Heady
Co-Founder & CEO
07/2021 – Current (exiting; see status note below)·Baltimore, MD
Context
Heady is a cannabis marketing agency serving retailers and wholesale brands across every digital channel — websites, CRM, content strategy, social media, PR, and all layers of SEO (local, technical, content-led, domain authority). Tim ran the agency (sales, client management, finance, operations); his business partner leads the SEO function.
Business model: expert-level marketing without expert headcount. Overseas contractors executing on proprietary workflows built by Heady's partners. Ships productized software so brands and other agencies can access the playbook directly.
Numbers
- ~$108k/yr per retainer ($9k/mo) as the standard contract size.SalesStrategy
- 3–5 clients lost across 4 years — ultra-low churn, surviving major leadership changes at nearly every client brand.SalesManagement
- $90k/mo → $1.1M/mo email-attributed revenue for a 6-store retail chain via Alpine IQ lifecycle work.GTMData
- +38% organic traffic, +85% non-branded clicks over 5 months for a cannabis CPG brand.GTMData
Status (07/07/2026)
Tim is in the process of exiting Heady. His partner has made an offer to acquire Tim's controlling stake, making Tim purely passive. Both partners are aligned: Tim wants to move on to other things because he is not passionate about cannabis itself — he was passionate about helping the clients.
Frame for job search: Heady is a completed, still-operating success. Tim is available.
Why Tim founded Heady
Leaving Jane, Tim saw cannabis brands using overpriced, charlatan-y agencies that didn't know what they were doing. He had the deep Web/SEO background from MyFinance, and had built enough CRM, PR, and design expertise across Jane to add those to the service offering. Heady would be a system, not a headcount play.
Products shipped
HeadyOS
The core product. An operating system that:
Foundation for everything Heady does internally. Offered on a DIY basis to any cannabis brand that wants to run it themselves.
- Connects to cannabis brand data sources: Google Search Console, Web Analytics, POS data, CRM data, lab-results data, and more.
- Automatically executes marketing workflows end-to-end — planning content for SEO, scaling CRM, designing social media assets.
- Replaces what a business would otherwise hire for: help desk, web monitoring, SEO strategy, retention strategy.
- Executes deliverables on the user's behalf: research, analysis, copywriting, design.
Other products
- StrainInsights.AI — launched June 2025.
- CannabisContent.AI — launched September 2025.
- Custom & turnkey website "themes" for wholesale and retail brands covering SEO, subscriber growth, and UX.
- Scalable page frameworks for deals / brands / categories driving both SEO and CRM performance.
Interview-safe stories
- "HeadyOS runs the agency." Tim can walk through the specific data sources → workflows → deliverables loop. Great story for AI Product roles.AIProductStrategy
- "Ultra-low churn in a chaotic industry." 3–5 clients lost across 4 years while every client brand had leadership turnover.SalesManagement
- "6 stores from $90k to $1.1M/mo in email." Alpine IQ case study.GTMData
- "Why I'm leaving." Honest, non-defensive answer: not passionate about cannabis; passionate about helping clients. Ready for a more focused seat than agency Founder.Strategy
Skills exercised
Company founding + running, agency P&L, sales, client management, product management of AI workflows, hiring/managing distributed contractors, SEO strategy at every layer, CRM lifecycle strategy (Alpine IQ specifically), GA4, Google Search Console, AI workflow architecture at production scale.