How to Form a Winning Sales Enablement Tech Stack in 2022

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Written by
David Levy

Sales enablement software makes selling more personal and effective.

Investing in the right tools can increase the ROI across your organization by giving reps access to content that helps them sell confidently and capably.

However, without the proper knowledge, it can be easy to fall into the trap of not investing in the right software for your organization.

Table of contents:

What is Sales Enablement Software?

Sales enablement software are tools sales teams use to directly increase their sales effectiveness.

Sales enablement software gives your sellers:

  1. Tools to level up your sales team at each stage of the sales cycle
  2. A system to manage to manage materials and content that is seamlessly integrated into the sellers workflow

Tools to improve each stage of the sales cycle includes:

  • More efficient prospecting
  • Better discovery and qualification 
  • Improved objection handling
  • Better pre-call prep
  • Closing on next steps
  • Higher converting sales meetings 
  • More effective and dynamic follow-up sequences 
  • Improved sales analysis and decision making 

A system to manage materials and content that is seamlessly integrated into the sellers workflow. Content can then be broken down into 2 parts: 

  1. Sales content for buyers
  2. Internal sales materials (i.e., battlecards, sales playbooks, and objection handling scenarios)

An effective sales enablement tech stack will help improve: 

  • Sales onboarding and ramp time
  • Sales effectiveness
  • Sales efficiency
  • Sales productivity
  • Reporting
  • Communication

5 Reasons to Invest in Sales Enablement Software

“How you sell is more important than what you sell.” — Andy Paul, author of Sell Without Selling Out.  

Sales enablement software streamlines HOW you sell with tools to increase efficiency and results throughout your entire sales cycle. 

Below I’ll go over 5 reasons to invest in sales enablement software.

1. Improve customer experience for prospects

Customers spend 17% more money with a company known for excellent service.

Once a lead enters your pipeline, sales enablement software enhances the customer journey throughout the sales process from beginning to closing. 

Prospects value a relevant and personalized experience — and when they get that, it increases the odds of winning the deal.

In 2021 (and years prior), call recording and transcription software were staples of information gathering for sales reps to not miss a beat in providing prospects the personalized experience they need. 

But in 2022, sales technology has evolved.

Aircover is a sales enablement solution that offers real-time, in-meeting insights to help build relationships and deliver relevant information, resulting in a higher-quality customer experience. 

Aircover lets reps bookmark important moments of a sales meeting where action items are discussed. Those bookmarks can then be shared with the sales team, along with directions on how and when to execute the action.

Aircover also uses AI to auto-detect action items with specific phrases (i.e., “As a next step, can you send me pricing?”) to provide prompt, personalized follow-up.

Automatically tracking action items helps reps prioritize the prospect's needs without missing anything due to human error.

This improves customer experience by ensuring your prospects' needs are met consistently.

2. Improve sales effectiveness across the organization

76% of organizations say that sales enablement has contributed to a boost in sales between 6% and 20%.

Sales enablement software helps reps across your organization by having access to the tools necessary to sell more effectively. At each sales cycle stage, reps can access the right tools, content, and workflows to help them move a deal forward.

Modern sales teams are choosing to supplement traditional, offline sales content with a new form of online dynamic content. This new form of content can be broken down into bite-sized pieces and used in a live customer meeting.

Additionally, sales enablement software can help automate non-revenue generating activities, so your reps can focus more time on higher-ROI activities.

3. Increase scalability

Sales enablement software provides a system to aggregate your sales resources, enabling your sales reps to get up to speed on your sales practices faster.

Modern sales enablement software is contextually aware of the deal and gives information to sellers at the moment when and where they need it most. Historically, this meant delivering content to your CRM, but revenue leaders should no longer settle for that – now there are tools available that can meet sellers where they intersect with their buyer: integrated directly into the meeting platforms themselves.

With the scalability that sales enablement software allows, your organization will have more consistency, which frees up your sales leaders’ time. 

Sales leaders are already stretched thin and asked to do more with less — with modern sales enablement software, they get their time back thanks to:

  • Arming reps with AI sales assistants vs. needing to relisten to every call for insights
  • In-the-moment insights provided by software vs. the sales manager needing to get involved in almost all of their reps’ calls to move the deal forward
  • Improved reporting and analysis
  • Context-based insights on customers

4. Make better data-driven sales decisions

It’s likely that your organization already uses CRM insights to help reps sell more effectively. 

Sales teams now need to marry CRM data with information from other systems such as:

  • Real-time sales enablement platforms
  • Learning management system
  • Sales engagement software
  • Forecasting software

For example, tying an in-meeting sales platform to CRM can help you answer these questions: 

  • Are my discovery questions leading to higher deal values? 
  • Which questions were asked in the meeting before a deal was “closed won” or “closed lost”? 
  • What are the most common action items by sales stage?

5. Winning bigger deals based on selling value

Sales enablement software helps customer-facing teams sell value over features, beat the competition, charge a premium for their product or service, and build a strong brand. 

Use sales enablement software to teach your sales reps to lead with customer stories their buyer can identify with. 

Researchers Dan & Chip Heath found that 63% of people remember stories, but only 5% remember a statistic — because stories touch the emotional part of our brains, making them personal, relatable, and memorable. 

Traditionally reps would be trained on this selling method and find customer stories through a learning management system (LMS). 

But today, sales enablement tools can be used to reinforce and enhance sales story-telling training. 

For example, your sales team could have tools to help with:

  1. In-the-moment reminders to insert a customer story during sales calls.
  2. Having a customer story for each sales script based on customer type, and creating a system that not only stores, it, but can proactively surface it to the rep at the right time.

How to Build the Best Sales Enablement Tech Stack for Your Team

Building a top-notch sales enablement tech stack for your team is essential for success, and following these 6 steps will ensure you’re well informed when you make your choices. 

1. Audit your sales cycle

Begin by analyzing your sales data to pinpoint where your sales cycle needs improvement.  

Audit your sales cycle with these questions in mind:

  • What stages are deals falling off?
  • How close or far are you to monthly/quarterly KPIs?
  • What sales processes or outdated tools should be replaced?
  • What inefficiencies are slowing down the sales cycle?
  • How is one sales stage inefficiency affecting your process as a whole?
  • What is my competitive win rate? Which competitors do we need to get more intel on?

For example, after your audit, you discover a high number of deals evaporating in the “Evaluation” stage. This can result, for example, from limited discovery by the seller.

To fix this problem, in addition to call recording software to relisten to what went wrong, management can implement real-time, in-meeting sales technology to aid the seller live on their discovery calls. In-meeting sales technology will not only help the rep in-the-moment, but it will surface the gaps of where things went wrong for coaching opportunities. 

So, in this case, a new sales enablement software tool (the in-meeting sales platform) was used to fix a sales cycle problem (too many deals falling through during the evaluation phase).

2. Meet with stakeholders & decision-makers

Sales managers need to get feedback on their sales reps' issues.

Once they have their feedback, sales managers have to communicate the points of friction and challenges to the VP of Sales, who should then work with their sales enablement counterparts to fix those challenges. 

Some challenges have simple solutions, like asking better qualification questions. 

Other challenges require more specificity, like training reps to access the right insights at the right time to boost sales effectiveness

The pain points should drive the solution, which drives the enablement process changes or software that’ll be most effective.

3. Map out the sales KPIs that matter most

Figure out your most important metrics that determine sales productivity, then search for the sales enablement tools that can directly improve your numbers.

For example, if too many leads are dropping off in the demo stage, consider software to help reps qualify leads better. 

You could then invest in a real-time, in-meeting sales platform like Aircover to: 

  • Upload the qualification questions that uncover pain points so those questions can appear during meetings.
  • Capture the responses and sync those answers to your CRM
  • Ensure reps personalize their sales presentation based on answers to the qualification questions. 

4. Research & meet with peers at other companies 

Research and talk with your peers at other companies to provide valuable information to help you build your sales enablement tech stack. 

Follow these 3 steps:

  1. Learn everything you can when researching software through websites, articles, and landing pages.
  2. Speak with vendors and experts.
  3. Meet with peers in similar industry roles (ex., If you run sales enablement at a high growth, pre-IPO, Series D company, find an enablement leader with a similar company DNA).

5. Make a list of sales enablement tools

Combine the information you’ve collected to create a list of potential tools for your tech stack.

Along with those tools, include different vendors you’re considering. 

6. Decide on the tools that fit your organization’s needs

Create a “scoring” criteria to help narrow down the best tools. 

Narrow down the most needed based on your budget, organizational needs, and the insight you gleaned from peers at other companies. 

11 Essential Sales Enablement Software for a Winning Sales Tech Stack 

Below are 9 sales enablement technologies that’ll contribute to successful tech stacks in 2022. 

(You can use the information below to fuel your sales enablement research and decision-making.)

1. Real-time sales enablement software (Aircover)

Aircover offers live sales tools, content, and workflows, including:

  • In-meeting battlecards
  • Objection handling automation 
  • Customer stories
  • Action Item tracking
  • Discovery and qualification questions

Aircover is indispensable when onboarding new hires to train them and get them hitting their numbers quickly.

Keep your ramping and experienced sellers up-to-date on the latest messaging and product positioning.

Aircover features & use-cases:

Aircover is driven by technology and the future of work — their features focus on helping every customer-facing role speak in a unified voice around product, strategy, and ecosystem. 

Real-time sales enablement cards Provide reps with in-meeting dynamic content to help personalize their prospect's experience and arm them with vital information to help close more deals. The cards include:

Action Item Tracking & Scheduling — Provide an automated option for tracking action items, with a button for reps to bookmark crucial moments in a call. These action items get collected in-meeting to summarize the next steps, facilitate higher-level buyer communication, and drive deal momentum. All next steps are synced back to your CRM.

At the end of the call, to enforce best sales practices, book your next meeting using Aircover’s scheduler before the current one ends. 

People Insights — Help your team access relationship notes and buyer roles (champion, decision-maker, blocker, etc.). This is shared contextual info that your broader selling team can access, beneficial for SMEs, executives, product management, or other stakeholders who are part of the deal.

Ideal sales stage(s) to use Aircover used: Discovery call, Sales presentation, Sales demo

2. CRM

Customer relationship management (CRM) houses contact information and provides sales and marketing tools to attract and build relationships with access to:

  • sales and marketing automation 
  • Contact database
  • Pipelines 
  • Reporting & analytics 
  • Segmentation 
  • Quote management 
  • Forms
  • Task management 
  • Calendars 
  • Integrations 

CRM helps reps track and manage their deals.

Aircover integrates with your CRM to sync deal and meeting information between the 2 tools — 7 CRMs to consider:

Ideal sales stage(s) to be used: All stages 

3. Data Platforms

Data gathering software arms your SDRs with the ability to collect up-to-date contact information for your target prospects. Contacts can be segmented based on attributes, industry, and behavior for better personalization.

You can expect these features:

  • Data availability 
  • CRM integration 
  • Data cleansing
  • Market insights
  • Lead analysis

2 excellent data gathering tools are:

Ideal sales stage(s) to be used: Prospecting/lead generation

4. Learning management system

Learning management systems facilitate e-learning materials for team members — content can be hosted, managed, and delivered in 1 place to support learning curriculums based on:

  • The user’s role 
  • The products being sold 
  • The industry you’re selling to 

Learning management systems prep your reps to be audible-ready for their calls through sales training and behavior best practices. 

Your learning management system’s value compounds each time team members revisit and get re-certified on learning lessons per cycle (quarterly, yearly, etc.)

Look for these LMS features:

  • Certifications 
  • Course-builder 
  • Content delivery and tracking 
  • Learning paths 
  • Assignments
  • Quizzes 

3 learning management systems available are: 

5. Content management system

Content management systems attempt to centralize all content into one place by allowing you to store files, sales playbook, resources, whitepapers, and presentations that aid sales effectiveness. 

CMSs allow content to be managed, collaborated on, and updated to keep content relevant. It typically will need at least one person tagging and organizing content at all times, and given there are no constraints on the content itself, it can be difficult for sales to find what they are looking for amongst the abundant and  lengthy documents. That being said, if you have at least 1 FTE to manage it, it's a solid alternative to Google Drive.

Store these resources in your CMS:

  • Trainings 
  • Customer profiles 
  • Lead management protocols 
  • Sales methodology 
  • Sales messaging 
  • Sales plays 
  • Sales battlecards 
  • Sales presentations

Look for these CMS features:

  • Content importing 
  • Open APIs to integrate the data to/from other systems
  • Templates 
  • Content storage 
  • Alerts
  • Live presentation 
  • Screenshare
  • Reporting 

CMS examples include: 

6. Sales engagement 

Sales engagement” is using data to track how sellers are interacting with customers throughout the sales cycle.

Sales engagement platforms are tools that simplify this process. 

For instance, reps can create automated sales campaigns, track opens, clicks, and responses.

By adding sales engagement software to your tech stack, sales leaders can more effectively track activity metrics and discern which email copy is garnering the most responses.

Here are the upsides of sales engagement software: 

  • Track buyer engagement to focus on the right buyers
  • Automate repetitive tasks 
  • Sync with CRM
  • Establish an optimal sales cadence
  • Deal management
  • Reporting 

Examples of sales engagement software include:

Ideal sales stage(s) to be used: All sales stages

7. Forecasting

Forecasting tools accurately evaluate your pipeline and draw conclusions based on data.

As sales leaders notice trends in the sales data, they can implement changes to the sales process.

These changes might be direct, such as mentoring reps on needed improvements, or indirect, like updating your sales playbook to sell more effectively to a customer segment.

Forecasting typically happens in 2 ways:

  • Quantitative forecasting — forecast using data and trends (more objective and measurable)
  • Qualitative forecasting — forecast using intuition, expertise, and market research 

Here are 3 benefits of adding forecasting to your sales enablement tech stack:

  1. Accurately predict sales numbers and backward engineer the steps of success
  2. Help give priority to the most important deals 
  3. Increases revenue transparency

Look for these forecasting features:

  • Live sales forecasting 
  • Risk analysis 
  • Opportunity scoring 
  • Data segmentation 
  • Pipeline management 

Here are 2 examples of forecasting software to consider:

Ideal sales stage(s) to be used: Can influence actions at each sales stage. 

8. Outbound calling

Outbound calling automates dialing for your BDR/SDR team. 

The process begins by uploading your lead list into the system, then having it dial contacts back to back.

Automated dialers bring efficiency, especially for big BDR/SDR teams with massive contact lists. 

You can also track KPIs relating to the number of dials made, conversations, and number of booked meetings.

Outbound calling software features should include:

  • Caller ID customization 
  • Reports (number of incoming/outgoing calls, agent performance, call summaries, etc.)
  • Speed dialers 
  • Contact lists 
  • Voicemail drops
  • CRM integration capabilities 
  • Call recording 

Examples include: 

Ideal sales stage(s) to be used: Prospecting/lead generation, follow-up/nurturing

9. Sending platforms

Sending platforms are a marketplace of gifts that sellers can use to engage with their prospects — think of it as a direct mail approach to touchpoints.

Teams often limit themselves to only having “deal-related touchpoints” and forget more casual, personalized approaches. 

Sending merchandise to a prospect can keep you top of mind during your buyers’ busy schedule, and help your brand stand out from your competitors.

So when it comes time for your prospect to make a final buying decision, their buyer-seller relationship is stronger with you. 

Benefits of using sending platforms as part of your sale enablement tech stack include:

  • Automate the data collection, packaging, sending, and tracking of items 
  • Build customer loyalty through differentiation 
  • Personalize the buyer experience

Look for sender platforms features:

  • eGifts
  • Box bundles 
  • Branded merch 
  • CRM integration 
  • Marketing automation  

2 sender platform examples: 

Ideal sales stage(s) to be used: Prospecting/lead generation, nurturing/followup

10. Digital sales room

A digital sales room is a microsite where buyers and sellers can go for all content and engagement related to a deal. With a digital sales room, you no longer need to sift through content and messages scattered across Slack, email, Google Drive, PowerPoint, and the Website. Instead, this is all centrally hosted in a digital location for the buyer and seller to collaborate on.

The digital sales room also provides the sales team with an opportunity to brand the microsite and create a differentiated experience for their buyer. Additionally, there are helpful engagement analytics to help the selling team know which content is the most compelling to their buyers. 

2 digital sales room platform examples: 

Ideal sales stage(s) to be used: end-to-end after the marketing qualified lead becomes a sales accepted lead.

11. Sales compensation

Sales compensation involves everything from territory planning, rolling out the sales plan to your reps, revenue goals, commission tracking, to monitoring, and adjusting throughout the year. To the sales rep, they want to get paid on time and accurately. For RevOps, they are historically juggling complicated spreadsheets with the added stress of unhappy sellers that something is incorrect or late. For finance and the leadership team, they have very little visibility into the burn implications until after the quarter ends.

That is until sales compensation companies came about.

Look to these tools to help simplify and transform the way companies track and pay commissions using intuitive software.

2 sales compensation & performance examples:

A Final Review of Successful Sales Enablement Tech Stack Components 

Your sales enablement tech stacks should be an arsenal of software to drive higher sales numbers. 

Ideally, your tools should cover a wide range of use-cases from reporting, sales optimization, lead generation, and sales training.

Today, top-performing organizations are supplementing offline sales training with real-time, in-meeting support.

In other words, sales teams are now gaining live insights from Aircover in their meetings on the right objection handling, customer stories, competitive intel, and people insights that win deals.

Get early access to game-changing sales enablement software, Aircover, and bring the insights your sales team needs for future success.