Skip links

Sales Leader Interview – Eric Rosenthal

Managing Individuals, Individually

Eric Rosenthal is an experienced Sales Leader and Chief Revenue Officer who recently founded the sales leadership consultancy BlueSky Revenue Group. Previously, he led sales at Emissary,, CAKE Software, and CrowdTwist, among other senior sales roles at technology companies.

We sat down with Eric to get his take on fostering peer learning, the impacts of COVID-19, and advice for aspiring sales leaders.

In your experience managing remote sales teams, what have you found to be the best way to foster collaborative and peer learning?

There are a couple of ways that seem to be the main methods of communication for a lot of the companies I advise, starting with Slack. I like to keep open channels on the specific deals we’re working on. Another thing I’ve tried is having a channel where we put all of the deal questions into a general deal channel for the entire commercial team to see. This way, instead of there being siloed tidbits of information from me to an individual, the entire team can see it, respond, ask questions, jump in, etc. That way, the next time someone else has a similar question, they can reference this channel to see the solutions myself or other members of the team have come up with.

What are some of the obstacles that have arisen for sales organizations due to the COVID-19 crisis, and how should managers look to overcome them?

In general, the biggest obstacles are the changes to interpersonal relationships and the struggle of understanding a seller’s challenges when remote. For sales reps, the biggest differences are obviously that you’re not going to have as much face-to-face interaction with your sales leader and your colleagues, and you’re not going to be traveling as much. So, if you’re a salesperson who thrives on building relationships and face-to-face interactions, you will have to work with your sales leader to enhance and modify your selling strategy.

From a management perspective, I say half in jest that you have to “be better.” Managers will need to expand their coaching methods and look at their sellers and situations in much more granularity. A good leader always manages each one of his or her sellers in a different capacity. With everyone working remotely, you’re going to have to be able to build rapport with individuals you’re hiring over video-chat, who you haven’t met in person. You’re going to have to learn their strengths and weaknesses without being face-to-face. But this works both ways. You, as a sales leader, also have to let your sales reps have greater insight into who you are beyond just an email or message channel.

What do you think are the biggest risks of automation in the sales process for both managers and sales reps?

In general, I think that automation is necessary to help a sales team scale. Whether you’re a start-up, a mid-tier company, or a large company, automation is imperative to helping you manage and grow your business. However, you can’t rely solely on sales automation.

For managers to get useful information out of their sales automation or sales technology, it’s essential they understand their metrics. You shouldn’t have your sales-ops leader throw some numbers in front of you and then think that you understand what’s happening inside the organization. You have to truly understand what those numbers mean. Personally, I am a metrics-driven leader; I intimately know the reports and information I need to run my business, but I also need to be able to distinguish between the numbers in my sales automation tools that I’m getting and how a sales rep is actually performing beyond the numbers. Why are they successful, or why are they struggling?

For sales reps, there’s definitely a trade-off between outbound automation and personalization. I’m not an advocate of just bombarding clients with emails because I don’t think emails are an efficient manner of outreach these days. I think you do have to mix it up with phone calls, LinkedIn, videos, etc. You have to strike a balance between quantity and pure personalization where you’re only reaching out to a handful of contacts every week.

With that said, I think it’s important for the manager to understand that each salesperson is different. Some thrive on putting together videos, some thrive on the phone, others through email. You have to make sure you create an environment where you’re empowering them to take ownership of their outreach.

What are some of the biggest mistakes sales managers are making today?

I think some of the mistakes managers make are some of the mistakes they’ve been making for a while. The one that jumps out to me is managing each one of your sellers in a similar manner; expecting reps to work around your sales leadership methodology as opposed to using your sales leadership skills to mold them into better sellers. I always say as a sales leader that I’m not the star of the show—I’m the central support system. The sellers are front-facing and I need to be supportive of them and put them in environments where they can be most successful.

So, most important to me is to know your seller, know your team, and make sure you’re putting them in situations where they can be successful. You can’t have a 100-person sales team and manage every individual differently, but you can design a structure that allows your sellers to thrive.

Thanks, Eric, for the thoughtful takes on some of the issues currently facing the sales world! Stay tuned for another post in our Sales Leader Interview Series and check out the rest of the BuyerSight Blog for more interviews discussing sales, leadership, and more!

Share with your network

Leave a comment