Home BusinessAs Chicago Tech Scales, Product Teams Face a New Challenge: Focus at Scale

As Chicago Tech Scales, Product Teams Face a New Challenge: Focus at Scale

by Joseph Wilson
3 minutes read

doubletheWHY Formalizes an Approach Born from Years of Product Leadership Work

Chicago, IL — As Chicago’s technology ecosystem continues to mature, many product teams are encountering a familiar but increasingly complex challenge: maintaining focus as organizations scale. Roadmaps expand. Stakeholders multiply. Governance grows. Product decisions carry more weight and more noise than ever before.

doubletheWHY is not a framework lifted from a slide deck or a rebranded consulting methodology. It emerged from years of hands-on product leadership inside growing organizations, where tradeoffs are real, constraints are non-negotiable, and decisions carry operational consequences.

The approach was shaped in the work itself through lessons learned, missteps corrected, and patterns observed repeatedly across scaling teams. It reflects the realities companies face: competition, regulatory pressure, resource constraints, competing stakeholders, and the tension between speed and sustainability.

Rather than abstract theory, doubletheWHY formalizes what consistently proved effective in practice: clarifying ownership, sharpening decision-making, and designing structures that support focus instead of diluting it.

Founded by product executive and operator Brian Ongioni, doubletheWHY centers on one core belief: sustainable product success depends on clarity of why, not just speed of execution.

“Most teams don’t need more frameworks or more features,” said Ongioni. “They need help protecting focus as complexity increases. The work changes as you scale, from shipping to deciding, and that shift is often underestimated.”

The philosophy is not anti-technology, nor is it rooted in hype. doubletheWHY is grounded in core product principles that endure regardless of tools. Artificial intelligence, automation, and emerging technologies can be powerful accelerators, but they do not replace clarity of ownership, disciplined prioritization, or strong decision structures. The model supports any hybrid mix of technology, including AI, alongside the people and organizational systems required to use those tools effectively.

Rather than emerging as a traditional consulting launch, doubletheWHY reflects the codification of an approach already applied across startups, SMBs, and growth-stage organizations. The model emphasizes disciplined prioritization, problem-led thinking, and organizational readiness.

Ongioni remains embedded in product work, leading and building inside complex environments while also advising executive teams. He is known for articulating structural tensions many organizations experience but hesitate to address openly, particularly where leadership design, governance expansion, and product velocity collide.

As Chicago’s technology companies move beyond early-stage execution, product leadership becomes less about speed and more about coherence. The challenge shifts from building features to designing systems that allow teams to compound value over time rather than fragment under growth pressure.

doubletheWHY exists to support that transition.

In a companion essay published this week, Ongioni explores how product organizations unintentionally trade clarity for momentum as they scale and why focus should be treated as a product capability rather than a constraint.

“Focus isn’t about doing less,” Ongioni added. “It’s about creating force multipliers for the work that matters.”

“At scale, focus does not happen by accident. It has to be designed and defended.”

Ongioni is also the author of the upcoming book Focus Is a Feature, which examines how disciplined clarity and structural simplicity drive durable product success in growing organizations.

The full essay, “When Focus Becomes a Leadership Problem,” is available at doubletheWHY.com.


About doubletheWHY

doubletheWHY™ is a Chicago-based product leadership practice shaped by years of hands-on operating experience across startups and scaling organizations. It focuses on helping teams make better decisions by doubling down on the why behind what they build and being far more intentional about what they do not.

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