Head of Technology

📋 Description

• Who Are We? Decentralized Masters is leading the charge in global DeFi education. In just two years, we've expanded from a visionary duo of co-founders to a robust team of over 140 committed professionals. We are now recognized as one of the fastest-growing enterprises in the sector, with industry experts forecasting our rise to unicorn status by 2030. Operating on a self-sustaining model, we are poised to achieve an impressive $50 million in revenue this year alone.

• Our Impact While our growth has been extraordinary, we take even greater pride in the achievements of our clients. To date, we have empowered over 4,000 investors to enter the DeFi landscape. At Decentralized Masters, we don't just provide education; we foster a wealth of knowledge combined with a vibrant community, cutting-edge technology, and a team of leading DeFi and blockchain experts. Our dedication is to offer unparalleled resources aimed at long-term success in the DeFi and Web3 arenas, ensuring our members not only protect but also enhance their financial futures.

• Our Vision Our objective is to establish the largest and most influential DeFi ecosystem ever seen, beginning with setting the benchmark in DeFi education. This vision is ambitious, transformative, and ready to reshape the digital finance landscape.

• Are You Ready? This is more than just a job; it's a chance to influence the future of Web3 technology and education. Are you prepared to join us in our mission to redefine the possibilities in DeFi and beyond? Apply below, and let’s embark on this journey together.

• The Role This is a leadership opportunity to oversee the operational framework of an AI-native education company scaling towards $10M/month in revenue. You will report directly to the CPO and COO, collaborate across all business functions, and take ownership of the daily operations concerning automation, data, security, and administrative systems that keep DM running smoothly. Leadership sets the strategy; you make it happen. If your career has been at the crossroads of automation, team management, and revenue operations, and you are ready to exercise that expertise with real authority across various functions, this is the role for you.

• The Head of Technology plays a crucial role in driving measurable efficiency and scalability within DM's revenue engine through automation, data infrastructure, security operations, and a disciplined sprint cadence. This leader builds and maintains the technical systems that enable Marketing, Enrollment, Fulfillment, and Renewals to grow without a proportional increase in headcount. The Head of Technology is a vital partner to every revenue officer in the organization and works directly under the CPO and COO to ensure all capabilities are delivered on time, governed by design, and aligned with the company's quarterly objectives.

• Your Impact DM is evolving into an AI-native operating company. We have made significant strides: daily syncs powered by Recall.ai and n8n, AI transcript validation in the enrollment funnel, and Cowork-native workflows throughout the organization. We are enthusiastic about the possibilities when AI agents and automation are integrated into every operational function — Marketing, Enrollment, Fulfillment, Renewals, Data, and Security. This role is responsible for the operating system that turns this potential into tangible efficiency.

• Drive Automation Across the Revenue Engine. Identify, prioritize, and implement automation across Marketing, Enrollment, Fulfillment, and Renewals workflows that yield measurable efficiency gains, evaluated by outcomes delivered rather than planned roadmaps. Take full ownership of the digitization process for the member journey, from the initial ad click to renewal.

• Safeguard the Business and Member Trust. Manage the operational cadence for Security alongside the Security Specialist. Ensure access provisioning, deprovisioning, audit workflows, and threat-response procedures protect DM and its members from malicious activities and cyber incidents. Escalate policy decisions to the CPO and COO; do not independently set policy.

• Lead Data Infrastructure and Reporting. Oversee the Data function in collaboration with the Data Engineer. Provide reliable data products, attribution joins across ad-platform and funnel data, and the dashboards that Marketing, Enrollment, the C-suite, and the founders depend on for weekly decision-making.

• Scale AI-Native Operations. Promote widespread AI adoption throughout the company. Define the scope, construction, and evaluation of agentic systems and automation within DM. Ensure AI tools are accessible to the operators who can utilize them, with clear ownership and measurable impact.

• Run Sprint and Ticketing Operations. Manage the ticketing system intake pipeline and the Tech Team's master list in ClickUp. Conduct weekly sprint planning according to the quarterly priorities established by the CPO and COO. Maintain OKRs, efficiently communicate progress and risks to leadership, and achieve the quarterly KPIs: 18 sprint points per Tech Specialist weekly, deliver commitments within one day of their due date, and 125 sprint points per quarter classified as profit-generating.

• Build and Empower the Technology Team. Hire, manage, develop, and, when necessary, transition members of the Tech department. Enhance the team's capabilities over time, foster a culture of execution, and ensure that each team member is engaged in the highest-impact work possible.

• Manage Vendor Strategy and Relationships. Actively search for new vendors as DM’s needs evolve. Maintain strong relationships with existing partners. Recommend stack changes to the CPO and COO; commit to significant changes only with approval.

• Partner Across the Business. Translate operational needs from Marketing, Enrollment, Fulfillment, and Renewals officers into actionable automation, data, and tooling roadmaps. Facilitate change management and adoption so that what is delivered is actually utilized.

⛳️ Requirements

• Hybrid technical and operational leader. You have spent your career bridging both areas — defining what to create and managing the team that implements it. You have successfully launched real systems within a high-tempo revenue organization.

• Builder-operator mindset. You design the operational model that integrates people, process, data, and technology, and you personally ensure it is executed. You own architecture and delivery, not just the strategic vision.

• HubSpot architect. HubSpot serves as the operating system for DM. You have acted as an admin operator, not merely a user, with workflows spanning lead, deal, contact, and ticket objects. You can troubleshoot a broken sequence, redesign a pipeline, and establish new automation without disrupting existing operations.

• Modern automation architect. n8n (self-hosted), Zapier, and native API integrations are infrastructures you have built or led teams to develop — not just buzzwords. You have frequently weighed the trade-off between vendor solutions and in-house builds.

• Paid-traffic attribution depth. Hyros, Everflow, Google Analytics Suite (GA4, Tag Manager, BigQuery), Facebook Pixel, Google Pixel via GTM, PostHog, and server-side tracking through Stape.io or similar. You have configured each, resolved platform-side discrepancies, and confidently backed the data in discussions with operators spending substantial amounts on advertising.

• Email and marketing automation operator. ActiveCampaign or its equivalent (Klaviyo, HubSpot Marketing). You have managed deliverability, constructed segmentation logic, and synchronized campaign data with a CRM in a high-volume sending context.

• Web and capture infrastructure. Webflow, Typeform, Vidalytics, GoDaddy (DNS), and the GTM container that integrates them. You understand how landing pages, video players, and form capture work together to create a measurable conversion funnel.

• Member lifecycle and community platforms. Circle (community/membership), Aloware (telephony and SMS), PandaDoc (agreements), and the payment systems behind a recurring revenue model (Whop, Fanbasis, Hotmart, Mamopay, Stripe, CopeCart). You have established lifecycle automations across at least one of these stacks.

• Data and reporting infrastructure. You can interpret a Snowflake or BigQuery roadmap, provide feedback, and coordinate delivery without writing SQL yourself. Experience with Plecto, Looker, Tableau, or similar dashboarding tools for executive reporting.

• AI and automation practitioner. You have hands-on experience with LLMs, agentic frameworks, and AI adoption initiatives (Claude, ChatGPT, TypingMind, Cowork, n8n + LLM nodes) that resolved real business challenges. You understand the distinction between AI as a buzzword and AI as an operational asset.

• Security-aware operator. You have worked in environments with genuine privacy, security, and compliance demands, and you integrate governance into systems by design. Single Sign-On (SSO), access governance, audit logs, anti-phishing, and incident response are part of your lexicon. You can manage a Security Specialist without authoring policy yourself.

• Work OS operator. ClickUp is the system of record for the Tech function. You have established sprint cadences, custom fields, automations, and reporting in ClickUp (or Jira, Asana, Linear, Monday) at scale, and you know how to ensure that a PM function effectively drives throughput rather than just ceremonial processes.

• Cross-functional operator. You build trust with senior leaders across Marketing, Enrollment, Fulfillment, Renewals, and Finance. You are a true partner to function leaders whose workflows you are enhancing, not merely a service provider.

• People manager at scale. You have recruited, developed, and transitioned team members across multiple sub-teams and time zones. You establish sprint cadences, one-on-one systems, and performance standards that accommodate back-end developers, data engineers, and security specialists who may never share the same physical space.

• Vendor operator. You have overseen multi-vendor ecosystems, negotiated significant contracts, and proactively replaced underperforming tools before they became obstacles.

• KPI-disciplined. Sprint velocity, deadline adherence, profit-generating output, data SLAs, ticket-resolution time. You set metrics, review them weekly, and maintain honesty with yourself and your team when the data shows discrepancies.

• Resilient communicator. You translate complex technical work into clear business results for audiences ranging from operators to the C-suite. You navigate uncertainty with sound judgment and keep teams focused during rapid transformations.

• Bachelor's degree in Computer Science, Information Systems, or a related field. An advanced degree is a plus.

• 8+ years of senior leadership experience in technology operations, with 4+ years leading automation, data, or revenue-tech functions in a scaling organization.

• Familiarity with crypto, DeFi, online education, or high-ticket info-product businesses is beneficial.

🏝️ Benefits

• Competitive salary - aligned with experience and output, not merely credentials.

• Full access to DM courses and educational resources.

• Direct exposure to the founders and senior leadership - your contributions will be recognized.

• 100% remote and asynchronous-friendly culture.

• Annual team offsites.