Charles Gryor Derupe

Director of Content and Launch Readiness Enablement, Square

Content

How is sales enablement thinking about adoption of new sales tactics or strategies?

Square Director of Content and Launch Readiness Enablement • February 8

This answer is purely based on opinion, so please keep this in mind. I believe that any new tactics and strategies need to be relevant to the sales methodology set by the enablement team. Why? Reps, especially those that are "green" to the field, need a repeatable, consistent skill development st......Read More

982 Views

How do you bring other departments together (e.g., marketing, product) to support sales enablement efforts?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

I'll be honest, I've been in the Sales Enablement industry for a while and this is something that takes so much time to master and has so much nuance depending on your organization's structure. Here are some tactics I use that have helped me get 80+ people in my last annual strategy review. It bo......Read More

972 Views

How do you align sales enablement efforts with the overall goals and objectives of the sales organization?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

Big question, but I'm happy to share some small factors that can really help to align and at least surface areas that enablement professionals can miss: 1. Know when and by whom business reviews are created. Even if it's async, understanding the target numbers, target audiences, and key strate......Read More

896 Views

How do you stay up-to-date on industry trends and best practices in sales enablement?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

Great question! There are three specific ways I do this: 1. There are some annual reports done for Sales Enablement that come from third-party sources like Forrester and Gartner. These may be gated, but sometimes they are sent by tools vendors. 2. Use your tool vendor resources! I always ask......Read More

848 Views

How do you build and maintain a strong sales enablement culture within the sales organization?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

I think the easy answer here is "buy-in" from your leadership. But what does this actually mean? They can say it, but that doesn't always mean that they'll prioritize or even fund it for growth. The approach of top-down is 100% the way to go in my experience but here are a few tactics I and my pe......Read More

798 Views

How do you take “the classroom” and convert it to “real world experiences?” What’s the best way to do this at scale across a sales org?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

I very much understand how this is difficult, especially if you have a distributed workforce and if budget constraints don't give you the ability to get folks into one place. I'll share a common approach that my peers from across the industry use (since I focus mostly on content) that can help se......Read More

792 Views

What’s the best way to measure ramp effectiveness?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

It's essential to first understand the expectations of your sales leadership, common denominators between successful reps who achieve those expectations, and availability of data to your enablement program. Here are a couple of questions to ask before you get started in creating a measurement pla......Read More

783 Views

How do you incorporate customer feedback and insights into sales enablement efforts?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

This requires a good amount of cross-functional work, especially with your sales leaders. If you have a forum where there are weekly, monthly, or quarterly business reviews, I would request adding sections with a clear format that guides front-line leads to give you can get key insights gathered ......Read More

766 Views

How do you take feedback from the sales org and develop new sales content and strategies?

Charles Gryor Derupe

Square Director of Content and Launch Readiness Enablement • February 8

Thanks for the question! There are three ways that we go about this: Focus Groups, Open Requests, and Analytics. First, I'll mention that all content should point back to your team's goals and objectives. What are you trying to achieve as an organization and business? Who are your target audie......Read More