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GUIDEBOOK

How To Create A

Winning Sales Process

Four steps to define and execute 

sales process rigor. 

A Publication of

By Jim Eberlin, Founder & CEO

with bonus 

WORKBOOK!


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Introduction

Author: Jim Eberlin

A sure-fire method to extend the sales cycle, add confusion to the forecast, and lose 
more deals is to have an informal sales process.  Having a B2B sales process that’s too 
simplistic leads to inconsistency and confusion. Imagine if a recipe just listed “add 
ingredients, mix, then heat”. Or a football running play, like the counter, was described as 
“run, fake, handoff”.  You would not have much success in the outcome of either of those 
scenarios.  So, don’t expect much sales growth when you have a few general sales 
stages that lead a lot to the imagination.  Your reps will be all over the place when they 
strategize on next steps, report deal status or provide a forecast.  Your sales process has 
to be well aligned with the activity that goes into a successful sale – that is based on how 
your customers buy.  It should also help in making decisions on next steps and be 
consistently understood by the entire sales team (sales rep, sales ops, sales 
management).

According to CSO Insight’s 2015 Sales Enablement Optimization Study, those companies 
with “unaligned sales processes” deliver conversion rates as low as 8%.  There is also a 
significant negative impact on quota attainment. The difference in quota attainment 
between being unaligned and being mostly or fully aligned is 13%.”

The most successful sales organizations have a process that fits well with the activity 
required to sell more deals.  The entire sales team should understand the critical sales 
stages to move a deal through the pipeline and the exit criteria required to move to the 
next stage.  But what happens when we get new sales people?  Isn’t it hard to keep 
everyone informed on definitions of the sales process?  When to commit a deal to the 
forecast?  And considering that customer behaviors change, doesn’t that just exacerbate 
the problem?  

Enter the new modern automation of machine learning algorithms and predictive 
analytics to simplify alignment and improvement of your best sales activity and give your 
organization the edge it needs to continue sales growth.  So, before you lose any more 
deals, waste good leads or opportunities, extend the sales cycle or on-boarding time of a 
new rep – let’s give your sales process a health check.  The following will help you 
create, tweak or overhaul your sales process so that you can win more deals.


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“Enter the new modern automation of 

machine learning algorithms and 

predictive analytics to simplify 

alignment and improvement of your 

best sales activity and give your 

organization the edge it needs to 

continue sales growth. “


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I. SALES STAGES

Create stages within your sales process.

Your stages are created based on how your buyers behave.  The stages should 
have a clearly defined objective of what needs to be accomplished.  So, the 
starting point is to review your buyer’s journey and create the stages so that it is 
based on how they buy and the activity required for them to make a 
well-informed decision to buy.  

If your product is an evangelical sale, you will educate, ask questions and present 
the product, in that order.  If your product is based on a mature market (RFP-like, 
lots of buyers and sellers), you may ask more questions up front in the process, to 
fit in better rather than educate on changing their process, very different from the 
evangelical sale.  All of the qualifiers, based on your favorite methodology (ex. 
Challenger, Sandler) and your favorite acronym (ex. BANT, ANUM) are placed 
within these stages.  

The number of stages is based on the complexity and sales cycle of the sales 
process.  The simpler and quicker, the fewer stages.  The more complex and 
longer sales model, the more stages you’ll have.  The best way to decide this is to 
review stages in the buyer’s journey based on how you you need to win and how 
they buy.  

Your ideal customer profile (ICP) may affect your stages in the selling process.  
ICP includes things such as market, industry, size and other attributes that may 
affect how you sell to them.  So you may have different stages based on different 
ICP.  It’s also possible the stages remain the same on all of your sales processes 
but the milestones or exit criteria could be different.  It’s important to separate 
your sales processes – especially Enterprise sales vs. SMB sales – because the 
analytics will be different.


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II. STAGE MILESTONES

Define milestones or exit criteria.

Your milestones (also called Exit Criteria) are the activities required to meet the 
objective of the stage.  Once you complete the milestones (or at least the necessary 
ones) you will advance to the next stage.  The tendency will be to add too many 
milestones – so be careful of getting too detailed as you go through your buyer’s 
journey.  

The milestones – definitely early on will be to educate the buyers on why they’d 
want to change and to ask questions based on how best to qualify the buyers 
involved.  The milestones include questions, activities, and content to send at the 
appropriate time.  It also includes plays against competition and the other alternative 
decision of keeping the status quo.

Milestones are necessary because they tell a sales rep the next step in a process 
and they help us understand the status of the deal.  It’s important that you are not 
too rigid – you may have some milestones that are optional based on the scenario.  
Also, because many sales models are more fluid – milestones may not all happen in 
perfect sequence.  

The final stages can be closed won or closed lost.  If Closed lost, you’ll want to have 
categories based on the loss that include:  No-decision, Not a Fit, Competition (with 
name of competitor) or other reasons for a loss.  It’s important to have rules as to 
when to close a deal after so long with no activity.


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III. ANALYZE 

Analyze the sales process and sales team.

Now that the process is consistent and everyone knows where an opportunity 
belongs within stages and milestones – you can analyze the data.  Without a 
rigorous and well understood process, you have no basis to analyze effectiveness 
nor the ability to analyze and coach a sales rep.  This is how you get to an optimized 
process – you analyze, tweak, and coach to get better.

Effectiveness of Process 

The following are metrics to measure the effectiveness of the sales process:

Conversion Ratios – track how well deals advance through the sales process and 
where they get stuck by checking the conversion rate.  This helps in understanding 
what a qualified lead should include, whether the activities within each stage are 
working or if you to change activities to advance deals.  Analyze the trend of 
conversion rates – from close rate to percentage of conversions from one stage to 
the next.  

ASP (Average Selling Price) – track deal size and quantity.  A trending upward ASP is 
a sign of good progress.  Of course, more closes may fill the gap if ASP is not 
increasing.  

Win rates – analyzing two types of win rates will help optimize process effectiveness.  
A “comprehensive win rate” looks at all wins and losses to determine overall wins.  A 
“scheduled to win rate” looks at win rate of all deals that were scheduled to close 
within that sales period which helps understand how well the sales team 
understands how to close within deadlines and how realistic they are.  Win rates can 
identify “Happy Ears” (low scheduled to win rate) and “Sandbagger” behavior (uptick 
of win rate and end of period).   

Sales Cycle times – It is important to analyze how long it takes to close a deal.  But 
it’s just as important to look at how long a sales rep holds onto a deal before it is 
closed lost.  Once again, Happy Ears tendencies causes long sell cycles – these reps 
love to hold onto the hope.  Sandbaggers tend to open and close deals right after 
they close them – for an artificially low sell cycle.  


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Forecast accuracy – ability to create a forecast and analyze the actual results.  Measuring 
ICP and attributes of qualification within opportunities is important because sales reps 
have to be focused on the right kind of deals to hit the number.  

Pipeline activity – Understanding how many new opportunities, open opportunities and 
how often a close date is pushed into the following sales period helps to understand 
how well opportunities are worked and how well a sales rep understands their business.   

Having good pipeline hygiene is important for having good data for this kind of analysis.  
Analyzing by ICP and different opportunity sales model attributes provides a better 
understanding of the different sales processes.  For example, analyzing subscription 
renewals is going to be different than analyzing acquiring new mid-market business.  So 
the separation of sales processes helps.

Coaching Performance of Sales Rep

Coaching sales reps at 1:1 meetings is going to help them get better.  When you can talk 
about where deals get stuck in the sales process and what they may do to advance 
these deals – it’s important to have empirical data to support the conversation.  Having a 
consistent sales process and accurate numbers supports these kinds of 1:1 meetings.  
You can apply the same metrics mentioned above and compare them to peers.  Goals 
can be set at performance planning meetings (ex. Quarterly Business Reviews) and 
managing to them will help reps focus and attain their personal quotas.  


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IV. AUTOMATION 

Enforce and analyze the sales process.

Machine Learning, Predictive/Prescriptive Analytics and Rules: 

Automation should be used to enforce the sales process and to analyze it.  
Automation is available that will prescribe winning activities and guide the best 
behaviors.  This automation always keeps the reps knowing next steps and ensures 
nothing falls through the cracks.  

Analytics should do more than just provide the ability to dig into the numbers.  It 
should be prescriptive and help reps and managers know what to do next.  It should 
keep teams aligned and consistent in their process.  Automation is a huge time saver 
and helps to optimize the sales process.  

Companies that have followed these steps to implement a rigorous and winning 
sales process and that have applied supporting automation have experienced:

1.

Sales Cycle Time Reduction of >38% 

2.

Consistent forecast accuracy to within +5% of hitting the optimized number

3.

Win rate increase of >25% 

4.

Time savings of average 11 hours/week per person

5.

CRM data increases of 400% to provide sufficient and accurate information


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Applying these steps to your sales process will do more than optimize it and help you 
win more deals – it will onboard and ramp up sales reps easier and quicker.  And no 
more reliance on the emotion and qualitative input from the sales team.  That’s important 
but it needs to be combined with quantitative data that has empirical support for the 
forecast.  No more listening to the happy stories around an opportunity nor doubting the 
CRM data accuracy and timeliness.   

To learn more about how TopOPPS can get your team on a consistent sales process 
utilizing predictive and prescriptive analytics, please contact us at 

www.topopps.com

 or 

email at 

info@topopps.com

 

To apply these steps to your sales organization, 

complete the Workbook on following pages.

 

Jim Eberlin is the founder and CEO of TopOPPS. Previous to TopOPPS, Jim founded 
Gainsight, #48 in the Inc 5000, and Host Analytics, the leading solution for finance in the 
cloud. Jim has several years in executive management within the software industry and he 
serves the tech entrepreneurial community by sharing his experience in early through 
growth stage start-ups. 

www.topopps.com

Closing


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WORKBOOK

Sales Process Rigor

A Publication of

Jim Eberlin

Presented at AA-ISP UNITE


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11

Questions: Define Rigor for Your Sales Process

Rigor in your sales process is  going to improve performance – but you have to define rigor.  Ask 
yourself these questions to assess your personal sales process rigor:

1.

 Does the entire team (Management, Sales Ops and Reps) know the definition of each 
Stage?  And when to move the deal to the following stage?

2.

How much subjectivity and/or emotion goes into the judgement of what stage a deal 
belongs?

3.

Does any level of “Happy Ears” or “Sandbagging” occur in your sales process?

4.

How do you communicate these definitions to new sales reps?

5.

How does your management of deals/opportunities affect the sales forecast?  Is it easy to 
translate this information to help predict the forecast?  How effective is it?


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12

Questions: 

Sales Process Rigor Assessment:

1.

Does the sales team know everything that happens in each sales stage?  (Ex. Activity, 
questions, objections, negative responses)

2.

Do you have pre-emptive responses for negative activity or objections?

3.

How do you rank your opportunities?

4.

Do you use any of the data from what happens to the opportunities to help coach the 
sales reps?  To get them performing better?

5.

How well does your current process support your sales forecast?  Prevent surprises at the 
end of the sales process?  Do you rely only on the “happy stories” around a deal to rank it?


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13

Questions

Stages

Define stages – but stick with them so analytics can be applied.  Change milestones (exit criteria) 
within the stages – but don’t change the stages.

1.

What stages do your leads move through?  

2.

When do you promote them to an opportunity?  

3.

How do they move through the sales process post opportunity promotion?


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14

Questions

Exit Criteria (Milestones)

1.

How do you keep management, sales operations and sales reps all aligned on the sales 
process?

2.

How do you know to advance? Or regress an opportunity?

3.

How do you enforce the same consistent work flow for opportunity management?  Have 
you tried and failed before?


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Questions: Deal HealthScore

1.

Do you weigh stages?  How do you deal with large opportunities falling out vs. small ones?  
How accurate is your % weighing (what is the source)?

2.

How do deals fall out?  Do you put a time limit on how long a deal can stay in a certain 
stage?  How do you manage that?

3.

What is your ideal customer profile?  Are there certain roles and company characteristics 
that you track in order to close more deals?


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Questions: Sales Forecasting

1.

How do you apply Forecast categories or commit deals from the opportunities that you’re 
working to the forecast?

2.

How do you know which deals deserve your time?

3.

How many of your later stage deals fall out?

4.

Do you just apply all later stage deals to the forecast?  Or do you scrutinize them more 
before you commit them?  If so, what rules do you use?


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Questions: Metric Driven Coaching

1.

How do you coach sales performance so reps can get better?  Or, if you’re a rep, what metrics 
do you look at and try and beat in order to close more business each sales period?

2.

What metrics drive win rates?

3.

Can you rely on the metrics you look at?

4.

Do you only set bookings goals – or do you look at conversions, how long you hang onto deals 
and pipeline metrics?


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18

Take away – 6 Steps to a Rigorous Sales Process:

1.

Define what I consider a rigorous sales process

2.

How does my customer want to buy and how do I implement that in my sales process?

3.

Score deals – don’t rely on the flawed process of just weighting stages

4.

Add Momentum scores and Ideal Customer profile scores to the progress scores to rank 
deals

5.

Coach from sales process analytics for each sales rep (or reps – analyze your own 
performance)

6.

Use automation to help with admin on opportunities as well as analytics