Training your sales reps to be the best they can be will result in greater success for them and greater success for the company. 

In this checklist, we have provided a 90-day training outline which takes your new hire from fresh-faced hire to experienced deal-closer. 

The first 30 days concern creating a competent sales rep, able to deal with clients and perform their job well.

The second 30 day period is aimed at giving them an in-depth knowledge of the market, the company, and the product. Alongside this, the reps will shadow their colleagues to improve on their core purpose: selling. 

The final 30 days is intended to give the sales rep experience of the full pipeline from prospecting to closing. They should also experience duties outside of the day to day activities, like going to a conference. The final 30 days of the sales training process should shape them into the complete sales rep.

90 Day Sales Training Process

As you run this checklist, you will want to gain as much value from your employee as you can. In the first week, beyond the tasks listed in the outline, find productive work for them within your company which is appropriate to their level of experience.

After the first week, you may want to put them straight on the phones to help generate revenues immediately. Be sure to avoid passing them high priority clients. Potentially provide them with low priority leads, as their ultimate goal is to get comfortable on the phones early on. After the first 30 days, your new hire should be comfortable operating in sales alongside your other reps.

Record employee details

Use these form fields provided to record your new hire's details.

Ensure onboarding has been completed

When hiring a new employee there are various steps which must be completed. The hiring process must be legal and all documentation must be signed. The employee should also be made aware of the nature of their role and compensation in order to guarantee satisfaction for both parties. 

Use our checklist below to record the completion of some of the steps.

  • 1
    Explain the company
  • 2
    Ensure agreement on compensation
  • 3
    Provide a full job description
  • 4
    Sign all relevant contracts
  • 5
    Provide payment information for finance department
  • 6
    Undergo background checks where necessary

For a more detailed onboarding process, you can use our Salesperson Onboarding Checklist for Startups.

Week 1:

Analyze previous portfolio

If you're hiring someone who has worked previously within a sales environment, particularly within the same industry or sector as your company, they may have leads or contacts which could provide immediate benefit to the company.

Sit down for a conversation with your new employee to discuss any immediate value they could bring to the sales team.

Record the notes of this meeting in the form field below.

Introduce to internal communication systems

The first thing to focus on with your new hire is open channels of communication. They will have a lot of questions at first and providing them with their email, Slack account, and/or Yammer account will make this process easier and prevent them from feeling isolated.

Record this with the form field.

Presentation of product

One of the first steps of a sale is explaining the product to potential customers. Give your trainee time to research and understand the product. 

Have the employee present the product to you and assess their understanding. Require them to go into the greatest level of detail they can.

Record your notes below

Meet the team

Your team is going to be working closely together so they should know each other well. Later in the training, we will schedule shadowing exercises to share knowledge with the new hire.

Use this moment to have a relaxed meeting where people can chat and ask questions to build a sense of togetherness. 

Week 2:

Meet the different departments

Introduce your new hire to the different departments in the company. This gives a good opportunity to show them around the building and to provide them with points of contact. It also aids them in settling in by making every face a friendly one. 

Learn the product with the product team

Schedule time this week for a meeting with the product team or a member of the product team. This should give your hire the chance to learn about the product first hand from the people who make it. Make sure that this meeting covers all aspects of the product which the sales rep will need to know. 

If your product is a SaaS application you could discuss everything from UX to how the servers are organized. You could cover what the core product is and how the secondary services relate to that within the structure of the application. What languages is it built with?

Use our email widget to reach out to the product team.

Undertake sample tasks on CRM

An important part of many sales team's processes is their CRM. This allows calls to be tracked and pipelines to be measured. Your hire may have experience now with the basics of the CRM, but this is your opportunity to test their knowledge and help them improve

Create 3 walkthrough scenarios of varying complexity for your new employee to work through in your CRM.

Detail the scenarios below.

For more about CRMs check out this post on the best CRMs for small businesses.

Most CRMs have a range of training materials and courses which you can use as templates to creating your scenarios. See this video from HubSpot to get you started.

Week 3:

Learn about the company

Particularly when dealing with bigger clients where sales have to be signed off at various levels, having an in-depth knowledge of your company and its history and successes can be very important. The reputation of a company can give the credibility needed to pass a sale in a boardroom where one of your sales reps might not be present. 

Task your employee with researching the company further and understanding what strengths they may be able to use in future calls.

Deliver a practice demo of the product

To build on the product introduction session with the product team in the previous week, have the new employee give a presentation on how the service works. Treat this like any product demo they may have in future on a call. Ask them probing questions and analyze in depth whether they know where the value lies. 

Record your notes in the form field below.

Present a workflow map of internal sales processes

By the end of their third week, the new sales rep should have spent two weeks doing some work on the phones and should have a strong knowledge of the CRM

Have them create a workflow map of internal sales processes and present it to you. 

Here's a pdf from Salesforce which shows how to put together a professional map of sales processes.

Upload the workflow map below.

Week 4:

Learn the market

Set the new employee the task of learning more about the market. This may involve researching competitors and reading any reports they may have published. If you give them appropriate guidance in how you want them to approach this then you could use some of their research when compiling competitor analysis for your monthly sales report.

Upload their research in the form field below.

Prepare and deliver a product demo to a client

Given the levels of research your new employee will now have done on both the product and the market, assign them a product demo with a potential client. Join them on the call to assess their performance and give guidance where necessary. 

Record your notes in the form field.

Complete a full mock sale scenario

To round off the first month, play a short roleplay with your sales rep. Design a full sale process and play the willing client. Have them sell to you from start to finish. The goal here through their 3 weeks of practice on the phones and extensive research is for them to now be a competent salesperson who you are happy to have representing your company in any scenario.

Record your notes below.

There are a number of example mock sales videos online. Here's an example one:

Week 5:

Undergo the customer service training

As part of a rounded knowledge of the company, it is important to understand different departments. Customer service is of particular importance to a sales team. Knowledge of the product alone doesn't equal knowledge of how customers engage with the product, and the problems or difficulties they may have. This knowledge can help inform salespeople as to what obstacles customers may be experiencing which could hinder sales, in certain industries.

Have your employee undergo basic customer service training.

You can find more about customer support approaches here.

Shadow the senior sales team members

In this month we'll be beginning the shadowing program. The first step is to pass on the skills of the most experienced members of the team. Connect your new employee with the senior sales team and have the new hire shadow all of them one by one to learn different techniques and approaches

Use the email widget below to inform the first one.

Sit In on product team meetings

To continue broadening the knowledge of the company's operations, have the new hire sit in on product team meetings. This will help them understand constraints and help them learn the roadmap for the product in greater detail.

Week 6:

Shadow the customer service team

Follow the customer service training with a day spent shadowing the customer service team or a few members of that team. This will help them understand that role better and prepare them for a few days of customer support assistance which they will undertake in the coming weeks.

Shadow the junior sales team members

Now that your sales rep has shadowed the senior sales team members, allocate them people to shadow from the junior sales team. This will help them see the approaches others are taking to the job and learn directly from team members with the same responsibilities.

Sit in on research and development meetings

After sitting in on product meetings, next is to try the R&D department. This will open up the new knowledge of the roadmap to further scrutiny and analysis. The new hire can understand why the roadmap is as it is. And they can gain further knowledge into other potential changes to come in the future.

Week 7:

Deliver first week of customer support assistance

Sales reps can gain insight into customers and their behavior through spending time assisting with customer support.

Depending on the customer support structures in the company, the employee may be answering emails and messages or on the phones. Many customer support setups have a categorisation system for helping existing clients. A SaaS platform may have different levels of support depending on the payment plan of the client.

Provide the new hire with an entry level equivalent support role for their first foray into helpdesk activities. 

Choose a mentor from the sales team to shadow

Your new employee should have spent time with each member of the sales team and begun to learn something about each individual and their sales methods.

Give your sales rep the opportunity to choose their own mentor from the team. This will allow them to choose someone they feel they have a good working relationship with. Moreover, it tells you which of the existing team were performing well and assisting with training during the shadowing period.

Use the form field to record which mentor has been chosen.

Give a presentation relating to the product

After having sat in on both product meetings and research and development meetings, the employee should have a strong knowledge about the product and its roadmap going forward.

Give the rep an opportunity to pick an aspect of the product or a future stage of the product to give a presentation on. Have them choose something inventive to approach and to demonstrate creativity.

Week 8:

Deliver second week of customer support assistance

During the shifts spent providing customer assistance in their second week, the employee could be given a different category of support to work with. This may open the hire up to dealing with a range of different customers.

Use the form field below to record any performance notes passed on from the customer support team manager.

Share a sales portfolio with the mentor

Help consolidate the mentoring program by sharing a portfolio between the two reps. With this effort, you can help encourage a greater degree of skill sharing

If you have more than one trainee and are running a mentoring program across multiple team members you can create a sales competition between the mentors. With the right incentives, you can encourage the mentors to give everything to improve the performance of their partners.

Provide follow-up contact to existing clients

During this week have the trainee follow up with previous and existing clients to attempt to resell or upsell products or services. This can be a good way of making sure all contacts are qualified leads and will test a slightly different sales skillset.

Have the employee compile a report on these contacts.

This report could document how existing clients are experiencing the product or services and what would be required in order to upsell, or it could document why previous clients left and what would be required to bring them back. 

Week 9:

Support the sales prospecting team

To gain a full working knowledge of the sales pipeline, assign some time to the sales prospecting team. This broad knowledge of the complete sales process will benefit future sales, flexibility, and potential advancement in the company.  

For a complete process, you can use our Weekly Sales Prospecting Checklist.

Take on leads as own clients for closing

Have the new employee take on their own independent high-value leads for the closing stage. This will provide them with knowledge of the final step in the pipeline and by focusing on this your new hire has the chance to put numbers on the board; fuelling their confidence. 

For guidance on this stage of the pipeline, you can provide your trainee with our Closing the Sale Checklist.

Present research on previous week's client research

Make time for the new employee to present their research report on existing and previous clients.

You can upload this report using the form field below.

Week 10:

Continue with sales prospecting assistance

Have the employee continue to devote some hours to the sales prospecting over the course of this week. Check to see improvement on the previous week's performance.

Leave your notes on their prospecting performance in the form field below.

Focus on existing clients

Continue to focus on closing the deals of the existing leads assigned in the previous week. Set the target of completing these deals for this week, and begin to take on more closing opportunities in the next.

Help another team member close a large sale

If you have a high-level corporate sale on the table which is of significant value to the company, assign your new trainee to assist in closing the deal.

This may mean accompanying the leader to other offices for pitches to boards or it may mean lending a hand in working out pricing for a bespoke solution.

Use the form fields to identify the sale.

Week 11:

Write an article on the training experience

Give the new employee the chance to write a short article about their experience within the company so far, and the nature of the training

If you use content marketing strategies, you could craft the brief to fit the needs of the marketing team. Alternatively, this article could be published as a blog post used for future recruitment services.

Upload the article here.

Take on new clients for closing

Resume taking on new clients who are at or close to the closing stage. 

In the following week, the trainee will be declared officially a full member of the sales team. To help them accelerate into the full role, this task will give them a series of deals they can close to raise their confidence to new levels.

Go off-site to an industry conference

Now they are inches away from being an equal player on the team, send them to a conference or trades-fair. This will help them identify themselves within the industry and gain broader knowledge.

Use the form field to record the event.

Week 12:

Become a full member of the sales team

Give your sales team member a big pat on the back as you publicly declare them to be a full member of the team.

This public display brings recognition from their coworkers and provides the employee with a memorable moment of achievement and belonging

Hold review session with mentor

Sit in on a meeting with the new team member and their mentor. Have them discuss the relationship and the development over time. Search for frank responses and probe for more information.

Record your notes below.

Write report of own training experience

Give the employee time in this week to write a detailed report of their training experiences. Encourage them to be honest in their critiques of their own performance, that of the team, and that of the program. 

Week 13:

Present report of training experience

Let your employee present this report to yourself or the team. Follow their presentation with questions. Try to probe for any weaknesses in the process and ask openly for any constructive criticism. 

Record your notes below.

Review performance with the sales team

Hold a team meeting to review the performance of the sales team as a whole but allocate time to focus on the new member of the team.

Ask for feedback; both positive and constructively negative. Peer reviews can show strengths or problems you may not have seen, and can also give insight into the dynamics of the team.

Enter your notes in the form field.

Have post-training review with sales team manager

Hold your final meeting of the training process with your new sales superstar. Review the performance in this checklist beforehand. Be open and honest with your employee and congratulate them on their successful integration.

Provide them with a clear breakdown of their standard week from now on. They should already feel they know this, but clarity is appreciated. 

You now have a fully trained sales professional. Well done.


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