Systems over campaigns
Andrew builds repeatable GTM infrastructure: outbound engines, lead scoring, marketing automation, and content systems, not one-off tactics that vanish when the sprint ends.
About
Andrew McGrath
Co-Founder and CMO of Vesara. Fractional CMO through Darwinian Ventures. Based in the San Francisco Bay Area, building go-to-market systems for AI-native companies.
Origin
The Path Here
Andrew McGrath started in Bay Area residential real estate, running marketing for a high-volume transaction team. The work taught velocity-based go-to-market, local market positioning, and how to build systems that produce consistent deal flow. Real estate was not a detour; it was the springboard. It taught the mechanics of repeatable revenue and client acquisition at speed.
The transition came when he recognized that the systems he was building for real estate applied to any market with a complex sale. He moved into tech and startups with the same operator instinct: if the motion is not repeatable, it is not a business. It is a streak.
He co-founded Maira AI as CEO, a voice-first AI agent fleet platform originally positioned toward real estate brokerages, later repositioned toward horizontal enterprise. He built the product, the brand, and the GTM motion, and led the company through its strategic pivot.
Today, Andrew is CMO of Vesara, co-founded with Andrew Boos, where he runs go-to-market strategy and the Enterprise AI Playbook newsletter. He also operates Darwinian Ventures, a fractional CMO practice serving AI-native startups at the zero-to-one stage, embedding with teams to build the infrastructure that turns early product into durable demand.
Selective
Advisory
Andrew McGrath serves as an advisor to a stealth-stage quantum computing startup focused on data optimization for financial models. The engagement sits at the intersection of his GTM expertise and emerging deep tech, selective by design, and held with the same operator standard he brings to founding and fractional work.
He does not treat advisory as a logo collection. When he advises, the brief is clear: help a serious team translate technical advantage into a market motion that can scale.
Principles
How I Work
Operator, not advisor
He embeds with the team. He writes the copy, builds the workflows, and ships the campaigns. Fractional in title, full-stack in practice.
AI-native GTM
AI tooling (automation, enrichment, content, analytics) is treated as core infrastructure, not a bolt-on. He builds the playbooks for how AI companies should market to other AI companies.
Take, not data
The best go-to-market starts with a strong point of view, not a dashboard. Data informs the system; conviction sets the direction.
Reference
Frequently Asked Questions
What does Andrew McGrath do?
Andrew McGrath is Co-Founder and CMO of Vesara, where he builds go-to-market strategy and publishes the Enterprise AI Playbook newsletter. He also operates Darwinian Ventures, a fractional CMO practice serving AI-native startups at the zero-to-one and one-to-ten stage. He is based in the San Francisco Bay Area.
What is Vesara?
Vesara is an AI advisory and GTM infrastructure firm co-founded by Andrew McGrath and Andrew Boos. Vesara helps enterprise organizations deploy AI with operator-grade go-to-market systems, and publishes the Enterprise AI Playbook newsletter. Learn more at https://vesara.ai.
What is Darwinian Ventures?
Darwinian Ventures is Andrew McGrath’s fractional CMO practice for AI-native startups. Engagements typically cover GTM strategy, positioning, outbound systems, paid acquisition, and marketing automation, with an emphasis on building repeatable infrastructure rather than one-off campaigns. Learn more at https://darwinian.com.
What industries does Andrew work in?
Andrew McGrath works primarily in enterprise AI and SaaS, with additional experience across recruiting and talent technology, search infrastructure, real estate technology, and selective advisory in quantum computing focused on data optimization for financial models.
What is the Enterprise AI Playbook?
The Enterprise AI Playbook is a weekly LinkedIn newsletter published under the Vesara brand by Andrew McGrath. It covers enterprise AI strategy, GTM for technical products, and the operator’s perspective on what is actually working in the field. Subscribe at https://www.linkedin.com/newsletters/the-enterprise-ai-playbook-7445918581823008768/.
Where is Andrew McGrath based?
Andrew McGrath is based in the San Francisco Bay Area, California, with ties to Sonoma County.