James Gilbert ππ»
3x CMO | Father of 4 | GTM Operator | AI-Driven GTM Strategy | Scaling Startups to Market Leaders
ex-PavilionRecent VP of Demand Generation at Bloomerang with a background as a 3X CMO.. I build revenue engines that scale.
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Over the last 22+ years I've helped startups, PE-backed companies, and growth-stage organizations transform marketing into a predictable driver of pipeline, revenue, and enterprise value. I thrive at the intersection of brand, demand generation, and AI-driven go-to-market strategy, translating innovation into market Start-up stages: Seed to Series D & $1M - $150MEnterprise experience at Cisco, Verizon, and AGCOCore expertise includes:- Building and scaling global marketing and growth organizations- Harnessing AI as a growth engine, with hands-on experience in agentic AI models, Voice AI, and leading platforms such as Claude (not just chat), n8n workflows, Replit, ChatGPT, Gemini, Perplexity, and more to transform marketing, customer experience, and operational efficiency- Partnering with CEOs, boards, and investors to guide companies through critical growth inflection points- Positioning organizations for long-term success through strategic storytelling, brand building, and market leadershipIn addition to my executive roles, I serve as an advisor to founders and leadership teams, an investor, and an author on the of future marketing, AI and modern go-to-market strategy. These roles keep me deeply connected to emerging technologies and the evolving growth landscape, enriching the perspective I bring to every company I help I bring a balance of strategic vision and operational rigor, ensuring marketing not only shapes the narrative but also drives measurable business impact in revenue not just pipeline. Today, I am focused on helping organizations harness AI and modern growth strategies to reach their next stage of expansion with clarity, momentum, and The power of humans in the world of AI has never been more important. Itβs the balance of how they work together that I help people Bringing a healthy combination of AI and humanity back to business.
GTM Index
- TDOOZ,JOB
- Advisor1Y 2M
Advisor
Tdooz, Inc.
Strategic advisor
- AYARA,JOB
- Advisor4M
Advisor
Ayara, LLC
Strategic Advisor for AI Building AI infrastructure and managing growth. Automating support and driving affiliates.
- PAVILIONJOB
- Member6Y 8M
Member
Pavilion
2X CMO School Graduate CRO School Graduate Revenue Architecture AI School
- BLOOMERANGJOB
- VP Demand Generation2Y 5M
Vice President Demand Generation
Bloomerang
Owned GTM growth across net-new and expansion for a nonprofit SaaS platform serving 25,000+ organizations. Led the AI-first GTM transformation. Team of 15, three directs. β’ Drove 68% of expansion revenue in 2024 and 2025 β’ Cut expansion deal velocity 52 β 22 days β’ Grew net-new revenue 28β42% YoY, with 21% unit growth β’ Raised ASP $3,200 β $5,500 net new, $1,100 β $1,700 expansion β’ Cut cost per opportunity 63% ($675 β $250) and cost per MQA 55% ($325 β $145) β’ Built and deployed agentic AI meeting bookers: 1,112 meetings, $5M pipeline, $2M closed β’ Set and guided the GEO/AIO strategy ahead of the market, then hired a dedicated owner β’ Bloomerang now ranks #1β2 across ChatGPT, Claude, Gemiβ¦
- GTM PARTNERSJOB
- GTM Ambassador2Y 10M
GTM Ambassador
GTM Partners
At GTM Partners, we assist companies with their go-to-market strategies.
- NOBLEJOB
- Advisor1Y
Advisor
noble
Marketing advisory
- CLOUDSPOTJOB
- Strategic Advisor1Y
Strategic Advisor
CloudSpot
Advised on their growth strategy. CloudSpot is a software for photographers.
- SENDOSOJOB
- Advisor3Y 2M
Advisor
Sendoso
- CMO COLLABORATIVEJOB
- SLC CMO Collaborative Chapβ¦1Y
SLC CMO Collaborative Chapter Leader
CMO Collaborative
- FLIP (FORMERLY REDROUTE)JOB
- Chief Mktg Officer1Y 4M
Chief Marketing Officer
Flip (formerly RedRoute)
Recruited to drive growth through Series A and establish a scalable foundation for marketing and demand generation. Highlights: - Built the marketing function from the ground up, developing demand generation engines across email, outbound, and partnerships - Led a complete rename, rebrand, and website relaunch within four months, amplifying growth without slowing momentum - Implemented AI-driven approaches for customer acquisition, retention analysis, and content-led marketing - Built a strong content ecosystem including a podcast and outbound engine that fueled community engagement - Positioned Flip as a category leader finalist at Pavilionβs 2023 awards - Achieved consistent results withβ¦
- Job: Tdooz, Inc. β Advisor Β· 2025-08 β present Β· 1y β Strategic advisor
- Job: Ayara, LLC β Advisor Β· 2026-06 β present Β· 2 mo β Strategic Advisor for AI Building AI infrastructure and managing growth. Automating support and driving affiliates.
- Job: Pavilion β Member Β· 2019-11 β 2026-07 Β· 6y 8mo β 2X CMO School Graduate CRO School Graduate Revenue Architecture AI School
- Job: Bloomerang β Vice President Demand Generation Β· 2024-01 β 2026-06 Β· 2y 5mo β Owned GTM growth across net-new and expansion for a nonprofit SaaS platform serving 25,000+ organizations. Led the AI-first GTM transformation. Team of 15, three directs. β’ Drove 68% of expansion revenue in 2024 and 2025 β’ Cut expansion deal velocity 52 β 22 days β’ Grew net-new revenue 28β42% YoY, with 21% unit growth β’ Raised ASP $3,200 β $5,500 net new, $1,100 β $1,700 expansion β’ Cut cost per opportunity 63% ($675 β $250) and cost per MQA 55% ($325 β $145) β’ Built and deployed agentic AI meeting bookers: 1,112 meetings, $5M pipeline, $2M closed β’ Set and guided the GEO/AIO strategy ahead of the market, then hired a dedicated owner β’ Bloomerang now ranks #1β2 across ChatGPT, Claude, Gemiβ¦
- Job: GTM Partners β GTM Ambassador Β· 2023-05 β 2026-03 Β· 2y 10mo β At GTM Partners, we assist companies with their go-to-market strategies.
- Job: noble β Advisor Β· 2024-06 β 2025-06 Β· 1y β Marketing advisory
- Job: CloudSpot β Strategic Advisor Β· 2023-10 β 2024-10 Β· 1y β Advised on their growth strategy. CloudSpot is a software for photographers.
- Job: Sendoso β Advisor Β· 2021-02 β 2024-04 Β· 3y 2mo
- Job: CMO Collaborative β SLC CMO Collaborative Chapter Leader Β· 2023-01 β 2024-01 Β· 1y
- Job: Flip (formerly RedRoute) β Chief Marketing Officer Β· 2022-05 β 2023-09 Β· 1y 4mo β Recruited to drive growth through Series A and establish a scalable foundation for marketing and demand generation. Highlights: - Built the marketing function from the ground up, developing demand generation engines across email, outbound, and partnerships - Led a complete rename, rebrand, and website relaunch within four months, amplifying growth without slowing momentum - Implemented AI-driven approaches for customer acquisition, retention analysis, and content-led marketing - Built a strong content ecosystem including a podcast and outbound engine that fueled community engagement - Positioned Flip as a category leader finalist at Pavilionβs 2023 awards - Achieved consistent results withβ¦
- School: Weber State University β Bachelor of Science (B.S.), Professional Sales
- School: Utah State University β Bachelor of Engineering - BE
Skills
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LeadMagic
ex-Amplemarket