Sales Execution

4 Keys to Coaching Enterprise Reps

Headshot photograph of Anthony Cessario, VP of Industries and Market Expansion at Clari

Anthony Cessario
VP of Sales, Enterprise at Clari



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Photograph of an enterprise sales team collaborating around a laptop
Photograph of an enterprise sales team collaborating around a laptop

If you are hiring correctly, your enterprise sales reps are some of the very best in the world at what they do. They likely don’t need you to teach them the fundamentals of selling (if so, you’re probably overpaying them) — but they absolutely do still need, want, and expect your help in continuously upping their game.

The key?

Do it in a way that doesn’t waste their time or yours. Here are 4 keys for effectively coaching your enterprise sales reps.

1. Coach your sales reps to be the CEO of their territory

Your enterprise reps are some of the highest-paid employees in the entire company. They are often running a multi-million dollar component of your most important business segment.

Empower them with this information. Don’t waste your time, or theirs, dictating how they should run their business. Instead, help them become CEOs of their territories and guide them as if you were one of their board advisors.

At Clari, we have a phenomenal board and set of advisors. When I get the pleasure of interacting with Silicon Valley icons like Carl Eschenbach, former President and COO of VMware and Steve Singh, Co-Founder of Concur, they never dictate to me how to run Enterprise Sales at Clari. They ask excellent questions and share thought-provoking stories.

Great enterprise reps (and CEOs) crave this same level of coaching. They are eager to improve and grow every day.

As CEOs, they want the autonomy and trust to manage their business through the lens of their unique and valuable experiences, but are still looking to you, their advisors, for small opportunities to up their game even just 1%, week after week.

2. Empower your sales reps to be world-class

There are only so many enterprise accounts out there in the world today. The executives in these companies are more educated than ever and are being sold/marketed to more than ever as well. It’s critical that you empower your enterprise reps with the knowledge that if they’re one of the select few actually getting time with these business leaders and even better, closing business with them, they are some of the very best in the world at what they do.

Find opportunities to remind them of this in an authentic way so they keep this frame of mind. In my experience, you see another gear in people when they come to realize that there are only a few people on the planet who can do what they do week in and week out.

However, for world-class performers, you need to provide world-class coaching, or they will find another team that values their contribution.

3. Skip the interrogation and coach with a POV

Enterprise reps want to be coached, not interrogated. The last thing your elite sellers want to do is regurgitate information, especially if they’ve painstakingly entered it into a sales system of record (CRM) already.

When you show up to one-on-one sales meetings asking for the same data they’ve just entered manually into their computer (P.S. almost no enterprise reps use their CRM’s mobile app — but if you want a good view of what it's like to use Clari's mobile app, you should read this story by one of our enterprise reps Maya Connet), your one-on-one sales meetings will quickly be flagged as a waste of time. Asking the reps to spend 30%+ of their time cataloging this data, and then not paying them the respect to actually look at it and draw meaningful insights before your meeting is a complete breakdown in trust.

Even leaders with the very best intentions often end up having reps report the news for 90%+ of one-on-one sales meetings, and coaching for maybe 5-10%.

It’s not easy for most leaders. There's tons of data out there. Finding a way to bring it together and create a point of view (POV) ahead of a weekly one-on-one sales meeting is the hard part, but it’s critical to running an effective coaching meeting.

When you come into these one-on-one sales meetings with a data-driven POV (as opposed to an opinion manufactured on the spot), it sets a different tone to the conversation. Reps will be eager to join these weekly meetings with you, as they will be getting valuable insight into their business.

4. Know where your sales reps want to take their career

Enterprise sales roles are one of the few positions in a company where you can have two people in the role that are at vastly different stages in their careers. There can be 3+ generations on a single enterprise sales team. Knowing exactly what career ambitions are held by each member of the team is extremely important if you want to motivate them to do meaningful work for you and the company.

Career development these days is a much more dynamic concept than ever before. It's not like our parents’ days when you hunkered down and climbed the ladder. That's just not how it works anymore. It's more like a climbing wall where everyone's kind of at a different point in their journey. Some people want to take risks, climb really fast, and hang upside down; while others just want to take the easy route, stay in shape, and cruise a little. As a leader, you’re holding the ropes and guiding them where to place their feet.

Maybe you have a rep who doesn’t want to be a leader, but they enjoy working with the product team. When you have this context, you can create experiences for them that they value and that will help them make progress both from a performance and a development perspective. Others might want to just maximize their W-2 due to the stage they’re at in their careers. I see this a lot. That’s also ok, and you can motivate/develop these folks appropriately as well for that result.

Understanding how your reps think about their career and what types of experiences they want to have is really important. And it's dynamic; it's always changing, so it’s something you need to check in on regularly.

At Clari, we have “progress huddles” 2 times a quarter. As leaders, we then do talent review meetings 2 times annually to ensure we’re finding/creating opportunities for all the unique cohorts of talent that we have across our teams.

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