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Principal Product Manager - Benefits

May 29, 2026

About this role As Principal Product Manager for Benefits, you'll shape how millions of people understand, access, and use the benefits their employers provide. Benefits are often the most valuable thing employees receive outside their paycheck, yet they remain confusing, fragmented, and underused. You are here to help change that. Working at the center of our platform, you'll define the strategy for how members discover what's available to them, navigate complex eligibility rules, and connect to the right care at the right moment. You will lead the product vision and roadmap for our unified benefits experience across medical, pharmacy, and ancillary programs, built on top of our internal platform and services. You’ll partner closely with engineering, design, data, and product peers across the organization to deliver feature‑complete, high‑reliability experiences that help people understand their benefits in a way that makes sense to them. This is a principal‑level, high‑leverage individual contributor role: you’ll be expected to set strategy, drive complex cross‑org delivery, mentor other PMs, and be the go‑to product leader for all things benefits at the organization. What you’ll do <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="1" data-aria-level="1">Define and evolve the product vision for how members discover, understand, and use their benefits. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="2" data-aria-level="1">Own the end-to-end product roadmap for member-facing benefits and enrollment features including Member-facing and administrative components </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="3" data-aria-level="1">Establish a single source of truth for benefit content and configuration, mapping legacy data and behaviors into a unified model with engineering and fellow PMs. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="4" data-aria-level="1">Translate executive and client commitments into a sequenced plan with explicit tradeoffs, dependencies, and cut lines, and keep that plan real as priorities shift. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="5" data-aria-level="1">Drive accuracy and efficiency in how we gather benefits information from employers, partnering with content management and implementation. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="6" data-aria-level="1">Define and instrument success metrics for benefits from task completion on "find what's covered" to OE error rates and digital ID card usage. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="7" data-aria-level="1">Partner with client implementation, clinical operations, and support leadership so engineering timelines leave room for training, UAT, and change management before launch. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="8" data-aria-level="1">Ship meaningful improvements on a fast, iterative cadence. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="9" data-aria-level="1">Represent benefits in executive and cross functional forums with crisp narratives, options, and recommendations. </li> </ul> What we’re looking for <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="6" data-aria-level="1">10+ years of product management experience, including significant time as a Senior or Lead PM owning complex, multi‑team products or platforms. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="7" data-aria-level="1">Deep familiarity with healthcare benefits and data including eligibility, plans and plan designs, accumulators/deductibles/OOP max, ID cards, coverage rules, and claims data, and how they show up in member‑facing experiences. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="8" data-aria-level="1">Proven track record shipping both internal and external product experiences in a B2B2C or enterprise SaaS context with an emphasis on reliability, correctness, and configuration flexibility. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="9" data-aria-level="1">Demonstrated success leading cross‑org, cross‑platform initiatives (spanning multiple apps, services, or interfaces) with hard external dates and real operational consequences. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="10" data-aria-level="1">Strong product sense: you can take dense benefit and platform constraints and turn them into flows that feel simple and trustworthy to members. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="11" data-aria-level="1">Exceptional communication and influence skills — equally effective with engineers, designers, clinical leaders, client teams, and executives. </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="12" data-aria-level="1">Naturally curious individuals who enjoy discovering how things work and finding ways to improve upon them </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="13" data-aria-level="1">Humble attitudes and a penchant for solving hard problems </li> </ul> <ul> <li data-leveltext="" data-font="Symbol" data-listid="9" data-list-defn-props="{" 335552541":1,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"multilevel"}"="" data-aria-posinset="14" data-aria-level="1">Experience in startup environments is a plus! </li> </ul> Location You must be authorized to work in the United States. Depending on the position we may have a preference to a specific location, but are generally open to remote work anywhere in the US.  Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out <div class="content-pay-transparency"><div class="pay-input"><div class="title">As a remote position, the salary range for this role is:</div><div class="pay-range">$180,000—$195,000 USD</div></div></div><div class="content-conclusion">Who we are Transcarent is the One Place for Health and Careᵀᴹ, bringing medical, pharmacy, and point solutions together with the WayFindingᵀᴹ experience, the first and only generative AI-powered health and care platform for health consumers. Our WayFinding experience, paired with transparent and consumer-driven pharmacy care, 2nd.MD expert medical opinions, and virtual primary care, works seamlessly with comprehensive Care Experiences – Cancer Care, Surgery Care, and Weight Health – to support people with all of their health needs, simple or serious. More than 1,700 employers and health plans rely on us to provide information, guidance, and care, empowering health consumers with more choice, an experience they love, access to higher-quality care, and lower costs for 21 million Members. For more information, visit <a class="Hyperlink SCXW17643364 BCX0" href="http://transcarent.com/" target="_blank">transcarent.com</a>, and follow us on <a class="Hyperlink SCXW17643364 BCX0" href="https://www.linkedin.com/company/transcarent/" target="_blank">LinkedIn</a>.<span class="EOP SCXW17643364 BCX0" data-ccp-props="{" 134233117":false,"134233118":false,"201341983":0,"335551550":1,"335551620":1,"335559685":0,"335559737":0,"335559738":0,"335559739":0,"335559740":240}"=""> At Transcarent, our values guide everything we do: <ul> <li>People First: We prioritize our Members, clients, and each other in every decision</li> <li>Care: Every decision starts with improving health and care for our Members</li> <li>Resilience: We push boundaries and take the uncharted path to change an industry</li> <li>Results: We take ownership, solve with speed, and deliver for our people and each other</li> <li>Humble and Human: We lead with humility, bring fun to tough moments, and go further together</li> </ul> Total Rewards Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal equity. Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options. Our benefits and perks programs include, but are not limited to: <ul> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559684":-2,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="1" data-aria-level="1">Competitive medical, dental, and vision coverage </li> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559684":-2,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="1" data-aria-level="1">Competitive 401(k) Plan with a generous company match </li> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559684":-2,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="2" data-aria-level="1">Flexible Time Off/Paid Time Off, 13 paid holidays </li> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559684":-2,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="3" data-aria-level="1">Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance </li> <li data-leveltext="" data-font="Symbol" data-listid="1" data-list-defn-props="{" 335552541":1,"335559684":-2,"335559685":720,"335559991":360,"469769226":"symbol","469769242":[8226],"469777803":"left","469777804":"","469777815":"hybridmultilevel"}"="" data-aria-posinset="4" data-aria-level="1">Mental Health and Wellness benefits </li> </ul> Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out! Research shows that candidates from underrepresented backgrounds often don’t apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren’t looking for someone who checks each box on a page; we’re looking for active learners and people who care about disrupting the current health and care with their unique experiences. </div>

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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...