Executive Summary
The state of sales training: why it fails, and what works.
Revenue is lagging, and sales leaders are facing questions about growth they can't answer. If you're the CEO or CSO, what will you tell them?
In 2019, the Harvard Business Review reported that organizations spent $359 billion globally on sales training in 2016. Was it worth it? In most cases, businesses did not achieve a high ROI from their sales training investments. The two leading reasons: faulty strategy and faulty execution.
If you don't start with the right sales strategy, you may spend months training your salespeople on the wrong sales plays. And on execution, studies have found that a one-time or short-term training event never works. If you're lucky, one in ten salespeople will improve somewhat, because learners retain almost nothing from a short-term training event.
What works is a customized, robust, and long-term sales enablement program that embeds best practices into your salespeople's muscle memory. It begins with training your frontline sales leaders, the ultimate owners of sales enablement. Then they train, coach, and reinforce your salespeople, not just one time but consistently over time, supported by stage-appropriate marketing content and the right technologies.
Nearly 74% of companies now have a sales enablement function in their organization — 19% year-over-year adoption growth. Having a dedicated sales enablement function correlates with significant business impact.
LinkedIn study
| Metric | Value | Context |
|---|---|---|
| Improvement in customer retention | +9 pts | |
| Improvement in quota attainment | +8 pts | |
| Improvement in win rates | +4 pts |
Aberdeen study
| Metric | Value | Context |
|---|---|---|
| More proposal quotes or RFP responses delivered to prospects | 52% | |
| Higher overall team attainment of sales quota | 32% | |
| More salespeople achieved individual quotas | 24% | |
| Higher lead conversion rates | 23% |
Highpoint study
| Metric | Value | Context |
|---|---|---|
| Increase in win rates | +12 pts | |
| More likely to have high sales rep engagement | 10% | |
| More likely to exceed executive expectations | 2× |
The factors critical to sales enablement success.
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Ideal customer profilesIdentify your buyers’ unique characteristics. The ICP is a foundational, organization-wide function of sales success, driving targeted account list creation, segmentation, and organizational structure. — Gartner
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Buyer personasClarify your buyers' wants and needs. Understanding your ideal customers' buyer persona is crucial for maximizing your sales organization's ROI. — Demand Science
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Data analyticsData and analytics, combined with a personalized approach to sales performance management, are helping sales executives coach their reps on best practices and significantly improve growth. — McKinsey
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Tech stackProgressive CSOs and CROs are aggressively fortifying their sales tech stacks, deploying technologies that cover the entire end-to-end revenue growth process. — Gartner
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Sales playbookA playbook is a roadmap that helps your sales team achieve optimal sales, guiding them with best practices through typical processes and large challenges while reducing new-hire onboarding time. — Bold CEO
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Buyer's journeyToday's buying process is more complex than ever: more stakeholders, more digital interactions, longer cycle times. A buyer's journey map is critical to achieving more effective sales. — Forrester
To achieve their revenue goals, company leaders need to advance sales training from a tactical to a strategic mindset.
| Metric | Value | Context |
|---|---|---|
| of organizations experience higher buyer engagement when they've had sales enablement processes in place for over two years | 48% | Highpoint |
Too often, companies don't have a clear sales strategy. This leads to predictable results. Their salespeople don't perform optimally. Deals are lost. Win rates are low. Opportunities are squandered. In the worst cases, sales training programs can introduce or reinforce bad selling behavior. Bottom line: salespeople won't consistently achieve their revenue goals.
Organizations often assume sales training is the remedy. But sales training is just a tactic. It's not a strategy. An often-quoted 2016 study by ES Research found that between 85% and 90% of sales training programs have no lasting impact after 120 days. In 2019, the Harvard Business Journal asked whether the $359 billion organizations spent globally on training in 2016 was worth it. The conclusion? No.
- 75% of managers were dissatisfied with their company's learning and development function
- 70% of employees said they don't have mastery of the skills needed to do their jobs
- Only 12% of employees applied the new skills to their jobs
How to take a strategic approach
A strategic approach requires sales leaders to step back and view their sales program in its entirety: What are our specific sales challenges? What are our revenue goals, including opportunities and win rates? How well do we understand our ideal customers, including how they buy? What is the root cause holding us back? How are changing market conditions impacting our results? And if we implement sales enablement, how will we know when it’s working? Once you answer these questions, you’ve arrived at a starting point for a strategic sales enablement program aimed at revenue growth.
Done right, sales enablement delivers a clear path forward for opportunities, win rates, and revenue that reaches, or exceeds, the metrics important to your company.
— Dan Bernoske, CEO and Founder
Elevating your sales success to meet a private equity firm's financial vision requires you to put yourself in the mindset of your buyers.
| Metric | Value | Context |
|---|---|---|
| higher win rates experienced by companies whose sales skills training exceeded their expectations | 52.6% | Sales Readiness Group |
When salespeople are not hitting their sales quotas, sales leaders must ask themselves the tough questions: Why aren't we reaching our sales goals? Why aren't my salespeople consistently making their numbers? You can conduct sales analysis, price your products correctly, and deploy the latest technology. But at the end of the day, sales is all about the people who talk to your company's potential buyers. It's all about the salespeople on the frontlines.
Salespeople must understand how your buyers buy
Being in sync with your buyers requires your salespeople to understand them, including how they buy. Then they must be skilled in guiding buyers through the buyers' journey at every step, including the key inflection points and milestones each buyer needs to overcome before they will move toward a sale. Your sales enablement program must include the lessons and modules that teach these specific skills, customized to each company's exact buyers' needs and challenges. That's why cookie-cutter training programs never work.
Build your salespeople's muscle memory
Even a few sales superstars won’t ensure your company consistently reaches its monthly, quarterly, and annual goals. Your entire team needs to move in the same direction, executing at the highest possible level, fully in sync with your buyers’ expectations, with a system in which new hires can ramp up quickly. Every salesperson needs to develop sales muscle memory so your sales program becomes deeply ingrained and predictable.
Sales enablement is the last mile of your growth strategy. Done right, a portfolio company trains and reinforces the skills and behaviors that its salespeople need to consistently perform at a world-class level.
— George de los Reyes, CRO, Managing Partner
To move the sales process forward successfully, salespeople must have access to stage-appropriate marketing materials at every step of the buyer's journey.
| Metric | Value | Context |
|---|---|---|
| of companies are not likely to engage with a seller who reaches out with irrelevant information | 61% |
Buyers and prospects need to move at their own pace, stage by stage, through the buyer's journey. Imagine you've never skied before but want to try it. You walk into a ski shop for the first time. A salesperson rushes up and asks what type of new skis you're looking for: "We just got in the new Rossignol 86 Tis. The titanal construction will give you great stability on black diamond slopes. Which ones do you want to look at?" Intimidated by the sales spiel, you back toward the door and leave, never to return.
Then you try a smaller ski shop. The clerk asks, "Welcome. Have you been skiing long?" "No, I’ve never skied. But I am curious." "It can be a lot of fun. Let’s start with why you want to learn how to ski." You have just been empowered to learn at your own pace. You decide to give this store your business. Lesson learned: be stage appropriate. Meet your buyer where they are in the journey and help them get to where they want to go at their pace, not yours.
Right materials at the right time
There are typically five to seven stages in a B2B buying cycle, from awareness to close, and usually multiple buyers who enter the journey at different stages. Executives are looking for business-case insight to explain the why; the actual users are looking for how-to insight. Without the right marketing support for each stage, you'll handicap your salespeople. Organizations that clearly map their buyer's journey and provide the right stage-appropriate materials set their salespeople up for greater success.
An important aspect of sales that many organizations get wrong is that they don't create stage-appropriate sales materials across the entire buyer's journey.
— Bill Piacitelli, Partner
As sales leaders, it's our job to ensure our sales teams are given what they need to continuously uplevel their skill set. One thing they need is a sales strategy playbook.
| Metric | Value | Context |
|---|---|---|
| in quota attainment when salespeople are better engaged | +30 pts | Highspot |
Launching a sales enablement program is one of the most impactful initiatives a sales leader can undertake. A critical step that is often overlooked is the sales playbook. It provides a standardized framework that documents a repeatable process to guide the entire sales team, ensuring every salesperson uses the same approach and methodology.
Every salesperson on the same page
- Buyer persona descriptions: knowing a buyer's unique characteristics, objections, pain points, and decision-making processes lets salespeople tailor their approach and messaging for each scenario
- Real-world sales processes: the scripts a salesperson should say to prospects, whether they're pitching, prospecting, nurturing, or closing
- Sales stage sequencing: how to take a prospect from problem awareness through a purchase decision, with insight into the buyer's mindset and how to get past objections at each step
Salespeople want to be successful. They don't want to struggle to meet their sales targets and their employer's revenue goals. A playbook is an important way to empower them to improve their performance. When you hand them a playbook, they feel more confident and ready to succeed. That is sales enablement at its finest.
When you hand your salespeople a playbook, they feel more confident and ready to succeed. That is sales enablement at its finest.
— Bill Piacitelli, Partner
You can transform an entire sales team's performance with proper sales enablement. You just need to know how to do it the right way.
| Metric | Value | Context |
|---|---|---|
| higher win rates for companies that aligned their sales process with their buyer’s journey | 10% | CSO Insights, Miller Heiman |
| higher quota attainment for the same companies | 14% |
"We’ve trained them on everything they need to know. Why are we still losing sales?" A frustrated EVP of sales asked me this after a new competitor launched and win rates plummeted. Monthly one-way training sessions on why we were better only made the win rate keep dropping. In desperation, we turned to sales enablement and observed conversations between our salespeople and prospects. At least 90% of the time, our salespeople were not asking prospects the right questions.
We designed a four-week program called "compliment, plant, explain." Week 1: teach sales leaders how a best-practices conversation should go. Week 2: sales leaders teach the approach to salespeople. Week 3: salespeople roleplay the messaging back to their leaders. Week 4: certify each salesperson on the new skill. The result? In four weeks, our win rate improved by 9%. This is the power of sales enablement done right.
What's missing from sales training today?
What's missing is real-life application and feedback. Humans learn new skills by immediately applying what they've learned and receiving feedback right away. Studying human memory, German psychologist Hermann Ebbinghaus found that if new information isn't applied immediately, we forget about 75% of it after just six days. At the Cortado Group, we model effective sales skills, give ample opportunity to practice in a variety of settings, observe performance, and provide immediate feedback and coaching until salespeople consistently demonstrate proficiency.
If you want a sales training program that sticks, you need a sales enablement program that ensures your salespeople gain new sales muscle memory.
— Sarah Bedwell, Consulting Principal, GTM Enablement
Sales enablement tells salespeople two essential things: what actions move a buyer toward a close-win deal, and what actions to stop taking because they aren’t working. Technology and data provide insight into both.
| Metric | Value | Context |
|---|---|---|
| gain in retention after implementing sales enablement | +5 pts | Sales Enablement Pro |
| improvement in win rates | +1 pt | |
| lift in attainment | +3 pts |
To reach super-seller status, salespeople need to know the impact of their actions based on factual data rather than guessing. They need to know what prospects and customers are experiencing, their buying journey, and their buying signals. Accessing and sharing this insight requires the right processes, systems, technologies, and measurement tools. We design successful systems by capturing data at each step of the buyer’s journey, from opportunity, to prospect, to account.
What an intelligence-backed program unlocks
- Move prospects to win-close: with outcome data gained over time, salespeople learn exactly what moves prospects closer to a sale, and what will never close, so they spend their time on true opportunities
- Forecast sales outcomes: layering sales enablement data onto a forecasting engine includes prospects in the equation, making wins, losses, and revenue more predictable
- Capitalize on digital conversations: recorded conversations are a treasure trove of tonal inflection, common terms, and competitor mentions, used to train salespeople to spot challenges and learn why a prospect chose a competitor
Sales enablement should be viewed as the science of improving and proceduralizing the right moves at every step of the buyer's journey. When we do that, we know what's working and what's not. Then we know the best path toward close-win deals versus closed-lost deals.
While it's easy to be skeptical about making an investment in sales enablement, when it's correctly implemented and supported, it's clear as day that these programs improve go-to-market performance.
— Jessica Pearson, RevOps Practice Leader
Twelve steps across four phases, from analysis to support.
A — Analysis
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1
Identify ICPClearly define your company's ideal customer profile
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2
Buyers' processDetermine how your buyers make their buying decisions
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3
Critical momentsIdentify the critical moments along your buyers' journey
B — Alignment
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Align journeyAlign your sales process to your buyers' journey
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Sales skillsIdentify skills your salespeople need to remove friction
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3
Training toolsCreate sales training tools to teach salespeople
C — Enablement
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Train directorsTrain your sales directors first
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2
Train repsAssign sales directors to train the salespeople
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3
Ongoing coachingContinue reinforcing the new sales skills
D — Support
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Marketing supportCreate materials to support the sales journey
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2
Technology supportIntegrate sales with your automated systems
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3
PlaybookEmpower your sales reps with a best practices guide
Medical education company overcomes sales gaps and boosts sales.
Founded in 1999, this portfolio company improves patient care by creating specialized education programs in six clinical areas, such as oncology and infectious diseases. The Riverside Company purchased the company in 2020 and launched Cortado Group's Sales Enablement 2.0 in 2023 to elevate sales performance, expand its brand on the global stage, and grow through larger contracts and acquisitions.
Challenge: a sales process that wasn't sustainable
By 2022, the sales division was missing revenue milestones, including close-win rate, sales cycle speed, and average sales price. Best practices were siloed within six clinical sales teams, experienced salespeople were retiring, new salespeople were arriving through acquisitions, and its largest vertical was slowing. Hiring clinical experts who can also sell wasn't viable, so the company chose to improve the sales skills of its existing subject matter experts through a formalized sales enablement program.
Solution: turn SMEs into salespeople
Through sales enablement, the company gathered the best practices of its six divisions into one holistic sales process every subject matter expert could use across the organization.
Cortado Group was the only firm that got it. They came back with a comprehensive, customized sales enablement plan that included timelines, milestones, and measures of success.
— Chris Davy, Managing Director of Commercial Growth, The Riverside Company
Process: extract sales best practices
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1
Documented their buyers' journey and personas
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2
Designed a sales process strategically aligned to that buyers' journey
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3
Codified the skills a salesperson needed to execute the sales process
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4
Built those skills into a scalable e-learning program
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5
Put the entire team through the training program
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6
Enabled the skills to stick by coaching the frontline managers week over week with 1:1 observation and feedback
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Empowered the frontline managers to coach their own teams
Results: salespeople's confidence in their skills, over 8 weeks
| Metric | Value | Context |
|---|---|---|
| ability to describe buyer personas and the process they go through to make a sales decision | +48% | |
| ability to develop a compelling grant idea to submit at the assigned quality level | +47% | |
| ability to create and run an engagement strategy while supporters are considering a deal | +42% | |
| ability to perform all the above in full compliance | +41% |
If you want to grow and scale, there has to be a systematic approach, and that is sales enablement.
— Portfolio company's Chief Strategy Officer
Ready for a sales growth consultation? Consider your answers.
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Have you deeply researched your real-life buyers and how they make a purchase decision?
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Have you designed a strategic sales process that aligns with how they buy?
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Have you identified the sales skills that will help your salespeople consistently deliver the desired outcomes?
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Have you both trained and consistently reinforced the right sales skills with your team?
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Have you embedded your buyer-centric sales process into your CRM?
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Have you provided the right marketing and technology resources to help your sales team perform their new skills successfully?