Account Executive - Midmarket

| Chicago



We here at Jellyvision are the proud parents of ALEX®, an interactive employee communications platform that happens to share some DNA (and a sense of humor) with the smash-hit trivia video game YOU DON’T KNOW ®, created by Jellyvision's founder. ALEX makes navigating tricky decisions—like choosing and using employee benefits or improving your financial wellness—easier, faster, and more helpful, not to mention entertaining. The success of the ALEX platform has exceeded our wildest dreams, (except for the part right before we woke up where our mom was riding a giraffe), which is why we need talented folks like you to help us help ALEX take over the world…er…continue to grow and succeed.

Reporting to the Director of Sales you will be contributing to the growth of ALEX by generating sales for our new ALEX Small to Medium Business (SMB) team. As a member of the ALEX SMB team, you will sell a wide range of products that helps employers help their employees choose and use their benefits, and plan for their overall financial well-being. Our products are sold both to brokers, who are our target customers in the small business space, and direct to employers.

Day to day, you’ll build and manage partnerships with the industry’s most innovative brokers, as well as reach out to new small and medium business prospects in an assigned geographical territory, dazzling them with ALEX products and closing deals left and right.  You will have the support of a team of inside sales reps, but will be responsible for reaching out to both cold and pre-qualified leads.

Why should you be interested in bringing your considerable sales chops to this particular opportunity?  Well, we seem to have a bit of a good thing going.  ALEX is well established and growing quickly. It isn’t utility enterprise software, like payroll or CRM; instead it’s an entirely new concept in employee communication, and it “shows” well.  Accordingly, the sales challenge isn’t as much differentiating ourselves from the competition, as it is shifting conversations from costs/price to value/benefits.  And the benefits are pretty impressive – we’ve got great case studies and a strong value proposition for the product.  We currently license ALEX on an annual recurring fee basis to more than 800 companies, many of which can be found sitting on the Fortune 500 list.  Our products are award-winning and extremely highly regarded, a great marketing team is already in place, and we’ve got amazing account and implementation teams to take care of clients once deals close.

So what will I do on this rock star team?  Specifically, you will be responsible for:

  • Prospecting from an existing book of business, calling, setting meetings, and making new friends, both with employers and brokers alike.
  • On the employer side, managing the full life cycle of an opportunity: pitching hundreds of qualified companies, creating relationships, negotiating and finally, closing an insane amount of new business. Once you have the green light from the client side, you’ll work closely with our implementation team to develop a statement of work and shepherd the deal through legal review to close.
  • On the broker side: hosting lunch and learns, providing support to help brokers pitch ALEX to their own customers, and doing a lot of listening to bring broker pains and opportunities to our product team so we’re constantly evolving our platform and approach to better serve their needs.
  • Meticulously tracking activities in Salesforce.
  • Reporting progress against daily, weekly, and quarterly goals.
  • Efficiently managing complex and, at times, long sales cycles.
  • Sharing what you’re learning with your team. We’re big into helping each other win, and do better with collaborators than lone wolves.

While we’re big believers that the right “DNA” and cultural fit are what makes for a successful hire, we’ll take an early shine to candidates with the following background, skills, and experience:

  • Proven sales chops.  Ideally, 2+ years of sales experience, preferably in the technology industry selling B2B. A solid SaaS software or benefits background would be helpful.
  • Experience prospecting, cold calling and securing appointments as well as closing new business.
  • Excellent verbal and written communication skills – the ability to talk and write with confidence, charisma, and competence for a wide variety of audiences.
  • Mad people skills. You’ll need to make a killer first impression, and then maintain active engagement with new and existing leads by being creative in your follow up efforts.
  • You must be a relationship builder – interacting with prospective clients and partners in a way that projects Jellyvision’s sense of fun paired with the unmistakable je ne sais quoi of hard-core competence.
  • You should also be able to challenge people in a charming way – for example, if you walk away every time a prospect says they don’t have the budget, you will leave sales on the table.  But you need to know how to address those budget concerns thoughtfully, in a way that doesn’t feel pushy.  Which means you’ll also need...
  • Great listening skills, as well as humility.  We aren’t the right solution all the time for everyone, and we’re believers in “seeking first to understand” before we make our pitch.  We get that people want to do business with people they like. If the timing isn’t right, but you form a relationship that can yield fruit in another season, well, that’s a key part of the job.
  • Killer sales instincts and drive.  Someone with a good gut for which leads are worth running down.  And the stamina to run them down.  And the drive to always want to close one more deal next week than you did this week.  Or two more.  Why not three if you hit two last week?  What would happen if you pushed for four?  (Are we beating a dead horse yet?  Probably.  But if you automatically started thinking, “Five, I could do Five.” then we want to talk to you.)
  • Innate curiosity and the ability to act on it.  You’ll have to be able to quickly understand prospects’ industry and core business processes, and how our solution could solve some of their problems.
  • Excellent market research skills, coupled with great instincts for the market.  You’ll need to be great at market research and analysis to evaluate the market for ALEX and develop a winning sales strategy.
  • Technical savvy - or at least a comfort level with discussing and understanding technical issues.  We need someone who can learn and understand product solutions and features.
  • Ability to play well with others.  Sales at Jellyvision is a team effort.  You’ll work closely with the other sales team members, the marketing team, and members of the creative, engineering, and implementation staffs.
  • Organization and time management skills in spades. You’ll be maintaining a large pipeline of leads and opportunities, so the ability to keep everything sorted out is key.
  • Proficiency in MS Office, Outlook, Google Alerts, Advanced Google searching techniques and
  • A phenomenal sense of humor.  Yes, it will make you more effective.  It’s also a job requirement at Jellyvision.

NOTE: Although our Account Executives will be managing geographic territories, we’re largely phone, email, and WebEx based in our sales. The ideal candidate will be based in Chicago, working out of our Lincoln Park office.

Well, look at that!  We asked a few of our Account Executives on your behalf.  Check it out here:

We knew you'd say that.  Here are a few more specific videos from the team:
David shares his favorite client success story:
Jessica shares why she loves to demo at Jellyvision:
Omar shares his definition of “sales” and his approach to the sales process:


Yes. We share a commitment to excellence and a desire to work in a comfortable, friendly atmosphere, so we only hire nice, bright, funny people who are willing to work hard.  Our credo is a simple one: be helpful. And we think we can be most helpful if our workforce is as diverse in thought, perspective, and culture as the people who use our products. We are looking to add amazing folks to our team who will bring diversity across many lines, including race, ethnicity, religion, sexual orientation, age, marital status, disability, gender identity, sex, and country of origin.

ARE THERE ANY PERKS? Yes, we love perks.


  • Competitive pay, 401(k) with matching and benefits. We pay 100% of the cost of premiums for medical, dental, vision, disability and life insurance for our employees (as long as you qualify for our tobacco-free discount; if you’re a tobacco user, your medical premiums will be higher than $0). We also cover a really nice chunk of the cost of premiums for spouse/dependent medical, dental and vision insurance.
  • Casual dress and a flexible schedule. Come in a sweatshirt, jeans, whatever, like everyone else here.
  • Creative work environment. We are lucky to work in a place that is full of intelligent, talented and innovative folks. Although most hours the place is deathly quiet (we're a focused bunch), this is punctuated with hilarious outbursts and general merriment, which makes a nice way to spend the day.
  • Free food. Every week, we stock our kitchen with free healthy snack foods, and we have a catered lunch every other week to give people a reason to hang out and eat together.
  • Easy transportation and lots of love for folks who bike to work. We’re really close to the North/Clybourn red line stop and the Halsted (#8) bus (right by the Apple Store and Mega Whole Foods too), and we have a transit FSA that allows you to dedicate pre-tax dollars to public transportation expenses. A number of our employees like to bike to work, so we also have bike storage, showers and lockers in the office.  And for those without their own bike in the city, we offer free divvy memberships – complete with Jellyvision bike helmets you can borrow from the office.
  • Did we mention our yoga class? We bring a pro instructor right to the office. Fully subsidized by Jellyvision and fully optional, btw.
  • Oh! And we have a massage chair. Not just any massage chair, my friend. It’s the HumanTouch HT 5320 WholeBody™ Massage Chair. Feeling a little stiff? Sit down. Relax. Feel better? Good. Okay, back to work.



We look forward to hearing about you and what you do. Make sure your application includes:


  • cover letter that highlights three reasons you think you’d be great for the gig, focusing on how your past experience has prepared you for this kind of position. Writing is key to all we do, and we weigh cover letters heavily.  We love a cover letter that really shows us your personality (check out our company bios to see the wide range of personalities we’ve already got in house), but don’t stress if you’re not a comedian. You don’t have to be funny. Just be yourself. We’re mostly interested in learning who you are, what you love to do, and why you’d love to do it here with us.
  • Your resume  


You will receive an auto-reply confirming that we've received your application.

Please know that every single application we receive is read by a real live human being. However that kind of thoughtful review takes time, so it may take us a little while to get back to you (but we will, we promise). In the meantime, NO FOLLOW UP PHONE CALLS OR EMAILS, PLEASE. It’s not that we don’t love hearing from you. It’s just that time spent responding to follow ups could be spent…well…reading your application. Please rest assured that if you received a confirmation from Recruiting Robot, we’ve got your application, and will get back to you really soon. We knew you’d understand.

If you still have pressing questions in the meantime, please feel free to check out our handy-dandy FAQ page!


Thanks for your interest in Jellyvision!

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848 W Eastman St # 104 , Chicago, IL 60642
848 W Eastman St # 104 , Chicago, IL 60642

Perks of working here

401(K) Matching
Casual Dress
Company Equity
Health Benefits
Some Meals Provided
Stocked Kitchen
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