Sales Manager

| 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.


Jellyvision is at a really exciting place in its history as a company – growing like crazy and with serious goals for future growth and product expansion. As we expand our sales team, we need to add a management layer with talent for coaching high performing Account Executives (AEs) through a consultative enterprise SaaS sales process, increasing conversion rates, and closing deals left and right. We’re looking for smart, seasoned, analytical managers who know how to both use data to drive decisions and also like to roll up their sleeves and dive in to help move deals forward. 

Our talented and typically hilarious AEs are supported by two rock solid functions:  1. Our team of inside appointment setters – our Business Development Representatives (BDRs) – who prospect, cold call, and set appointments for AEs to speak with interested companies and 2. our Sales Operations function that helps us track and analyze our activities.  This isn’t a start-from-scratch gig, but rather a help-us-organize-as-we-grow one.  

More specifically, our Sales Managers are responsible for:

  • Managing performance and coaching your team.
    • You’ll meet with your Account Executives (likely 7 to 10 people) one-on-one weekly to review their pipeline, process compliance, and evaluate progress towards goals. You’ll be responsible for mentoring your team and identifying coachable moments, helping each AE diagnose and correct approaches that are holding them back, and reinforcing effective strategies and behavior. This will require a lot of time spent in the numbers and dashboard to proactively identify gaps in pipeline performance.
    • You’ll routinely attend pre-qualifying calls and follow-up meetings with each of your Account Executives to understand their selling techniques and gain insight into coachable moments.
    • Working with other sales leaders, you’ll participate in and lead team meetings and daily stand-ups.
  • Hiring and training.
    • As we continue to grow, you’ll be involved heavily in the hiring process for your team: sourcing candidates, interviewing, participating in auditions (an important part of Jellyvision hiring) and helping us make the right decisions as we scale our team.
    • To set up your new hires for success, you’ll share your ideas for refining and expanding our AE training and on-boarding program – we welcome thoughts on how best to get new hires up to speed on Jellyvision’s sales process, learn the ins and outs of ALEX, most effectively shadow other Account Executives, etc.
    • And once folks are on board, you’ll provide continuous training and feedback to all team members.
  • Assisting with large strategic opportunities.
    • With our VP of Sales, you’ll develop selling strategies to activate and nurture national partnerships.
    • You’ll help your AEs with big opportunities, including covering for them when they’re out, by demonstrating best practices around preparation and research, sitting in on calls, and moving the sale forward through a sometimes long and involved sales process.
    • You’ll work closely with colleagues across the company to assist your team in negotiating and closing strategic deals.
  • Maintaining a close eye on team dynamics.
    • Each Jellyvision salesperson calls into a specific territory. Working closely with the VP of Sales, you’ll work to manage the territory split for a growing team of salespeople.
    • You’ll manage the relationships between your AEs and the BDRs they work with to increase their efficiency and productivity.
    • You’ll help foster and enable a culture of collaboration, support, and fun.
  • Close communication with the VP of Sales and Executive team.
    • Each week, you’ll provide an accurate forecast of sales progress for your team.
    • Each month, you’ll report on individual and team dynamics and performance.
    • Lastly, you’ll keep the VP of Sales and Executive team informed on the insights your team gathers on market changes and dynamics as they speak daily with leaders in the HR space. 


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 management experience.Ideally, 4+ years of experience managing employees in an Enterprise sales environment, preferably in the HR or SaaS Sales Industry. We’re looking for managers who love working with people and coaching their team members to perform to the best of their abilities. If you have a network of great AE and BDR candidates, that will come in handy.
  • Experience cold-calling, hunting, and closing new Enterprise business.Ours is not a transactional sale but rather an involved, multi-constituent enterprise one.  The wisdom you’ll share with your team to make them better salespeople will come from lessons you learned and knowledge you gained from years of being a successful salesperson yourself, one who constantly meets and exceeds sales targets by understanding how to capture attention, show real value, and nurture relationships over time.
  • Organization and time managementskills in spades. Sales at Jellyvision is fast-paced. This role will require you to excel at the tasks directly in front of you, while also keeping your eye on the big picture. Serious organizational chops are required to manage all of that in a company growing as quickly as ours – and it’s an important thing to model for your team.
  • A student/learner mindset. This is perhaps unusual but our sales leadership is chock full of people who are eager to continually benchmark and improve our efforts.  We’re always tinkering.  It will help if you read books on sales methodologies and have a quant-y, math-y mindset.  Also, we have a very tech-enabled organization.  If you don’t like to dabble in new technologies to create efficiencies, we’re probably not the best home for you.
  • Creative problem-solving skills.The sales process for our Enterprise deals can be lengthy. When your Account Executive hits a roadblock, you’ll want to get involved and come up with solutions to keep the process moving towards a deal.
  • You must be a relationship builder– trust and communication are the pillars of any relationship. And you need to be skilled at building authentic, trusting relationships both internally and externally. Having people skills and developing a rapport with everyone on your team will contribute to your success as the leader of a hungry, hard-working, and driven Account Executive team.
  • You should also be able tochallenge people in a charming way. Giving advice and constructive criticism is a fine art. You should know each of your individual team members well and adapt your approach to each of them in a way that brings out the best in them every day.
  • A good eye for talent– As our sales team continues to grow, you’ll be responsible for helping to find and identify the next great Jellyvision salespeople. We’re looking for smart, driven people interested in sales who have hustle and are great culture fits for the team. And once those folks are on board, you’ll need to…
  • …Be able to lead by example and maximize the talent of your team. To gain insight into how each of your Account Executives are doing, each month you’ll attend 2 pre-qualifying calls and one follow-up meeting per each rep.
  • Excellent verbal and written communication skills– the ability to talk and write with confidence, charisma, and competence for a wide variety of audiences.
  • 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 legal, creative, engineering, and implementation staffs.
  • A great sense of humor. Yes, it will make you more effective.  It’s also a job requirement at Jellyvision and a seriously important component of our 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 and meditation classes? 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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