Senior SEO & AI-Forward Digital Marketing Strategist (Cannabis + Beyond)

Part-Time | Remote | $30-35/hr | 60–80 hrs/monthWinston Digital Marketing is seeking a versatile, tactical, and AI-savvy Senior SEO Strategist to step into a mission-critical role supporting two major cannabis brands and some other clients. Our current lead is exiting, and we need someone ready to roll up their sleeves and lead the charge this week.

Who We’re Looking For:

This isn’t a "set it and forget it" SEO gig. We’re looking for someone who:

Owns SEO end-to-end: Strategy, implementation, audits, content, tech fixes, and structured data.

Can navigate dev roadblocks: You’ll need to speak developer, prioritize ruthlessly, and make things happen even when resources are limited.

Uses AI daily: You’re leveraging tools like GPT, Surfer, Screaming Frog, ChatGPT plug-ins, even agents or workflows — or at least understand the stack.

Understands omnichannel marketing: Ideally, you know enough about Paid Search and Social to see how SEO fits into a broader growth plan.

Can lead others: You’ll help support junior SEO and content team members, even if you’re not directly managing them.

About the Role

Hours: 60–80 per month (30–40 biweekly)Pay: $40–$60/hr depending on experienceStart: ASAP – we're looking to fill this within the next 7 daysLocation: Remote, must be based in the U.S. or Canada

About Us

Winston Digital is a performance-focused, AI-forward digital agency. We work with some of the biggest cannabis brands, major players in finance, and even local businesses who want Navy SEALs, not the Navy. We’re small, agile, and strategic. Our SEO work spans enterprise builds to gritty technical cleanups and everything in between.

We’re also not afraid of the future. We embrace AI, not as a crutch, but as a force multiplier. If you're someone who’s using AI to move faster and think smarter (but still has great instincts), you'll thrive here.

Apply now with a brief intro and relevant experience. To be considered please include:

Examples of dev-roadblocks you’ve solvedHow you’re using AI in your daily workExperience with cannabis or other regulated markets