Rethinking Sales Enablement Training for Long-Term Impact
Guest Blog
You’re anxiously preparing for sales and revenue kickoff (SKO/RKO) or the arrival of a brand new cohort of account executives. As you rush to put the final touches on your latest training content, you have a nagging feeling. You worry that although the new material will initially excite your salesforce, it will soon be forgotten, languishing in your learning management system (LMS) but rarely applied in the real world.
Conversely, perhaps you’re the first enablement and training hire for a rapidly scaling startup. You want to be able to build a program that establishes a winning sales motion and supports your investors’ lofty revenue goals. However, you know that good intentions (and expensive sales enablement platforms) aren’t enough to ensure sales success.
You want your teams to know how to sell the product and be able to self-service when they need additional enablement content or training. How do you rethink sales enablement programs to promote more resonant learning and cultivate a feeling of trust and security between enablement and the sales teams?
In this blog, we’ll discuss a framework for tackling sales enablement training for stickier learning.
What’s Happening in Sales Enablement?
With economic uncertainties persisting, winning new business requires even more precision. Thus, tech vendors are holding steady in investing in sales enablement and effectiveness. However, there are signs that cross-functional alignment is suffering.
Here are some key stats to know:
61% of executives surveyed are investing more in enablement to help drive go-to-market effectiveness in 2025 - nearly 2x more than in 2024
87% of sales leaders surveyed saw sales enablement as Extremely or Very Important to driving sales efficiency, but only around 50% had implemented sales enablement
Product Marketing Alliance’s 2024 State of Product Marketing report showed a decrease in the portion of product marketers who cite working with sales enablement as a primary responsibility (64% vs 67% in 2023).
Furthermore, the percentage of product marketers who engaged with sales enablement tools decreased from 55% to 42% over the same time period
This data emphasizes the continued importance of sales enablement. Concerningly, though, it suggests that sales enablement might be getting more siloed.
Successful sales enablement programs exist symbiotically within their broader go-to-market ecosystem. In this blog, we’ll examine how to build these programs for sustained success.
Sales Enablement Success Starts with Training
Having a successful sales enablement program is only possible when good habits are established from the very first day of employment. Investing the right amount of time upfront can pay great dividends down the road.
According to Highspot’s State of Sales Enablement 2024, 76% of executives believe that investment in sales enablement has helped to improve their company’s sales performance.
So, what does a good training program look like?
First, it starts with a 90-day onboarding program. This doesn’t mean that training is all a new sales representative spends their time on in the beginning. Rather, there needs to be time set aside for new hires to absorb what they need to know to be successful:
Self-learning. Provide a variety of self-guided materials including reading, interactive digital modules (including virtual instructor-led training or vILT), and self-led research.
Group learning. Traditional classroom-style learning is also very effective, fostering active discussion and providing opportunities to work through real-life scenarios. Depending on the content and need for interactivity, these can be delivered by live or virtual instructors.
1:1 coaching. New hires should be given individualized objectives and plans from their leaders and meet regularly with them to discuss progress on goals.
Peer mentoring. Similarly, new hires should be paired with high-performing sales representatives who are closer to them in tenure and seniority. These relationships are meant to provide more on-the-ground advice and a safe place to discuss strategies and challenges with someone who has been there before.
Ultimately, the right mix for your company will depend on the complexity of your offerings, resources, and nuances of your typical sales motion.
What should new sales team members be learning?
In my view, there are seven core building blocks of sales enablement training:
Sales Skills. Even if you only hire experienced salespeople, it is always a good idea to review foundational sales skills in the context of your organization and its products and services. There are nuances that change across different industries, segments, and target buyers, and it cannot be assumed that past skills will seamlessly translate into a new company.
While the precise details will look different in every company, it is generally a good idea to focus on six key skills: technical know-how, business acumen, approaching prospects and clients with a consultative approach, relationship building, collaboration, and adaptability.
Competitive Landscape. Many markets, especially in software, are seeing a proliferation of potential competitors. It is important to break down the landscape for new hires. Among the areas to focus on are understanding which competitors are most relevant (a best practice is to create three tiers of competitors based on frequency of going to head-to-head and applicability to Ideal Customer Profiles).
Ideal Customer Profiles (ICPs). Speaking of competitive relevance, it is important to establish who the customer is. An ideal customer profile (ICP) describes a business’s ideal customer based on attributes like demographics, behavior patterns, needs, and pain points. Sharing customer case studies are a great way to drive the ICP home – and arm salespeople with usable content.
Selling at your organization. No two organizations sell the same way. Sales funnels and cycles vary greatly in terms of length, number and intensity of touchpoints, and tactics used. It is important to cultivate a strong understanding of your company’s processes and the different sales tools (i.e. CRM, prospecting and outreach, and social selling, among others) available to facilitate their work.
Product. While we don’t necessarily expect all salespeople to become technical experts, they should develop a deep practical understanding of the product. A good enablement program should prepare salespeople to succinctly describe:
What makes your product different
How it helps customers achieve desired outcomes
Business benefits of key features.
Messaging. Messaging is the means by which a company and product’s positioning is communicated to target audiences. Messaging is strategically designed to evoke particular emotions and actions from a target audience – and is a conduit for conveying brand values.
Ecosystem. Most tech products today exist in a broader ecosystem of complementary and related solutions, as well as implementation and support partners. It is important that sellers understand where their product fits in these broader networks as it is a critical consideration in many deals.
We recommend assessing for mastery of this knowledge continuously throughout the 90 days. Command of foundational concepts should be assessed weekly during the first 30 days, with assessment of more advanced and abstract concepts coming at 60 and 90 days. These assessment milestones can be integrated into 30/60/90 day onboarding goals.
Don’t forget about continuous learning
Technology products evolve constantly and in the fast-paced world of sales, people forget things. For these reasons, sales enablement programs should be built with a commitment to continuous learning. Some examples of how continuous learning can be promoted:
Regular virtual and in-person live training. Seeing technology in motion can be much more effective for understanding than reading about it or watching a canned demo.
Explainer videos. These are great assets for marketing and customer success and should also be required watching for sales.
Summary pages. Summary pages used as part of support or SEO pages can also be offered as a sales reference resource.
Enablement channels. A dedicated channel in Slack can promote on-the-fly knowledge sharing and learning.
Gamification. Create and incentivize interactive assessments and friendly competitions to encourage self-motivated learning.
Feedback surveys. Provide anonymous surveys to understand potential gaps in confidence and understanding or just which type of knowledge your sales team can’t get enough of.
Manager reinforcement and coaching. In both 1:1 and team settings, provide targeted coaching beyond the first 90 days.
Office hours. Sales enablement leaders can block off time each week where team members can pop in to ask any burning questions. This is a great way to learn what’s really on everyone’s minds.
Scenario training. Having the occasional in-person or virtual role play training allows colleagues to learn from each other and build muscle memory to apply in real-life situations. The most valuable aspect of these training sessions are the discussions that they promote: How would you do it differently? What did you find effective? Were there any missed opportunities? This type of learning is especially effective at turning conceptualization into execution.
Making it Work Long-Term
After having trained your new sales team members and acquainting them with their supporting colleagues, they are all set for self-sufficiency, right? In many ways, yes. However, this does not mean that training has ended. In fact, training never ends. Rather, it morphs from learning to polishing and reinforcement of what has been learned as well as adapting to changes in the market.
For this reason, sales enablement should always remain a cross-functional initiative. Product marketing, product management, customer success, and implementation should openly be involved in curriculum development and the training process. This is not just for their expertise, but to promote ongoing knowledge sharing and consistency in messaging.
Conclusion
A successful sales enablement strategy hinges on great training and alignment across go-to-market. Building these practices into your organization from the start and cultivating alignment across GTM functions should set your sales enablement team up for success.
Need help creating powerful messaging and content for your sales enablement program? Greenefield Consulting can help! Contact us for a free consultation.
If you’re looking to operationalize this approach, Cathy DeBurro is an experienced learning and development leader and facilitator providing sales enablement consulting services.