Outmarket AI appoints Mike Ryan as Senior Vice President of Marketing

Outmarket AI has appointed Mike Ryan as Senior Vice President of Marketing, adding marketing leadership as the company expands its AI platform for insurance agencies and brokerages.

Mike's career has included work across freight technology at project44 and AI-powered customer service at Crescendo. His move to Outmarket AI brings experience from industries where complex operations and substantial manual workloads create opportunities for technology-led change.

In his new role, Mike will lead the company's marketing efforts, with a focus on increasing awareness of Outmarket across the US insurance agency and brokerage market.

Bringing AI to the insurance industry

Mike sees insurance as a significant opportunity for AI adoption, particularly because of the manual work that continues to shape many brokerage operations.

Insurance professionals regularly handle complex documentation, policy comparisons, coverage reviews and client servicing tasks. These activities require accuracy and industry knowledge, yet can consume time that account managers and brokers could otherwise devote to advising clients.

Outmarket AI is developing technology to automate these workflows, helping insurance professionals work more efficiently while maintaining their focus on client relationships and business decisions.

Mike's experience across freight and customer service technology provides a background in markets where automation must work within established operational processes.

Making brokers more effective with AI

Outmarket's approach centres on giving insurance professionals greater capacity without removing the expertise and relationships that underpin their work.

Its platform connects with agency management systems and automates tasks across commercial insurance, employee benefits, personal lines and specialty insurance. Capabilities include proposal generation, policy comparisons, coverage gap analysis and other document-intensive workflows.

The company's proposition is that AI can take on repetitive administrative work while enabling brokers and account managers to concentrate on more valuable activities, including advising clients and identifying risks.

For Mike, communicating this distinction will be central to the marketing opportunity: positioning AI as a way to strengthen the work of insurance professionals rather than simply replace existing processes.

Customer advocacy and market adoption

In announcing his appointment, Mike highlighted customer advocacy as one of the reasons he chose Outmarket AI. He pointed to referrals from agencies and customers who recommend the platform to their peers, describing the response as unlike anything he had previously experienced.

Outmarket has reported adoption across more than 300 agencies and over 10,000 users. The company also says that more than a quarter of the 100 largest US insurance agencies use its platform.

These indicators provide a foundation for its next phase of growth, as the company seeks to reach more agencies and brokerages that have yet to select an AI platform for their operations.

Mike's marketing remit will focus on translating that customer traction into broader market awareness and adoption.

A leadership team focused on insurance AI

Mike joins a leadership team that combines technology, product and insurance expertise.

Co-founder and CEO Vishal Sankhla previously held product leadership roles at Ethos, alongside engineering experience at Meta and Uber. Co-founder and CTO Anshu Jain brings experience in AI and knowledge systems, including work associated with IBM Watson. Alpesh Patel has also contributed experience in insurance technology and go-to-market development.

The team is building around the view that insurance requires AI systems designed for its specific workflows, documents and operational requirements, rather than generic automation alone.

Mike's arrival adds dedicated senior marketing leadership to that effort as Outmarket works to communicate its proposition to a wider market.

Scaling after a $34.5 million Series B

Mike joins as Outmarket AI enters its next stage of growth following a $34.5 million Series B funding round led by SignalFire, announced in September 2026. Fika Ventures, Permanent Capital Ventures, TTV Capital and Dash Fund also participated.

The round followed the company's $17 million Series A and brought its total funding to $56.5 million, according to the company.

Outmarket has said it will use the funding to accelerate product development and expand its capabilities across insurance workflows, with plans to extend its offering to carriers as well.

For Mike, the opportunity is to build the marketing engine behind that expansion and ensure more insurance agencies understand how AI can support their operations.

About Outmarket AI

Outmarket AI is an artificial intelligence company building a platform for insurance agencies and brokerages. Its technology automates workflows across commercial insurance, employee benefits, personal lines and specialty insurance, including policy analysis, proposal generation and coverage checks. The company aims to reduce manual work and help insurance professionals focus on client service and business growth.

Source: Mike Ryan's LinkedIn announcement