The secret to mic-drop demos workshop - Oct 6 at 10am EST.Sign up now!
The Quick and Easy SaaS Sales Coaching Cheat Sheet

The Quick and Easy SaaS Sales Coaching Cheat Sheet

Anirban Banerjee
Anirban Banerjee
February 2, 2022
5 min read

You can’t bake a cake with burrito ingredients and you can’t sell SaaS with generic sales coaching. 

B2B sales teams are competing against savvy buyers who know exactly what they want and salespeople need to be ready to handle their inquiries with thoughtful answers to difficult questions.

SaaS (Software as a Service) sales coaching does exactly that – it helps sales reps stay-up-to date on the latest tools and tricks in SaaS sales and gives sales trainers the strategies they need to help their sales teams win.

SaaS sales coaching for the win!

How far does SaaS sales coaching fall from the sales coaching tree?

People who have been on both sides of the equation know – compared to most other products, selling SaaS and tech is tougher. Here are a few reasons why:

  • Buying a SaaS product may mean significant changes in a company’s systems or processes. This can lead to resistance. 
  • The onboarding process may require extensive training for teams, especially in case of products like CRMs where the impact is company-wide. This needs time commitment.
  • Most SaaS sales have a longer sales cycle and require multiple touch points before a close
  • SaaS products usually come with multi-month and year deals, so companies are extra careful before signing on.

Because of all of these reasons, your sales reps need to bring their A-game every day. They need to be able to clearly emphasize the value propositions of their software, tell a cohesive story and tie case studies to the specific client use case in order to create a convincing pitch.. 

Why do you need this sales coaching cheat sheet?

“I know my product. I have sold my product more than just once and I can teach my sales team how to do this. And if we’re spending time and coaching reps, when would they bring in more clients?”

Here’s a scenario – One of your salespeople closed ten deals last month. However, another closed twenty. Now, if the efforts you’re putting towards improving their performance are common and equalized, then how is one of them closing more deals?

The answer to this lies in the statement itself. You are giving the same demo sessions, same knowledge training and onboarding all your reps for the same sales training programs. And yet, each of your reps is different in a thousand little ways, so how can the same training take?

What you should be doing?

It’s simple – Your coaching needs to be personalized for each rep. Let’s break that down further:

  • Identify the problems faced by your sales reps
  • Keep track of what they are doing, where they are lacking
  • Schedule regular meetings with them to discuss those sales roadblocks
  • Ask them what could improve their sales and coach them accordingly
Personalize sales coaching.

Of course, in a busy sales environment, where both you and your reps burn the midnight oil regularly, it is not easy to take out time to do all of this. But if you do what you’ve always been doing, you’ll get the results you’ve always been getting. Change in results demands a change in inputs! And this is where this no BS sales coaching cheat sheet comes in. 

What is the best way to get started with SaaS sales coaching? 

  • Focus on how you can improve your average and low-performing sales reps. 
  • Use a sales intelligence tool (like Wingman) to record and refer to your salespeople’s prospecting/sales calls.
  • Help your salespeople set their own goals. Remember, your job as a SaaS sales coach is to help your team reflect and realize their key areas for improvement.
  • Advice them to be S.M.A.R.T. with their goals. The goals should be specific, measurable, attainable, realistic and time-constrained. Have faith in this approach; it can make things a lot transparent, accountable and easy to track and follow.
  • Be mindful - measure what matters! Choose your sales metrics wisely.
  • Offer opportunities to fast-track your sales reps’ professional development. Upskill them for the new in-demand SaaS product features and the action plan to sell them right!

The SaaS sales coaching cheat sheet

SaaS sales coaching cheat sheet

Let’s begin with some of the most common sales coaching models. We’ve gone down this rabbit hole quite a bit further in another blog, but here’s a refresher..

Common sales coaching models for SaaS sales 

GROW: Goals, Reality, Options, Will

Using this model, you can help your sales team set clear goals for themselves - based on where they currently stand and what they want to accomplish, how they can approach that and what they are willing to do to achieve their goals.

OSKAR: Objective, Scale, Know-how, Affirm+Action, Review

This model involves listening to your rep’s sales woes and deriving an action plan, followed up by following up with them to track the progress. Set an objective, mark its achievability on a scale of 1-10 and help your coachee derive methods to achieve it and pick the best way to act on it.

CLEAR: Contract, Listen, Explore, Action, Review

Here, the coach and coachee together lay out a “contract”, basically a set of guidelines of how the sessions will go. Listen intently to the coachee and ask probing questions to helm them explore various options that they can then action. As the last step, the coachee will review YOUR performance as a coach (yup, this flips the script!)

CLEAR: Contract, Listen, Explore, Action, Review

AOR: Activities, Objectives, Results

With its data-driven approach, this model enables you to coach in real time by tracking sales processes, calls and downfalls (without micromanaging, of course!). Track your team’s sales-tivities; based on that, help them define objectives to improve the concerned sales metrics and track that to ensure growth.

CIGAR: Current reality, Ideal situation, Gaps, Action, Review

With CIGAR, you can burn up the gaps your sales reps are facing in their sales cycle. Have a transparent discussion to map out the gaps between your current reality and the ideal situation. Help reps decide on a course of action to eliminate those obstacles and assess if they have achieved the ideal situation or not.

Prepping for a sales coaching session

Prepping for sales coaching sessions.

Here are a few coaching-prep tips that can make your sales coaching session a veritable “golden hour.”

  • Get a pre-session update 

Ask your leads to update you about how their week has been sale-wise. They can  send you a video or audio 24 hours prior to the coaching session talking about everything they’d like to improve their coaching experience.

  • Dig into your coachee’s sales calls

Leverage sales intelligence tools (like Wingman) to listen to the highlights of pre-recorded sales conversations of your coachee. This will help you identify exactly where they are lagging, giving you specific areas that your sales rep needs to be coached for. 

  • Choose metrics that need attention

Let’s say your coachee repeatedly stumbles at the first sales call. Going through the numbers, you see their average call duration is quite low, especially for that crucial first call. Well, now you know what to focus on!

Questions to ask during your coaching session

Each session is different, because each rep is different, but some questions are always helpful in unearthing specific roadblocks and birthing insights. Here are some of them..

  • What deals have you won and which ones were you not able to convert?
  • Do you know the reason the deal didn’t go further than a particular stage in the funnel?
  • Did you course-correct your method of selling? What strategies did you follow?
  • What are you doing right with the deals you are closing? Can you figure out a way to apply that to all of your deals and see if it works?
  • Do you think having more technical knowledge about our SaaS product would ease things for you?
  • What sales activities do you execute the best? And where exactly do you feel things start to go south?

Now, let’s use an example to see how you can frame problem-specific, catalytic questions.

Say you have a sales rep who is good at prospecting, gets through the first call, gets the SaaS product demo booked and knows the ins and outs of the technology behind it. However, these demos rarely lead to sales. Here’s a series of questions that you can ask your rep to coach them on how to resolve this. 

  • How do your prospects sound on the first call? 
  • Do you make any efforts to build a relationship with them?
  • If not, why? Do you think you’re lacking at lead engagement and building customer relationships?
  • What do you think would help change that for you? Would you like to be onboard any sales training for the same? 
  • While you are giving the demo, do you consider the size of the enterprise and the budget the lead is willing to spend? Did you make an effort to base your demo session on those factors?
  • How do you make the lead see how our product solves their needs?
  • How do your leads sound during the demo? If they don’t sound confident, what measures did you take to change that?

Best practices for SaaS sales coaching

Focus on your reps’ wellbeing

With a lot of sales having gone virtual, your reps are forced to change their routines while still hitting their sales quotas. It’s quite possible that their mental health is affected due to this. We’re all humans in the end - see how you can support them to bring their best selves to work.

Are your reps doing well lately (mental health wise)?

Work on one metric at a time

Making plans to improve too many things at once might overwhelm your sales rep. Focus on improving only one key performance indicator through a sales coaching session. 

Ask your rep to create an action plan

If your rep needs to increase the number of sales calls they are making every day, you can create a measurable, attainable and trackable action plan for another week. Help them set a value for how many calls they want to make per day in order to improve the metric in the long run.

Follow the data-driven approach

Data-driven approach

When you have so much enterprise data, sales intelligence and analytics tools available – just go ahead and leverage them as much as you can! Use rep-specific data by listening to their pre-recorded calls and identifying moments that led to a lost deal; use that data in your coaching session.

Follow up or bust

People mostly forget what they have learned within a month of coaching. Hold your reps accountable for their progress and regularly follow up to ensure that the lessons stick. This ensures you don’t have to begin the whole process again some time in the future.

Tip: Document everything you can! This will help you come to better conclusions and guide your sales rep in the current and future coaching sessions. You won’t have to start from scratch the next time. Just refer to your notes!

Document, document, document!

What NOT to do in SaaS sales coaching

Walk in unprepared

Each minute of a session is valuable. Make sure that as a coach, you do your homework. This means reading up on your coachee’s performance data, listening to their recent calls and even creating a list of specific talking points.

Overwhelm your reps 

If you ask too many questions at once and talk about making improvements to too many sales metrics, you might just end up overwhelming your reps - defeating the whole purpose of sales coaching.

Keep it together.

Try to clone yourself

Your goal is to make your reps reflect on their sales processes to identify areas of improvement, set goals and achieve them. If you tell them exactly what to do, you aren’t really helping them think for themselves. At best, you should offer them multiple options and ask them to pick a solution that fits. 

Forget that the session ever happened

Do your reps remember the sessions?!

Yes, we’re saying this again, because it’s just that important! Follow up with your sales reps, hold them accountable for their goals and give regular feedback! SaaS sales coaching is NOT one-and-done

If you want to be a good coach, you know data lies at the heart of your SaaS sales coaching cheat sheet. If you have no record of the metrics you need to track/improve, what are you even going to base your goals and action plans on?

That’s where Wingman comes in: 

You want to analyze your rep’s on-call behavior?

Our sales intelligence software gives you critical insights into your rep’s sales calls such as talk/lead ratio, moments of hesitation, repetitive questions asked and more.

Wingman: Call transcript

Do you want to get quick insights into your team’s sales conversations for pre-coaching prep?

Our AI-powered sales highlights give you the most actionable metrics based on their analysis of your sales transcripts. 


Wingman: Team call log

Now that you’ve been through most result-driven coaching models and dos and don’ts of SaaS sales coaching - you can leverage this SaaS sales coaching cheat sheet to coach your sales reps to be super-salesmen!

Have Wingman by your side!


Real-time sales coaching software that helps your team win deals with confidence

Book a Demo
In this article

Liked this article?

Subscribe to our newsletter and stay up to date.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

Related articles