[Hiring] Head of Technology @Decentralized Masters

Role Description

This is a leadership opportunity to run the operating engine of an AI-native education company scaling toward $10M/month in revenue. You will report directly to the CPO and COO, partner across every function in the business, and own day-to-day responsibility for the automation, data, security, and administrative systems that make DM run. Leadership sets the strategy. You make it ship.

If you have spent your career at the intersection of automation, team management, and revenue operations, and you are ready to apply that judgment with real authority across a four-function span, this is the role.

The Head of Technology is responsible for unlocking measurable efficiency and scale across DM's revenue engine through:

• Automation
• Data infrastructure
• Security operations
• Disciplined sprint cadence

This leader builds and operates the technical systems that allow Marketing, Enrollment, Fulfillment, and Renewals to grow without scaling headcount proportionally. The Head of Technology is a critical partner to every revenue officer in the business and works under the direct supervision of the CPO and COO to ensure every capability is shipped on time, governed by design, and aligned to the company's quarterly objectives.

Your Impact

DM is becoming an AI-native operating company. We have taken meaningful first steps:

• Daily syncs powered by Recall.ai and n8n
• AI transcript validation in the enrollment funnel
• Cowork-native workflows across the org

This role owns the operating system that converts that potential into real efficiency.

• Drive Automation Across the Revenue Engine: Identify, prioritize, and deliver automation across Marketing, Enrollment, Fulfillment, and Renewals workflows that produce measurable efficiency gains.
• Safeguard the Business and Member Trust: Run the operating cadence for Security alongside the Security Specialist.
• Lead Data Infrastructure and Reporting: Deliver trusted data products and dashboards that Marketing, Enrollment, the C-suite, and the founders rely on for weekly decisions.
• Scale AI-Native Operations: Drive massive AI adoption across the company.
• Run Sprint and Ticketing Operations: Own the ticketing system intake pipeline and run weekly sprint planning.
• Build and Empower the Technology Team: Hire, manage, develop, and when necessary exit members of the Tech department.
• Manage Vendor Strategy and Relationships: Proactively source new vendors as DM's needs evolve.
• Partner Across the Business: Translate operational needs from various officers into executable automation, data, and tooling roadmaps.

Qualifications

• Hybrid technical and operational leader with experience in defining and managing systems.
• Builder-operator mindset, owning architecture and delivery.
• HubSpot architect with admin operator experience.
• Modern automation architect with experience in n8n, Zapier, and API integrations.
• Paid-traffic attribution depth with experience in Hyros, Everflow, Google Analytics Suite, etc.
• Email and marketing automation operator experience.
• Web and capture infrastructure knowledge.
• Experience with member lifecycle and community platforms.
• Data and reporting infrastructure experience.
• AI and automation practitioner with hands-on experience.
• Security-aware operator with experience in compliance requirements.
• Work OS operator experience with ClickUp or similar tools.
• Cross-functional operator with trust-building skills.
• People manager at scale with experience in hiring and developing teams.
• Vendor operator with experience in managing multi-vendor stacks.
• KPI-disciplined with experience in setting and reviewing metrics.
• Resilient communicator with the ability to translate technical work into business outcomes.
• Bachelor's degree in Computer Science, Information Systems, or related field; advanced degree a plus.
• 8+ years senior leadership across technology operations, with 4+ years leading automation, data, or revenue-tech functions.
• Familiarity with crypto, DeFi, online education, or high-ticket info-product businesses is a plus.

Requirements

• Prior hands-on experience with the following tools is expected:
• CRM and Lifecycle: HubSpot, ActiveCampaign
• Automation Platforms: n8n, Zapier
• Web, Capture, and Domains: Webflow, Typeform, Vidalytics, GoDaddy, Cloudflare
• Attribution and Analytics: Hyros, Everflow, Google Analytics Suite, Facebook Pixel, PostHog, Stape.io
• Member Lifecycle and Community: Circle, Aloware, PandaDoc
• Payments and Renewals: Whop, Fanbasis, Hotmart, Mamopay, Stripe, CopeCart
• Data and Reporting: Plecto, Snowflake, BigQuery
• Work OS and Comms: ClickUp, Slack, Google Workspace, Zoom
• Security: Google Workspace Audit and Investigation, SSO, Cloudflare, Supabase
• AI Tooling: Claude, TypingMind, n8n LLM nodes
• Design and Collaboration: Figma, 1Password

Benefits

• Competitive salary - benchmarked to experience and output, not just credentials
• Full access to DM courses and educational resources
• Direct exposure to the founders and senior leadership - your work will be seen
• 100% remote and async-friendly culture
• Team Offsites annually