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Tommy MassaroTM
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Tommy Massaro

@tommymassaro

I build and scale complex digital products through product strategy, UX, design systems, and hands-on implementation.

United States
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What I'm looking for

I'm looking to lead hands-on product design for complex products, partnering closely with product and engineering to turn strategy, customer insight, and experimentation into shipped outcomes.

I lead product design for a stealth data privacy platform, shaping its product vision, user experience, and design system while moving between Figma and the codebase to ship ideas.

Previously, I led design for Moov Technologies’ two-sided marketplace and internal CRM, simplifying complex workflows and taking features from concept through production. At JobPixel, I built the brand, product experience, design system, marketing site, and go-to-market materials as the company grew into a mature HR technology platform.

I co-founded 36 Labs, where I led product, design, front-end execution, experimentation, and performance marketing as the company grew to roughly $20M in annual revenue before its acquisition by MUNDOmedia. Over 20+ years, I’ve also built products at PlayPhone and Fli Digital, combining customer insight, real-time data, and business outcomes to guide design decisions.

Experience

Work history, roles, and key accomplishments

Stealth Startup logoSS
Current

Principal Product Designer

May 2025 - Present (1 year 5 months)

Leading product design for an early-stage data privacy platform, shaping the product vision, user experience, and design system as the company grows. I work hands-on across product strategy, UX, visual design, prototyping, and implementation, often moving directly between Figma and the codebase to explore and ship new ideas.

Private Investor logoPI
Current

Angel Investor

Jan 2010 - Present (16 years 9 months)

Current Investments:
True Laurel (San Francisco), Curated, Apartment List, Polychain Capital, One Local, Azora Therapeutics, Vertical Finance, JobPixel

Exits:
Fli Digital (acquired by Game Theory, LLC, Aug 2010)
Open Install (acquired by AVG Technologies, Dec 2011)
Bright.com (acquired by LinkedIn, Feb 2014)
36 Labs (acquired by MUNDOmedia Oct 2016)
TrueBill (acquired by Rocket Companies, Dec

Moov Technologies Inc. logoMI

Director of Product Design

Jan 2023 - May 2025 (2 years 4 months)

Led product design across Moov’s two-sided marketplace and the internal CRM used to operate the business. Worked closely with product and engineering to simplify complex workflows, establish product patterns, and take new features from early concepts through production.

JobPixel logoJO

Head of Design

Nov 2020 - Jan 2023 (2 years 2 months)

Joined JobPixel early as both Head of Design and an investor, helping shape the company from its earliest stages. I built the design foundation from the ground up, including the brand, product experience, design system, marketing site, and go-to-market materials, while working closely with product, engineering, and leadership as the platform evolved.
JobPixel grew from an early-stage idea into a m

36 Labs, LLC logoLL

Co-Founder | VP of Product & Design

Jan 2014 - Nov 2020 (6 years 10 months)

Co-founded 36 Labs as part of a small, hands-on team building and scaling performance marketing products. I led all aspects of product and design, from defining new product ideas and user experiences to front-end execution and optimization.
I was also deeply involved in the performance side of the business, managing millions of dollars in media spend and using real-time data to shape both product

PlayPhone logoPL

Head of Design & User Experience

Aug 2012 - May 2014 (1 year 9 months)

Led design at PlayPhone, a mobile social gaming platform powering app stores and gaming experiences for major wireless carriers around the world. I was responsible for product design and user experience across consumer-facing products, partner experiences, and the broader platform ecosystem.
The role meant designing for scale across carriers, developers, and millions of mobile users, while working

Mobile Plus, Inc. logoMI

Executive Director

Mar 2012 - Sep 2012 (6 months)

Worked as Executive Director at Mobile Plus, Inc..

Social Hour, Inc. logoSI

Executive Director [New York]

Aug 2010 - Mar 2012 (1 year 7 months)

Worked as Executive Director [New York] at Social Hour, Inc..

Fli Digital, Inc. logoFI

Co-Founder & Managing Partner

May 2002 - Aug 2010 (8 years 3 months)

Co-founded Fli Digital as a boutique design agency specializing in brand identity, print, and web design. Our work included websites, brochures, marketing collateral, trade show booths and displays, presentations, and broader brand systems that helped companies communicate consistently across physical and digital channels.

As the business evolved, we moved beyond client services and into product

Imojo logoIM

Creative Director

Nov 1999 - Jun 2001 (1 year 7 months)

Worked as Creative Director at Imojo.

Education

Degrees, certifications, and relevant coursework

RT

Rochester Institute of Technology

BFA, Industrial Design

1995 - 1999

Rochester Institute of Technology logoRT

Rochester Institute of Technology

Bachelor of Fine Arts, Industrial Design

1995 - 1999

Pursued a Bachelor of Fine Arts in Industrial Design, developing a strong foundation in design thinking and creative problem-solving.

Tech stack

Software and tools used professionally

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