Career Success Story: Charles Chuman's Path to High-Growth Sales

Charles Chuman's career might be described as a laundry list of places, faces, and causes. Work opportunities and learning goals have taken him from Chicago to Lebanon, then on to Iraq, Jordan, and the United Arab Emirates, before returning stateside to Indiana, Washington D.C., and finally back to the Windy City. He has worked as a journalist covering Middle East politics while studying Arabic as a graduate student at American University of Beirut. He's developed new market strategy for a startup investment firm, rallied supporters as a field organizer for Obama For America, and contributed to efforts around energy policy in D.C. Throughout the diverse turns and reaches of his career path, the common element has been early-stage interaction with the seminal ideas of the day: Middle East, Obama, energy, startups. And now, healthcare tech.

A graduate of our spring 2015 sales training course in Chicago, Charles champions healthcare innovation for a growth-stage Chicago startup. I caught up with Charles to learn more about his new role:[bctt tweet="Interview with @charleschuman, #startup #sales executive at @ContextHealth."]

Tell us about your job at ContextMedia

I am a healthcare sales executive at ContextMedia:Health. We provide preventive, condition-specific education through digital means in the space where patients make the most decisions about their health—the point-of-care. We provide free televisions, tablets, digital wallboards, and wireless internet to healthcare systems, hospitals, clinics, and doctors offices to educate patients, empower patients with information, and assist doctors and their staff through our digital platforms. It is my job to bring our products to the attention of medical professionals and bring them on board as members.[bctt tweet="At @ContextHealth, we provide preventive digital ed at the point-of-care. -@charleschuman"]


What is a typical day like?

I usually arrive at work before 8am. Breakfast and coffee are provided.

From 8:15-11:30, I am on the phone with doctor's offices and hospitals. I manage my sales pipeline to make sure that I have structured out my calls in advance. I usually like to have a group of new prospects (cold calls), follow-ups with offices that have expressed interest in our service, and a few objection calls.

The company provides lunch. I always try to touch base with our other teams during this time. It is useful for salespeople to keep up to date with what is happening in other departments: product, marketing, onboarding, account management, accounting, and Salesforce developers.

I'm back on the phone for most of the afternoon. Then, from 5-6:15pm I sort through leads and plan out my schedule for the next day.

Many evenings throughout the week, you'll find me trying to recruit new candidates at networking events around the city. If you're interested in a job in almost any field (but especially in sales), send me your résumé.

ContextMedia seems to be more of a scaleup than a startup. What do you like about working for a company at this growth stage?

This is my first job in business-world sales. I wanted to learn from one of the best sales teams in the city.

More importantly, I wanted to see a company scale. The startup process is important, but so is the scaling process. ContextMedia bootstrapped, so we are inventing everything internally and figuring everything out for ourselves. As big of a company as we have become, we still have a startup spirit because we only have ourselves to rely on. There are not venture capital experts, consultants, or invested channel partners showing up and telling us that we need to hire someone or make specific changes. We own our decisions.[bctt tweet="As a scaleup that #bootstrapped, we own our decisions for @ContextMedia, says @charleschuman"]

Maintaining company culture is difficult in a scaling company. ContextMedia's founders have seen companies change in negative ways during their scaling process and decided that the talent team will maintain our culture. It makes it more difficult to hire people, hence more difficult to scale as rapidly as desired. However, it keeps the company strong in the long run.

When startups succeed, scaling occurs rapidly. It is useful to have seen the transition and be able to provide that advice to other startups in the future whether as an investor, mentor, Startup Institute instructor, or otherwise.[bctt tweet="When #startups succeed, #scaling occurs rapidly. I've seen that transition. -@charleschuman"]

Tell us about your interview process. Why do you think you ultimately got the gig?

ContextMedia has a long and thorough interviewing process. The process starts with a phone interview. Our talent team is very friendly and asks the usual interview questions in a comfortable manner: Why ContextMedia? Why this role? What motivates you? Tell me about a time when...

The second round is an in-person interview, generally with a team member and a department manager. For me, I spoke with the top sales rep and one of our sales managers. This is where many applicants begin to drop out. Our managers are very good at making candidates feel comfortable and letting them know about the company. We want to hire people who really, truly want to work at ContextMedia. Equally as important, we want people who truly want to work in the area they are applying for. Since we are scaling, we want salespeople or accountants who want to work in sales or accounting and do not one day hope to work in product or marketing.

The third round is a telephone-based situational interview. The majority of candidates do not make it through this round. During three separate situational calls back-to-back, candidates are asked to role play their future role in the company. For salespeople, these are three mock cold calls. The traits we are looking for most are adaptability, empathy, and friendliness.

The fourth round is usually with a manager, a member of senior leadership, and a co-founder.[bctt tweet="Traits @ContextMedia looks for in #salespeople? Adaptability + empathy - @charleschuman"]

At each step, a candidate must show a combination of ethics, competitiveness, grittiness, and friendliness, and must remain consistent as to why she wants to work in the specific role she is applying for.

What does an aspiring startup salesperson need to know about the Chicago tech scene?

Meet as many people as possible. The Chicago startup scene is growing rapidly, but we are in constant communication. Every company is eager to hire salespeople. The important thing is to find the right company culture and product for you. The best way to find out how a company really operates is by meeting the people who work there.[bctt tweet="Every #Chicago startup needs #salespeople, says @charleschuman. Get out and meet people."]

What advice do you have for incoming students in our sales training program?

Network as much as humanly possible. The sales course at Startup Institute is a wonderful period in your life, but it is brief. Make sure to make the most of it.

Start scheduling coffee chats during your second week of the program. Ease your way into them. Start by asking Startup Institute alumni and instructors. We're non-judgmental and have been in the exact place you're in right now.[bctt tweet="Start to build your #network with @StartupInst alumni + instructors, says @charleschuman" via="no"]

After you feel comfortable, work your way up to the highest levels, not necessarily in terms of job title, but in terms of your own personal comfort level. Figure out if a certain person intimidates you and why, and work your way up to asking them for a coffee chat.

The more you network and the more you schedule coffee chats, the more you will come to understand yourself, what other people find interesting about you, and how you will fit into the startup scene. This is critical intelligence that you can use to craft your own personal elevator pitch. You will learn the language startup people use, what catches their attention, what books they've read, what companies are booming, what products don't actually work, and more. It's invaluable, and it's only available to you for a very short period of time.[bctt tweet="The more you #network, the more you'll come to understand yourself, says @charleschuman"]

Interested in launching your tech sales career? Our free sales and account management course guide will tell you everything you need to know about our eight-week program.