ProductPlan Acquires Winware.ai, Taps New CEO for AI Certainty

DENVER, CO – January 12, 2026 – ProductPlan, a long-standing leader in product lifecycle management software, today announced a definitive move to reshape its future with the acquisition of Winware.ai, an AI-native customer and market research platform. The acquisition not only signals a deep strategic pivot toward artificial intelligence but also installs Winware.ai’s founder and CEO, Steven Cohn, as the new chief executive of ProductPlan. The combined entity aims to create a singular, AI-driven Product Intelligence Platform designed to address one of the most persistent challenges in software development: uncertainty.

A Strategic Pivot to AI-Driven Certainty

The acquisition arrives as the product management software market is undergoing a seismic shift, with AI integration evolving from a novelty to a competitive necessity. Major players like Aha!, Asana, and Atlassian’s Jira Product Discovery have been embedding AI functionalities to summarize feedback, automate tasks, and generate content. However, ProductPlan’s move represents a more aggressive strategy: instead of building AI features incrementally, it has acquired a company built from the ground up on AI and placed its visionary at the helm.

This is about more than just adding features. It’s about fundamentally changing the decision-making process. As part of the transaction, new CEO Steven Cohn articulated the core problem his technology aims to solve. "What product teams struggle with today isn't execution, it's certainty," said Cohn. "I built Winware around agentic and generative AI to bring first-party customer and market intelligence directly into product decisions. Bringing that capability into ProductPlan allows teams to plan and prioritize with confidence before decisions become commitments."

Winware.ai’s technology uses agentic AI to proactively gather first-party customer and market insights, while its generative AI capabilities analyze and translate that data into actionable outputs for planning, positioning, and go-to-market strategies. This approach moves beyond passive data analysis, creating a system that actively helps product teams understand what to build and why. For ProductPlan’s more than 1,000 enterprise and mid-market customers—who have collectively created over 860,000 roadmaps on the platform—this promises a new layer of data-driven confidence behind their strategic initiatives.

The Return of a Category Creator

The appointment of Steven Cohn as CEO is as significant as the technology he brings. Cohn is a multi-time founder with a proven track record of identifying and capitalizing on critical gaps in the product development space. He previously founded Validately, an early and influential user research platform that simplified moderated testing for product teams. Validately was acquired by UserZoom in 2019, where it was integrated to bolster its user experience insights offerings.

Cohn’s career has been defined by building tools that give product teams clarity. His experience at companies that were later acquired by giants like TripAdvisor and LivingSocial honed his understanding of operating under intense market pressure. With Winware.ai, he once again targeted a core industry pain point: the disconnect between raw customer feedback and high-stakes product investment decisions. His return to a CEO role, this time at the helm of a scaled platform like ProductPlan, signals an ambition to solve this problem at a massive scale.

This leadership change positions ProductPlan not just as a tool for visualizing roadmaps, but as a strategic partner guided by a leader who has spent his career at the intersection of user research and product decision-making. His background suggests a future for the company that is deeply focused on embedding verifiable, first-party intelligence into every stage of the product lifecycle.

De-risking Innovation from Idea to Monetization

The business imperative behind this acquisition is clear: reducing the financial and reputational risks of product failure. In a landscape where resources are tight and the pressure to deliver ROI is immense, the combined platform aims to provide a competitive edge by de-risking innovation. By integrating Winware's intelligence layer, ProductPlan can help organizations move beyond intuition-based planning and anchor their decisions in real-time market and customer data.

This strategy is strongly supported by ProductPlan's backer, Bow River Capital. Abdullah Ghuman, a board member and Vice President with Bow River Capital’s Software Growth Equity Team, commented on the evolving market demands. "As product organizations adapt to a rapidly changing, AI-driven landscape, the demands placed on product teams have increased significantly," Ghuman stated. "Roadmaps remain essential, but teams now need deeper decision intelligence behind them. By combining ProductPlan's scale and trust with Winware's AI-powered, agentic intelligence, we're creating a platform that reduces product risk across the entire development lifecycle."

Bow River Capital’s investment thesis often focuses on scaling founder-led SaaS companies by enhancing their go-to-market and operational execution. This acquisition fits that playbook perfectly, transforming an established roadmapping tool into a next-generation intelligence platform poised for significant growth. The goal is to help teams move from idea to monetization with greater speed and a much higher probability of success.

The Path to an Integrated Product Intelligence Platform

The fusion of ProductPlan and Winware.ai is not merely a branding exercise. The companies have laid out a timeline for a full technical and operational merger. Winware's capabilities will be integrated into the ProductPlan platform over the coming months, with broader customer access to the newly christened Product Intelligence Platform scheduled for April 2026.

Ben Jubenville, who is transitioning from his role as President and CEO of ProductPlan to a senior board and strategic advisory position, endorsed the move as a natural evolution for the company. "Product teams are under more pressure than ever to move fast and stay focused. We've always been about helping them stay aligned and execute efficiently," said Jubenville. "Bringing Winware into the platform gives them a new intelligence layer that focuses resources on the right work and drives better outcomes."

Jubenville's transition to an advisory role suggests a carefully orchestrated leadership change designed for continuity and strategic alignment. While the integration of two distinct platforms presents inevitable technical and cultural challenges, the unified vision articulated by both the old and new leadership provides a strong foundation. Together, the new ProductPlan is embarking on an ambitious mission: to build an AI-native system that serves as an indispensable guide for product teams, telling them precisely what to build, why it matters, and how to win in an increasingly competitive market.