Account Executive - Enterprise

| 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 JACK®, 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 Enterprise Sales, you will be contributing to the growth of ALEX by generating sales for our ALEX Enterprise product. The target market for ALEX Enterprise clients is large employers with 3,001+ benefits-eligible employees. At the Enterprise level, ALEX is both configurable and customizable, allowing our largest clients to create a unique ALEX experience for their employees.

As an experienced sales rep, you know that selling Enterprise-level products to Fortune 500 (and similar) clients results in a long sales cycle. You will work your way through HR hierarchies to ensure that we know the timing of the buy, the purchasing process, and which decision makers need to be at the table to make the deal happen. And you’ll need to do all that networking, relationship building, and jumping through procurement hoops with a Jellyvision sense of humor and panache (yes, we just wanted to use the word “panache” in a job posting). In a nutshell, you’ll be using your consultative sales skills and experience to build relationships with HR professionals at large companies, and use those relationships to inform your sales process for each potential client so that you can get the deal done.

And why should you be interested in bringing your considerable sales chops to this particular opportunity? Well, we seem to have a good thing going. ALEX is licensed on an annually recurring fee basis and is used by millions of employees at more than 800 companies —including 70 of the Fortune 500® and more than a third of Barron’s list of the ‘“World’s Most Respected Companies” based in the US. And now with ALEX Express, we’re adding small and medium sized businesses to our impressive list of clients. ALEX is award-winning and extremely highly regarded, a great marketing team is already in place, and you will have the support of an inside sales team setting appointments for you.

So what will you do on this rock star team? Specifically, Account Executives for ALEX Enterprise are responsible for:

  • Closing significant net new business with Enterprise-sized customers.
  • Building a thorough territory plan that includes:
    • Key partnerships
    • Target accounts
    • A deep understanding of the territory dynamics
  • Managing a sales cycle that can be complex and long – or sometimes incredibly short if you talk to the right people at the right time. Throughout the process, you should plan on leveraging your creativity to keep a dialogue going with dozens of key prospects. On average, an Enterprise sales cycle lasts approximately 5-6 months from initial contact to close.
  • Mastering the art and the science of the pitch by delivering engaging presentations online or in person with executive level decision makers.
  • Negotiating price and contractual terms with almost all new customers. You must be skilled at identifying who is going to be involved in approving the purchase (legal, CFOs, CEOs, etc.). Since you will have been the main point of contact throughout the long sales process, when the deal reaches the contract negotiation stage, you’ll be a driving force to keep potential deals moving through the procurement process smoothly, all while exhibiting constant Jellyvision charm.
  • Finally, be prepared to become close friends with We’re meticulous about tracking everything and expect you to be as well.

We’re looking for smart, seasoned, likable, numbers-driven sales folks who are used to blowing their quotas out of the water and are looking for a new challenge. We’ll take an early shine to candidates with the following background, skills, and experience:

  • Proven sales chops. Ideally, 5+ years of sales experience, preferably in the technology industry selling B2B. A solid technology, agency, or benefits background selling into large organizations (Fortune 1000) would be helpful. We’re looking for sales folks who have experience meeting and beating a quota in the neighborhood of seven figures.
  • Experience working your way through the purchasing process at large companies. If only it were as simple as finding the right person, explaining the value prop and getting a signature on a piece of paper, right? ALEX Enterprise is most often a nuanced sale that requires bringing together a number of decision makers, mastering complex procurement processes, negotiating contract terms, and constantly overcoming roadblocks until the deal is done. If your specialty is figuring out the right people to approach and the path to take to land a big-name logo, we’d like to talk to you.
  • Killer sales instincts and drive. Someone with a good gut for which opportunities are worth running down. And the stamina to run them down. And the drive to always want to close one more deal next month than you did this month. Or two more. Why not three if you hit two last month? 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.). 
  • 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.
  • 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.
  • 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 in a way that projects Jellyvision’s sense of fun paired with the unmistakable je ne sais quoi that reeks 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.
  • 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.
  • 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.
  • Proficiency in MS Office, Outlook, Google Alerts, Advanced Google searching techniques and (experience with marketing automation tools such as Eloqua or Marketo is a plus).
  • A phenomenal sense of humor.  Yes, it will make you more effective.  It’s also a job requirement at Jellyvision.

Well, what do ya know!  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:
Our newly promoted VP of Sales 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, stock options 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.


To be considered, we need:

  1. A cover letter that highlights 3 reasons you think you’d be great for the gig, along with your sales stats for the past several years, target vs. actual.  Writing is key to all that we do, and we weigh cover letters heavily.  Show us how you’d engage us as if we were a prospective client.
  2. Your resume

You should 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. (Yes, we know that a good salesperson should always follow up, but trust us here.)  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!

Thank you 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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