that what we have is valuable and can help your business succeed. Give me three minutes to change your mind.”

Your sales reps need to know how to respond to common questions and concerns from customers without resorting to obvious answers. That way, as thornier, more complex issues inevitably arise, they can focus all their energy on solving them. Turn your sales reps into better listeners. They won’t need to spend as much time thinking about what to say next during a call and can focus on what the prospect’s really saying.

Drive Home the Core Value of Your Product

Your reps might be amazing at sales but still fail because they know nothing about your business. Cover the basics. Get your sales reps to use your product and read support articles. Have them study your market, industry, and competition. They need to understand your product inside and out and its core value proposition.

Go one step further and make them feel your customers' pain. Create real-life scenarios where they can step into your customers' shoes.

HubSpot, for example, has each new sales rep create a blog and generate traffic for it—which they typically fail at. Then, they use HubSpot’s suite of SEO marketing tools to alleviate this pain. New sales reps see firsthand how powerfully HubSpot’s product helps their customers achieve their marketing goals.

That way, when your sales reps talk to prospects, they can honestly say, “I’ve been there. Let me show you how our product will resolve this for you.”

2. Train in the Shadows

The next step to onboarding your sales reps is to have them shadow you. You want to show them how your company conducts sales while providing an environment for you to teach them and assess their progress.

Have them follow you around and observe how you do your job—manage deals, send emails, follow up, qualify opportunities, prospect, and close deals. Let them draw their conclusions and analyze what you’re doing.

Don’t use the shadowing phase to tell new reps how to do sales. Many people fall into the trap during onboarding because they don’t recognize that there are multiple ways to achieve success in sales. What works for you won’t necessarily work for your new reps.

It seems counterintuitive, but the most important thing you’re trying to achieve during the shadowing stage of onboarding isn’t telling your new sales reps what to do—it’s to get them thinking about how they would do things.

You want to cultivate a “figure shit out” frame of mind in your new reps, which is ultimately what drives success in sales. You want your sales reps to become agile and capable of handling a variety of situations on their own terms.

"[Coaching] is the one-on-one time where a rep can be challenged to think more creatively – to find a new answer. It is not something you push onto your reps, but rather interactive – some input along with a lot of what could be possible."Lori Richardson, Founder and CEO, Score More Sales

For example, say you’re preparing for a big presentation or demo. Sit your new reps down next to you. Tell them how the demo is structured, who you’re giving it to, and how you got in touch with the prospect.

Have them sit in on the demo, and when it’s over, do a post-game recap. Turn around and ask:

  • “How do you feel the call/demo went?”
  • “Was anything unclear?”
  • “What would you have done differently?”
  • “What’s your take on this prospect?”
  • “Will they buy or not? Why?”

During the shadowing phase, have your new sales reps watch you, but allow them to draw conclusions based on their own analysis of the situation and form their own opinions.

Gauge their analytical skills and how well they paid attention during the process. Only once that’s done should you give your feedback: "Here are the things I believe you recognized correctly: ... . Here's what I think you missed: ... . And here’s where I disagree with your interpretation … ."

3. Practice Constantly

By this point in onboarding, your sales reps have a high-level understanding of your sales process. But you can’t just put your sales process down onto a piece of paper and expect your new reps to read it, walk out the door, and magically close deals. That’s not how sales works.

You need to ensure that all this information really sinks in and becomes second nature for your new hires. The only way to do that is to have them practice constantly. Practice is a framework and a mindset at the same time, and as a manager, you have to inspire your reps to constantly improve.

Sales is like swimming—to learn, you have to get wet. But give your new sales reps a swim vest and a safety net so they don’t drown immediately. Lead them along in baby steps.


Create mock sales situations so your new reps can practice their sales repertoire.

Take the role of a prospect, and have your reps practice on you. Have them give presentations and demos. Let them write cold emails. Get them to make real phone calls with you on the other end. Get them used to talking on the phone.

"There’s no better way for sellers to practice what they say before they have to do it in real-time. Sales role-playing... is the best way to discover if what you say makes sense, if you create any stumbling blocks, what questions you’ll be asked and how to best respond to them."Jill Konrath, author of the sales books Selling to Big Companies and SNAP Selling.

When you give feedback on a mock call or demo, don’t overwhelm new reps with a hundred things you think they did wrong. They won’t be able to process all of it immediately and will only come out of it with their confidence in tatters.

Build up your sales reps properly to enable their success. Focus on one weakness at a time and coach them through it.

Real-World Scenarios

Then it’s time to get your new hires out into the world—real life is the only sales coach that really matters. But do it gradually, so if they mess up (and they will), it won’t shatter their confidence or damage your business.

Give them old leads and prospects to contact or small inbound leads. Have them cold call or email these prospects while you listen in. You want to get them into the groove of talking to prospects and building relationships, but at the same time, allow for mistakes. As they improve, you can give them more responsibility.

Put your reps in situations where it’s okay if they mess up. You want to see how they handle failure. Do they let it get to them and shake their confidence, or do they rebound better and faster than before?

No test will ensure your new sales reps will be 100 percent ready for the job. After a certain point, they’ll have to sink or swim on their own—and the only way to find out is to cut the apron strings and push them out there. But by adequately onboarding them and gradually exposing them to real-life scenarios, you maximize their chances of success.

4. Prune Your Team

Not all of your sales reps will work out. Even with the best hiring practices and the most fantastic onboarding, some of your reps won’t fit your company. Don’t lead them on. They’ll resent you for it in the long run, and it’ll drain your business. For everyone’s sake, you want to make sure your sales team is working optimally.

Anthony Iannarino, President and Chief Sales Officer of SOLUTIONS Staffing, agrees, "You have to protect your culture from infection, and that means releasing anyone that threatens that culture. Sooner rather than later."

If you’re wondering, “Is this working or not? Is this person right for us?” about a new rep, the answer is probably no. If you have doubts, those doubts probably point to a bad fit. Let them go as cleanly and humanely as you can.

You want multiple moments where you think, “Yes, this person will be a part of our team. I see the future of our company with this person in it.” You want to think, “Holy shit! This person is amazing. I’m so glad I found them.”

These reps will bring that drive, initiative, and energy to your company daily. They’re the ones who will build the future of your company.

Learning Never Ends

Looking through the steps above, onboarding seems like a lot of work. And it is. You must be patient with your new reps and equip them for maximum success. They won’t always learn as quickly or as efficiently as you’d like—but they’re investments in your company's future, and you need to treat them as such.

By making your sales process explicit, you force yourself to look inward and reevaluate your sales process from a fresh perspective. When you onboard the right way, you empower your sales reps to succeed and grow your business and learn invaluable lessons on how to continually evolve and improve.

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