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FMLA Leave Specialist @ Tilt

March 11, 2026

FMLA/Leave Specialist @ Tilt

Tilt (check us out here) is looking for a Leave Success Manager to join our team and help us scale our business by working closely with our customer’s employees to provide seamless onboarding and ongoing support as they navigate the leave journey from start to finish.

Who are we?

Our mission is big: make leave not suck. We are building a product that makes it easy for people to switch between work and life. If you join us, you’ll be part of a fearless band of humans helping employers balance empathy with economics. We’re changing the status quo and it’s hard. You should know that now. You should also know that joining Tilt means the opportunity to be a change-maker.

Who are you?

As a member of the Customer Success Team you will have a few years of experience in a customer facing role, preferably in the healthcare or human resources industry, and a passion for helping people when it matters most. You are highly organized and thrive in an environment where your ability to empathize, research, and serve others is celebrated.

Day-to-day, you will get your hands dirty by:

Managing the lifecycle of employees on leave through Tilt software and various support channels

Providing troubleshooting support for employees and their managers

Partnering with internal experts to serve as a resource for employees on leave - answering questions around U.S. state and federal leave laws, state paid family and medical programs, healthcare providers, insurance carriers, and company policies

Advocating for the customer internally by working across multiple departments

Ongoing development of your platform and industry knowledge around leave management and compliance

Collaborating with each accounts’ Customer Success Manager (CSM) to help prove value to our stakeholders

Communicating directly with regulatory agencies, healthcare and insurance providers, and other third parties if/when necessary

You’re a great fit if

2+ years of experience in a customer success or support and have extensive knowledge in paid and unpaid Leave of Absence across the United States

Passion for helping people solve their problems and navigate abstract regulations

Ability to research policies and compliance literature – interpreting and translating knowledge to a non-policy savvy audience

Clear, articulate, and empathetic communication style – you deliver your message with respect, confidence, and compassion

Thrive in a fast paced environment, embrace technology and enjoy learning new tools and are able to easily change gears and switch between multiple platforms to get the job done

Naturally self-directed, organized, and resourceful with the ability to multitask, managing and switching priorities as needed

Bilingual (English/Spanish) preferred, we serve a diverse community, and this helps us meet folks where they are

You thrive in a collaborative environment where diversity and inclusion is celebrated

You’re familiar with the leave compliance space

You have experience working with a startup and/or with a B2B SaaS business

Virtues/Competencies

1. Health & Family First

You've proven to be able to integrate all aspects of your life in a way that produces excellent work and ensures you care for what matters most in your life

You get things done at a pace consistent with the business needs

You consistently show up prepared, dependable and follow through on commitments

2. Autonomy + Team. Always

You are highly organized and can manage multiple priorities and deadlines at once

You are focused on scale and building - you understand that pace is equally as important as quality

3. Be Curious

When you don’t have all of the answers, you dig in and ask questions

You don’t let negative assumptions drive your actions and instead assume positive intent and find truth

You are intentional in discovering the paths of self development Tilt has to offer and seek out opportunities to engage in professional growth

4. Love Our Customers

You lead with empathy and compassion, meeting customers where they are and supporting them with intention and care

You take the time to deeply understand customers’ needs, goals, and challenges, not just the task at hand

You communicate openly and honestly, even when conversations are difficult

5. Fearlessly Flexible

You embrace change and navigate ambiguity with confidence and curiosity

You take initiative and make progress even when direction isn’t fully defined

Total Compensation

The projected annual salary range starts at $60,000 USD plus stock options (ISOs), because we believe everyone should have some stake in our business. We are people-first and this ain’t some PR jazz, we truly give a damn about our peeps!

Additional benefits include:

Comprehensive medical, dental, and vision benefits paid at 100% for all employees and 50% for dependents.

401k + match (100% match on the first 3%, 50% match on the next 2%)

$50 monthly to spend on “What Matters Most”

Responsible Time Off - take what you need, when you need it!

More about our amazing Perks and Benefits can be found here!

More about Tilt

Tilt’s mission is big: make leave not suck. We are building a product that makes it easy for people to switch between work and life. If you join us, you’ll be part of a fearless band of humans helping employers balance empathy with economics. We’re changing the status quo and it’s hard. You should know that now. You should also know that joining Tilt means the opportunity to be a change-maker. We’re thinkers, doers, revolutionaries, dreamers, get shit done-ers, and bold enough to tackle a really complex space.

Remote Work & Flexibility

We are a fully remote company. We are committed to being fearlessly flexible and ensuring that all employees are set up and have the autonomy to do their best work, as well as have the balance to care for their health, family and life outside of work. Overall, we trust our team and are focused on outcomes not outputs.

Equal Opportunity Employer

We celebrate and support our differences. We believe in the power of equality which is why we are an equal opportunity employer. Employment at Tilt is based solely on a person’s merit and qualifications related to their professional competence. Tilt does not discriminate against any employee or applicant because of race, color, creed, religion, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy, or any other basis protected by law. We comply with all applicable national, state, and local laws pertaining to nondiscrimination and equal opportunity.

You must be authorized to work in the US.

So what do you say? Do you want to join our team?

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...