Opportunities Within Our Portfolio

At MassMutual Ventures, we are fortunate to have been early and long-term partners to our portfolio of category-defining businesses that are located across the globe. Learn more about their available opportunities below.

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Product Designer (Contractor) @ fast-growing, mission-driven startup

Gain Life

Product, Design

Boston, MA, USA · Remote

Posted on Jul 23, 2025

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Title: Product Designer (Contractor)

Location: Fully remote

Company overview
Gain Life is where efficiency meets simplicity in insurance. We streamline complex claims workflows into faster, clearer experiences for customers while freeing insurance professionals from repetitive tasks to deliver exceptional outcomes. We do this with the industry's most configurable and comprehensive platform for automating insurance workflows. We're a mission-driven, remote-first company, born out of Harvard University’s Innovation Lab, and are backed by world class investors in MassMutual, General Catalyst, and Unusual Ventures. Learn more at www.gainlife.com.

What we’re looking for:
We’re looking for a Product Design Contractor (aka: UIUX designer) who is passionate about design and who wants to make a positive impact with their work. You’ll lead and execute on research and design for new features as well as improve the experience of existing ones. We’re looking for someone who can work both autonomously and collaboratively with our product lead, design lead, and team at large, and is willing to work flexible hours based on the needs of the company, with the opportunity to grow into a more permanent part-time or full-time role based on quality and speed of output, team fit, and future product design needs. For context, you'd be joining a small-ish team (~25 people), that moves fast, values excellence, collaboration, creative problem-solving, and has high expectations of one another.

Responsibilities:

Execute on design needs for any stage of the design process: from journey maps, wireframes, prototypes, to high-fidelity mockups
Help conduct interviews and/or usability testing as part of key design validation steps
Understand design implications from multiple lenses (i.e. end users, clients, business objectives, data analytics, product roadmap), and deliver thoughtful solutions with all those puzzle pieces in mind
Walk through design solutions with both internal and external stakeholders, iterating based on feedback
Work closely with product and engineering to ensure design specifications are clearly defined and understood
Participate in sprint processes and help assure the integrity of designs in the final products

Must-have Qualifications:

3+ years of experience as a product (UI/UX) designer, working on software applications
Comfortable working on a cross-functional team; not afraid to voice your opinions and raise concerns as needed
Excited to uncover customer pain points, needs, and wants
Positive, can-do attitude; comfortable in ambiguous situations, and can work autonomously
Strong verbal communication skills; can speak confidently to the problems you’re solving and how the solutions impact the product as a whole
Strong written communication skills; can effectively document design specifications for your engineering teammates
Strong critical and quick thinking; can know when to challenge and ask the right questions to unblock progress, ensure alignment, and increase speed to output

Nice-to-have Qualifications:

Worked on a product that has a content management system (CMS) component
Familiar with agile processes and sprint ceremonies
Iterating on design based on data and analytics
Fluent in using Figma
Have used PostHog, or similar data analytics tool(s)

To apply:
Please submit your application here on Wellfound, and additionally email 'info at gainlife.com' with a link to your portfolio and why you think you'd be a great fit.

Thanks,

Sean (Co-founder)

p.s. Please no recruiters. We also ask that you please don't reach out directly to a member of our team about this opportunity over email, phone, or LinkedIn. Sorry, but these messages/submissions will not be replied to.

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