Justin S.

Partner & Co-Founder at Remix Partners

Justin Massa is a seasoned innovation leader and generative AI strategist who helps growing businesses transform AI experiments into tangible growth engines. As Partner and Co-Founder of Remix Partners, a boutique consultancy focused on GenAI strategy for SMBs, Justin bridges the gap between cutting-edge technology and practical business application. Based in the Greater Chicago Area, he combines decades of experience in design thinking, data science, and entrepreneurship to guide leaders through the 'jagged frontier' of AI capabilities. Justin's journey began as the founder and CEO of Food Genius, a foodservice data and analytics startup he launched in 2010. The company quickly gained traction, serving major clients like Dine Equity, Kraft, Unilever, and Safeway, and earning accolades such as a Chicago Innovation 'Up-and-Comer' Award and a spot on Entrepreneur Magazine’s 100 Brilliant Companies list. In 2017, Food Genius was acquired by US Foods, where it drove over $150 million in incremental sales by 2019 and continues as an independent unit. This exit honed his skills in scaling data-driven ventures. [LinkedIn](https://www.linkedin.com/in/justinmassa) Joining IDEO in 2015, Justin rose to Partner, leading business development for North America and pioneering the integration of data science into design thinking. He co-led the acquisition of Datascope Analytics, expanding IDEO's capabilities and exceeding revenue targets by 30% in the first year while maintaining 100% retention. His work emphasized venture design, B2B products, and strategy at the intersection of data and design. He also served as a founding member of IDEO's Helix DE&I team. [S2G Investments podcast](https://www.youtube.com/watch?v=60zGY0JPkfw) Post-IDEO, Justin held roles like Senior Vice President at Newlab, a deep-tech venture platform supporting 900+ entrepreneurs raising $2B+ in capital, and Owner of Midwest Quality Consulting, where demand for his AI expertise inspired Remix Partners' formation in 2025 with co-founder Jason Rubinstein. Today, he also teaches Generative AI Business Strategy as an adjunct professor at Illinois Tech, publishes AI for SMBs Weekly on Substack, and serves on boards for Northern Illinois Food Bank and 1848 Ventures. [Remix Partners](https://www.linkedin.com/company/remixpartners) Justin's pragmatic approach demystifies AI for executives. He advocates CEOs directly using tools, likening it to learning to ride a bike—hands-on experimentation over theory. His frameworks, like the 'technique, jig, tool' implementation paths and three-layer AI ethics (creation, operation, application), help prioritize high-impact use cases. He emphasizes testing AI's evolving frontier, balancing automation with augmentation, and involving legal teams in governance. At Remix, they use a promiscuous model strategy (Claude, ChatGPT, Gemini, etc.), costing ~$250/user/month but saving hours weekly. [IDEO U](https://www.youtube.com/watch?v=tpP2htIL1E0) Through podcasts like 'Beyond the Hype' with S2G Investments and IDEO U sessions, Justin shares case studies from firms like Red Antler 'buying back' employee time for strategic work. His philosophy: AI won't replace teams but reshape workflows, turning ad-hoc pilots into AI-first cultures. With 11,916 LinkedIn followers and active on X (@justinmassa), Justin remains a sought-after voice in AI strategy, blending optimism with realism for sustainable transformation. (Word count: 512)

Key Insights from Justin S.

The jagged frontier, where AI outperforms in some tasks but fails in others, and its capabilities are continuously in flux.

— Justin S. on AI Capabilities

CEOs must be direct users of AI tools. Think of learning AI like learning to ride a bike: no amount of theory substitutes for falling, getting back up, and finally figuring it out.

— Justin S. on Leadership in AI

Three paths to integrating AI: technique (low lift), jig (custom tool), tool (enterprise software).

— Justin S. on AI Implementation

AI won’t replace your team—but it will reshape how they work, buying back time for creative, strategic pursuits.

— Justin S. on Workforce Transformation

Notable Quotes from Justin S.

"Model monogamy might be holding your business back."

— Justin S.

"Everything works with everything—your choice of AI no longer depends on your office suite."

— Justin S.

"Tackle AI resistance by creating culture, confidence, and clarity."

— Justin S.

"The fast fashion era of SaaS is very soon."

— Justin S.

Frequently Asked Questions about Justin S.

How can SMBs prioritize AI investments without getting overwhelmed by hype?

Justin recommends the AI Opportunity Matrix, plotting capabilities by business differentiation importance and AI disruption risk. Identify bottlenecks like repetitive tasks or missed opportunities, then map to high-value areas. Start with low-lift 'techniques' using frontier models like Claude or ChatGPT before custom 'jigs' or enterprise 'tools.' Develop model fluency across providers—avoid monogamy—and experiment hands-on. At Remix Partners, they maintain multi-model subscriptions (~$250/month/person) for optimal task matching, emphasizing ROI through time savings and opportunity creation over cost-cutting alone. Governance evolves across creation, operation, and application layers, with legal involvement. [AI for SMBs](https://aiforsmbs.remixpartners.ai)

What is the 'jagged frontier' in AI and why does it matter?

Coined by Justin, the 'jagged frontier' describes AI's uneven capabilities—excelling in some areas while failing unpredictably in others, with constant flux. Unlike productized AI that trims edges for consistency, frontier models offer power but require governance. Leaders must test edges regularly to track evolution, prioritizing where AI augments differentiation. This mindset shifts from hype to pragmatic strategy, as Justin advises in podcasts: use models promiscuously, prototype rapidly, and abstract task-level wins to systems. [S2G Podcast](https://www.youtube.com/watch?v=60zGY0JPkfw)

How has Justin's experience at IDEO and Food Genius shaped his AI approach?

At Food Genius, Justin scaled data analytics to $150MM+ sales impact post-US Foods acquisition, teaching data-business alignment. At IDEO, he integrated data science via Datascope acquisition, exceeding revenue 30% with perfect retention, blending design and tech. These inform Remix's GenAI focus: strategy-proficiency-planning-guidance. He teaches at Illinois Tech, publishes weekly insights, and boards nonprofits/VCs, ensuring real-world grounding. [LinkedIn](https://www.linkedin.com/in/justinmassa)

What role does ethics and governance play in enterprise AI adoption?

Justin outlines three layers: creation (model training), operation (deployment), application (business use)—each needing evolving policies. Legal teams must engage, especially application-level, as capabilities shift. Build AI-first cultures via change management, pilots, and roadmaps. Remix provides ongoing market intel and reviews to filter noise, ensuring ethical, impactful scaling. [IDEO U](https://www.ideou.com/blogs/inspiration/how-to-invest-in-ai-for-your-business)

Justin S. — Areas of Expertise

  • Generative AI Strategy
  • AI for SMBs
  • Design Thinking & Data Science
  • Business Transformation
  • Innovation Consulting
  • Venture Design
  • AI-driven strategies

Justin S. — Show Appearances

  • Mornings in the Lab (2025-05-09)

Justin S. — Signal Brief

Signal Score: 21/100

Generated 2026-04-16T01:26:37.809Z