2. hiring & onboarding

sales onboarding: 
how to structure your sales onboarding plan to kickstart your new sales team

Reading time:  7 min  |  Time to finish this chapter: 19 min

It’s not every day you welcome a new sales representative into your company, so do your best to make a great impression. First of all, experiencing a great first day influences the newbie’s commitment and connectedness with the company. Then, you also spent a lot of time hiring this new employee, so it’d be a shame to underestimate their onboarding.

Companies invest in onboarding because it increases employee retention. The cost of losing an employee is extreme. Taking both the cost-per-hire and the cost-per-vacancy into consideration, it can go up to 2 times their annual salary! Well done onboarding improves productivity and performance by almost 40% - starting already with the first day.

Sales Onboarding

Let's get you on board

Sales Onboarding - a balanced mixture of theory and practice

Onboarding is the process of integrating a new employee into your team and company. Depending on the position type, it can take between a few weeks up to several months. Let’s say it starts with the newbies’ first day and ends when they can work mostly independently. 

Obviously, for sales representatives, it’s not (or should not be!) only about getting to know the position, company, vision, etc. A big chunk of their onboarding plan is practical sales training. Ideally, they get a chance to speak to their first potential customers and get familiar with the job’s nature.

Contrary to just watching presentations, studying the solution, and shadowing colleagues for months - we don’t strive for this setup. That’s one of the perks of being a smaller company. 

Sales onboarding requires a lot of planning, especially if you plan to include your team with constantly full calendars. Onboarding should be preceded by preboarding, including some administration towards the new sales team member. 

Pre versus On

The essential difference between preboarding and onboarding

The preboarding process starts after you shake hands or sign a contract with the newbie. This period can take up to several months; some people need to finish their previous jobs, some take a sabbatical, and some might still browse the job market, even if just out of curiosity.

In all these cases, you need to be in touch with your new employee. You’ll get a chance to address their questions and start creating an emotional bond. 


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What are the pre-boarding activities you can do:

Simply put, do anything that will open the door to questions. Addressing questions, together with showing you’re ready for them to come and honestly care, will make a great impression and a significant difference on their 1st day.

The period between signing a contract and the 1st day gives your new hire space to “look around” and see other fantastic positions to apply for.

You don’t want that to happen, so create an emotional bond by preboarding and increase the chances they’ll actually start working for you! 

Apart from all of this, schedule, plan, and organize. Become a planning freak! That’s how you maintain control.

What about teams?

Few ideas to keep your onboarding plan together

Set up a team-focus approach. Have your whole team deliver the individual training. This will ensure the newbie has the interaction with the veterans and also acclimatize quicker to the team.

At the same time, it won’t hurt the veterans to do a mental recap of what they already know. Educating others will extend their know-how. Give the newbie access to all materials so they can always get back to it. For all activities, set clear expectations. 

With all new sales representatives, immediately set “leader < > sales representative” status update meetings.

In SALESDOCk, we meet weekly. Dedicate this timeslot to catching up on what happened last week, removing possible obstacles, and setting the next steps for the following week.

It’s great to have a checklist of what needs to happen and already happened. There are many HR or Project Management tools, but if you don’t want to invest in them now, an excel sheet will do.

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How we think about this in Raynet? Read detailed look of our CEO Martin Bazala from our new office. Yes, we rebuild casino!

Martin Bazala / CEO

Here's the meeting room, here's the cafeteria

1st day at work - Just like your mother-in-law was coming for a visit

Clean up! Clean up the office, clean up the new sales representative’s table. Have a complete setup ready - computer, mouse, something to write with, a notebook, etc., and add some gifts, such as a box of chocolate, company merch, a “new team member” t-shirt, etc. Get them great sales books; they’ll come in handy. We recommend Proactive Selling and Selling Above and Below the Line from Skip Miller. His approaches to sales are to be adopted!  

We usually start the 1st day with breakfast and chat. We introduce the newbie to their buddy, leader, and other team members they need to know.

Then we do orientation - show them where and how to make a coffee!

Then jump straight into the onboarding/sales training plan - getting to know the company, its vision, some self-study and presentation preparation, tools introduction, and finally a happy hour with the team:

9:00 - 9:45
Team meet, Orientation, Coffee/Tea & Light Breakfast
9:45 - 10:30 Led by Jakub & Michal
SALESDOCk @ Banana.bi - Story & Vision & Team
10:45 - 11:45 Led by Buddy Martin
Team meet, Orientation, Coffee/Tea & Light Breakfast
11:45 - 12:30 Team
Team Lunch & Table foosball/chill
12:30 - 13:00 Team
Our Industry executive summary - presentation
13:00 - 14:00 Led by Jana
Tools: Intro, Login & Setup
The Office & Equipment; Email; Google Drive; Documents; Asana; Slack; Chrome; LinkedIn
14:00 - 14:30 Led by Buddy Martin
Our Organization
Week by Week; Roles; Metrics; Career plan
14:30 - 16:00 Led by Antonín
Our magic CRM intro
16:00 Team
Team Happy Hour

As you see, the first day is not that different from any non-sales positions. Most sales-based training happens in the following days and weeks. 

Settling in

The first week of your new sales representative’s onboarding

We admit it; we made it tense! We’ve received the feedback. But if you want to kick-start the new sales representative, that’s what you need to do. Mix up studying of what you do, your industry, clients, competitors, etc., with practical training. 

The practical training we deliver on the first week are:

These are immediately followed by the mockups and practical parts; creating templates and emailing clients, making a call script and calling clients, building a network, and posting the first post on LinkedIn. 

Since the new sales representatives are still quite nervous and have questions, the buddy pays a lot of attention. To make sure they’re not losing the path, we have daily “sales standup meetings” at the end of each day. We discuss what they learned, adjust the information if needed, and set the next steps. 

Activity report in RAYNET

When you use a calendar in RAYNET CRM it is automatically monitoring sales rep activities. So the activity report is just click away…


Weekend is coming!

Top tip: Make the newbie’s first day Thursday or Friday 

Leaders, managers, buddies, etc., are less busy at the end of the week and will have the time to pay attention to the new sales representative. Sadly, a significant portion of newbies experienced a lack of attention on their first day. Just ask around you.

Your first day!
8:00 – 8:30
Morning Stand Up
8:30 – 11:30
Industry Training & Customer Inteview
11:30 – 12:00
Lunch & chill
12:30 – 15:30 Jakub
Industry Training & Customer Inteview, Competitive Landscape
15:30 – 16:30
Recap, Tools & Admin
16:30 – 17:00
Buddy Martin
Sales Team Stand Up
8:00 – 8:30
Morning Stand Up
8:30 – 12:00
Martin B.
Cold Call training & Call Scripts
12:00 – 13:00
Lunch & chill
13:00 – 15:00
Martin M.
Mockups and Objections
15:00 – 16:30
Martin M.
20 Customer Calls
16:30 – 17:00 Jakub
Sales Team Stand Up
8:00 – 8:30
Morning Stand Up
8:30 – 12:00
Martin M.
Mockups and Objections, 20 Customer Calls
12:00 – 13:00
Lunch & chill
13:00 – 16:30
Cold e-maily Training
16:30 – 17:00 Jakub
Sales Team Stand Up
8:00 – 8:30
Morning Stand Up
8:30 – 12:00
Martin B.
LinkedIn Setup & training
12:00 – 13:00
Lunch & chill
13:00 – 14:30
Martin M.
Mockups and Objections
15:00 – 16:30
Martin M.
20 Customer Calls
16:00 – 16:30 Jakub
Inbox & Asana Zero & Team Stand Up

Week after week

The following 11 weeks of your new sales representative’s onboarding

After the newbies receive their first training, we let them practice and get used to their daily routine. Throughout the following 11 weeks, we check on their work, do mockups, roleplays, shadowing, and keep adding more training and tasks: 

  • Week 2 - Creating a product case study, demo training, studying competitors

  • Week 3 - Our sales methodology, meeting structure, need discovery training

  • Week 4 - Our sales process

  • Week 5 - Features Advantages Benefits training

  • Week 6 - Story Telling training

By week 6, there’s a lot of new information for the sales representative to absorb, so we slow down and deliver new training bi-weekly. We focus more on practicing and role-playing. 

  • Week 8 - Objections Handling

  • Week 10 - “Bob and Mary” (decision maker and user-buyer) perspective training

  • Week 12 - Rapport building training

What's next?

After the 12 weeks of onboarding pass

We ask the new sales representative to fill in a feedback form. As a young company, we experience changes constantly, and, hand in hand, we keep optimizing the onboarding process.

Right after an onboarding ends, you should have enough inputs to decide whether you made a good hire. If you’re wondering whether this person is a right fit for your sales team, the answer is most probably no. Doubts are always a bad sign. If you have them, let the person go. Your current sales team is too precious to be infected by a bad hire. 

If you’re happy with the hire, set proper KPIs and a bonus structure. Now, they’re ready to leave the nest.

Wrap up

Our first few onboardings weren’t the smoothest. That’s only natural.

So, if you’re setting it up for the first time, prepare for a lot of iteration and optimization. What truly helps is to ask for feedback once they complete the onboarding. Mix theoretical training with a lot of practice - roleplays, shadowing, and mockups. 

Don’t forget that everyone has a different learning pace and that learning actually never ends. Provide the environment to feel good and succeed.

Enjoy the fresh energy a new employee brings into the company. 


7 effective ways to find the best sales reps and how to keep them

You can be the best headhunter, but when you have nothing to offer to your potential salespeople, you won’t seal the deal. How do you attract and keep the best of the best? More in this chapter.


"SALESDOCk is one of Startup Wise Guys' trusted partners in working with early-stage technology businesses. Their involvement has succeeded in helping teams to excel.