Mike Gilson / CEO, Conversica / San Francisco

Executive Profile

Michael
Gilson

Chief Executive Officer · Conversica

The operator who inherited a conversational AI company and immediately asked the question no one else was asking: what happens when the data the AI runs on has been sitting untouched in a dealer's CRM for a decade?

1.5B

AI Conversations Powered

$148M

Total Funding Raised

2,000+

Enterprise Teams Served

Who He Is

Running the machine that taught AI to follow up

Michael Gilson became CEO of Conversica in April 2025. He walked into a company with $148 million in venture backing, a platform that had already processed over a billion and a half conversations, and a product that could engage leads, prospects, and customers across email, SMS, and web chat - in six languages, with no human required.

That's the inheritance. What Gilson did with it is more interesting. Within months, he greenlighted a full rebrand - Conversica became "The Conversation Company" in August 2025. The renaming wasn't cosmetic. It was an acknowledgment that the product had outgrown its original job description: automated sales follow-up. The new framing covers the entire customer lifecycle - acquisition, service, retention - and positions AI agents not as a single point solution but as the connective tissue of every customer-facing team.

Before taking the top seat, Gilson spent years in enterprise SaaS, working across organizations including Wiser Solutions, Revient Inc., and Telestream, a video workflow technology company whose products sit inside broadcast operations and media workflows around the world. The experience running products for highly technical, data-intensive buyers shows up in how Gilson thinks about Conversica's edge: it's not the conversation itself, it's the data underneath it.

He holds a BA from Princeton University, graduating in 2010 - the same year Conversica's original AI assistant, AVA, first went to market commercially.

Fast Facts

1.5B

Conversations powered
across all customers

$24.6M

Annual Recurring
Revenue (2024)

200+

Employees across
the organization

Languages supported
by AI agents

2007

Founded — originally
a car dealer CRM

The starting point for really any modern AI system is really the data and the data foundation.

- Michael Gilson, CEO, Conversica

The Story

From a Bellingham car dealer CRM to 1.5 billion conversations

The company Gilson now leads started as something entirely different. In 2007, Ben Brigham launched AutoFerret.com in Bellingham, Washington - a CRM built for automotive dealerships. The original product was straightforward: help dealers track leads. What happened next was more unusual.

The team began experimenting with AI-driven communication, building AVA - Automated Virtual Assistant - to handle the relentless follow-up work that sales reps either avoided or couldn't scale. AVA began selling commercially in 2010. By 2013, the company had raised a $16M Series A from Kennet Partners, relocated to Foster City, California, and set its sights on markets beyond automotive. The name changed to Conversica in 2014, signaling a clean break from its origins as a car dealer tool.

By the time Gilson arrived as CEO, Conversica had raised $148M across six funding rounds, including a $25M Series E in April 2022, backed by investors including Providence Strategic Growth. The platform had evolved well past a follow-up bot - it now supported multi-channel conversations across email, SMS, and web chat, with deep integrations into Salesforce, HubSpot, Marketo, Eloqua, and the automotive-specific stacks like VinSolutions, DealerSocket, and CDK.

Gilson's first public move after taking the CEO seat was to zero in on automotive again - but this time with a sharper lens. His argument, laid out in a February 2026 appearance on the Car Dealership Guy podcast, was simple and uncomfortable: dealers are sitting on millions of dollars in dormant customer data that the AI can activate. The data has always been there. The activation layer hasn't.

"A lot of that data gets wasted," Gilson said. "You can't really leverage it in a way that can really make you more money." It was the kind of observation that only makes sense when you've spent time in both sides of the problem - enterprise SaaS product cycles and the unglamorous reality of how data rots inside CRMs that nobody fully maintains.

The August 2025 rebrand to "The Conversation Company" was a bet on something larger. Gilson was signaling that the product wasn't just for sales teams chasing inbound leads anymore. AI agents could manage the entire arc of a customer relationship - from first touch to renewal to service follow-up. Sports teams. Higher education institutions. Financial services firms. Car dealers. The vertical list got longer because the underlying technology had become genuinely flexible.

Industry Focus

The industries Gilson is betting on

🚗

Automotive

Dealerships use Conversica's AI agents to re-engage dormant leads, surface hidden data in DMS systems, and close the gap between inquiry and sale. Gilson's personal focus since taking over - and a return to the company's roots.

🏟️

Sports & Entertainment

Sports teams use the platform to identify fan revenue opportunities buried in ticketing and CRM data. The Conversica Customer Forum for Sports and Live Entertainment launched under Gilson in 2025.

🏢

Enterprise

Fortune 500 companies like T-Mobile, ServiceNow, and Iron Mountain use Conversica's Revenue Digital Assistants to handle lead nurturing, customer success outreach, and pipeline acceleration at scale.

🎓

Higher Education

Universities and colleges use AI agents to engage prospective students across the enrollment funnel - from first inquiry through application, acceptance, and orientation - without overwhelming admissions staff.

💰

Financial Services

Banks and financial firms deploy Conversica for compliant, AI-driven outreach that meets regulatory requirements while maintaining the cadence and personalization that builds client relationships.

📡

Telecom

Telecom operators use the platform for automated follow-up, upsell campaigns, and customer retention - markets where volume is enormous and human-to-human follow-up simply can't keep pace.

"A lot of that data gets wasted. You can't really leverage it in a way that can really make you more money."

- Michael Gilson, on dealership data, Daily Dealer Live, February 2026

Career Timeline

How he got here

2006-2010

Studies at Princeton University, graduating with a Bachelor of Arts.

2010s

Early career in enterprise SaaS and data analytics. Holds roles at Wiser Solutions, a retail intelligence platform, and Revient Inc., building operator instincts across B2B software companies.

2010s-2020s

Joins Telestream, a media technology company whose video workflow software is used by broadcast organizations globally. Develops deep experience with technically complex, data-intensive enterprise buyers.

Pre-2025

Moves into a senior operating role at Conversica, gaining deep knowledge of the product and go-to-market before ascending to the CEO seat.

April 2025

Appointed CEO of Conversica, taking over leadership of a $148M venture-backed conversational AI company with 200+ employees and 2,000+ enterprise customers.

August 2025

Leads full rebrand: Conversica becomes "The Conversation Company," repositioning from a sales-tool point solution to a full customer lifecycle AI platform spanning acquisition, service, and retention.

2025

Launches Conversica Customer Forum for Sports and Live Entertainment, accelerating the company's vertical expansion into ticketing, fan engagement, and sports CRM intelligence.

February 2026

Appears on Daily Dealer Live (Car Dealership Guy Podcast) to discuss how AI can unlock millions in latent revenue hidden inside dealer databases. The episode surfaces Gilson's thesis on AI as an activation layer for dormant enterprise data.

Watch

Dealers sitting on millions - Gilson explains why

In this episode of Daily Dealer Live (Car Dealership Guy Podcast), Michael Gilson makes the case that the automotive industry's biggest AI opportunity isn't acquiring new data - it's activating the customer and transaction data that's already sitting dormant inside dealer systems.

His argument: the data foundation is the differentiator. Dealers who figure out how to make their existing data legible to AI will have a structural advantage over those who keep buying new leads.

Daily Dealer Live / Car Dealership Guy Podcast / February 2026

Scrapbook

Details worth keeping

Conversica, the company Gilson now runs, started as AutoFerret.com - a car dealership CRM built in 2007 in Bellingham, Washington. His automotive focus is less a pivot than a homecoming.

Gilson graduated from Princeton in 2010 - the same year Conversica's AI assistant AVA first went to market commercially. He and the company grew up in parallel without knowing it.

The platform Gilson oversees has powered over 1.5 billion conversations - more human-AI interactions than the entire population of China, one automated follow-up at a time.

Conversica's AI agents work in six languages: English, French, German, Spanish, Portuguese, and Japanese - letting a single US-based sales team conduct nuanced outreach across global markets simultaneously.

Before Gilson's rebrand, Conversica's tagline was "Revenue Digital Assistants." After August 2025, it became "The Conversation Company." Same product. Bigger ambition. Different buyer conversation.

Technology