Corp Dev at an AI Company
Corporate Development at Conversica (The Wins)
When I took over in October 2019, we envisioned Corporate Development as the jet fuel for Conversica’s growth—$150M in Series D capital would fund not just operations but strategic acquisitions that vaulted us into adjacent markets. The pandemic grounded that vision quickly, with only $20M raised. But that didn’t stop us from pursuing high-leverage, non-linear growth.
Over five years, we assessed dozens of M&A opportunities, partnerships, and strategic combinations. What worked? We developed a repeatable framework for evaluating accretive, cash-neutral opportunities—built around team quality, product adjacency, and GTM synergies. These weren’t moonshots. They were pragmatic, fast-moving deals aimed at accelerating time-to-product or time-to-market.
Our deal discipline matured. By 2024, we were capable of standing up an M&A case with valuation logic, earnout scenarios, and detailed integration blueprints—something that wasn’t the case pre-2020. Our pipeline included companies in conversational AI, agent assist, and lead conversion analytics—each evaluated against Conversica’s core AI thesis.
One standout: the Commerce AI startup opportunity. Structured to bring a team, a product, and 18+ months of self-funded runway in exchange for just 5% of Conversica common stock. It would have immediately accelerated our roadmap, required no new cash, and injected entrepreneurial energy into our team. A clean win—on paper.
Corporate Development – Strategic Headwinds (The Losses)
The greatest obstacle wasn’t opportunity—it was inertia. The Board’s risk posture calcified during the pandemic and never fully thawed. Despite presenting multiple low-dilution, high-upside deals, we faced consistent pushback. Deals that could’ve delivered non-linear scale were sidelined by “strategic conservatism.”
That same Commerce AI deal? Rejected by the Board—despite it being equity-light, self-funded, and squarely aligned with our GTM direction. Not because the business case was weak, but because institutional fear outweighed strategic vision.
We also underestimated the cultural drag of trying to “sell” transformative ideas in an environment conditioned to play defense. Even internally, aligning stakeholders around inorganic growth took more energy than closing the deals themselves.
Ultimately, we lost more to hesitation than execution. Corporate Development at Conversica wasn’t a failure of ideas—it was a failure of courage.
Advice From One CEO to Another – Building Corporate Development in AI GTM
- Set the Board Contract Early
Make M&A part of your charter from Day 1. Don’t just ask for permission later—bake Corp Dev into your CEO mandate upfront. - Use Equity Like a Weapon, Not a Shield
Cap tables don’t build companies—teams do. Use your stock to attract great people, not just fund raises. - Avoid the “Big Deal” Trap
You don’t need $100M acquisitions to make impact. Focus on product tuck-ins, talent grabs, or tech accelerants. Think nimble. - Create a Deal Culture Internally
Make it normal to evaluate external plays. Involve Product, Finance, GTM early. M&A should feel like a muscle, not a moonshot. - Get Buy-in When You Don’t Need It
Build Board alignment before the deal. Pitch phantom deals quarterly to test appetite and calibrate response before it matters. - Marry Corp Dev to Product Strategy
Every deal should answer: “Does this accelerate our roadmap or customer value?” If it doesn’t, walk. - Don’t Just Model ROI—Model Belief
Numbers alone won’t win. Storytelling matters. Paint a vision they can believe in, not just approve.
Conclusion
Conversica’s Corporate Development story is one of vision constrained by governance. We built the tools, sourced the deals, and structured the moves—but were met with strategic caution rather than catalytic support. Still, the frameworks remain. The playbook is written. For the next chapter—or the next CEO—those tools are ready to be unleashed.
Inorganic growth is like catching lightning—rare, powerful, and fleeting. But only those who carry the rod ever get struck. Make sure you’re holding it when the storm comes.
