We won't beat around the bush- the world of benefits is hard. It's time for something better than options that fail to deliver and waste countless millions on unused resources. That's why Jellyvision is your partner to reinvent how employees choose and use benefits. Our sophisticated technology delights and guides your people to make better benefits decisions — leading them, and you, to a more prosperous future.

jellyvision

Who we are
Jellyvision makes<a href="https://www.jellyvision.com/"> ALEX®</a>, the employee decision-support platform trusted by thousands of employers and millions of people to make smart benefits choices. We’ve done that profitably, at scale, for a long time—over $600M in lifetime sales, without losing our soul or our sense of humor.
Now we’re taking on an even messier problem: Medicare.
A small, senior team is building MyALEXHealth™, a digital Medicare guide designed to help people move from employer coverage into Medicare with clarity, confidence, and dignity. Our goal is simple and ambitious: reduce decision stress, improve plan fit, and help people feel good—not overwhelmed—about one of the most important health and financial decisions they’ll ever make.
This is an incubation-stage product. Translation: ambiguity is a feature, not a bug.&nbsp;
What’s the role?
We need someone who can write the way people actually talk (warm, clever, human), about Medicare (a subject that fights back), inside strict federal compliance (poetry with your hands tied), while architecting the branching logic beneath the words, coaxing an AI voice into sounding like someone you'd trust, and steering the whole thing through carrier and CMS review without a single detail slipping.&nbsp;&nbsp;
If that list made you tired, we understand. If it made you a little excited, keep reading.&nbsp;&nbsp;
You are, first and last, a great writer. Everything else serves that.&nbsp;&nbsp;
Quick gut check on the voice we're after: someone decided the Part D coverage gap should be called "the donut hole," so a hole in your drug coverage would sound like a pastry. That move, making the scary thing feel like an inside joke the two of you are in on, is the whole gig. If you already have three better nicknames for Medicare's weirder corners, we should talk.
What you’ll do to be successful&nbsp;
1) Write like a human being
<ul>
<li>Draft interactive, branching advisor conversations that feel like a smart friend, not a robot reading a policy. Write the linear stuff too: teaser and marketing videos, articles, and UX copy down to the button label and the error state.&nbsp;</li>
<li>Keep voice and tone consistent so product and marketing read as one brand.&nbsp;</li>
</ul>
The bar: people forget they're being walked through Medicare and just feel helped.&nbsp;
2) Structure the branching and conditional logic so it's followable, buildable, and testable
<ul>
<li>Hand engineers requirements, not riddles: here's the script, and here's what it needs the system to do.&nbsp;</li>
<li>Understand how data comes back from APIs and write so the words hold up against the real, messy data, not just the happy path.&nbsp;</li>
</ul>
The bar: fewer "wait, the logic doesn't work that way" moments after handoff.&nbsp;
3) Direct the sound
<ul>
<li>Generate and shape AI voiceover for our host so it sounds like a person, not a GPS.</li>
<li>Direct live VO talent when a project calls for it, and pick the takes that land.&nbsp;</li>
<li>Edit, mix, and caption to a clean, launch-ready standard. We'll train the technical mechanics; the ear is on you.&nbsp;</li>
</ul>
The bar: the voice sounds real, and audio never becomes the bottleneck.&nbsp;
4) Get it live, and get it cleared
<ul>
<li>Own content in our CMS from first draft to live URL, and QA it against your own script.</li>
<li>Prep scripts for compliance review so they're accurate to the Medicare program and true to the letter of federal rules.&nbsp;</li>
<li>Work with team leadership on carrier and CMS feedback: sorting what needs a real change from what needs a clarifying reply, and making the change without killing the writing.&nbsp;</li>
</ul>
The bar: content clears review in few rounds, with the charm intact.&nbsp;
And the part that ties it all together: you own the script, then you coach it to life. Designers, engineers, and collaborators build with you, not for you. The vision and the translation come from you, and you bring people along by making them want to nail it. Think showrunner, not assembly line.&nbsp;
Experience &amp; skills you’ll need
<ul>
<li>5+ years of experience in a writing-led, multi-disciplinary role spanning some combination of interactive content, UX writing, conversational design, content strategy, or digital storytelling.</li>
<li>You write like people talk, and you're funny without visibly trying.&nbsp;&nbsp;</li>
<li>You think in systems. Branching logic and messy data don't scare you; they kind of delight you.&nbsp;&nbsp;</li>
<li>You have an ear. You can hear when a VO line runs a beat too long or lands a shade too chipper.&nbsp;&nbsp;</li>
<li>You sweat the details. In compliance, "close enough" is how brands get in trouble, and you catch the thing everyone else skims.&nbsp;&nbsp;</li>
<li>You treat AI as a power tool, not a threat. You know where it speeds you up and where it makes slop, and you never ship the slop.&nbsp;&nbsp;</li>
<li>You have the portfolio to prove it: real work where you made something complicated feel simple and something dry feel alive. Interactive, editorial, advertising, or education backgrounds all fit.&nbsp;</li>
</ul>
We'll teach you the rest: Medicare's rulebook, our in-house tools (some with zero documentation), and the audio-mixing mechanics. Bring the instincts. We'll bring the manuals.&nbsp;
The Details&nbsp;
<ul>
<li>Location: Remote</li>
<li>Salary Range: $115,000 - $130,000&nbsp;</li>
</ul>
What Jellyvision will give you
Check out our benefits<a href="https://www.jellyvision.com/about-us/careers/"> here</a>!
Jellyvision is committed to continuous evolution and fostering a more diverse and inclusive workplace where everyone is welcomed, valued, and respected. It doesn’t matter your race, ethnicity, religion, age, disability, sexual orientation, gender, gender identity/expression, country of origin, genetic information, veteran status, marital status, pregnancy or related condition (including breastfeeding), criminal histories consistent with legal requirements or any other basis protected by law...we just want amazing people who are willing to grow along with us.
Although we have a Chicago-based HQ that employees are welcome to work out of whether they’re local or just visiting, this position is also eligible for work by a remote employee out of AZ, CA, CO, CT,&nbsp; FL, GA, IL, IN, KY, MA, MI, MN, NC, NY, OH, OR, PA, SC, TN, TX, UT, VA, WA or WI.
<hr>
How to apply: write to us
We’re looking for writers so a resume alone won’t cut it for us. Skip the "why I'm a great fit" generic cover letter and submit this info instead to that section (in one document):
<ol>
<li>A short sample of you. About 150 words, any format, that shows us your voice. Make us feel something, or make us laugh once.&nbsp;&nbsp;</li>
<li>Since you're attaching your portfolio, choose two of your favorite pieces from it and write one line each on what was actually hard about them.</li>
</ol>

Sr. UX Writer

Senior Director, Customer Operations
Who we are
Jellyvision is redefining how organizations experience benefits by bringing everything together in one modern, intelligent home. With ALEX Home, we combine our award-winning <a href="https://www.jellyvision.com/">ALEX®</a> decision support with a flexible benefits administration platform, giving employers and employees a simpler, smarter way to manage benefits year-round.
Our mission is to help organizations reduce complexity, lighten administrative burden, and drive real employee understanding and utilization without forcing rip-and-replace decisions. We meet teams where they are today and give them a clear path to what’s next.
The people behind Jellyvision are creative problem solvers who care deeply about getting it right. We debate ideas, give real feedback, and sweat the details because those details are what turn complicated problems into great experiences for real humans.
We’re a human-first company that trusts smart people to do great work. We value curiosity, kindness, and willingness to try new things, learn fast, and try again. You won’t just show up to do a job, you’ll help build what’s next, solve real problems, and have some fun doing it.&nbsp;
How you’ll help
We're looking for a Senior Director of Customer Operations to lead the team responsible for bringing our products to life for customers. You'll set the strategy, guide a team of leaders, and help us continuously improve how we onboard, implement, and support customers across our growing portfolio of products.
This is an exciting moment for the team. In addition to our core ALEX product, you'll help shape and scale implementation operations for two newer offerings: ALEX Home and our benefits administration platform. You'll play a key role in determining how we grow, where we invest, and what it takes to deliver a consistently great experience as our business evolves.
You'll lead a talented group of directors and the teams they support, creating the structure, clarity, and alignment needed to do great work at scale. You'll oversee capacity planning across our products, balancing internal resources with vendor and broker partnerships as we grow. And you’ll partner closely with leaders across Jellyvision to turn big ideas into scalable ways of working that improve experiences for both our customers and our teams.
What you’ll do to be successful
1.) Lead a team that does great work
Lead a group of talented directors and support them in leading their own teams across multiple product lines. Your focus will be creating clarity, removing obstacles, and helping people do their best work and achieve strong results.
<ul>
<li>Oversee ongoing implementation staffing, including full time and seasonal talent.</li>
<li>Coach and develop directors and their teams, helping them navigate everything from day-to-day challenges to high stake, complex, customer situations.</li>
<li>Build a culture rooted in accountability, collaboration, and continuous improvement.</li>
</ul>
2.) Build systems that scale
As our products and customer base grow, the way we work needs to grow with them. You'll use data, customer feedback, and team insights to identify opportunities for improvement and lead initiatives that make our operations more effective, efficient, and scalable.
<ul>
<li>Develop, execute, and define measures for strategic initiatives that support the company’s long-term vision and team/company goals.</li>
<li>Partner with the Chief Customer Officer to monitor team progress, wins, challenges, risks, and overall strategy.</li>
<li>Proactively identify and lead high impact initiatives that improve how we deliver for customers and scale operations.</li>
<li>Anticipate future operational needs and design scalable systems, processes, and talent strategies to meet them.</li>
<li>Manage implementation capacity across product lines, balancing customer demand, seasonality, and business priorities</li>
<li>Build and maintain strong relationships with vendor and broker partners and drive consistent delivery quality across the full product portfolio.</li>
</ul>
3.) Manage customer implementations across all product lines
You'll own implementation delivery across our product portfolio, helping ensure customers have a smooth, successful experience from kickoff through launch.
<ul>
<li>Scale implementation operations for ALEX Home customers.&nbsp;</li>
<li>Lead the buildout of the implementation model for our benefits administration product, defining the operating model, staffing approach, and customer experience from the ground up.</li>
<li>Establish shared standards while recognizing the unique needs of different products and customer segments.</li>
<li>Ensure quality, consistency, and accountability across every implementation experience.</li>
<li>Partner directly with key customers as a senior point of contact, building relationships that reinforce trust in Jellyvision's service and stepping in to lead resolution when escalations require senior engagement.</li>
</ul>
4.) Bring people together to solve problems
Some of the most important work in this role happens through partnership.
<ul>
<li>Collaborate with leaders in Customer Operations, Revenue, Product and other departments to improve customer outcomes, operational effectiveness, and future planning.</li>
<li>Build strong cross functional relationships that help teams stay aligned, move quickly, and execute effectively.</li>
<li>Bring the voice of implementation and customer operations into strategic conversations and company planning.</li>
<li>Build and apply deep product and industry expertise, in order to enable Jellyvision to continue providing an optimal customer experience</li>
<li>Balance strategic thinking with hands on problem solving, helping teams navigate both the "what's next" and the "how do we get there.”</li>
<li>Serve as a key integration point between product, operations, and vendor/broker partners as Jellyvision expands its suite of offerings.</li>
</ul>
Experience &amp; skills you’ll need
<ul>
<li>12+ years of experience successfully managing employees in an Implementation or Project Management environment, preferably in the HR or SaaS space.</li>
<li>In addition to 10+ years management experience, a successful track record implementing and onboarding Enterprise customers in a customer facing role.</li>
<li>Demonstrated experience leading implementations across multiple product lines simultaneously, ideally including benefits administration platforms or HR technology products.</li>
<li>A track record of building high performing teams and creating environments where people do their best work.</li>
<li>Experience managing a distributed workforce, including offshore or nearshore teams and third-party vendor/broker relationships.</li>
<li>Proven ability to manage capacity in an implementation or professional services environment, including forecasting and vendor management.</li>
<li>A knack for developing positive relationships across the organization to drive influence and align teams with cross functional initiatives.</li>
<li>A willingness to operate and make decisions in the absence of clear data, and an ability to pivot quickly and keep your team motivated as business needs change.</li>
<li>A strategic mindset with the ability to zoom out and align day-to-day execution with broader business goals.</li>
<li>A bias for action. Comfortable with ambiguity, driven to create clarity, and known for getting things done.</li>
<li>Strong executive presence and communication skills; able to influence and collaborate at all levels of the organization.</li>
</ul>
The Details&nbsp;
<ul>
<li>Location: Remote&nbsp;</li>
<li>Salary Range: $170,000 - $190,000</li>
<li>Other: this position is eligible for bonus and equity</li>
</ul>
Additional Compensation:&nbsp;
The salary range listed for this role reflects what we expect to pay, but where someone lands within that range depends on a few things, like their skills, relevant experience, qualifications, and how the role fits within our overall compensation philosophy, including internal equity and the budget for the role.
Compensation is more than just base salary. We also offer a comprehensive benefits package designed to support you at work and outside of it. Check them out <a href="https://www.jellyvision.com/about-us/careers/">here</a>!
Our Talent Acquisition team will walk you through the full package and answer any questions throughout the interview process, so you'll know exactly what to expect.
Our commitment&nbsp;
Jellyvision is committed to continuous evolution and to building a workplace where everyone feels welcome, valued, respected, and empowered to do their best work.&nbsp;
It doesn’t matter your race, ethnicity, religion, age, disability, sexual orientation, gender, gender identity/expression, country of origin, genetic information, veteran status, marital status, pregnancy or related condition (including breastfeeding), criminal histories consistent with legal requirements or any other basis protected by law.
At the end of the day, we're looking for great people who are excited to learn and grow along with us. And while we’ve listed what we’re looking for in this role, we’re always looking to add other attributes, and skills that make Jellyvision even better. The point we’re getting at, we encourage you to apply - even if your background doesn't perfectly match every qualification.
A note on location: While our headquarters is based in Chicago, and employees are always welcome to work from the office whether they're local or just passing through, this role is also open to remote candidates residing in AZ, CA, CO, CT, FL, GA, IL, IN, KY, MA, MI, MN, NC, NY, OH, OR, PA, SC, TN, TX, UT, VA, WA or WI.

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