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How To Increase Your Win Rate With Data-Driven Sales Coaching

Sales Coaching To Increase Your Win Rate
Training & Coaching

In my last article, I discussed the winning formula for hiring A-Players and how recruitment is the first major challenge of any sales manager/SVP.  The second biggest problem sales manager/SVP face is around coaching. One of the greatest struggles we face on a daily basis is figuring out how to optimize the time we spend coaching reps to ensure it’s as productive as possible and we understand where the gaps are in our team(s) before poor performance becomes a problem for them. By problem, I mean the CEO is breathing down your neck! As a sales manager, you should be spending roughly 40% of your time in productive, tailored and measurable 1-1/group coaching sessions. By the way, pulling one or two random calls or listening to demos side-by-side while on your laptop checking emails is neither productive nor efficient.

As your team/division grows from one or two reps to 50+ reps, without a structured, data-driven approach to coaching you can expect the following three problems as an SVP:

  1. Low morale and high churn of reps who don’t feel valued or developed.
  2. Low win rates and therefore high discounts to drag everything over the line.
  3. Your sales managers constantly in a reactive, stressed, and fire-fighting mental state.  

Trust me, we experienced these problems ourselves during the first 18 months or so at Epos Now, and it massively stunted our growth. When you’re growing 200%+ per year, your people problems are going to compound even more than normal, and, if you’re not providing coaching and development, expect a tough, stressful time as a sales manager/SVP.  

However, after hours of experimenting and hard work, we ended up increasing the win rate (open opportunities to closed won %) of our sales teams by 40% using the following data-driven coaching methodology.  We have taken the below methodology over to the United States and grown the business organically by 1,700% in the first year.

First off, all of your reps and teams should have activity led KPIs in place based on a benchmark of the top performers/ideal performance. Below is an example breakdown of a weekly KPI tracker for the SAAS industry. For the purpose of this exercise I am using an Excel report to show the information; however, all of this data should automatically be available in SFDC. Additionally, your sales process should be intelligent enough to have a click-to-dial technology to automatically log calls and talk-time, have built-in workflows to move opportunities between stages (upgrade to SalesForce Lightning if you haven’t already), record the number of demos automatically, and create dynamic proposals based on products assigned to the opportunity.

Once you’ve got the activity KPIs in place, it’s now time to check in weekly with the rep (preferably first thing on a Monday) to conduct an activity and pipeline review.

We can see from the below results that there are some inconsistencies across the month. Using the training scenarios and checklists below, our sales managers can instantly provide targeted, structured feedback to the rep each week.

Scenario 1: If calls are high, but talk-time is low (See Week 1 as an example)

In the week 1 coaching sessions we would check to see if the rep is:

  1. Calling the lead within 5 minutes
  2. Leaving a voicemail
  3. Sending a ‘Can’t Contact’ email template
  4. Using Google/Social Media to find alternate contact numbers for the lead
  5. Calling the business at the right time based on the industry vertical
  6. Calling the lead more than once a day
  7. Texting the lead
  8. Using a localised State phone number

Scenario 2: If number of demos booked are high but demos completed are low (See Week 2 as an example)

In the week 2 coaching sessions we would listen to a few discovery calls and check to see if the rep is:

  1. Exceeding 70% call quality based on your discovery call scorecard
  2. Sending out a calendar confirmation email while the customer is still on the phone
  3. Making a confirmation call/sending a confirmation email the morning of the demo
  4. Turning up on time for the demo
  5. Getting an alternative number/cell number from the lead contact just in case

Scenario 3: If number of opps generated is low and pipeline amount is high (See Week 3 as an example)

In the week 3 coaching sessions we would check to see if the rep is:

  1. One or two larger deals are skewing figures
  2. Call activity is also low, resulting in lack of discovery calls  
  3. The rep is exceeding 70% call quality based on your discovery call scorecard

Scenario 4: If number of opps generated is high, but pipeline amount is low (See Week 4 as an example)

In the week 4 coaching sessions we would check to see if the rep is:

  1. Has a majority of opps stuck in the Qualification/Discovery/Demo Booked stages
  2. Is qualifying the lead properly – listen to a call stuck in discovery to see if rep is probing the pain points and building urgency
  3. Is sending proposals to every opp they’ve demoed

Scenario 5: If demos completed are high but win rate is low at the end of the month

We would check to see if the rep is:

  1. Asking deeper qualifying questions before beginning the demo to better understand the customer journey. I.E. “How does your current customer journey work?” or “If I could give you a magic wand what would be the three things you’d improve in your business.” This will quickly disqualify prospects who require specialist functionality without getting 20 minutes in and realizing you’re not a good fit for the customer.
  2. Providing options and pricing at the end of the demo and testing for hesitancy by listening to the last 10 minutes of the demo. For more information watch the video on how I do this here:
  3. Setting up a next step (task) in SFDC for a closing call within a day or two of the demo (Think Zero-time Selling)
  4. Checking whether there are any other decision makers involved

Scenario 6: If overall activity numbers are low (at the end of the month)

In the monthly 1-1 we would check to see if the rep is:

  1. Still motivated and desires to be “on the bus.”
  2. Concerned about anything outside of work  

To wrap up, if sales managers/SVP’s can have these types of quality conversations with their reps on a weekly basis it will resolve the three most critical problems I highlighted at the start of the article. It’s never too late to change your coaching processes and up your game. A time commitment combined with a dedication to seeing improvement in your team will undoubtedly lead to managers seeing a drastic, measurable improvement in win rates and decreased churn and stress.


David Duncan

David Duncan is an award-winning VP of sales for the 13th fastest growing Tech company in the UK and fastest growing POS company in the world (all organically funded, no VC!). He's a results-driven sales leader with a proven track record of 156% annual growth for 4 years in the UK before spearheading the US expansion in 2016 with 1,300% organic growth YTD.

Contact David at