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Sales Training and Onboarding

An Early Playbook for Training and Onboarding Your Salespeople

January 2, 2023
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5 min read

Finding and hiring that perfect candidate for your sales organization can be very difficult, but that’s only half the battle. To get your new team members performing at their peak potential as quickly as possible, you need to have excellent training and onboarding.

Focusing on sales training and onboarding during a sales team’s infancy might not seem as enticing since it doesn’t necessarily yield an immediate payoff, however, you’ll notice a steep long-term improvement in how your sales organization scales.

Until your new hire is capable of producing at their full potential, they can actually be a significant drain on your resources. For example, it takes about 5.3 months for the average new sales representative at a SaaS company to be fully activated– that’s nearly half a year of losing money per new hire!

Getting that activation number down must be  prioritized for any savvy growth-oriented founder. In the following article, we’ll teach you how to install a sales training and onboarding program that can scale with your organization.

What is Sales Training?

If you don’t come from a formal sales background, you’ll still be able to find many similarities between most educational programs and sales training – modules, assignments, practices, and templates.

The primary goal of sales training is to teach salespeople how to have strategic and tactical conversations with your customers. However, each organization has its “special sauce” that naturally develops in the wild.

Your sales training program is a repeatable process that transforms your new hires into competent and revenue-producing team members. These sorts of programs are usually very template heavy in order to help new sales representatives understand the sequence and flow of what a successful deal looks like so they can repeat it at scale.

The basic requirements of any sales training program are:

How Long is a Startup Sales Training Program?

  1. Complete understanding of your product offering and the acute business pain it solves
  2. Basic understandings of your sales technology
  3. A fundamental understanding of how to crush the commission plan set out for them

How Long is a Startup Sales Training Program?

Most startup sales programs are generally a fast-paced 2-3 weeks.

Startups need their sales talent to ramp up quickly, but they need to find a balance between proper onboarding and effective, meaningful training.

Sales training, however, is an ongoing process. Your formal sales process can be as long as a few months until your salesperson starts hitting their full expectations. Check-ins and maintenance training are various intervals that are important touchpoints that should be utilized to keep your sales recruits focused and up-to-date with company goals as they evolve.

How to Manage a Sales Training and Onboarding Program

The management role for a startup sales training program usually falls on one of the founding team members or early top managers. Keep in mind that whoever you have running your sales training must have the proper bandwidth and focus to do so.

If you instinctively tap your top-performing sales representative to train all your recruits, you could put their own performance at odds with the time they must spend on their training program.

That being said, the best way to manage an early-stage sales training program is to start small and scale up, all while keeping excellent documentation in case you need to onboard a new training manager.

Use Google Docs and calendars, and then eventually move to a housing program in Guru or something similar.

You can use a rudimentary Sales Training Worksheet to track the progress of your trainees.

Sales Training Prep Work

Before your training and onboarding starts, knock out some simple prep work that ensures a consistently high-quality experience for new trainees while also setting accurate expectations.

When a new hire accepts their offer, they should be crystal clear on their next steps and expectations. Whether you plan to onboard them virtually or physically, make sure they have everything they need: every email, document, any company swag, and calendar invites. It should feel like you’ve been eagerly awaiting new hire’s arrival for weeks.

Stress that learning, especially for a career in sales, is an active experience– not a passive one.


  1. Create your accountability documents before Day 1 starts.
  2. Review all pertinent call recordings you plan to show your trainees.
  3. Read through all the sales presentations and demos you plan on showcasing.
  4. Put together a list of sales book recommendations.
  5. Overview your explanation of all relevant tech that will be used.
  6. Set the sales training calendar

Startup Sales Training Topics

There is a lot to cover in an onboarding class in a short period of time, so make sure you leave nothing to be purely verbally communicated. Your time does not scale, your documents do – create extremely high-quality and clear documentation, absent of anything overly proprietary.

Here is a running list of training topics:

  1. Administration Documents such as payroll, insurance, stock-option plan, W-2s, etc. You don’t want to just dump these on your trainee’s desk. Dedicate the time and resources to fil these out with new hires, helping them curb any misunderstanding or anxiety over logistics.
  2. Your company culture such as your values, principles, and what makes your company unique. Why should new hires be excited to work for you and shoot for the moon?
  3. Business Metrics and an explanation of what primary criteria focuses on, and how your new sales representatives will be evaluated.
  4. Technical and logistical training is particularly important if your product is fairly technical so trainees are able to intelligently explain your value proposition.
  5. Market overview and a full stack breakout of all the players, including ancillaries, in your company’s market.
  6. Your Sales Playbook that goes over critical items such as demos, cold calling templates, objection handling, competitive selling, and slide decks.
  7. Software and Sales Tools is crucial if your trainee’s role requires using multiple platforms (i.e., CRMs like Salesforce) to be successful. Guide them through any and all tech and make sure they’re set up on every platform they need to be. Show them the most useful features (for example, how to undo send on Gmail), chrome extensions, voicemail apps, how to take screenshots, demo software, etc.
  8. Basic tools and sales etiquette are especially for new hires coming out of college. Show them how to send cal invites and proper email meeting etiquette.
  9. Scheduling best and expectations, as well as general customer buying cycles.

Best Onboarding Live Training Routines for Startup Sales Teams

Live training and performance is a very important aspect of teaching your new hires the sales ropes. Your sales training program needs to ensure your sales representatives are as comfortable as they can be before they start dialing actual customers.

Performance Training:

Start with mock introductory call presentations where trainees present their intro call shpiels in a group setting for constructive feedback.

Establish the setting properly (you’re cold calling the secretary of a key decision maker) and rotate topics until everyone masters each angle. [10] [11] [12] These mock introductory calls are best performed in a group setting, and are excellent for objection handling training.

To take mock calls a step further, pair teammates together and have one act as a prospect and one as a sales representative. Giving each representative a seat on the other side of the sales process can help them understand how prospects think from an intimate point of view.

Performance training mock calls should be split around different segments of the sales process:

Lead generation, cold calling, negotiation, and deal closing.


This brief apprenticeship of sorts helps new representatives see how your more seasoned sales operators handle the nuances of your sales process.

In shadowing exercises, a new rep will listen in (likely on speaker phone) on the live calls of experienced reps. A brief Q&A session after each call will allow each new representative to probe further into the specifics of sales and common on-the-ground best practices.

However, be careful not to eat too much time and productivity from high-performing reps. To help scale your high-performing reps time, have them record their live calls for new sales representatives to watch on their own.

Setting your new reps up for early success:

Start your newly trained sales representatives on the shallow end of the pool by sending them highly qualified or inbound leads to get their confidence. To facilitate the process, pair them with an experienced representative to get some quick wins.

Call recordings:

Record the sales calls of your new representatives and review them as a team. Seek out opportunities to improve in a constructive manner while also highlighting what aspects your representatives performed well.

Pass these recorded calls to experienced and senior representatives to build their management skills and scale your time.

Final Thoughts - Ongoing Training

Sales training is an overlooked and under-resourced component of sales teams both new and mature. With a little grunt work and some nurturing, you can install a basic sales training and onboarding process that will ensure your sales reps feel supported before they even arrive for their first day.

Structure ongoing learning sessions built into each representative’s weekly schedule, even if it's just an hour or two per week to go over best practices.

One common thread you’ll hear from top-producing sales representatives is that they’re constantly on the edge trying to learn how to do their job better. Startups that embrace a culture of self-improvement and on-going training tend to produce rockstar sales people.

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