Are we in a sales hiring drought? 5 top Chicago startups let us know what they think

by Sam Dewey
July 23, 2015

Have you caught wind of the most recent hiring rumor? This summer’s heat has apparently brought on a sales drought. Companies in the area are more than willing to hire for sales, but they’re having a bit of trouble locating true all-stars to add to their teams. To get the inside scoop, we sat down with five top Chicago startups who are successfully building their sales teams in spite of the reported drought.



Who they’re looking for: “We’re building a team of elite salespeople that have aptitude, humility and grit,” said Philip de Guzman, Executive Business Liaison at ContextMedia. “The future of any industry can be unpredictable, and hiring for aptitude over experience makes for a nimble team that can adapt to change. Humility ensures that we hire team players that are open to feedback and approach work with our patients in mind. Lastly, by hiring for grit, we're building a team that holds itself accountable and will get creative to hit goals. We don't follow a script at CM, so we want people who are comfortable letting their personalities show!”

Difficulty level of finding talent: 7

Why’s it so tough: “Chicago is home to some of the best salespeople in the world, so finding salespeople is easy,” de Guzman said. “The tricky part is figuring out which of them are mission-driven, embody our values, and can generate demand. Our team isn't just trying to hit their quotas every day; we want salespeople who get up in the morning motivated to improve the lives of the the millions of patients we impact.”

Current sales team size: 62

Dream team size: They’re looking to more than double: 125.

See ContextMedia jobs here



Who they’re looking for: “We target folks with 2-4 years of experience who are intrinsically driven and enthusiastic about sales,” said Kristy Nittskoff, VISANOW’s Director of Talent Development. “As we grow as an organization, there are plenty of advancement opportunities so we really look for people who want to advance quickly.  Experience in a tech company helps, due to the fast-paced nature of our work.”

Difficulty level of finding talent: 6. “Our Sales Recruiters are really hitting their stride and the candidates coming in are fantastic,” Nittskoff said. “Four months ago, I would have said 9 but word is spreading fast on what an amazing environment we have here and the unbelievable opportunity that we have in front of us.”

Why’s it so tough: “We face some stiff competition! Our recruiters are very proactive in their approach, but building relationships with the right people takes time. It’s often the case that a candidate is considering multiple offers or wasn’t really looking for something new in the first place. In those situations, we need to really convey the benefits of joining our awesome team that provides employees with the chance to change lives every day,” she said.

Current sales team size: Including sales and client managers, they’re sitting at 72 — up from 30 in January.

Dream team size: 107, by the end of this year. “As we continue to scale, this number will of course grow,” said Nittskoff. “Sales is our biggest area of growth but there is no shortage of opportunities on our Tech, Marketing, and Finance teams.  In total, our plan is have 212 coworkers company-wide at the end of the year.”

See VISANOW jobs here



Who they’re looking for: “We really stress that each team member has their own entrepreneurial spirit, are willing to own their responsibilities, and have an attitude that meshes well with the rest of the team,” said Brian Sparker, ReviewTrackers’ head of content marketing.  

Difficulty level of finding talent: 8. “We're laying the foundation for a world-class sales team, and finding the right people early on in this process is crucial,” he said. “We're lucky to have found David DiPasquale, our Chief Revenue Officer, who has already made an impact on our talent search with his leadership and experience.”

Why’s it so tough: “There are so many great companies with amazing talent in the Chicago area. Identifying the type of person you want to target is fairly easy, but the challenge is hiring the right person at the right time,” Sparker said.

Current sales team size: 5 full-time, each of whom wears many different hats.

Dream team size: They’re looking to double their sales team by the end of the year.

See ReviewTrackers jobs here



Who they’re looking for: They’re hunting for workers who are driven, hungry, self-motivated, and have an entrepreneurial mindset.

Difficulty level of finding talent: “I would place us mid-range,” said Hireology’s Director of Talent, Melissa Ryan. “We have been lucky to be named as one of Crain’s Best Places to Work in Chicago, and it has allowed us to be more selective throughout our hiring process. We have a great culture, great benefits, like equity, that allow us to attract top talent.”

Why’s it so tough: “A great challenge for us is to keep up with the sales hiring volume that a company growing at our pace demands,” Ryan said. “It's a good problem to have. But by using our software, we have an advantage over other companies in selecting more qualified talent for our open roles.”

Current sales team size: 32

Dream team size: 40 by the end of 2015, 75-100 by the end of 2016

See Hireology jobs here



Who they’re looking for: When hiring for sales, UrbanBound wants to see tenacity and resilience. They also want someone goal-oriented and inquisitive.

Difficulty level of finding talent: 8

Why’s it so tough: “[It's particularly challenging to find] the combination of someone who is comfortable working in a startup environment and moving fast, but can also see the bigger picture,” said UrbanBound’s Director of Talent, Libby Keribar. “There are so many great corporate sales organization here in Chicago that finding great startup sales talent can be a challenge.”

Current sales team size: 12, with three new hires starting early August.

Dream team size: 20

See UrbanBound Jobs here

Have a tip for us or know of a company that deserves coverage? Email us via [email protected].

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