A Peek Into Chicago Sales Jobs

Four Chicago sales employees talk about their first months on the job.
Written by Avery Komlofske
December 14, 2021Updated: December 14, 2021

Now is the time to apply to that sales position you’ve been dreaming about.

Sales is a field built on transferable skills — if you can sell in one place, you have what you need to sell anywhere. And with nearly a thousand open sales jobs on Built In Chicago alone, there are plenty of opportunities to seize.

Having the luxury of choice, though, has its own difficulties. How do you find the sales job that’s right for you? 

There are significant factors to consider: the product you’d be selling, the company culture and values, and the positives and challenges of working for a specific organization. Ultimately, the best way to learn the realities of working in a position is to talk to people who are already there. 

To get a glimpse into the new hire experience, Built In Chicago talked to recently-hired sales employees from Upwork, Infutor, PerkSpot and Key2Act. These employees opened up about their experiences as new members of their teams, including the challenges they face, how they fit into their company and what they particularly value about working there. 

 

A couch and table in Key2Act's office.
Key2Act

 

Sarah Abusoud
Business Development Representative

 

What attracted you to apply for a role at your current employer in the first place?

I was attracted to Upwork because of its innovation, its mission to create economic opportunities to better people’s lives and its diverse and inclusive company culture. 

Upwork is a people first-organization so I knew I’d be joining a company that prioritizes its employees, which would keep me engaged and motivated to do my best each and every day. Upwork’s business model is one I’m passionate about — it’s additive for the economy and helps people attain control and freedom over their businesses and independent careers. Additionally, Upwork makes a dedicated strategic investment in diversity, inclusion and belonging, both within its corporate teams and on the Upwork platform, which creates a positive impact on society.

 

Which skill or experience do you think helped distinguish you during your job search?

As a marketing and sales student at the University of Wisconsin-Parkside, I had the opportunity to participate in sales competitions and career growth opportunities that served as building blocks to my success today. I’ve participated in international sales competitions that were based on real-life corporate sales scenarios, ranging from initial cold outreach to closing the sale. Having ranked as a top 10 performer in each competition, I learned the value of storytelling and that leaning into my unique strengths — like being trilingual and strong interpersonal skills — help me form genuine connections with people that I meet. I’m grateful for the endless support from my career coach and the complimentary sales coursework that laid the foundation for my career.

I learned the value of storytelling and that leaning into my unique strengths help me form genuine connections with people that I meet.”

 

What do you enjoy most about selling your company’s product or service, and what do you find most challenging?

The most enjoyable parts of selling Upwork Enterprise are building strong relationships, being a resource for organizations looking to accomplish big goals and supporting what is most important to my clients and their company. When you love what you sell, it shows — I am proud to sell a solution that makes clients’ lives easier, enriches their company culture, drives revenue and fills critical talent gaps. 

In sales, there is always a challenge selling a product or service and seeing if it is a true fit for your client. At Upwork, our business model requires innovative thinking and an understanding of what the workforce can and should be — as opposed to what it used to be. It can be challenging to change the status quo, but with our network of high-quality freelancers, need-specific solutions, customer success stories and unique labor insights we are uniquely positioned to address the tremendous market opportunity in front of us.

 

 

Conor McMahon
Customer Success Manager

 

What attracted you to apply for a role at your current employer in the first place?

Prior to working at Infutor, my experience as a customer success manager was specifically in the SAAS space, selling out of the box solutions. I wanted to join a growing organization with a collaborative team that made data-driven decisions. My decision to join Infutor has been the best professional decision I’ve made and I’m grateful to be part of such an amazing organization.

 

Which skill or experience do you think helped distinguish you during your job search?

I started my professional journey as an account executive and have since transitioned into customer success. While I enjoy working alongside our customers to help them achieve their business objectives, the opportunity to sell within those organizations comes naturally to me. 

I believe my curiosity and creativity differentiated me from others during my job search. I’ve been empowered to provide input and feedback as a new employee — not given a script and told to forget the knowledge I’ve acquired during my path. I’m grateful to have joined the team and have found my new home here with the Infutor family.

I’ve been empowered to provide input and feedback as a new employee — not given a script and told to forget the knowledge I’ve acquired during my path.”

 

What do you enjoy most about selling your company’s product or service, and what do you find most challenging?

I love that we have products that can provide tremendous value to many different customer profiles. No one use case is the same as another — each solution is creatively put together between Infutor and our customers. The process to determine the best product or products for each customer is collaborative and engaging — while this does provide a great deal of flexibility, it also presents unique challenges we might not have seen or solved for previously.

 

 

Ellen Donaghy
Account Executive

 

What attracted you to apply for a role at your current employer in the first place?

It was really the quality of the product. I understood it, I could see the value of it and I could visualize myself authentically promoting it to a client.

 

Which skill or experience do you think helped distinguish you during your job search?

I really wanted it. I had applied previously and came up a tiny bit short in the interview process. This time around, I could really articulate all the areas where I had improved and how I could apply that experience at PerkSpot.

I understood the product, I could see the value of it and I could visualize myself authentically promoting it to a client.”

 

What do you enjoy most about selling your company’s product or service, and what do you find most challenging?

It’s got real value. I use it, my coworkers use it and we brag about how we’re using it, which gives me so many use cases for how the customer’s end users will use it. The challenging part is that it’s a no-cost solution to a problem that doesn’t have a native timeline — budget cycles, seasonal hiring patterns, open enrollment or review periods — so if the initial enthusiasm for the product wears off before the deal closes, getting the buyer to the finish line can be challenging. Luckily, there is a strong team I can lean on for support.

 

 

Ron Vallejo
Business Development Manager

 

What attracted you to apply for a role at your current employer in the first place?

I believe that Key2Acts’ technology needs to be offered to as many people as possible.

 

Which skill or experience do you think helped distinguish you during your job search?

My history in my field, actually — since I come from the customer base that Key2Act calls on.

I enjoy making my customers’ lives easier with what we do.”

 

What do you enjoy most about selling your company’s product or service, and what do you find most challenging?

I enjoy making my customers’ lives easier with what we do. The hard part is slowing the potential customer down so they can see that we can help them make more money and simplify their workflow to get the job done and make their customer happy.

 

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