Getting Started in Sales Enablement

Phil Stern By: Phil Stern  |  July 24, 2020

We find that there are two primary ways to support the success of your salespeople: sales efficiency and sales effectiveness. Sales efficiency relates to your systems, processes, data, tools and partnership with marketing and sales operations. It’s the efficiency of the system you build in which your sellers sell. Sales effectiveness relates to how your salespeople perform when they’re engaged with, or working to engage with, prospects and customers.

Sales enablement is the intersection of Sales Efficiency and Sales Effectiveness; it exists to help create highly effective salespeople.

And—sales enablement is an investment. By supporting the development of your salespeople and working to make them as effective as possible, you impact a number of key metrics that contribute to the growth engine of your business. These can include, but are not limited to, bookings per rep, the ratio of a rep’s annual bookings to their annual earnings (aka ACV:OTE), and customer acquisition costs.

In addition to driving these metrics, better prepared sellers can also provide your prospects with a better buying experience, thus creating a strong perception of your company from the start. In other words, sales enablement may be an investment worth making.

Structuring a Sales Enablement Program

Enabling successful sellers is a lot of work. And creating comprehensive sales enablement programs requires more than just an investment in training on a specific sales methodology or coaching in your 1:1s.

Sales enablement involves developing programs in the following four areas:

Each of these areas can be key to the long-term success of your sellers, as well as their growth and satisfaction in their roles on your teams.

  • Sales Skills and Systems: Training your sellers on sales methodology, objection handling, discovery strategies, tactics, tools and techniques. This program helps your sellers adopt and practice skills for engaging with prospects and closing deals, while using technology effectively and efficiently.
  • Product Knowledge: Training your sellers on your product and the value it provides to your customers. This knowledge gives sellers a higher degree of confidence so they can focus on the buyer and not have to dig through materials or connect with a product manager to answer questions.
  • Buyers, Markets, Competitors: Helps your sellers understand who they are selling to, your ideal customer profile (ICP), their needs and challenges. It also helps your sellers understand the markets in which you operate. Broader market knowledge can help them approach their conversations with greater empathy for the customers and position the value of your product in a more compelling manner. Also, it helps your sellers know your competition.
  • Professionalism & Career Development: Supports the growth of your sales team beyond the skills they need in their immediate role. This includes professional development and career coaching. Investing in this category can go a long way in retaining your top performers.

Can’t build a full program? Start somewhere.

Many companies lack the resources to develop these types of full-fledged programs. More to the point, many companies can’t hire a dedicated sales enablement team member. Companies large and small, bootstrapped and well-funded, brand new and established all seem to struggle with sales enablement to some degree. This may be because it is challenging to cleanly show the ROI of enablement programs.

Nevertheless, if you want to build a high-performing sales team, we believe it is critical to invest somewhere in the realm of sales enablement.

So even if you don’t have the budget to bring on a dedicated team member right now, here are four suggestions to get your sales enablement program off the ground:

  1. Prioritize sales skills and product knowledge. Helping your sellers gain confidence will have the most immediate impact on their results. These trainings can be delivered by your product and marketing teams and/or a small investment in an outside sales trainer, supplemented by consistent reinforcement training led by you or another sales leader.
  2. Document everything you want your sellers to learn. Even if you can’t develop a full program right now, write everything down and start thinking about a sequence in which you’d like to deliver the trainings to your teams. If team members or cross-functional partners in your business have bandwidth, ask them to contribute specific training content as well. That way, your training manuals will be queued up when you’re ready to launch your program.
  3. Make it a team effort. Share your interest in sales enablement with your team of sellers. Ask them what they’ve seen at prior companies. Ask them what would be most impactful to their success. Seek out team members who have a passion for learning and might want to help.
  4. Create a centralized location to store all content. Many companies create content to support the success of their sales team, and it never gets beyond the outbox or hard drive of the person who created it. By creating a centralized location (shared drive, accessible from anywhere), and establishing a clear file structure, you will better set your team up to find the content they need when they need it.

We believe sales enablement is the process of taking your sales efforts to the next level. It requires an investment in your team and your process that spans every aspect of the sales experience. It can be a lot to take on, but it can also be approached in bite-sized chunks. Don’t let the weight of the program intimidate you from getting started. Your sales team will thank you.


Phil Stern
Phil is a Vice President at Mainsail. He leads the firm’s Center of Excellence for Sales and is responsible for helping Mainsail’s portfolio companies optimize their growth strategies and deploy sales practices.
More by Phil Stern
This content piece has been prepared solely for informational purposes. The content piece does not constitute an offer to sell or the solicitation of an offer to purchase any security. The information in this content piece is not presented with a view to providing investment advice with respect to any security, or making any claim as to the past, current or future performance thereof, and Mainsail Management Company, LLC (“Mainsail” or “Mainsail Partners”) expressly disclaims the use of this content piece for such purposes.

The information herein is based on the author’s opinions and views and there can be no assurance other third-party analyses would reach the same conclusions as those provided herein. The information herein is not and may not be relied on in any manner as, legal, tax, business or investment advice.

Certain information contained in this content piece has been obtained from published and non‐published sources prepared by other parties, which in certain cases have not been updated through the date hereof. While such information is believed to be reliable for the purposes of this content piece, neither Mainsail nor the author assume any responsibility for the accuracy or completeness of such information and such information has not been independently verified by either of them. The content piece will not be updated or otherwise revised to reflect information that subsequently becomes available, or circumstances existing or changes occurring after the date hereof, or for any other reason.

Certain information contained herein constitutes “forward-looking statements,” which can be identified by the use of terms such as “may,” “will,” “should,” “could,” “would,” “predicts,” “potential,” “continue,” “expects,” “anticipates,” “projects,” “future,” “targets,” “intends,” “plans,” “believes,” “estimates” (or the negatives thereof) or other variations thereon or comparable terminology. Forward looking statements are subject to a number of risks and uncertainties, which are beyond the control of Mainsail. Actual results, performance, prospects or opportunities could differ materially from those expressed in or implied by the forward-looking statements. Additional risks of which Mainsail is not currently aware also could cause actual results to differ. In light of these risks, uncertainties and assumptions, you should not place undue reliance on any forward-looking statements. The forward-looking events discussed in this content piece may not occur. Mainsail undertakes no obligation to update or revise any forward-looking statements, whether as a result of new information, future events or otherwise.

No representation, warranty or undertaking, express or implied, is given as to the accuracy or completeness of the information or opinions contained in the enclosed materials by Mainsail and no liability is accepted by such persons for the accuracy or completeness of any such information or opinions. For additional important disclosures, please click here