Empathy, candor, resilience: What 8 Chicago sales leaders look for in new hires

by Michael Hines
August 30, 2018

All sales teams share a similar goal: to win clients by providing solutions for their problems. But the traits needed for salespeople to successfully turn prospects into customers varies from company to company.

We recently spoke to sales leaders at eight Chicago tech companies to learn more about what they look for in new salespeople, along with how their culture and training set employees up for success.

 

Relativity Chicago sales team

Relativity’s e-discovery technology is used by businesses, law firms, government agencies, and more to analyze and organize data contained in legal documents. While legal technology is relatively new, Senior Account Executive Adrienne Knight said Relativity’s customers know their stuff, which is why it’s important for her teammates to have a deep understanding of both the e-discovery industry and how the company’s tech can meet the customer’s needs.

 

What makes your sales team’s culture unique?

Our sales team’s culture is very collaborative. We put a significant emphasis on client success with our product. Everyone in the organization is working toward one goal, which is to make sure that our clients are able to be successful using our products.

You need to ... deeply understand our technology and the e-discovery industry.”

 

What are the most important traits needed to be successful on your team, and why?

You need to have the ability to not only manage relationships with your clients, but also to be able to deeply understand our technology and the e-discovery industry. We work with very educated buyers, and often act as partners to our customers to help them create a solution that fits their needs through the extensibility of Relativity.

 

What training or programs do you offer to help salespeople succeed?

We have a ton of continuing education available internally, both sales-focused and product-focused. Additionally, Relativity offers employees funds every year to apply toward external continuing education. This very unique benefit is usually used for external sales training of some sort.

 

tron Chicago sales team

Sales is a big component of any media technology company, but especially so for one with a reach like tronc’s. The company operates publications like the Chicago Tribune, Baltimore Sun and New York Daily News. Sales Team Lead Brian Geraghty said collaborative training and a light atmosphere help keep his salespeople sharp

 

What makes your sales team’s culture unique?

We keep things fun and goal-oriented. We currently have a sales contest going, and the winners will be taking a day off to head to Wrigley to watch the Cubs get a W. I’m also a part of our activities team, which schedules after-work events that range from movies at the park to bags tournaments on our building’s rooftop.

Our highest performers are able to connect with clients and understand their needs.”

 

What are the most important traits needed to be successful on your team, and why?

The most important traits needed are empathy, resilience and self-discipline. Our highest performers are able to connect with clients and understand their needs to form the best solutions. Resilience and self-discipline are essential to sticking to a consistent daily plan that leads to success.

 

What training or programs do you offer to help salespeople succeed?

I like to do mock calls with my team. This collaborative environment helps reps open up to one another and teaches them to work together. We often perform screen shares with our clients to present information and share the features and benefits of our offerings. I constantly work with each rep to fine-tune their presentations and practice the portion of the sales call they need to strengthen.

 

SpotMe Chicago sales team

SpotMe helps companies create apps to stoke engagement at both live events and during virtual and hybrid company meetings. While sales teams often have a reputation for attracting extroverts, according to CEO Pierre Metrailler, the most successful salespeople at his company tend to be introverted.

 

What makes your sales team’s culture unique?

We do not want to be salesy. We just want to be helpful. Onboarding, training, kick-off calls, remote or onsite support — every customer interaction is an opportunity to provide best practices, share samples and technical tips, make recommendations, and, more generally, offer our consultative approach. By constantly rubbing shoulders with our customers, we create the long-lasting relationships that have been driving our growth.

We do not want to be salesy. We just want to be helpful.”

 

What are the most important traits needed to be successful on your team, and why?

Tenacity, empathy and intelligence. Sales is arguably the toughest job on Earth, and it is all about having the discipline to persistently try, follow up, build resilience and not take rejection personally. While having drive and a hunter’s mentality is an absolute must, at SpotMe, the most successful salespeople are introverts who understand the power of quiet, and, more than anything else, truly enjoy listening to customers.

 

What training or programs do you offer to help salespeople succeed?

Training starts with a six-month onboarding program. Sales is lonely, so every new hire is assigned an onboarding sponsor. We encourage our sales team to experience the product firsthand at events, and product knowledge is supplemented by best practices, which are shared in our App of the Month program and in quarterly meetings. These highlight our unique event apps and their design process. Everyone on the sales team looks forward to our annual sales kickoff, which is when our worldwide team gathers for three days of strategizing, learning, sharing, team building and celebrating.

 

Hireology Chicago sales team
PHOTO VIA CHRIS MURPHY

Hireology provides companies with a single solution for managing the hiring process from recruitment to onboarding, as well as for managing payroll, benefits and time. When asked what trait makes someone on his team successful, VP of Sales Max Lowenbaum kept it simple: culture fit.

 

What makes your sales team’s culture unique?

The one word I would use to describe Hireology’s sales culture is “intentional.” There is a reason behind everything that we do and who we are, and that reason is to help our employees and our company grow. This makes us work hard, get better and have fun. There are lots of growth-minded companies, but the way we do it here is unique to Hireology, and it’s by design.  

We look for people who are genuinely inspired and excited by the opportunity.”

 

What are the most important traits needed to be successful on your team, and why?

The most important trait for us is culture fit. No matter how great someone can be at the job, if they don't add to our culture and make other great people want to work at Hireology, they won't be happy here and our company won't benefit from having them. We look for people who are genuinely inspired and excited by the opportunity to work at our company, in our markets and on our product. We can teach them everything else.  

 

What training or programs do you offer to help salespeople succeed?

We have a formal two-week onboarding program and then ad-hoc training moving forward. We are constantly focused on helping our reps improve, and employee growth is critical to the success of our company. Additionally, we’re currently looking to add a dedicated resource, a sales trainer, to our team to help us further our goals on sales training and skill improvement.

 

ReviewTrackers Chicago sales team

ReviewTrackers’ software helps businesses keep track of their online reputations and increase the amount of customer feedback they receive. To Director of Sales Jeff Pearlman, the key to being successful on his team is balancing collaboration with competition.

 

What makes your sales team’s culture unique?

Our top salesperson is extremely competitive. At the same time, he’ll stop what he’s doing to help people around him. He’ll do whatever he can to help other sales reps because he knows that’s what’s going to help the company.

We have a career progression plan built so that people can get promoted up to four times a year. If someone hits 150 percent of their quota in a quarter, they move up in terms of title and pay. If someone averages 100 percent of their goal across two, three, or four quarters, they move up a level. People really have the opportunity to grow within their sales roles to take on bigger titles and more responsibility.

People really have the opportunity to grow within their sales roles to take on bigger titles and more responsibility.”

 

What are the most important traits needed to be successful on your team, and why?

For me, it’s constant practice and being coachable. If you can take the things you are learning, implement them and practice, then you are going to set yourself apart from the pack. There’s a difference between the reps who come in and practice five pitches before they make their first cold call of the day, versus the one who just jumps into a call. If you work hard and are willing to learn through constant feedback, we will give you the tools you need to be successful.

 

What training or programs do you offer to help salespeople succeed?

We have a weekly, hour-long training session for the whole sales team that ranges from how you set an agenda for a meeting to how to negotiate pricing, run discovery and review the value of our product at the end of a call. I also do one-on-one training with every rep so that we can identify certain things that need improvement. I’ll also jump on calls with them to be a fly on the wall and give feedback afterward, or to actively participate in the call and help train people by showing them how I would handle certain situations.

 

Affinitiv Chicago sales team

Affinitiv is a marketing technology company that works exclusively with automotive manufacturers, dealership groups and individual dealers. Chief Revenue Officer Tim O’Neill said that although culture can’t be quantified, it’s still extremely important to a sales team.

 

What makes your sales team’s culture unique?

You cannot measure a team’s culture like you measure monthly revenue, meetings and pipeline activity, but this does not mean it’s not important. I would describe Affinitiv’s sales culture in a few words: healthy competition, accountability, a common vision, trust and communication. Our team has the ability to quickly identify opportunities and work towards solving business issues for our clients.

We have a work hard, play hard culture that rewards people for overachievement. What makes us unique is that our sales leadership is part and parcel to the process. We don’t ask anyone to do something we are not willing to do. We have a very open and honest culture that promotes healthy debate.

We have a work hard, play hard culture that rewards people for overachievement.”

 

What are the most important traits needed to be successful on your team, and why?

We look for individuals who understand the daily risks and challenges of selling. We look for people who understand that activity does not equal productivity. We want people who have the will to win and who don’t make excuses for missing goals. Great salespeople can anticipate a client’s needs, and we want individuals who are focused on solving business issues and have solid business conversations. We want people who know what it takes to meet and exceed goals through solid planning and managing the right type of activity.

 

What training or programs do you offer to help salespeople succeed?

We rely heavily on our sales leaders to become an integral part of the day-to-day training, and not just around our product and sales processes. A big part of our training is built around role playing to ensure we have a consistent message. We also have a great learning management system that gives all of our associates quick access to sales strategies and tactics.

 

Spark Hire Chicago sales team

Spark Hire’s video interviewing platform is used by over 4,000 companies to streamline the interviewing process. Sales Manager Jeremy Tolan described his team as “interdependent” and motivated by the success of the collective, not just the individual.

 

What makes your sales team’s culture unique?

Interdependence is at the heart of our culture. We have systems in place where team members are individually motivated by their entire team’s success. Moreover, a team member’s performance is largely dependent on the performance of other team members, so everyone makes sure to set each other up to be as successful as possible. This interdependence has naturally helped make us an exceptionally tight-knit group.

Successful team members walk in each day passionate about contributing.”

 

What are the most important traits needed to be successful on your team, and why?

Accountability is king. To be successful, you need to be dependable. Being proactive and facing challenges head on with a positive attitude is crucial. We also look for those who think swiftly, and are adaptable and available to help others and our processes improve. Having fun is paramount. Successful team members walk in each day passionate about contributing.

 

What training or programs do you offer to help salespeople succeed?

Every new hire goes through an in-depth, formal training program featuring a mix of classroom-style training and shadowing. During this time, new hires learn about our company, product, customers, processes and tools. New hires begin work with a manager or team lead shadowing them, to ensure good habits are formed and that all of their questions get answered. The training doesn’t stop there, though. Ongoing training initiatives are delivered in weekly team meetings and one on one to foster employee growth and performance improvements.

 

Upwork Chicago sales team

 

Upwork’s platform connects companies in need of talent with freelancers specializing in everything from mobile development to accounting and design. VP of Enterprise Sales Robert Merritt said his sales team’s culture is heavily influenced by its commitment to Upwork’s mission.

 

What makes your sales team’s culture unique?

Upwork’s sales organization is a very mission- and vision-forward team. We’re passionate about connecting companies with great talent and creating economic opportunity globally so that people live better lives. We believe selling is our craft, and providing solutions to our customers problems is what we strive to do daily. We are a results-first team.

Selling is our craft, and providing solutions to our customers problems is what we strive to do daily.”

 

What are the most important traits needed to be successful on your team, and why?

We bring a growth mindset to all that we do. We seek the difficult and embrace the challenge. Our team is also customer-obsessed. We are the “voice of the client” and are more than just an organization delivering service or support. Being world-class is also important, as we are constantly striving to out-practice and outplay our competition. Our sales team members are also relentless in their commitment to our community.

Finally, we are a sales culture built upon candor. Candor gets more people involved and invites dialogue, which creates an idea-rich environment. Candor generates speed, where the best ideas are surfaced, debated, improved and then decided upon. Candor facilitates collaboration, which leads to both personal and professional growth for everyone in our group.

 

What training or programs do you offer to help salespeople succeed?

We offer a fully developed month-long orientation, called Hustle, that completely immerses a new hire in all things Upwork. Hustle is a combination of Upwork training as well as role-specific training, and it equips new employees with everything needed to get off to a fast start. We have additional training programs to help employees expand their skill sets and knowledge as they move past the six-month mark. Lastly, we have a leadership development program called “On-Deck” that provides future leaders with mentoring, coaching and the development curriculum needed to succeed once they advance to the next level.

 

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