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
Advisor
Tdooz, Inc.
- AYARA,JOB
- Advisor2M
Advisor
Ayara, LLC
- PAVILIONJOB
- Member6Y 8M
Member
Pavilion
- BLOOMERANGJOB
- VP Demand Generation2Y 5M
Vice President Demand Generation
Bloomerang
- GTM PARTNERSJOB
- GTM Ambassador2Y 10M
GTM Ambassador
GTM Partners
- NOBLEJOB
- Advisor1Y
Advisor
noble
- CLOUDSPOTJOB
- Strategic Advisor1Y
Strategic Advisor
CloudSpot
- 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)
- Job: Pavilion β Member Β· 2019-11 β 2026-07
- Job: Sendoso β Advisor Β· 2021-02 β 2024-04
- Job: CloudSpot β Strategic Advisor Β· 2023-10 β 2024-10
- Job: Tdooz, Inc. β Advisor Β· 2025-08 β present
- Job: Flip (formerly RedRoute) β Chief Marketing Officer Β· 2022-05 β 2023-09
- Job: Ayara, LLC β Advisor Β· 2026-06 β present
- Job: noble β Advisor Β· 2024-06 β 2025-06
- Job: Bloomerang β Vice President Demand Generation Β· 2024-01 β 2026-06
- Job: CMO Collaborative β SLC CMO Collaborative Chapter Leader Β· 2023-01 β 2024-01
- Job: GTM Partners β GTM Ambassador Β· 2023-05 β 2026-03
Skills
Playbooks
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