Using a salesperson onboarding checklist

Since the average cost of recruiting, hiring, and training an employee is typically 200% of an employee’s annual salary, you want to make sure they actually stick around.

According to HubSpot, in an Allied Workforce Mobility Survey it was revealed that only 66% of companies train their new employees.

On average, the cost of onboarding a new hire is just $67. Compare this to the cost of recruiting, hiring and training a sales employee (over $100,000), and you've got a clear, logical reason to use a proper salesperson onboarding process.

Record checklist details

In this Salesperson Onboarding Checklists for Startups, you will be presented with the following form fields, which you are required to populate with your own specific data. More information is provided for each form field via linkage to our help pages:

To begin the Salesperson Onboarding Checklist for Startups, enter the required details into the form fields below.

This is a stop task, which means you cannot progress in this checklist until the required form fields are complete.

At the end of this checklist, there is the option to decide whether the employee needs further orientation. Your response to this task needs approving. Fill in the details of your manager (or other relevant personnel), to approve your decision.

Employee Handbook:

Record employee details

The first step in the salesperson onboarding checklist for startups is to record the details of the new employee. Use the form fields below to record their name, date of hire, contact details and any extra information you may choose to include.

Formulate desired outcome

Once a suitable candidate has been selected, onboarding (introduction to responsibilities, culture, tools, environment and colleagues) starts.

To know when the onboarding process is over, you first have to formulate ideas of what it will involve and the goals you're aiming to meet. Record a copy of these goals with the form field below.

For example, you may consider the following sub-checklist:

  • 1
    Familiarity with company purpose
  • 2
    Understanding of company beliefs
  • 3
    Induction into company culture
  • 4
    Explanation of customer base
  • 5
    Familiarization with products
  • 6
    Understanding of the competition
  • 7
    Training to use all required tools
  • 8
    Orientation into your sales process
  • 9
    Explanation of how your keep clients on

Consider all of these points and, based on the new hire's past experience, ask yourself 'how reasonable is it that they complete these goals within X weeks?' This 'reasonableness test' will be different for each candidate and should give you an idea of how long you're going to be working on onboarding them.


Explain your mission statement

If your firm hasn't decided on a mission statement, follow this guide to ensure you separate your good ideas from the bad ones. 

If you have one already, provide a copy to your new employee. This could be in the handbook, or in the slideshow of the orientation session.


Explain company goals

Explain your company's goals in as few words as possible in your handbook, using these recommendations:

  1. Your explanation should not be more than a few sentences.
  2. Explain the problem your potential customers are experiencing.
  3. Explain how you solve the problem you’ve outlined.
  4. What is the end result of your service or product? Does it save money, make their life easier or give them new opportunities?
  5. If possible, make your explanation relate to the person you are speaking to. Has the problem you are solving affected them? Do they know anyone with this problem? The more interactive you can make your pitch, the higher the chances that your audience will be receptive to it.

You might also want to explain in more depth, later down the line or in a group session, about your company history.


Explain company culture

Next up, in the employee handbook you must explain company culture.

Company culture is not just about relationships outside of work or office parties, it is mostly to do with how employees interact in the workplace, during work hours. 

“Culture guides discretionary behavior and it picks up where the employee handbook leaves off. Culture tells us how to respond to an unprecedented service request. It tells us whether to risk telling our bosses about our new ideas, and whether to surface or hide problems. Employees make hundreds of decisions on their own every day, and culture is our guide. Culture tells us what to do when the CEO isn’t in the room, which is of course most of the time.” 

Culture includes:

  • How employees feel about their boss and each other
  • How employees interact with each other
  • Amount and quality of communication
  • Willingness of employees to help each other, even though it's 'not in their job description'
  • Workspace innovation, e.g. communal areas, outdoor areas
  • Work retreats, group activities and holidays

To ensure the best results, refer to this Amazing Workplace interview for guidance.


Explain who you customers are and why they buy from you

Do you have a portrait of your ideal customer or various customer personas? Explaining this will help your new sales hire understand how to sell to the right people effectively.

If you don't have a customer profile refer to these five steps in creating an ideal customer profile. It will help your employees when dealing with customers and will ensure your company is using the right target material to promote your business.


Explain what they buy and why

Next, you need to make sure that the handbook explains what customers buy and why.

  • Do different customer personas buy certain packages or price points?
  • What do they use it for?

Answering these questions helps your new sales hire understand more about your customers and your products.


Know the competition

A fully informed salesperson should know exactly what they're up against, and so this is what you must confer through the handbook.

  • Is there a competitor selling a similar product?
  • How does it differ from yours?
  • Do you often lose customers to them for a specific reason?

Warn the new hires about what they might be losing sales to so they can work out the best strategy to combat it.


Hold orientation with the required tools

If your new hire is familiar with your CRM, communication system, pipeline software, or even telephone extension system, make sure to provide as much or little training as they feel they need.

Assess them on it at the end of this checklist. 


Teach about finding and selling to prospects

Whether they will be actively involved in lead generation or not, it is necessary to tell new hires what kinds of background their prospects are coming from. Whether you're selling to HR managers, social media marketers or mothers, the approach will be different in every case.

If you're looking to optimize the process, check out these 10 actionable tips on finding prospects for your new business.


Supply 10-15 common questions

In your employee handbook you need to be preparing the salesperson for the kinds of questions they will encounter from real customers. As such, you need to include some of the more common questions which are asked.

To make sure that the new hire is fully aware of what will likely be asked of them, be sure to include 10-15 of the most common questions which your customers ask.

For more information, check out's post on salesperson onboarding.

Include 10-12 common objections

Much like with the common questions, your customers will likely have common objections which the salesperson needs to be prepared for. As such, note 10-15 of the most common customer objections (eg: "I don't have time to talk to you") in the form field below.

For more information, check out's post on salesperson onboarding.

Supply responses for each question and objection

Now that you have your questions and objections, you need to supply the correct responses so that the hire can learn them by heart. The responses to everything should be included along with the questions and objections, potentially with a short descrtiption of why those answers are correct too.

For more information, check out's post on salesperson onboarding.

Keep your customers over time

Churn, or cancellation rate, is one of the biggest plagues of businesses. Teaching your sales people how to form solid relationships with customers is one effective way to stop the process before it even starts. 

If you have a company-specific way to keep customers on board, ensure you fully explain it to new hires. If you need tips, check this great article by Zach Bulygo, and this post by Jason Lemkin on SaaS-specific problems.

(Sources: &

Before the first day:

Send a welcome letter

The first stage of preparation for the employee's first day is to send them a welcome letter. This will usually take the form of an email, such as the sample email below. Remember to include a copy of the employee handbook!


Provide a full job description

Remind them of the full description on the job site they applied through. Alternatively, you can provide them with a new, more in-depth version with a full list of responsibilities.

Click here for a great example job description


Send performance goals

Provide the new hire with your performance statistics, strategy for the future, and be clear about what they are expected to do to help you meet those goals.

To manage their workflow easily, create a Trello board and add tasks as cards.

Test them on the handbook material

Once they've had a chance to study the handbook and learn the common questions and objections your customers will say to them, you need to test that the answers have sunk in.

Give them a call and make sure that their responses are up to snuff; do so by combining a random selection of the questions and objections you previously supplied.

Ensure that they test out the product

Trying to sell a product which you're not familiar with is a huge handicap, so you must now ensure that your employee tests out your product themselves thoroughly. The main aim here is to ensure that the value of your product is abundantly clear.

Make them go through your onboarding flow, give them tasks to carry out which take advantage of your best features, listen to what feedback they have to give; whatever you do, just make sure that they thoroughly understand the product they will be tasked with selling.

Make them read support conversations

Once the salesperson is familiar with your product through testing, you should introduce them to your customer base by getting them to read (or even interact with) your support conversations.

This is a fantastic way to show both the breadth of questions and objections they will later be faced with, but also give them a sense of the background and desires of your customers first hand.

Schedule any required extra training

For any hires who need extra training using your CRM, or more help with sales techniques, schedule a 1-on-1 meeting using Google Calendar and share the event with them over email. Record the date and time of this meeting with the form field below.

See this article from ITWorld for more details.

(Source: &

Assign a staff member as buddy

Assign your new hire an experienced buddy they can come to with any concerns, after or during the onboarding process. Record the name of their "mentor" in the form field below.

More experienced sales reps are a great asset for helping with new employee onboarding because they've been through the process themselves and know the ins and outs of your company.

Remember that any mentor should not be telling the hire how to do their sales. Instead, the new hire should be shown the issues they will face and be allowed to think creatively about how they will go about solving them.

Get them to listen in on sales meetings, then ask questions on how they thought it went.


First day:

Tour of the facilities

The next step in the salesperson onboarding checklist for startups is to give the new hire a tour of the facilities on their first day.

If you are situated in an office, it's useful and exciting for new hires to be shown the area, the different departments, the break room, where to get food and drink, etc.

Take them out to lunch

In small companies, the personal touch goes a long way towards making new hires feel welcome and confident, especially in a people-based job like sales.

The small investment of taking them out to lunch on their first day and getting to know them (by not talking about business!) is well worth making.


Have an end-of-day meeting

An end-of-first-day meeting is a great time to catch any issues or concerns from the first day at work. Note any issues they have in the form field below

Remember to track if there has been any improvement during your daily meetings over the course of their first week.

Following six weeks:

Meet with them regularly during the first week

Most easily-dealt-with problems, like issues with software, will arise over the course of the first week and can be resolved quickly. Hence, you need to keep meeting with them regularly during this time.

This extra care and attention will go a long way in building trust between you and your new employee and make them feel as if they can talk to you about anything concerning them in the future. 

Engage in roleplay until they are ready for live calls

Even if your new hire performed amazingly well with memorizing the handbook and fielding answers to the calls they have listened in on with their mentor, they need to be put through their paces thoroughly before you can let them loose on your customers.

Take on the role of a prospect and make the sales hire practice on you. Make them give presentations and demos, write cold emails, have live phone calls with you.

Schedule weekly 1-on-1 meetings

As time goes on, you won't need to check up on how your new employee is doing so regularly. Limiting correspondence to weekly meetings means that the most important issues of the week can be ironed out on the spot.

It's best not to schedule a meeting like this on Friday, so action can be taken straight afterwards. Also, ensure that you do not overload them with feedback - focus on a few key areas of improvement at a time, as this will not only make it clear what they have to focus on before the next meeting, but they also avoid walking away with their confidence in tatters.


Break them in slowly

Once the hire is ready for live customers, start off by giving them old leads to contact, or at most small inbound leads. Essentially, only give them a task with a real customer if it's okay for them to mess up, and ensure that you're always listening in.

Assess the outcome

Decide whether the employee needs more orientation or is good to go by looking at the following aspects and comparing them to your expectations:

  • Project completion
  • Testing
  • Practice certifications
  • On the job evaluation

Bring in their assigned buddy for the assessment to help you clear up anything you're not sure about.

Assessing the outcome of this process will help you to refine your salesperson onboarding in the future.

Deciding whether more orientation is needed for the employee is an approval task.


Will be submitted for approval:
  • Assess the outcome
    Will be submitted


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