How to Measure & Increase Sales Effectiveness

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Written by
David Levy

This guide uncovers how to boost sales effectiveness. These insights will help your organization reach the sales excellence needed to stay competitive. 

Companies that drive sales performance year-round have reliable sales systems that make an effective selling foundation.

If you’re looking to boost sales effectiveness, you need to streamline sales efficiently and measure your progress. 

Keep reading to gain practical insights on improving organization-wide selling at each stage of the sales process!

Table of contents:

What Is Sales Effectiveness?

Sales effectiveness refers to how well a salesperson or organization reaches sales KPIs throughout the selling process.

In other words, improved sales effectiveness = winning more deals.

But you can’t improve your sales effectiveness if you don’t know how well your organization is performing.

That’s why having a system in place to measure your sales effectiveness will automatically set you ahead of the pack. 

According to Salesforce’s 3rd Edition State of Sales report, 57% of sales reps expect to miss their quota.

Hitting sales quotas consistently requires evaluating sales effectiveness at each stage of the sales process for needed improvements.

That’s because each stage of a sales process influences the next (and your larger overall outcomes). 

For example, improving your effectiveness on discovery calls will move more prospects to the demo stage, which in turn, will move more to later stages (proof-of-concept, legal/security, negotiation, etc), which leads to a higher average of won deals.

At a more tactical level, let’s say deals are falling through because reps aren’t connecting with decision-makers until too late in the sales process.

Managers can train their account executives to fix this ineffective process by qualifying for decision-makers (DM) early on. That way, the AE can either get the DM involved in the sales process early on, or at the very least, qualify their champion has buy-in from management.

Here’s another example: 

Imagine your lead-to-SQO ratios are low.

Revamping the qualification process in your sales playbook to ensure your reps are asking the right questions to the right personas may be the solution. 

No matter what issues with sales effectiveness you want to improve, you have to measure your business’ performance to identify them. 

Monitoring relevant KPIs (such as the following) give you this crucial insight:

  • Average sales cycle length
  • Revenue
  • Revenue added per sales rep
  • Opportunity-to-win ratio
  • Funnel conversion rates more broadly (i.e. MQL-to-SQO by revenue and count)

Winning deals in today’s fast-paced, hyper-competitive market especially requires one feature inherent in all successful systems: efficiency. 

In fact, sales efficiency accelerates the sales process, which can multiply your wins. 

With that said, let’s concretely distinguish sales effectiveness from sales efficiency, so you know how to leverage this information to better equip your sales team to close deals. 

Sales Effectiveness x Sales Efficiency = Sales Productivity

Sales effectiveness is the ability to reach a sales objective at each stage.

Sales efficiency reflects the speed at which you can reach those sales goals. 

Together, sales effectiveness and sales efficiency generate sales productivity. 

According to a survey, 71% of C-level executives credited their business’ growth to increased sales productivity. 

So does your organization’s sales productivity meet your standard for success?

One way to calculate this is to compare sales productivity with your sales quotas. Take the average revenue per rep in a given timeframe and compare that with the revenue sales quota.

Here’s an example:

A SaaS company generates $450,000 in new revenue in Q2 from a sales team of 5. 

This means the average sales productivity for each salesperson was $90,000. 

You can compare the rate of sales productivity with quotas to calculate whether your reps are hitting or missing quotas, which tells you sales effectiveness and/or efficiency needs to be improved.

What Is Required To Sell Effectively? 10 Essential Elements

Before you focus on optimizing your sales effectiveness across every stage of the sales process, you need to have a squared away sales structure.

Let’s go over 10 essential elements that will help.

1. Sales enablement resources

Sales enablement bridges knowledge gaps and distributes critical sales information (the kind otherwise siloed by top-performing or long-time reps) company-wide.

Enablement resources that result in more effective selling include:

Many of these sales enablement tools should be organized in your sales playbook. 

By consistently improving your sales playbook year-round, you stay ahead of the constantly (and I mean constantly) changing market. 

In fact, according to Hubspot’s Global Sales Enablement Survey, 65% of sales leaders who surpass revenue goals have a dedicated sales enablement team.

2. Thorough training 

Thorough training helps team members retain information over time.

Consistent training allows your organization to speed up the slow ramp-up times that plague so many companies.

Thorough training should accompass the commercial, technological, and competitive domains.

Aircover offers sales enablement tools that help reps access up-to-date sales information so they can clearly understand the latest competitive intel while they are live, in-meeting, with a customer.

3. KPIs

You can’t steer a ship to the right place if you don’t know where you’re headed.

In fact, you might be headed the wrong way. 

That’s why sales KPIs are a must-have in your sales arsenal.

If your CRM shows that over 60% of your reps are on track to miss quota, you can have data-driven discussions with sales leaders about making changes that improve sales effectiveness. 

Ideally, you identify where in the funnel the prospects are falling out. For example, if it’s during your demo phase, that may signal an improvement is needed in discovery. If marketing is sending over a high volume of marketing qualified leads, but AE’s are disqualifying right away, there could be a larger issue around ICP and the leads being brought into the funnel.

Here are some must-do’s when setting and tracking KPI goals:

  • Establish or revisit your sales objective
  • Evaluate your current process
  • Set realistic goals with short and long-term timelines
  • Ensure sales incentives are driving the right behavior
  • Have a collective KPI goal agreement with sales leaders, stakeholders, and C-level executives 
  • Track progress and make tweaks along the way

4. A high-performing team 

A high-performing team naturally results from great training, sales enablement, and realistic KPIs.

You know that your team is performing well when its members:

  • Know the customer
  • Lead with value over features
  • Understand your industry and competitive landscape in an in-depth way 
  • Are clear about the buyer journey
  • Grasp the ins and outs of your product 
  • Are hitting their sales KPIs

Building a high-performing team doesn’t happen overnight.

On the other hand, making daily incremental shifts to the sales team can culminate in drastic improvements by the year’s end.

5. Effective marketing

Marketing brings prospects to your doorstep, but it needs to be effective for your company to gain a satisfying ROI. 

Effective marketing works in tandem with your business objectives to deliver on the KPIs that matter (and move leads through your sales cycle).

Whether your organization runs email campaigns, PPC campaigns, SEO, social media ads, or offline marketing strategies, zeroing in on key metrics will help you identify where to spend your marketing budget for best results. 

Effective marketing also gives your account executives plenty of opportunities to sharpen their sales abilities by driving inbound leads. Ultimately, effective marketing happens with plenty of collaboration with sales, to understand the quality of the leads and if the right ICP is being targeted. 

6. Thorough qualification 

Targeting every company under the sun will hurt your sales efficiency and effectiveness. 

That’s because not everyone is a good fit for your brand. In fact, MarketingSherpa reports that only 27% of B2B leads will truly be qualified to buy from you.

So how do you distinguish a qualified lead from ones that aren’t a match? 

You develop an ideal customer profile (ICP) and create discovery qualification questions that help reps speak with leads who can gain the highest value from the product or service itself. 

Your sales qualification questions should be stored in the sales playbook along with accompanying battlecards.

MEDDPICC, BANT, SPIN, and other sales methodologies can give you a strong framework and a more predictable process to scale across tens, hundreds, or thousands of reps.

When you center your qualification questions around a framework, you can derive more insights throughout the sales process of what is working vs. what is not – ultimately, leading to improved sales efficiency and effectiveness.

7. Building trust 

So how do reps develop trust?

Here are 4 strategies you can use to establish credibility:

  1. Ask great questions - These show the prospect you care about their situation, allowing them to reveal important contextual information you can use to serve them better later in the call or at a different stage in the buying process.
  1. Educate the buyer - This can be through asking great questions, surfacing pain the prospect did not know they had, sharing relevant customer stories to help guide the buyer, industry/market knowledge, etc,, they establish themselves as authorities prospects can turn to for answers. 
  1. Build rapport - People buy from people. Be yourself, add value to your conversations, and always try harder than the rep at your competitor. 
  1. Provide testimonials & case studies - Showing successful customer experiences positively shapes prospects’ perceptions of your product and company. They allow the buyer to envision themselves experiencing a similar outcome. 

8. Great sales mentoring & coaching 

A huge number of sales organizations neglect to coach their teams – citing lack of time – to improve rep performance. 

This is a big mistake.

For one, sales reps are often focused on deals and hitting quota for this quarter, so it's difficult for them to have a long game perspective.  

A lack of long-term coaching can lead to perpetual bad sales habits, missed quotas, and lost opportunities. 

Coaching and enablement doesn’t have to be overly burdensome, especially thanks to technology. Team leads can employ the following multifaceted approach to coaching their reps:

  • One-on-one in-person coaching 
  • Sales meetings 
  • Call recording software
  • Live sales enablement tools, such as Aircover

9. Clear understanding of the customer

You have to understand your audience to sell to it effectively.

This can involve creating an ICP that includes demographics and behavioral data to identify ideal product-market fit.

Your ICP provides focus to all members of the revenue team: marketing to bring leads into the funnel and nurture them, and sales to focus their efforts on the right types of buyers. This is especially important for early-stage sales efforts when you are finding product market-fit. 

Because no matter how creative your GTM strategy or robust your sales enablement tools are, your sales team won’t reach its full potential without deeply understanding your buyer.

10. Repeating what works

There’s no need to recreate the wheel. 

If the systems you rely on work, keep them in place. 

At the same time, look out for unhealthy business patterns that need to be eliminated or tweaked. 

If you use and regularly update a sales playbook and battlecards, you’re already documenting effective strategies (and probably noticing the ones that yield more/less results).

Continue to lean on these resources to improve your sales effectiveness. Additionally, look to be different from the competition, investing in new technologies and processes to drive greater results.

You can take those tools a step further by integrating them with Aircover’s real-time sales enablement tools so reps can access the most effective solutions during calls with prospects. 

How to Measure Sales Effectiveness

Metrics accurately and objectively measure sales effectiveness. That said, watch for these essential sales effectiveness metrics:

  • Average sales cycle length
  • Total revenue
  • Revenue per sales rep
  • Opportunity-to-win ratio
  • Win-rate
  • Sales efficiency ratio
  • Quota attainment average 
  • Average selling price 
  • Competitive win-rate
  • Lead-to-SQO ratio

11 Rules & Tips to Improve Sales Effectiveness

If you want to boost sales effectiveness, you should implement the following practices right away. 

1. Evaluate the current process

Take an inventory of how your sales process looks right now.

Start with your CRM’s pipeline.

When looking at your pipeline, play close attention to where deals are falling and why. Take a look at your win/loss reports to identify trends that may be flying under the radar.

Evaluating your sales process doesn’t just end internally though, it’s also essential to hear what your customers are saying about interactions with your sales team.

You can get that kind of anecdotal information by running customer interviews.

If time or lack of available labor to conduct these interviews is an issue, consider hiring an external firm to survey your customers for you. 

Use this valuable feedback as a starting point for making the right adjustments.

2. Review sales enablement 

Sometimes a company’s sales enablement is so outdated, you can find it on a floppy disk. 

Using ancient sales enablement in a modern marketplace is an enormous obstacle to sales effectiveness. 

The solution?

Gauge when your materials were created to get an idea of how fresh the content is. 

Given the velocity of changes in the market, battlecards covering competitors from even just 6 months ago might be completely irrelevant today.

Is your sales enablement content up to date with your customer wins? 

Is there specific content for each of your ICPs? 

What about information about your product’s use-cases and the vertical market?

Is your team trained up on your latest roadmap?

These are all important questions to keep in mind when reviewing sales enablement relevance.

3. Gauge sales enablement compliance

Sales enablement compliance is sometimes overlooked which can lead to a “leaking bucket phenomenon” where sales value-adds are present but underutilized.

This is why identifying compliance is a perpetual sale effectiveness rule!

Ask these questions to determine the level of sales enablement compliance in your organization:

  • How engaged and active are reps during sales enablement sessions? 
  • Are reps asking questions? 
  • Are reps using sales enablement materials?
  • Which sales enablement materials are reps using before, during, and after calls?

If your reps aren’t using sales enablement resources consistently, it may be time to refresh your team on their benefits. 

Just like customers have to see the value of your product to buy it, your sellers need to see the value of your enablement content to use it.

The best enablement content helps guide buyers through the sales process, overcome objections, or provide information in a digestible format for the rep to use in their next call.

4. Look for sales enablement improvements

When looking to make sales enablement improvements, focus on each resource’s main objective. Then work to make that resource as digestible as possible so reps can get what they need from it quickly.

Here are some questions to keep in mind when making improvements:

  • Are your reps retaining content from training? 
  • Do they have access to the latest competitive intel and product information?
  • What feedback do reps have about their experience with your sales playbook?
  • Is sales enablement digitally accessible? 

Part of the improvement process is swapping or supplementing ineffective sales enablement tools.

If in the past you had to rely on offline coaching meetings to train your sales team, you can adopt Aircover to complement training with in-the-moment information during customer calls.

5. Set KPI goals for the quarter

Ideally, KPIs should be set each quarter and for each stage of the sales process. 

Here are some examples of quarter-based KPI goals:

  • Improve lead-to-SQO rate by 5% in Q3 
  • Shorten average sales cycle length by 7 days in Q4 
  • Shorten lead to opportunity days by 3 in Q1

When setting and tracking KPIs, note edge cases that might spike your metrics up. For example, a deal that sits in your negotiation stage for longer than usual may slightly inflate your average sales cycle.

6. Change approach to sales training 

Yes, it can be daunting to add that “cool” new tool. 

But oftentimes that’s what’s needed to jumpstart more effective training.

My point is this:

Don’t rely exclusively on video training or meetings. 

If you haven’t already, think of adding tools like battlecards, which give reps a more dynamic view of the market and more digestible information. 

Another great way of adding a new dynamic to training is peer-to-peer sales case studies.

Here’s how to do it:

  • Elevate sellers who closed a deal very strategically as well as those who ran a textbook approach to landing a new customer.
  • Then, give them opportunities to present their deal to the broader sales team.

At the end of the day, reps want to learn from the best sellers because that’s where they find the motivation to enhance their performance. 

7. Apply working principles & iterate on gaps

Identify principles that work and apply them to the holes that cause deals to fall through.

Is the competition consistently winning? 

Do you need to qualify leads more effectively? 

Is there a gap in product knowledge?

Look into what competitors are doing to position themselves to win in the marketplace and cross-reference that with your gaps. 

Revisit your ideal customer profile to make sure you’re tailoring the sales process to them specifically. 

Talk to as many customers as you can to learn why they were looking for a solution and why they chose you over other vendors. 

Notice any other trends your research reveals and apply important takeaways to your training and enablement.

Your insights can power your GTM team to create customer personas that inform how you personalize your sales process.

9. Have active sales coaching 

Ongoing sales coaching enforces increased sales effectiveness.

Coaches ask the right questions, review sales calls, give feedback, and set an outstanding example.

The right coaching can even help the lowest performing reps improve and boost sales confidence!

Even though reps tend to sell individually, belonging to a sales organization is a team sport. 

Every rep’s ability to sell at a high level depends on the systems put in place by other people in your business.

10. Ensure sales training is consistent 

Occasional training and one-off reminders about sales enablement tools isn’t going to yield the results you want. 

The key to sales effectiveness is consistency and integrating it directly into the reps’ workflow. 

Reinforce consistent sales enablement practice by taking time during weekly meetings to ask reps about the enablement tools they’re using in calls and why.

There is only so much training you can offer your reps. Compliment your training with tools to reinforce product knowledge, competitive intel, and customer stories that can naturally work within your team’s daily processes.

11. Work collaboratively with the product team 

Synergies between product and sales is critical for success.

Set up a revenue/product sync to collaborate with your product team and brainstorm ways to improve your roadmap. This discussion should be hyper-focused on the customer, their feedback, and features to drive additional value/stickiness/churn prevention within your accounts.

Ideally, you should focus on product requests that:

  • Are causing you to lose deals (i.e. customers selecting the competition because your product/service is lacking something they want/need.)
  • Can add more value to current customers (land and expand)
  • Can help to retain existing customer segments (i.e. make you more sticky)

The market is constantly changing. 

Continuously enhancing your product to meet those changes will significantly help your sales team improve its sales effectiveness. 

Practical Advice to Improve Sales Effectiveness at Every Stage

Take a look at the following tips for the most common 7 stages of the B2B sales process and how you can improve sales effectiveness at each one. 


  • Research prospects before the call to gain the information you can use to build rapport. Refer to ICPs as well for customer patterns.
  • Have a relevant elevator pitch. If it isn’t already, include an elevator pitch in your sales playbook and battlecards.
  • Set an agenda to manage the call.
  • Ask probing questions to uncover pain points and qualify prospects.
  • Clearly set next steps for prospects to follow.


  • Align your demo with the information gathered during discovery. 
  • Rather than showcasing all your product’s features, highlight the ones that specifically fix the pain mentioned in the previous stage.
  • Apply key demo protocols outlined in your sales playbook to keep your meeting on track.
  • If the demo is a recorded video sales call, gain feedback from sales leaders on what to improve. 
  • Make note of questions that come up during the demo questions and apply them to future battlecards.


  • Use a POC if a trial is needed.
  • Put tight guardrails on the scope of the POC (from both a use-case and timing perspective), while ensuring that it solves the buyer's pain. 
  • If there is a large time gap between a demo and a POC, deploy the following tactics to add value:
  • Providing additional product information.
  • Have your product team present the product roadmap. 
  • Invite executive leadership to discuss the vision of the company.
  • Allow customer success leadership to highlight your strong customer support process. 


  • Once you have a verbal “yes” from the prospect, keep the momentum going by kicking off the legal process. 
  • Determine the documents needed to legally secure the sale terms.


  • Similar to legal, this should be done once you’ve received verbal confirmation that there is nothing holding the prospect back.


  • Schedule a meeting with key decision makers to discuss any additional terms.
  • Ideally, you should have presented pricing, ROI calculators, and other tools to align value with buyer pain to help your champion justify the price after a successful POC.


  • Once you reach a deal and process legal documents, begin the onboarding processes.
  • Introduce the buyer to your customer success team, professional services, and/or their technical account manager. Ensure they continue to receive white glove treatment like you showed them during the pre-sales process.

Wrapping Up: Why Sharpening Sales Effectiveness Is Always Ongoing 

At some point, your sales enablement may need an overhaul. 

That might sound intimidating, but making the necessary changes will allow each stage of your sales cycle to shine, leading to better overall sales performance.

If you’re consistently monitoring your sales effectiveness, you’ll be able to catch changes as they’re needed. That will happen frequently — in today’s market, what’s effective right now will be different by next year. 

But the work of refinement is worth it. Lagging behind can stop your business from growing.

Your existing competitors are enhancing their offerings while dozens of new competitors are entering your space, especially in high-growth sectors like Cloud, AI, and Cybersecurity. 

Set your business apart by leveraging AI-powered tools that make your selling more effective.

If you’re ready to see what technology-backed sales enablement can do for your meetings, get early access to Aircover’s sales tools today!