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Sales Leader Interview Series – Kent Summers

Two Types of Sales Reps

Kent Summers is a seasoned technology executive with 30 years of contributions to the Boston entrepreneurship community. Today, Kent focuses his time on helping founders navigate the startup world and teaches B2B sales classes at both Harvard and MIT.

We sat down with Kent to discuss the transition from outside to remote sales, implementing automation tools, and received some great tips on sales management!

What are your thoughts on selling remotely versus more traditional outside sales?

You have to focus on the techniques and methods that will help make your salespeople more effective in a remote environment; for example, helping them develop new skills for becoming effective selling via Zoom versus in person. There isn’t a sales person on the planet that will tell you that not meeting people face-to-face is a good idea, especially for higher value products, longer sales cycles, etc. It’s easier to continue the conversation remote once the relationship has been established, but actually developing a new relationship remotely is much more challenging. So, the transition to a remote environment is a significant compromise that you need to make, especially for hunters versus those salespeople who are responsible for maximizing the yield within an account.

What is one way to assess sales skill without using the typical performance metrics?

I think the quality of your sales reps can be determined just by asking them good questions during discussions, such as, “What if…? How would you react to this, that? What did you discuss? How did you navigate the conversation?…” There are basically two types of reps: those who chase transactions and those who tend to slow down their sales process and focus on the quality of their interactions and building relationships. It turns out that for the second group, transactions just happen to occur naturally, and for the reps who tend to chase transactions and skip some steps in the sales process, transactions tend to be more elusive. So, you can pretty much tell just by a simple interview where a rep’s mindset is with respect to the sales process, the steps they’re taking, or whether they’re taking shortcuts, and thus discern a level of quality. 

What are your thoughts on using automation tools with a sales team, and what should managers do to maximize returns on these products?

Like anything that helps with efficiency and scale, there are positive and negative aspects, and you have to achieve some kind of balance, provided it doesn’t impact performance. For example, if you build dashboards that give you a perspective on the data that you capture, you can spend much more time focusing on value-add functions, and you’re now in a much better position than you were. 

Automation can be great, as long as you’re thinking about how it helps you become more effective as a manager. Think about the leading indicators, the outcome measures you need as a manager, and the extent to which you can automate different views and perspectives. As long as you’re focusing on the metrics that actually impact the quality and performance of your team, automation can be a big advantage for a sales manager. At the end of the day, however, a manager needs to understand that efficiency is on the x-axis, and performance is on the y-axis—they’re not on the same axis and at some point you do get diminishing returns.

What is your best sales coaching advice?

First, sales reps really must believe that there’s a benefit to being coached. If you’re working with somebody that fundamentally does not see the value in being coached, you’re wasting your time. So, one of my most important criteria for building organizations is that the reps want to be coached and they truly see the value in it.

Second, rather than having regularly scheduled coaching sessions, I’m a big believer in having the sales rep request sessions for coaching, because it usually means that they have a good reason for doing so. They’ve probably accumulated two or three things that they’re struggling with and know that they can benefit from a coaching session. During a meeting that is regularly scheduled, they will have to artificially come up with those things to discuss. 

In terms of the method itself, I’m a big believer in team coaching as opposed to one-on-one coaching, because one-on-one coaching is just one person’s opinion versus another’s. And while somebody might have years more experience, at the end of the day, it could just be viewed as an opinion. By contrast, if you bring two or three people with different perspectives on sales topics, the coaching tends to stick a lot better and have a lot more credence because they can see two or three smart people agreeing on the same thing.

Thanks, Kent, for the great sales insight and coaching advice! Stay tuned next week for another post in our Sales Leader Interview Series, and check out the BuyerSight Blog for additional interviews with sales experts.

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