The legal technology sector is seeing a surge in artificial intelligence applications and one company, Definely, is bolstering its leadership team to meet the growing demand. On Monday, February 16, 2026, Definely announced the appointment of John Connolly as its new Chief Product Officer (CPO). This strategic hire comes as law firms and in-house legal departments increasingly seek AI-powered tools to streamline contract review and manage rising workloads.
Connolly joins Definely from Meta, where he served as Director of Product Management until March 2025. His experience encompasses a broad range of tech companies, including roles as CPO for multiple venture capital- and private equity-backed scale-ups, VP of Strategy and Business Development at Expedia, and CPO of SpringerNature, according to Definely’s official announcement. He brings over 20 years of product experience to the role.
A Shift in Leadership at Definely
Connolly’s appointment marks a transition in Definely’s product leadership. He succeeds Bruce Elliott, who is moving into the position of Principal Product Manager after joining the company in 2020. This internal shift allows Definely to leverage Elliott’s existing knowledge while bringing in Connolly’s extensive experience in scaling complex platforms and leading research and development teams, particularly within regulated industries.
Navigating a Competitive Landscape
The timing of Connolly’s arrival is significant. The market for AI-driven contract analysis is becoming increasingly competitive. Vendors specializing in contract review are facing challenges from both emerging “vibe-coders” and established technology giants like Anthropic, which are integrating AI capabilities into their existing platforms. Despite the increased competition, demand for these tools is growing as legal professionals recognize the potential benefits of AI in managing complex legal documents.
Definely differentiates itself by integrating directly within Microsoft Word, rather than requiring lawyers to switch to a separate system. This approach aims to minimize disruption to existing workflows and maximize the efficiency of AI-powered tools. The company focuses on providing out-of-the-box solutions to address common challenges faced by legal teams, increasing the value and usability of generative AI products.
Connolly’s Vision for Definely
As CPO, Connolly will be responsible for supporting the executive team in product development and aligning Definely’s product roadmap with the company’s overall business strategy. He emphasized the importance of successfully implementing AI to deliver tangible business value, stating, “Definely is addressing one of the biggest challenges facing businesses today – the successful use of AI to deliver real business value.” He also highlighted the need to balance efficiency with the preservation of human understanding and professional integrity, particularly in a field where errors can have significant financial and reputational consequences.
Nnamdi Emelifeonwu, Co-Founder & CEO of Definely, echoed this sentiment, noting that Connolly’s experience in both large technology companies and high-growth startups will be instrumental in driving the company’s international expansion and delivering innovative solutions to the legal sector. According to the company’s press release, Emelifeonwu stated, “John is a versatile leader with a proven track record…combining technical depth, commercial strategy and board-level leadership.”
Connolly’s LinkedIn profile, as reported by Startpage, further details his extensive background in product leadership and his connections within the tech industry.
Definely’s growth trajectory is also linked to events like the Legal Innovators California conference, scheduled for June 10 and 11, which showcases the latest advancements in legal technology. The company’s focus on AI-powered contract analysis positions it within a rapidly evolving market, and Connolly’s leadership will be crucial as Definely navigates this landscape.
Looking ahead, Definely will likely continue to refine its AI capabilities and expand its integration with other legal tools. The company’s success will depend on its ability to deliver reliable, user-friendly solutions that address the specific needs of legal professionals. The next key development to watch will be the rollout of new features and integrations based on Connolly’s strategic direction in the coming months.
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