How to on-board SaaS sales reps and set them up for success

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So you’ve completed the arduous and lengthy hiring process. You’ve culled a pool of tens, maybe even hundreds of applicants, and interviewed your top five. You’ve played personality detective in interview after interview, trying to work out who’s right for the role, right for your company, and knowledgeable about the industry.

Now what?

Well, as a sales leader, you need to ensure that your new hire is as productive as possible, as fast as possible. This concept is known as ramp time.

Ramp time is the amount of time it takes to get a new hire fully productive. Depending on the type of business, it can be anywhere between 1 and 24 months. A lot of different factors affect the total length of ramp time — everything from the type of product you have to the sort of customers you attract.

But it probably goes without saying that the shorter your ramp time, the faster your revenue grows, so what you want to do is make it as brief as possible.

When we’re talking about ramp time in the context of a high-growth SaaS business, you can see it’s super important not only for your profits but also for the culture of the business. I mean, imagine if you bring in four or five new hires and after seven or eight months, they’re still dragging their heels and not fully up-to-speed with the business. It will create a really negative atmosphere on the sales floor and that’s why it’s in the interest of everybody to make ramp time lightning fast.

Ramp time is reduced if on-boarding is effective.

So what does an effective on-boarding program look like?

It differs from company to company: some provide intensive six-week professional education programs with incredibly deep dives into the company culture and sales processes; others offer on-the-job training and just expect people to hit the ground running.

In my opinion, for on-boarding to be successful, you need to blend the above two approaches. Provide a classroom-style learning environment in your company so that your new hire can acquire the minimum viable skills and market knowledge, but don’t hold them back from going out into the wild and actually picking up the phone to have conversations with customers. The ultimate learning experience!

A good on-boarding program is one that gives new hires all of the answers and tools they might need to perform straight away. A great on-boarding program is one that trains new hires to ask the right questions and find answers themselves.

A great on-boarding program is one that trains new hires to ask the right questions and find answers themselves.

Here’s a process that you can follow for the first week of on-boarding for a new hire.

Now let’s take a look at each of the key areas of this diagram.

Company & Culture

Obviously, the first thing you need to do when you begin to on-board a new hire is to make sure they are set up for success. In other words, set up their physical environment for success — make sure they have a computer login, give them access to all the systems that they’ll need to use, and make sure they’ve got a clean desk. You could even pimp up their office space a little bit with a plant or two, or a personalised coffee cup. If you’ve got some company merch in the form of a t-shirt, hat or business card, give it to them as a great ice-breaker welcome!

Next, it’s important to take them through a nice introduction to your company, even if you think they should already know all the details from the interview. Now they’re in, they need to understand who’s who in the zoo! Make sure you tell them who they can talk to if they encounter a challenge, how often their pay hits their bank account, and who in IT can assist them if their computer starts misbehaving. Also, make it clear who their direct manager or point-of-contact is.

Once you’ve got all of that out of the way, start thinking about how you can help them understand the goals of your business, why it is you are creating your unique product or service, and who your ideal customer is. This all boils down to your company vision, values and mission statement.

You want them to have this information so that they can then use it as a framework for tackling your customer’s unique challenges, which we’ll go into in the next section. And remember, this isn’t an exhaustive lesson. Their education and integration into the company is going to continue well beyond this initial on-boarding process.


Think about the minimum viable information that you can share with them to ensure that they’re going to be successful. Pick your battles. Do they need to be able to perform an in-depth presentation after their first week in the role? Probably not. Do they need to understand how to navigate between the different sections of your software or identify what the difference is between an administration and an end user portal? Absolutely.

The idea of this initial introduction to the product is to give them the bones from which they can hang their muscle of customer knowledge. Armed with this context of how customers actually use the technology they will be in a much better position to empathise with the customer’s challenges and understand how your solution will be able to impact the customer’s business.


Next you’ve got to think about providing training relevant to what’s important for your customers. This is where you can teach your new hires to ask the right questions. You do that by helping them understand what impact they’re looking to achieve.

Typically, when people are looking to purchase new software, they’re looking to do four things:

  1. Make money,
  2. Save money,
  3. Create efficiencies with UI/UX, and
  4. Stay out of jail by making sure they’re keeping themselves compliant.

This goes beyond the typical facade which we see advertised on many vendor websites, and actually understanding the IMPACT your customers are looking to achieve in their business and how it is that your company can help them achieve that.

The next element you need to help your new hire master is understanding which critical events your customers are working towards. A critical event is one which generates dire consequences for them if they miss that date.

So, say for example someone needs to implement a new CRM system. They decide they need to implement the new system by the end of the year, so that they’re effectively set up for success for the following year. And what happens if they miss that date? They’ll start thinking about rolling it out the next quarter.

Now that doesn’t sound critical. That sounds compelling. To make it more critical, you may emphasize that if they miss that date and it’s of high importance to their company, then their job is going to be at risk. That definitely changes how they’ll think about things.

So it’s important to understand what critical events are important to your customers and convey this to your new hire as a vital consideration in the sales process.

Your reps are now armed with some great information that can potentially help your customers, but a big mistake that many companies fall into is letting them into the wild with this new information.

The challenge is that new reps, armed with this information, are keen to tell everyone about their new found knowledge. They are falling into the dummy curve trap of talking, more than listening and asking questions. Check out this graph below for how it impacts sales over time.

To accelerate their path to become a seasoned pro, you need to equip them to tell third party customer stories about former customers, the challenges they were facing, how they implemented your solution to solve that problem, and the actual impact that it created, while not mentioning your company. This does two things for the customer:

  1. Helps them feel like they are not alone
  2. Makes you sound like an expert who helps a lot of people in the industry

Understanding the Minimum Viable Knowledge for each new hire

It’s now time to really hone in on what the minimum viable knowledge that your new hire needs in order to succeed in their role. I’m going to break this down into two different streams.

Firstly, we’re going to look at a junior sales development rep (SDR) whose job it is to generate leads for the account executive. Secondly, we’re going to look at the account executive who needs to be able to take the lead that has been generated by their junior sales development rep and progress it through to the next stage of the sales cycle.

Sales Development Reps (SDRs)

So looking at the SDR outputs, one of the core elements of their role is research, right? Researching to see who’s going to be the next customer to call, researching why your solution is going to be of value to them… you get the idea.

Here’s where you’re going to leverage that classroom scenario and applied learning principle I talked about earlier. Ideally, you’ll follow these three steps:

  1. Give your new hire a task to go and identify and conduct research on 10 companies which are potential business targets.
  2. Get your new hire to create emails in your companies framework. This not only demonstrates that they are writing professional emails, it also demonstrates that they understand the core value proposition of the business.
  3. Have your new hire conduct role plays with their colleagues for each company they have just researched.

Once they’ve done this, they’ll have a better understanding of your customer and what they need to do in their role because they’ve literally walked the walk.

Account Executive

The key skill of an account executive is to have a great conversation with the customer, diagnose whether there is a potential fit, and prescribe a solution.

The first step is to create a detailed call plan. This will help new hires understand the hypothesis of needs and get familiar with some of the core questions that they need to ask to be able to qualify and progress an opportunity. Within that learning scenario, you may ask them to present call plans for 5 scenarios.

Similar to the SDR’s, the next stage of the applied learning process is where these new hires do role-plays to replicate exactly what those conversations would sound like.

Again, these are things that can happen within the safe confines of a classroom environment and are best done with either brand new hires, colleagues, or potentially people who have experience in the role.

Now, these skills obviously aren’t all they’re going to require to be successful in their role. But they will pick up a lot more when they’re actually on the phones and engaging with customers. Get them in there as soon as possible to accelerate the on-boarding process. They don’t actually need to be 100% ready when it comes to engaging with customers.

Remember how I said that a good on-boarding program provides new hires with all of the answers, but a great on-boarding program teaches their reps to ask the right questions?

Even if they don’t know the answer, that’s perfectly okay. Customers appreciate it when sales reps are honest with them and say something as simple as, “I’m actually not sure of the answer to that question. Let me ask the right people within our organisation and get back to you later today with the most accurate answer possible.”

Encourage your new hires to ask your customers follow-up questions, such as “Can you help me understand why that is important to you?” and “in an ideal world, what would you like this answer to be?”

This sort of applied learning will make their on-boarding time much quicker.

Summing up

In summary, on-boarding is never an easy or quick process. When you think about it, you’re teaching new skills to adults, which is akin to teaching an old dog new tricks.

Therefore you should approach it with patience and an analytical mind. Make sure you measure the results of your on-boarding program and measure your ramp time from employee to employee.

It may vary from department to department, but decreasing your ramp time should be a goal across the board. It’s a key part of building a scalable sales organisation.

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