Director of Operations

About TheFutureSociety LLCTheFutureSociety LLC is a fast-growing digital media and membership company built around three brands: • The Tarot Ship: a YouTube channel with a deeply engaged global audience – 286k subs • Great Awakener: a premium all-livestream membership platform for astrology, spirituality and consciousness education • MAX: an AI-powered astrology platform currently in Beta phase This is a revenue-generating startup approaching its first anniversary in August, with strong subscriber growth and multiple product lines launching in 2026. The ideal candidate will be building, executing and running the business day-to-day, including a membership platform, an AI product and a distributed team with roadmap, so the Founder can focus on content creation and community. The Founder is a well-known astrologer, psychic and tarot reader, with a background as an award-winning journalist and former EVP of a global tech company. The RoleWe're looking for a Head of Operations who can own and run the entire operational side of a growing membership and spirituality business. You will make sure nothing falls through the cracks, the team stays accountable, campaigns go out on time, KPIs are met, the company grows and the CEO never has to ask "what's the status?"This is a player-coach role. We are a small team. You know everyone's name, cover for them when needed, and are close enough to the work to catch problems before they escalate. You will execute, not just plan strategy. We value builders over brief writers.The 90-day benchmark: The Founder should be spending fewer than 5 hours per week on operational matters. That's how we measure success in this role. What You'll OwnCampaigns & Revenue Growth• Plan and execute email campaigns (win-back, promotional, product launches) with defined KPIs: open rates, click-through rates, and conversion targets• Own Stripe billing: monitor MRR, track churn, working with billing specialist for recover failed payments, investigate anomalies• Build and manage automated sequences (dunning, abandoned checkout recovery, cancellation deflection) using Make.com, Kit and Stripe webhooks• Deliver brief, weekly financial snapshots: cash-to-bank, subscriber counts, churn rate, campaign resultsTeam & Contractor Management• Own all hiring end-to-end: sourcing, screening, interviewing, and onboarding (subject to CEO approval for final candidates)• Manage a distributed team across US, Ireland, Brazil, and Chicago• Oversee and collaborate with research, creative, developers and the billing specialist and customer support function — set quotas, monitor performance, and ensure response SLAs are met• Execute contractor payments monthly; coordinate with bookkeeper for reconciliation• Manage US employee payroll and contractor records through Gusto: onboarding, offboarding, 1099s, and compliance• Enforce accountability through clear deadlines, KPIs, and reporting cadence — not just SOPs Guest & Instructor Relations• Help source, vet and onboard guest experts and instructors for Great Awakener and YouTube livestream programming• Conduct pre-appearance interviews and briefings to ensure guests are on-brand, prepared, and aligned with the platform's tone and audience• Manage the instructor pipeline: contracts, scheduling, technical setup and post-appearance follow-up Product, Automations, Systems & Technical Delivery• Oversee product delivery for MAX (AI astrology platform) and Great Awakener membership features• Manage any developer sprints, QA testing and launch readiness• Coordinate with any external dev teams to ensure deliverables meet deadlines and specifications• Use AI-assistant tools, such as ChatGPT or Claude (Code), to fix any technical bugs• Support the build and maintain operational automations using Make.com, Stripe, Kit, Supabase and SlackContent & Brand Operations• Own the content calendar and ensure publishing flows on schedule; run weekly all-hands meeting• Serve as quality gate for all public-facing content: social posts, emails, course materials, newsletters, community communication and platform announcements• Coordinate social media posting strategy and/or oversee social media team member(s), such as video editor Legal, Compliance & Vendor Management• Manage vendor relationships: developers, insurance, legal, accounting, SaaS subscriptions• Support legal matters: coordinate with attorneys, prepare documentation, follow up on deadlines• Ensure operational compliance: S-Corp requirements, contractor 1099s, insurance renewals RequirementsMust Have• 5+ years of operations experience — including 2+ years at a successful startup, creator business or subscription/membership company• Hands-on experience with Stripe: billing, subscriptions, dunning, payment links, coupons• Experience running all-in hiring cycles: sourcing, screening, interviewing, contracts and onboarding in a small team environment• Experience running email marketing campaigns with KPIs using Kit, Mailchimp or similar• Abil