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From Sales Strategy to Mastering the Sales Pipeline to the 
Production Plan

Changes in strategy, go to market, sales coverage, revenue 
engine performance and sales productivity require defining and 
aligning the underlying performance measures that drive 
execution.

The Revenue Engine: Revenue is maximized when demand 
is optimized across the Demand Waterfall and through the 
Buyer-Aligned Sales Process and Customer Lifecycle

Sales Performance levers That Drive Results:  Four key 
performance levers enable sales performance modeling and 
predictability:  volume, conversion rate/win rate, deal size and 
cycle time.

More Predictability drives greater sales performance through 
sales motions that are prioritized on higher probabiliity 
opportunities and less on deals that are not ready.

Requires understanding sales pipeline analytics, pipeline 
requirements, pipeline segmentation and stakeholder 
alignment

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Sales Strategy, Market Coverage and the Revenue Engine

Sales Performance Levers That Drive Results

Volume

Conversion Rate

Deal Size

Cycle Time

More Predictability

Mastering the Sales Pipeline 

Pipeline Analytics

Pipeline Requirements

Sales Production Plan

Stakeholder Alignment

Sales Management Process & Cadence

Forecast Management

An Example Putting it all Together

Agenda

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Speakers

Robert Muñoz

Research Director, Sales Operations 

Strategies

Forrester|SiriusDecisions

Jim Eberlin

Chief Executive Officer

TopOPPS


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Sales Strategy to Sales Coverage

Changes continually happen throughout an organization and those changes should be associated 
with strategies for how an organization chooses to grow.  Growth strategies can take different 
forms:

Entering new markets

Going after new buyers or new buyer personas within existing markets 

Going after new offers with the introduction of new products.

Maybe by Acquiring another company

Leveraging technology that enables a better solution or buyer experience.

These are all valid ways to grow an organization and that growth needs to be associated with 
sales coverage.  Sales coverage can be in the form of:

Having all the different sales roles covered, whether it’s a hunter/farmer, a hybrid of 
inside/outside reps, or direct and indirect channel sales

Accounting for the coverage and the level of specialization each rep is going to have and 
whether it’s an inside sales rep or a BDR that hands off to a field rep and a field rep that 
hands off to a customer success manager.  

What sales engagement looks like.  Will it be face to face or over the phone, etc. 

How much do we expect that our sellers are going to self generate in terms of pipeline 
versus how much is going to be provided through marketing, telemarketing, channels, etc.

The sales process impacts the ease or difficulty by which sales reps work opportunities 
from early stage, all the way through to closed

In summary, sales strategy needs to be insync with a sales coverage 

model to take advantage of the strategy.


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The Revenue Engine

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The  end  to  end  revenue  engine  begins  with  demand,  works  through  the  sales  process  and 
includes ensuring customer success after the sale for year over year renewal.  

Generating demand is independent of whether it’s inbound or outbound via tele prospecting or 
from targeting specific accounts.  It includes how marketing engages with leads and qualifies 
them to a certain point when they are ready for sales to engage them. Once they are qualified, 
sales will develop and work them through to close-won. Now, they become a customer and we 
manage that customer experience, trying to, develop them and certainly retain that customer and 
hopefully continue to cross sell and upsell those accounts.

This is the full revenue engine.  Any strategy that grows the business should be focused on trying 
to maximize the revenue engine end to end and not one particular segment.

This guidebook focuses on the opportunity side of the revenue engine once that demand is 
converted to an opportunity.  It focuses on:

The revenue engine from opportunity to “close-won”

How to be successful managing this portion of the sales revenue engine

Managing the sales pipeline to improving the performance of the revenue engine

How to plan and be successful in managing the pipeline to support the longer term 
multi-quarter production plan.


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Sales Performance Levers That Drive Results

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When thinking about sales performance and improving the performance of the revenue engine, 
there’s four key levers that need to be understood and managed. 

These are four core metrics that are really foundational  to understanding for any sales 
pipeline.  There are others metrics less foundational that AI is able to leverage to provide many 
additional insights, but for setting sales leadership up for success, these four metrics are key. 

These four core metrics need to be measured across a number of different categories and market 
segments, both on a historic basis and on a proforma basis to model future sales and make sales 
more predictable.  Examples of other categories to measure these metrics include:

By sales rep, sales manager and sales hierarchy - to understand variances in sales rep 
performance

Seasonality – to understand how the drivers are impacted by the sales cycle over time

Demand source – to understand the differences when opportunities are sourced by sales, 
marketing, partner channel, sales development reps, etc.

Industry - to understand the differences across different industries

Prospect size - to understand differences across Enterprise sales, mid-market sales and 
SMB

Sales type - breaking down sales by New, Cross-sell/Upsell and renewal

The first metric to focus on is volume.  This identifies how much is needed at each stage in your in your 
pipeline in your demand waterfall. This tracks the number of leads, and the number of opportunities.  All 
things being equal, more is better.  There is a minimum volume required. 


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The second metric to focus on is conversion rate.  How are the leads converting to opportunities, 
and how are the opportunities converting to “close-won”.  Win rate is a form of a conversion rate.  
Conversion rate also measures how efficient opportunities are getting converted from sales stage 
one to sales stage two and from sales stage two to stage three, and so on. Conversion rate is one 
of those key metrics to use to fine tune the revenue engine to ensure it is performing the best as  
possibly.

The third metric is deal size.  It identifies the average size of a lead or an opportunity that is won.  
It is important to track it for both new deals, as well as growth.or expansion and cross sell upsell 
type deals. 

The fourth core metric is cycle time. It identifies how long it take for an opportunity to move from 
the moment it enters that pipeline to when it is closed.  All things being equal, if we can reduce the 
cycle time we can bring a customer on board sooner we can recognize revenue quicker we can 
free up the rep to go pursue another deal.  From that standpoint cycle time is a metric that we 
want to be smaller as opposed to larger.  

These four core metrics need to be measured across a number of different categories and market 
segments, both on a historic basis and on a proforma basis to model future sales and make sales 
more predictable.  Examples of other categories to measure are the same as those listed on the 
previous page.

These are four core metrics that are really foundational  to understanding any 

sales pipeline.

Sales Performance Levers That Drive Results


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Another Key Driver of Sales Performance is Predictability

In addition to the strategies we employ to grow sales, the processes and organization structure 
we put in place to manage coverage, and the four key levers that drive results, sales teams 
must to focus on the motions that sales reps take to prioritize their actions on specific sales 
opportunities that have a higher probably of closing. 

Sales Reps need to spend less time on: trying to close deals that are not ready; or pull-in deals 
from other periods due to short-falls in this period.  It is important not to waste motions trying to 
pull in deals and take a hit from discounting or doing other unnatural things to close opportunities.  
Part of having a predictable outcome is minimizing the actions that result in giving away margin.

Having more predictable outcomes is being able to minimize actions by having adequate pipeline.

Production planning of sales is not just about the current month or current quarter’s sales pipeline. 
It  is  about  looking  out  four  quarters  to  insure  a  constant  stream  of  new  opportunities  filling  the 
sales pipeline.  It is about knowing what an adequate pipeline is and creating it proactively on a 
regular basis.  It is also about understand the segmentation of the pipeline and key metrics that 
drive  results  so  adequate  bookings  close  on  a  regular  basis.    Predictability  comes  first  from 
having adequate pipeline volume, and second having forecast predictability. 

Sales pipeline predictability is driven out of data.  It is important not to burden the sales reps to 
input that data.  That is yesterday’s paradigm.  The data needs to be automatically captured, as 
much as possible.  Where it is not possible, it needs to be as efficient and streamlined..

Opportunity  predictability  prioritizes  those  opportunities  most  likely  to  close  based  on  some 
predictive opportunity score that signals a high likelihood of closing the opportunity in the current 
period.  Opportunity predictability can be aided by guidance in terms of what are the actions that 
advance the deal to the next stage and potentially be able to close the deal that much sooner.


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Elements That Drive Pipeline Predictability

The following four elements drive pipeline predictability:

The first step to master the pipeline is to understand your pipeline and the four key foundational 
metrics: win rate, cycle times, new vs existing opportunities and demand mix.  The first step is to 
go back through history and understand your analytics, where you been, what’s been the 
performance. It is important to understand the metrics like win rate and cycle time across your 
pipeline segmentation.   Examples include: new vs existing sales pipeline and how much of the 
mix of the pipeline was generated by marketing or other sources versus self generated by reps, 
etc.

Once there is a  historic basis of past results you have the necessary information to begin to 
define the goals for your sales team and what is required in terms of pipeline size to hit those 
goals.  Once there is an understanding of history a production plan can be built, starting with how 
much pipeline is needed and how to generate it for each month.

Managing the pipeline is about clarity on how to move opportunities from one stage to the next 
stage as effectively as possible.  It is about leveraging the intelligence and having guided next 
best actions for reps that will help to prioritize the deals.  It is also about having a regular cadence 
of the deal reviews.

Once these first three items are in motion you are able to deliver the forecast with a high degree 
of accuracy.  From these first three steps you understand how much pipeline you need and the 
pipeline coverage so you can more consistently deliver on the targeted number.  

In addition to these three previous steps, it is important to have a consistent forecast process 
along with predictive capability that uses the data and applies the signals we may or may not see.  
The predictive process is able to correlate the signals to outcomes and create a very informed 
forecast process. 


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Digging Deeper into 4 Elements for Mastering the Pipeline

The first step is to understand the sales pipeline along a number of different segments, but none 
are more important than understanding it along three core buckets: 

The portion of the sales pipeline that net new business, net new customers

The portion of the pipeline that is expansion of within existing customers 

The portion of the business that is renewal of existing customers 

Additional Market Segments
Beyond  these  core  buckets  you  may  want  to  also  understand  how  it  breaks  down  between 
enterprise accounts, mid market accounts and small accounts.  The reason and determination of 
which  segments  to  monitor  is  dependent  on  those  segments  that  have  different  sales  cycles.  
Some  segments  will  have  higher  or  lower  win  rates  or  different  deal  sizes  or  cycle  times.    It  is 
important  to  break  them  out  in  each  category  to  have  realistic  multipliers  for  each  to  determine 
pipeline requirements, sales coverage and the sales forecast.

The  image  on  the  following  page  provides  an  example.    There  are  three  target  categories  of 
pipeline  opportunities  to  understand  as  well  as  understanding  how  much  of  that  pipeline  is  self 
generated  by  sales  reps  versus  how  much  is  from  marketing,  your  SDR  team  or  sales  channel 
partners.  Next apply the historic average deal size, win rate and cycle times appropriate for each 
segment.    While  collecting  this  information  may  seem  daunting,  the  best  practice  is  to  go  back 
through  sales  pipeline  history  and  analyze  it  to  understand  what  history  looks  like.    Some 
technologies are able to answer this just by syncing with your CRM system.  This is the first step 
to mastering the sales pipeline.  

The image on the next page shows what it looks like.

The best practice is to go back through pipeline history and analyze these 

four key metrics by your sales pipeline segmentation:  new, cross sell/upsell, 

renewal; and enterprise, midsize companies, small companies.


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Digging Deeper into 4 Elements for Mastering the Pipeline

The second step, is to define the pipeline requirements for each month of the fiscal year.  This 
needs to define how much is needed to be created each month vs how much is needed to close 
each month.  The “how much” is broken into each of the different market segments.  The example 
shows the breakdown by, New, Cross-sell/Upsell and Renewal.

Knowing “how much” by segment by month/quarter is required to manage the pipeline.  Without it 
you  will  start  to  “make  deals”  at  the  end  of  the  sales  period  if  your  pipeline  started  up  short  of 
these targets and you will undoubtedly give up margin to create those sales.

If  you  were  doing  this  manually  in  Excel  you  could  have  just  one  combined  view  of  the  total 
pipeline, but it is much more powerful and actionable when you understand what is working and 
areas in the sales pipeline where you may be coming up short.

At this point we have defined the pipeline goals for each sales period for both to be created and to 
be closed in the period.


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Digging Deeper into 4 Elements for Mastering the Pipeline

The  best  way  to  interpret  this  graph  is  to  assume  a  win  rate.    In  this  example  assume  30%.  
Then you could read up from 30% to understand the target pipeline size for the beginning of the 
sales  period.   As  an  example,  the  target  pipeline  needed  for  the  first  month  of  the  quarter  is 
about 1.33 times your bookings goal for month 1.  It is 2.43 your bookings goal in month 2 and 
3.33  your  booking  goal  for  month  3.    The  multiplier  is  increasing  because  of  the  sales  cycles 
within the quarter.  

Before we leave this topic it is important to define the calculation for sales pipeline size.  

To calculate the pipeline size for New & Cross-sell/Upsell market requires we first calculate the 
pipeline size factor as:

Once that is calculated we can calculate the required sales pipeline needed as:

The renewal pipeline requirements is calculated as: 

When  you  start  to  think  of  the  variable  nature  of  average  win  rate  across  periods  and  due  to 
seasonality in comparison to your pipeline size needed you start to see a graph like this: 


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Improving Forecast Accuracy & Reducing Sales Effort

Interestingly,  the  multiplier  varies  depending  on  your  average  win  rate  and  your  cycle  times.  
Many times we think 3x or 4x pipeline needed for the quarter but it really varies across months 
within the quarter.

Because  of  the  variable  nature  of  the  factors  to  calculate  the  required  sales  pipeline,  it  is 
important  to  have  a  tool  to  calculate  it.    The  levels  of  detail  can  get  overwhelming  and  error 
prone if using Excel.

Here  is  what  the  pipeline  size  requirements  look  like  for  both  the  closed  pipeline  and  for  the 
newly created sales pipeline.

The above image shows both the size of the pipeline that is need to close and the size pipeline 
needed at the beginning of each month so there is adequate pipeline to hit the bookings target.   
From these to numbers you can calculate how much needs to be created given your current sales 
pipeline.  This allows the creation of pipeline in advance when it is needed.  

It is important to have a view that represents a production plan that for every month of the year, 
ideally, broken down by new, expansion and renewal pipeline.  This tells you how much of the 
current goal is covered by my current pipeline and how much of my goal is based on what needs 
to created.  This identifies one perspective of the the risk in the plan.  

Understanding the pipeline needed on day one of each month is about teeing up the sales period 
for success.  The pipeline will change and pipeline requirements will change as you work through 
each sales period over the year and this is where predictive forecasting helps fine tune your 
needs and recalculate your forecast.  The monthly pipeline requirements are all about setting up 
to have adequate pipeline in the first place.

The following page shows a sample of a detailed sales production plan: 

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Improving Forecast Accuracy & Reducing Sales Effort

The following diagram below is 

representative of what you want to be able to do to have you set up 

for  increase the likelihood of you being able to not only be have a high degree of forecast 
accuracy to deliver your number but have enough pipeline. So your sales teams aren’t doing all 
sorts of unnatural things.

.

This information is very helpful to understand how sales is tracking tracking under 
or over monthly targets.  If there is a consistent tracking over or under it is the time 
to  reset your pipeline expectations for the team.


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While sales operations needs to be aligned on coverage, it also needs to be aligned with HR and 
sales enablement on the hiring and ramp up of new reps.

The  third  area  to  align  on  how  much  pipeline  is  to  be  delivered  by  the  demand  sources  like 
marketing  and  channels.    It  is  important  that  everyone  understands  their  commitment.  It  is  a  lot 
harder for a rep to deliver pipeline.  It takes a lot more energy and time for them to develop their 
entire pipeline versus having 30% – 50% sourced for them.

Lastly it is important to align on sales reps goals and quotas, including factoring in the number of 
accounts  in  their  territories,  the  mix  of  new  versus  expansion  on  existing  accounts  and  the 
number of opportunities they can successfully manage.  Well qualified leads shouldn’t be ignored 
because the sales rep is tied up with more qualified leads.

Stakeholder Alignment

The last thing to call out, assuming the sales pipeline is mastered and the production plan is built, 
is to have alignment across stakeholders.  Categories to align on include:

Seasonality

Headcount

Demand Source 

FLM/Rep Pipeline Goals

It  is  important  to  align  with  the  finance  and  marketing  on  the  seasonality  of  revenue  by  month.  
There  is  typically  seasonality  within  sales  periods  and  from  sales  period  to  sales  period.    Sales 
may build early in the year, then it slacks off and builds again at a higher rate from September to 
December.  It is important to understand that seasonality when building the plan.

It is also important to align the number of full time equivalents needed to support the sales plan.  
Delivering on the right amount of sales pipeline is wasted if the necessary headcount isn’t in place 
to close the opportunities.  As an example, if the fourth quarter is your big quarter, it is important  
be  staffed  appropriately  to  drive  demand  and  closed  deals.   Things  need  to  be  factored  in    like 
attrition rate as well as adequate time to fill open positions and ramp up new reps.


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A foundation of sales management is the establishment of sales stages to measure sales process 
along  the  way  from  prospect  to  “close-won”.    It  is  important  that  sales  stages  in  your  CRM  are 
aligned  to  the  way  buyers  buy.    Maybe  its  six  sales  stages.  Maybe  it’s  only  five  sales  stages, 
stages vary from company to company, but the key is:

The sales process and sales pipeline is divided into stages

The sales stages align with the buyer’s buying process.  

Healthy opportunities moves from one stage to the next, to the next until they close.

Opportunities should not show up in the pipeline today and have nothing happen to them for three 
months and then all of a sudden they magically appears closed one right. That’s not the behavior 
of a healthy pipeline and that’s not the path to predictable performance.  It is important to ensure 
that that pipeline is being managed appropriately.  The diagram below identifies a healthy sales 
management process and cadence:

Sales Management Process and Cadence

A key to ensuring a healthy sales management process is to have a regular sales management 
cadence for managing opportunities. That cadence may be a weekly or bi-weekly tactical meeting 
between the sales rep and sales manager to review the sales pipeline and individual 
opportunities.  The purpose is to understand top deals and assess rep performance. It may also 
include the forecasts roll up. A predictive forecasting solution can really aid this process. 

It’s also helpful to stagger some meetings on a monthly basis by having a slightly different focus in 
addition to the forecast.  The focus may include understanding key trends or or major gaps that 
appear on a monthly basis.  

The last management process cycle is the Quarterly Business Reviews[QBR]. That is a quarterly 
review where sales reps and sales teams analyze their strategic accounts to understand the 
outlook for the current and next quarters.  It should also include a strategic look at the sales 
approach, what is working, what is not and  looking at the performance of the territory and 
accounts as a whole. 


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Once a company has completed the first three steps toward mastering the sales pipeline they can 
focus on forecast management.  For this step it is important to consider using a tool that gives you 
a  forward  looking  predictive  projection  of  your  sales  and  supports  the  best  practice  sales 
processes.    That  tool  should  help  guide  the  sales  by  prioritizing  those  deals  that  have  higher 
likelihood  to  close.    That  puts  sales  managers,  sales  reps  and  sales  teams  in  a  much  better 
position to deliver on the target with a high level of accuracy. 

Forecast Management

Generally, forecast accuracy has been associated with the four outer circles in the diagram above:  
Opportunity Amount, Sales Stage, Forecast Category and Close Date.  It has been about the 
dollar amount of the opportunity, sales stage of the opportunity as either an early, mid or late 
stage opportunity.  Then merging into the opportunity and the forecast category,  is it a commit or 
upside, and what is the close date.  These are four things that have historically always driven 
forecasts and they are still relevant.  

What is new and key is the ability to include activity data.  Activity data influences predictability 
and forecast accuracy by interpreting the activity.  As an example, an account with a higher level 
of activity can be said to have a higher level of engagement and that could generate much better 
outcome.  Sales activity needs to be both quantitative, how many and qualitative, what was said.

Predictive forecast solution can improve your ability to interpret this information and deliver on 
your number in a much more meaningful way.


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The following is an example of what a production planning solution looks like using 

TopOPPS

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Putting it all Together

The screen we are viewing is is for Chris Cross a Sales VP.      This actual and forecast 
information represents totals for her team.  Market segmentation was one of the key points of the 
presentation and this screen can be filtered by multiple market segments.  Here we are filtering by 
sales rep hierarchy, but it could also be filtered by territory hierarchy, sales process, company size 
or any of the other opportunity attributes and market segmentation being tracked by the system.

To understand this screen, first divide it in half.  The bottom half of the screen       gives an 
understanding of past closed sales periods.  The top half of the screen,       starts with the most 
recent closed sales period (actual) and then projects out the next four sales periods.

The top half of the screen is where the forecast is managed:

Quota is the target

AI Projection/Actual      is the actual results for the first column and the AI projection for the 
future periods.

Category pipeline     is a perspective of what is in the category pipeline (Commit, upside, 
best case, etc).  The user can filter which categories to include in the pipeline

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Putting it all Together

Stage Pipeline       is what is in the staged pipeline, the user can select which stages to 
include in this row.

These four rows give the user a series of different perspectives on the sales pipeline and how it 
relates to the quota.

The next two rows focus on the sales pipeline coverage      .  The first shows what is required to 
hit future sales targets.  The second is the current actual coverage, so you can compare where 
you are at to where you need to be.  

The last row shows the current forecast called by the sales team        (sales rep/sales 
manager/sales leader depending on sales hierarchy filters applied).

The sales production plan goes beyond managing the sales pipeline to hit the 

current sales period target, it focuses on future sales periods to ensures you are 

building enough sales pipeline to hit the next four sales period targets.

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Hear from guest speaker Robert Munoz, Research Director, Sales Operations Strategies at Forester/SiriusDecisions to learn how artificial intelligence is taking the pain out of the sales process, not just by predictive forecasts but by improving sales productivity with AI assisted capabilities to help you the data and opportunities up-to-date.