<img src="https://ws.zoominfo.com/pixel/4z2e82sWyhmveGlCzuJa" width="1" height="1" style="display: none;">
Untitled presentation (1)

Best Practices for B2B Sales - Proactive Follow Up & Content Delivery

Authored by Ric Ratkowski on June 17, 2020

This blog provides more details into the next two of the six tactical best practices outlined in the blog “Best Practices for B2B Sales - Sales Pipeline”.  It focuses on:

  • Proactive follow up on opportunities in the sales pipeline
  • Proactive delivery of the right sales content and insights to members of the buying team and guidance to the sales team

It may feel like these two best practices could be consolidated into one called proactive selling. Both could be handled via alerting and prompting solutions or optimized with a process we call “Alerts Requiring Action”.    However, there are subtle differences between the two that make a big impact on sales. 

Proactive follow up is compliance based, it removes sales operations from the role of compliance police.  It helps insure the accuracy of the information in the CRM.  In many companies it may just be a report sent around with the note “Fix This.”  The challenge is the sales rep either stops what they are doing, figures out which tools to use, and fixes the issue, or they ignore the note and forget about it.  

Proactive delivery of the right sales content and insights is strategic, when coupled with AI it becomes a dynamic guided selling solution.  It helps the sales process become an unfair advantage against the company’s competitors.  It can be thought of as a digital playbook.

Proactive Follow Up

Proactive follow up helps maintain a clean pipeline and is a process for managing sales pipeline hygiene and making clear what is real in the pipeline.  It focuses on good practices that should be followed to keep all opportunities in your pipeline “clean”.  It includes clean up alerts like:  close date in the past; no next steps in place; close date not realistic; lead source not set, etc.  It also includes “at-risk” alerts like:  late stage opp - no meeting set; last email from prospect is negative and deal in commit; opportunity sponsor left; no decision maker on buying team, etc.

Generally underlying issues with pipeline accuracy and validity are usually less about technology and more about human behavior, i.e. getting the sales reps to update the opportunities.  By using AI driven alerts and prompts it helps the sales reps stay on top of what needs to be done.  By extending the alerts to “Alerts Requiring Action” it helps save sales rep time by resolving the alert from within the alert itself.

The following table breaks down the problem/business need and best practice summaries related to proactive follow up.  


Proactive follow up on opportunities in the sales pipeline


The best sales people make sure they are continuously following up with the buying team of their sales opportunities but the process isn’t easy.  Buying teams can have 3 - 10 people evaluating the product all with different perspectives, needs and neediness.  It is hard to keep it organized without a system to remind them to take action when appropriate.

Proactive follow up is part of a sales pipeline data cleansing process.  It insures the opportunities are up-to-date.  Ideally the data capture on emails, meetings, and meeting content is already automated as described in the blog posts from February 11th to March 23rd

Problem/Business Need

A key challenge in B-to-B sales is when the sales pipeline doesn’t reflect reality.  It is important that everything in the sales pipeline is always up-to-date so at any point in time it is easy to understand what is “real” in the sales pipeline, what are the “next steps” on every opportunity, and which opportunities are most likely to close in this sales period.  Without this information, the weekly Sales Rep and Sales Manager one-on-one calls become an interrogation rather than a strategy session and the sales forecast is based more on wish than reality.

When you start to evaluate reasons for a lack of quality in the sales pipeline it is because:

  • There are untouched or inactive deals that have neither advanced nor had recent activity.  
  • Stalled deals have remained in a sales stage for longer than typical for close-won deals
  • Deals have continually been pushed out sales period after sales period

Prompting the sales rep to update these compliance items will help remove the zombies in your sales pipeline.  

Successful sales is all about follow-up and managing key aspects and attributes of the sales opportunity.  Examples of key aspects of the sales process that needs to be continually monitored include:

  • Following up with every member of the buying team to educate them on “state of the art” and to overcome any issues/questions they may have.  Forgetting to follow up, or following up late is a good way to lose an opportunity.  
  • Making sure every opportunity has a sponsor at a decision making level
  • Identifying when key opportunity milestones are accomplished and the opportunity is being reflected in the right sales stage..  


The initial requirement is to prompt the sales rep, when appropriate to complete any or all sales pipeline hygiene items.  The requirement is extended to not just prompt them, but from within the prompt give them the opportunity to fix the problem.  If the projected close date is in the past, let them update it, if the sales stage needs to be moved up or back, let them up-date-it.

The need is to:

The need is to monitor all key compliance characteristics of a sales opportunity and prompt the sales rep to update them when appropriate.  Examples of things to check include:

  • Account Executive Clean Up Alerts
    • Opportunity in the pipeline with no meeting set in X days
    • Close date in the past
    • Current buying team doesn’t have buying power
    • Opportunity has no incoming correspondence in the last X days
    • Opportunity has pushed multiple times with no activity
    • Rep forecast not set 
    • Move close date out, not enough activity deal will not close this quarter
    • Meeting scheduled with no summary afterwards
    • Lead source not set
    • Close date not realistic move close date out x days
    • Close Lost does not have a reason
    • No contacts associated with the opportunity, ACTION: enter buying team
  • AT-Risk Alerts
    • Late Stage Opp - No meeting scheduled or account activity in last X days
    • Renewal customer with no communication
    • Last email from prospect is negative and deal in commit
    • Opportunity sponsor left, no decision maker on buying team





Sales reps update their SFA application manually, on a best efforts basis, when sales compliance items change and need updating.

Sales Operations is the compliance police and sends out emails asking sales reps to update certain fields based on things they catch when reviewing the sales pipeline.

Rules are coded in the CRM application to set flags that can be used in reports to identify settings that need updating.  Sales Operations sends out weekly reports to sales reps asking them to “Fix This”. 

A system that has a prompting/alerting mechanism designed to alert the sales reps on a continual basis of data items out of compliance and allowing them to make the changes from within the alert..

The Baseline is what currently happens in most companies.  In most companies, the sales pipeline is not regularly updated.

At the Good level, sales operations takes on the responsibility of prompting the sales reps to keep the sales opportunities up to date as it relates to opportunity compliance items.  The challenge is this is a fragile and tedious process during sales operations busy time these processes are often overlooked.

At the Better level, there starts to be a cadence to keeping the sales pipeline clean.  It still relies on the sales reps logging in to the appropriate application in the sales tech stack and updating the appropriate fields.  It also relies on the rules to be coded.  This sets up a fragile infrastructure that needs to be maintained and routinely updated by someone with a strong IT background.

At the Best level, the system is built to support prompting the sales reps, while they are in the application, to update compliance items on their opportunities.  As part of the prompts, the sales reps can take immediate action cleaning up the item.  This prompting and fixing of the problem becomes a daily cadence and the sales pipeline is always up to date with the latest information.  The system includes: pre-configured compliance rules;  company configured compliance rules and AI generated compliance rules based on company sales patterns.  The system also should allow rules to be set at the sales rep level, sales manager level, sales leadership level or company wide level.  

Proactive Delivery of the Right Sales Content

Proactive delivery of the right content to the right buyer persona at the right time is dynamic guided selling.  It is strategic and it extends beyond just content.  It delivers sales insights to the sales rep and sales insights to the sales manager they may not normally pick up on.  It is grounded in the sales cycles of prior close-won, close-lost opportunities.  It is not only designed to help the rep, it is designed to help the buying team understand how your solution can address their needs now and in the future by providing content to educate and inform them on “the current state of the art.”

Ideally your sales process is divided into sales stages.  Each stage includes sales milestones or sub-steps to hit before moving to the next stage and within some of these milestones are inflection points where buyer alignment is key and sales reps must manage through it with content to move the opportunity forward..  Dynamic guided selling is stage, milestone and inflection point aware and uses this as a framework to deliver insights.   

You can think of proactive delivery of content and insights as a digital sales playbook.  Sales playbooks are used in a non-digital world to define what a sales rep does in response to the buyer actions by a specific buyer persona. Playbooks started as a thick three-ring binder that reps consulted prior to a call and when evaluating next steps within an opportunity.  AI and today’s technology can automate and track this via “Alerts Requiring Action.”  These alerts can prescribe what to do and they typically link to content that describes what to say, or training resources or other resources like what to use/who to ask.

The following table breaks down the problem/business need and best practice summaries related to proactive delivery of the right sales content.


Proactive delivery of the right sales content


Providing content helps buyers understand “the current state of the art” and how your product fits into it. It also helps identify obstacles arising that kill the deal.    Content helps reinforce your message and move them past the obstacles.

Each sales stage is made up of milestones.  Milestones help gauge completion of critical steps that indicate the prospect is moving forward in the buying process and on to the next stage.  

Extending the concept of delivering the right content.  Systems today can also deliver sales insights to the sales team about the opportunity.  This isn’t  just delivery of content to the buyer, it could include recommending “in-the-moment” training or recommending performance based training for the sales rep.  It also serves as a benchmark and suggests when it is appropriate to move an opportunity to the next sales stage or back to a prior sales stage.  

Problem/Business Need

Common challenges most sales teams continue to face include:

  • At most companies, no one knows the common characteristics of good sales engagement and when to do what.  There may be a guesstimate of the sales process stages and milestones but it hasn’t been verified and there is no confidence in the process.
  • Also at most companies, no one knows when opportunities hit an inflection point and could easily pivot the buyer journey to close-lost.  Without knowing this, it is difficult to mitigate the threat by recommending appropriate action
  • There is a lack of opportunity management and sales process optimization because it is impossible to see what is going on with a sales opportunity.

The solution is to continuously monitor all opportunities and provide insight to the sales reps on next best action for each of the members of the buying team and help the selling team understand key inflection points in the buying process on an opportunity by opportunity basis.


Deconstruct the manual sales playbooks and integrate the processes via alerts, prompts and insight into the rep workflows.

Continuously monitor all opportunities and provide insight to the sales reps and sales managers on:

  • Next best action for each of the members of the buying team.
  • In-the-moment training for the sales rep
  • Coaching insights based on rep performance and based on specific situations in the sales opportunity  

Continuously monitor for changes in conversion rates, inflection points, and obstacles that require a continuous improvement to the sales process.  (See previous blog post on “Sales Process Review and Improvement” for more information).

The need is to automate:

The need is to automate the monitoring of all sales process characteristics of a sales opportunity and provide alerts, prompts and insights to guide the sales rep on how to handle the situation.  Examples of things to check include:

  • Provide insights and alerts when No Next Steps in place
  • Highlight opportunities with a loss of momentum and recommend next steps which could include:
    • Specific sales assets based on sales stage and milestone status
    • Specific training
    • Putting members of the buying team in a sales cadence or sequence
    • Coaching Video
  • Review Competitive Playbook for Competition Strategy 
  • Critical Inflection Point Send Value Review
  • Need project sponsor
  • Later stage opportunity not in Commit or best case 
  • Opportunity scheduled to close but no next steps/meetings set
  • Need to describe prospect need and pain for this opportunity
  • Milestones achieved, advance the stage
  • No recent emails sent to client, consider adding to a sequence





The strategic action to be taken on a specific opportunity is determined during the one-on-one coaching sessions

Companies leverage the traditional sales playbook to keep up on strategic sales tasks to guide the sales process

Traditional sales playbooks are semi-automated with the use of activity based reporting on events that signify inflection points.  Activities suggested by inflection points are manually completed.

Dynamic Guided Selling tools anticipate the sales process and deliver the right content at the right time, within the natural opportunity management and buyer interaction workflow of sales reps

At the Baseline the strategic actions to be taken are identified weekly during one-on-one coaching sessions.  The challenge is many of the coaching sessions are interrogations by the sales manager of the sales rep to understand the status of the opportunity, leaving little time for strategy discussion. [Spoiler Alert: our next blog will deal with how to eliminate the interrogations by enhancing the reporting/visualization of opportunity details.]

At the Good level, companies use traditional sales playbooks.  It is a step in the right direction, processes are identified and strategic assets are matched up to the sales stages and milestones. The challenge is it is a manual process and when times get busy strategic activities tend to slip through the cracks.

At the Better level, the playbooks are semi-automated through a series of reports and custom triggers set up in the SFA application.  The challenge is the coding is tedious and the solution is fragile when you consider the dynamic nature of the sales process.  It is an evolutionary step to a fully automated system as we describe at the best level.

At the Best level, the sales playbook is fully automated.  It is both manually configurable for outlier instances as well as AI driven to dynamically adjust to changes in the sales process.  It can show up along with the prompting and alerting mechanism for proactive follow-up.  This level of the best practice goes beyond just notifying the sales rep, it also allows them to take action and correct the problem from within the alert, so there is no need to switch to a different system.  The two pictures below provide an example of sales reps prompts and sales coaching insights to guide the sales process.  


The “Alerts Requiring Action” dialog box on the left appears as part of the sales pipeline.  By clicking on the alerts a dialog box is displayed (shown on the right) prompting the user to take action.


The above image is examples of performance based insights generated by AI.  The first insight suggests some Brainshark training to help the sales rep mitigate the issue.

Implementing this solution provides for a measurable, repeatable sales process.  It creates consistency in sales pipeline management and gives all sales reps a consistent plan of attack to follow.

Digital playbooks dynamically change the activities and assets offered to the prospect and are driven by sales activities in the context of sales stage, sales milestone, industry, offering, competitors. Conversely, as a rep moves through the playbook, completing tasks and accessing content, the opportunity record is automatically updated (e.g. moving to the next stage in the sales process), which frees up the sales rep’s time.

Next Blog

My next blog will complete the series of tactical best practices on B2B Sales for the sales pipeline component.  I will drill in on the last two best practices that relate to the sales pipeline that is:

  • Monitor the pipeline from many different perspectives
  • A focus on closing the best leads, nurturing the new leads and “close loss” opportunities as soon as possible

Subscribe to our newsletter!

Lists by Topic

see all

Leverage these best practices with automation and AI driven by TopOPPS

Learn how our customers are winning with artificial intelligence in their CRM:

  • Predictive Sales Forecasting
  • Automated Pipeline Management
  • Significantly More Updates from Reps

Watch Videos

More Recent Posts:

March 26, 2021

Best Practices for B2B Sales - Sales Analytics

The next four blogs focus on best practices related to sales analytics to support an accurate sales forecast.  The previous four best practice blog series of:  Data Access and Enrichment, Sales Pipeline, Sales Opportunity Management and Sales and Sales Management Process set the foundation for accurate, timely, and relevant sales analytics to support the sales forecast.  This is the fifth category of the blog series “Best Practices for B2B Sales Pipeline and Forecast Management started on January 21st of 2020.  The ultimate goal of the analytics is to provide fact-driven information, interpretation and insights  across the four key sales roles: ...

Sales Automation, Sales Operations, AI for Sales, sales best practices, Sales Analytics, Sales Metrics

March 10, 2021

Xactly Acquires TopOPPS to Revolutionize Revenue Operations

Xactly and AI forecasting company TopOPPS set a new standard fordata-driven decision making throughout the Revenue lifecycle SAN JOSE, Calif., March 10, 2021 — Today, Xactly, the leader in revenue intelligence solutions, announces the acquisition of TopOPPS, a company focused on artificial intelligence (AI), sales pipeline management and forecasting. With this strategic acquisition, Xactly is expanding beyond Sales Performance Management to deliver a first-of-its-kind, end-to-end platform for Revenue Operations (RevOps). The combination pairs Xactly’s rich empirical data set and purpose-built AI with TopOPPS’ capabilities in one platform to advance the quality and scope of data-driven decision making throughout the revenue lifecycle. By introducing behavioral data driven forecasting and pipeline management, a new standard of intelligence is redefining revenue performance and shattering status quo thinking. ...

Webinars & events, Sales Process, Artificial Intelligence, Sales Pipeline Management, Xactly Acquires TopOPPS

February 22, 2021

Best Practices for B2B Sales - Quarterly Business Review

This blog focuses on the fourth part of the Sales Management Process, the quarterly business review[QBR].  These meetings are held at the beginning of each quarter and in lieu of the monthly sales strategy meeting discussed in the last blog.  These meetings are an integral part of the sales management cadence described by this blog series..  The QBR meetings are individual presentations by the sales rep.  Each rep is given 30 to 60 minutes to review their performance for the previous quarter and their game plan for the new quarter.  The previous quarter review should include a few opportunity postmortems of both close-won and close-lost opportunities.  The QBR meetings are usually done within the first two weeks of the new quarter and set the stage for hitting the current quarter goals.  ...

sales technology, Sales Process, Sales Tools, Sales Pipeline Management, sales best practices, QBR, Quarterly Business Review

January 15, 2021

Best Practices For B2B Sales - Monthly Strategy Review

This blog focuses on the third part of the Sales Management Process, the monthly strategy review.  These meetings are held on a monthly basis, usually twice a quarter, at the beginning of the months when the quarterly business review[QBR] is not being held.  This is a team call with the sales manager and his/her sales team, plus sales support and marketing.  While it may not be feasible to invite marketing to all the one on one’s and sales forecast calls, they should attend the monthly sales meetings and the QBRs.  This will help align marketing and sales. ...

sales management, Sales Process, best practices, sales best practices

December 14, 2020

Best Practices for B2B Sales - Sales Forecast Call

This blog focuses on the second part of the Sales Management Process, the sales forecast calls.  The last three blogs focused on Sales Coaching and One-on-Ones, the first part of four parts that make up the Sales Management Process.     A Word of Caution Both One-on-Ones and Forecast Calls are weekly meetings, but don’t make your One-on-Ones the forecast call.  One-on-One time is for the sales rep.  This is the sales rep’s  sales development time.  It is your time to help them become  A-players.  The Sales Forecast Call is all  ...

Sales Calls, Sales Forecasts, sales best practices, Sales Forecast Call

November 21, 2020

Best Practices for B2B Sales - Sales Rep Coaching-Performance Reviews

This is a continuation of the previous two blogs on sales rep coaching.  This blog focuses on reviewing the sales rep’s overall performance during a one-on-one.  In a series of weekly one-on-one meetings this topic typically comes up once every four weeks.   ...

sales management, AI for Sales, best practices, sales best practices, Sales coaching, Sales One-On-Ones

October 30, 2020

Best Practices for B2B Sales - Weekly Pipeline/Opportunity Review

This is a continuation of the previous blog on sales rep coaching.  The prior blog reviewed how sales rep coaching fits within the sales management process and outlined best practices related to “call coaching”, one aspect of sales rep coaching.  This blog focuses another aspect of sales rep coaching --  sales pipeline reviews and detail opportunity reviews.  The next blog will focus on the third aspect of sales rep coaching, sales rep performance one-on-ones.   ...

sales management, Sales Process, Sales Pipeline Management, AI for Sales, automated sales rep coaching, sales best practices, Sales coaching

October 16, 2020

Best Practices for B2B Sales - Sales Rep Coaching and One-on-Ones

Sales rep coaching and sales manager/sales rep one-on-ones are the catalyst for sales optimization and sales growth. They are also the tool for increasing the sales rep proficiency and converting C and B quality sales reps to B and A players.  Some supporting research from CSO Insights reveals a correlation between quota attainment and coaching.  The study found the better the sales manager coaching the higher quota attainment.   ...

Sales Executives, Sales Tools, AI for Sales, sales best practices, Sales coaching, Sales One-On-Ones