Navigating Sales Management in a Remote World with Jesse Rome

The playbook for managing remote teams is rapidly evolving, and everyone is seeking the right tools to help them succeed. At Pathlight, we want to help every manager achieve their professional best, so we created the Virtual Manager Series.

In this series, we speak with real managers about their insights, tips, and tricks for successful management in this unprecedented time, so you can start implementing their best practices on your team tomorrow.

Introducing Jesse Rome

Jesse has been driving sales at Yelp for six years. He started in August 2014 and worked his way up — from making 80 cold calls a day in San Francisco to being selected as a Top Manager to help build and accelerate growth at the D.C. office.

Every company across the globe is making their own decisions about how and when to return to work in an office setting. Given COVID-19 guidelines from the CDC, the reality is that most companies will be operating with a hybrid model moving forward — allowing for employees to choose whether to continue working from home or head back into the office.

While there will be a group of employees who return to the office at every company, managers are far from a world without a large percentage of remote employees. The crucial time to determine best practices for remote management and put them into action is, of course, the present. Frontline managers will be coaching, motivating, and meeting with their employees from afar for many months to come. Jesse Rome is committed to paving the way for smooth and successful remote management.

Key Insights

Commit To A Routine

Rome makes it clear — “The most important thing everyone has to do is just establish a routine.” He pushes his team on creating and maintaining routines because it applies to all aspects of life. “It is the biggest thing that I’m very strict about with my team because it’s both personal and professional,” Rome says. A routine will not only help you and your reps focus, but it will also prevent burnout. He says, “I’m seeing a lot of people who bleed that sales pressure and they’re working through lunch and I’m stopping them. I have to say, ‘No. You committed to a routine, and that’s what’s going to keep you sane.”

“The sweet spot is right in the middle of management where you can give a suggestion and see the fruits of your labor pretty quickly— but it’s not just for you, it can have a widespread impact on ten others and other teams.”

To combat burnout, Rome says it’s about more than management — he commits to mentorship and teaches his team how to establish routines and work at a pace that can last. “I like to immerse myself in people’s lives and motivations, and be a mentor and a friend, so that I can see their growth.” He says, “the sweet spot is right in the middle of management where you can give a suggestion and see the fruits of your labor pretty quickly — but it’s not just for you, it can have a widespread impact on ten others and other teams.”

Creative Motivation

When it comes to the new world of remote work, “Overall, motivation is the biggest struggle,” Rome says. “The challenge is to motivate my team consistently.” He says, “You can’t always fall back on commission and say, ‘Don’t you want money? What’s your financial goal?’ That only works one out of four weeks.” Rome has learned that commission only serves as motivation at the beginning, and sometimes end, of the month. “It’s not going to work in the middle — that’s where you have to get creative,” he says.

“I have to be very creative in the ways that I try to motivate people. In my opinion, you have to do something new every week to keep it fresh,” Rome says. “Everybody just wants to learn something new every day, so that’s our responsibility as managers to teach them things constantly.”

He says external resources have been a huge help, “[I learn] about what other tech companies did during the Great Depression and other industries that have gone through recessions and how they’ve come out of it.” One article that impacted Rome was a Forbes article about advertising during a recession. He says it’s articles like these that he shares with his reps to expand their perspective on the current economic climate.

“When we come out of this, which we will, we’re not going to promote you based on what you did before COVID. We’re going to promote you based on what you did during it.”

Rome also makes sure his reps don’t get complacent and lose track of the future. “There are so many companies and people who are proving themselves when the going gets tough,” he says. He makes sure his reps know to never waste a crisis. Rome tells his team, “When we come out of this, which we will, we’re not going to promote you based on what you did before COVID. We’re going to promote you based on what you did during it.”

Every 15 Minutes Counts

Rome says, “During work from home, I am constantly thinking about where I’m going to get the greatest return on my time.” The concept of “return on time” is something he learned early on in his career as a manager. He says, “As a business you’re going to think about where you’re the greatest return on your investment. If you’re a manager, your investment is your time, so you should be constantly thinking about where you’re going to get the greatest return on your time.”

Rome says it doesn’t make sense to spend an hour with one person and not with anybody else. “During that hour you could have talked to three people for 20 minutes each, which would guarantee a result from at least one of those three people,” he says. Rome advises managers, “Always keep thinking, ‘Where can I get the greatest return on my time? Is it with the people that are working the hardest or the person that isn’t?” He says, “You should be thinking — ‘If I were to spend 15 minutes with anybody, who is going to drive me the most results?”

“If you’re a manager, your investment is your time, so you should be constantly thinking about where you’re going to get the greatest return on your time.”

He also reminds managers that it’s okay to think selfishly for a second; managers are still making a commission. He says, “You can also ask, ‘Where can I get the greatest return financially, out of my 15 minutes? That is something that we forget, but at the end of the day, there’s an “I” in business and an “I” in life. You’re going to get left behind if you’re not thinking about some of those things.”

Trust, But Verify

“One lesson that I learned from my first manager, that I think is applicable to working from home, is to trust, but verify,” Rome says. “She always told us that every time we did anything — trust everyone, but ask a few questions and verify.” He says this concept, which is the alternative to the “command and control” model of management, has always helped his approach to management, but has become especially prevalent since shifting to remote work. “[As a manager] you have to practice what you preach, in every way. When doing work from home, we’re just not sure what exactly our reps are doing. So it’s our job to get them to trust us.”

“I think it’s a responsibility as a corporate leader to make sure we’re verifying and getting to the truth.”

Rome tells his team, “I will trust you until you break that trust.” He says he lets them know he trusts them in order to empower them. At the same time, he says, “I’m verifying all of those things by digging deep in questions and looking into the backend to see what they did and didn’t do.” He says the practice is not necessarily the most fun part of his job, but he knows it is necessary. “I think it’s a responsibility as a corporate leader to make sure we’re verifying and getting to the truth.”

Tips and Tricks

What is one book you would recommend to read ASAP?

“Read Remote by Jason Fried and David Heinemeier Hansson. They kind of predicted a lot of the things that are going on now.”

How do you prevent employee burnout?

“When I see people working 100%, 100% of the time, I tell them, ‘This can’t last forever. It’s not sustainable. I always try to peel back 10%. If you see someone working nine hours a day, and one of those hours is lunch, that’s 10% so peel it back. You can work 100% those other 8 hours.”

How do you stay up-to-date with what’s going on in the world?

“Listen to podcasts. Listen to Pivot, specifically. It’s all about politics and tech perspective and macro economics.”

What is the best change someone can make tomorrow?

“Whatever amount of time that you used to use to commute to work, whether it’s 30 minutes or an hour, don’t replace that with sleep. Replace that with something for yourself. Wake up at the same time you usually would if you were commuting, but do something for yourself. I go for a walk with my dog or listen to a podcast.”

“Managers and hippos are both always hungry. Always trying to eat, and when we do, we always win.”

Rapid Fire

What is a manager’s spirit animal?

“A hippo is underwater for the most part — it sits off to the side, in the sun, but it is well-known and well-feared as one of the most vicious animals when it comes time to battle. As a manager, you’re not going to see me on every call. You’re not going to see me in every interaction. If you have to see me, it’s either because you’re in trouble or because I’m going to help you get this sale. And I’m going to be pretty intense about it because this is only going to help you. Managers and hippos are both always hungry. Always trying to eat, and when we do, we always win.”

What’s the best piece of advice you’ve ever received?

“If you think something, say something, and don’t wait to say it.”

Who has influenced your approach to management?

“My dad was a big person that influenced me on people leadership. He always promoted that idea of ‘If you fish for a man, he’ll eat for a day. If you teach a man to fish, then he’ll eat forever.’ So I don’t just do things for people, I teach them.”

What is the most important quality for a manager to possess?

“Humility. Too many managers think they’re perfect — we’re not.”

What is your favorite quote?

“Martin Luther King Jr. said, ‘The ultimate measure of a person is not where they stand in moments of comfort and convenience, but where they stand in times of challenge and controversy.’ As a parent, as a manager, as a person dealing with a pandemic — I try to put that quote and that power of a leader onto my people.”

Thank you to Jesse for sharing his invaluable insights. If you’re looking for ways to manage your team effectively in this new environment, check out the other interviews in our Virtual Manager Series or try the Pathlight platform for free.