Our VP of Growth, Brian Wool, comes to StorySlab with over 20 years of sales experience, including over 12 years in sales leadership. We asked him what his career has taught him about successful selling and how sales enablement can help refine that process. Here’s his perspective on how to motivate your sales team, maximize marketing dollars, and improve customer conversations—all with sales enablement.

What was the start of your sales career like and how did it help you become a better growth leader?

I spent my first 10 years in sales as an individual contributor, which is incredibly important as you evolve into sales leadership. Knowing what I did well and where I stumbled gives me the understanding I need to coach my team, as they’re probably making a lot of the same mistakes. 

In my first role, I was knocking on doors, selling information systems to automotive dealerships. I’d go in and ask for the owner, set up a meeting, then demo a computer system that would run their entire business. (This was in the mid-90s when most companies didn’t even have a website yet.)

SDRs didn’t exist then. There was no LinkedIn. There was no sales enablement. I was responsible for everything: research, outbound prospecting, scheduling meetings, and having those meetings. Now I leverage those experiences as an individual contributor to help my team think through the areas where they’re struggling. I can help play up their strengths and coach up weaknesses. I can help them figure out where opportunities went wrong and where they get tripped up.

What can sales leaders do to keep their team motivated while selling remotely? 

Help them think through creative ways to prospect. Get involved in more sales opportunities and be proactive in doing more deal reviews. Use whatever tools you’ve invested in. Have standups a few times a week, not just once. Share thought-provoking info that gets your team to ask questions and remain curious.

Now that a lot of outside sales reps are learning to sell remotely, make sure to keep the sales process as similar as possible. No matter where your reps are selling, the process should be the same. This will help reps get more comfortable and create a more consistent experience for your customers. Remote meetings are going to have a different vibe, but if you use a tool like StorySlab that works for both remote and face-to-face meetings, you can keep the experience more consistent.

How can sales enablement help maximize your marketing dollars?

Any company spends an enormous amount of time and money creating messaging around what the brand and company represent. There’s a huge investment in the marketing collateral and tech specifications for products. If you’re not capturing information and making it readily available for salespeople to have access to that info, a lot of those marketing dollars are wasted. Sales enablement helps you refine your message, drive insights on what’s working, and create a strong feedback loop for both salespeople and ensuring sales and marketing are aligned.

Take the investment you made in marketing and put those materials in the hands of your salespeople—the tip of the spear—so they can go into the marketplace and represent your brand, present your products, and get insights on what customers are engaging with. Then they can take that info back to marketing to help them better understand what customers and prospects are truly engaged with and what’s important to them. Then marketing can refine the message.

How can sales enablement help reps improve their conversations?

In the past, building effective cadences was up to the sales rep. They had to be highly organized for success. Now there are cadence tools like SalesLoft and Outreach that help salespeople leverage the data from their CRM and plan around the ideal customer profile.

So SalesLoft goes and generates leads into org, but now you have to figure out what’s happening inside those conversations. What’s being shared? In what order? What works on different types of buyers? You need to analyze your conversations so you can improve them.

Add StorySlab, and you start getting insights about what salespeople are talking about, how customers are engaging, and what they’re responding to. Gong does a great job with remote selling, but StorySlab works both remotely and in the field. In addition to helping inside sales reps, it can also help outside sales reps be much more productive.