Head of Technology

Decentralized Masters

2h•Remote

About The Position

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, and a 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. 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, and Cowork-native workflows across the org. We are excited about what's possible when AI agents and automation are applied to every operational function — Marketing, Enrollment, Fulfillment, Renewals, Data, and Security. This role owns the operating system that converts that potential into real efficiency.

Requirements

Hybrid technical and operational leader. You have spent your career spanning both sides — defining what to build and managing the team that builds it. You have shipped real systems with that judgment, in a high-tempo revenue org.
Builder-operator mindset. You design the operating model that connects people, process, data, and technology, and you personally make sure it ships. You own architecture and delivery, not just strategy.
HubSpot architect. HubSpot is the operating system of DM. You have been an admin operator, not just a user, with workflows that span lead, deal, contact, and ticket objects. You can diagnose a broken sequence, redesign a pipeline, and stand up new automation without breaking what is already live.
Modern automation architect. n8n (self-hosted), Zapier, and native API integrations are infrastructure you have built or led teams to build — not buzzwords. You have made the trade-off between vendor and in-house build dozens of times.
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 equivalent. You have configured each, debugged platform-side discrepancies, and stood behind the numbers in a room full of operators spending real money on ads.
Email and marketing automation operator. ActiveCampaign or equivalent (Klaviyo, HubSpot Marketing). You have run deliverability, built segmentation logic, and synced campaign data with a CRM in a high-volume sending environment.
Web and capture infrastructure. Webflow, Typeform, Vidalytics, GoDaddy (DNS), and the GTM container that ties them together. You understand how landing pages, video players, and form capture combine into a measurable conversion funnel.
Member lifecycle and community platforms. Circle (community / membership), Aloware (telephony and SMS), PandaDoc (agreements), and the payment rails behind a recurring revenue business (Whop, Fanbasis, Hotmart, Mamopay, Stripe, CopeCart). You have built lifecycle automations across at least one stack like this.
Data and reporting infrastructure. You can read a Snowflake or BigQuery roadmap, push back on it, and coordinate delivery without writing the SQL yourself. Plecto, Looker, Tableau, or equivalent dashboarding experience 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 solved real business problems. You know the difference between AI as a buzzword and AI as an operational tool.
Security-aware operator. You have operated in environments with real privacy, security, and compliance requirements, and you embed governance into systems by design. SSO, access governance, audit logs, anti-phishing, and incident response are part of your vocabulary. You can manage a Security Specialist without being a policy author yourself.
Work OS operator. ClickUp is the system of record for the Tech function. You have set up sprint cadences, custom fields, automations, and reporting in ClickUp (or Jira, Asana, Linear, Monday) at scale, and you know how to make a PM function actually drive throughput rather than ceremony.
Cross-functional operator. You build trust with senior leaders across Marketing, Enrollment, Fulfillment, Renewals, and Finance. You are a genuine partner to function leaders whose workflows you are transforming, not a service provider.
People manager at scale. You have hired, developed, and exited team members across multiple sub-teams and timezones. You build sprint cadences, 1:1 systems, and performance norms that work for back-end developers, data engineers, and security specialists who never sit in the same room as you.
Vendor operator. You have managed multi-vendor stacks, negotiated meaningful contracts, and proactively replaced underperforming tools before they became blockers.
KPI-disciplined. Sprint velocity, deadline reliability, profit-generating output, data SLAs, ticket-resolution time. You set the metric, you review it weekly, and you are honest with yourself and your team when the numbers are wrong.
Resilient communicator. You translate complex technical work into clear business outcomes for audiences from operators to the C-suite. You navigate ambiguity with steady judgment and keep teams focused during rapid transformation.
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 at a scaling business.

Nice To Haves

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

Responsibilities

Drive Automation Across the Revenue Engine. Identify, prioritize, and deliver automation across Marketing, Enrollment, Fulfillment, and Renewals workflows that produce measurable efficiency gains, measured by delivered outcomes, not roadmaps. Fully own the digitization of the member journey, from first ad click through renewal.
Safeguard the Business and Member Trust. Run the operating cadence for Security alongside the Security Specialist. Ensure access provisioning, deprovisioning, audit workflows, and threat-response procedures protect DM and its members from malicious actors and cyber incidents. Escalate policy decisions to the CPO and COO; do not set policy yourself.
Lead Data Infrastructure and Reporting. Lead the Data function alongside the Data Engineer. Deliver trusted data products, attribution joins across ad-platform and funnel data, and the 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. Define how agentic systems and automation get scoped, built, and measured inside DM. Make sure AI tooling reaches the operators who can use it, with clear ownership and measurable impact.
Run Sprint and Ticketing Operations. Own the ticketing system intake pipeline and the Tech Team master list in ClickUp. Run weekly sprint planning under the quarterly priorities set by the CPO and COO. Maintain OKRs, communicate progress and risk to leadership efficiently, and hit the quarterly KPIs: 18 sprint points per Tech Specialist per week sustained, ship commitments within 1 day of due date, 125 sprint points per quarter tagged as profit-generating.
Build and Empower the Technology Team. Hire, manage, develop, and when necessary exit members of the Tech department. Grow the team's capability over time, build a culture of execution, and make sure each person on the team is doing the highest-impact work they can.
Manage Vendor Strategy and Relationships. Proactively source new vendors as DM's needs evolve. Maintain strong relationships with existing partners. Recommend stack changes to the CPO and COO; commit to material moves only with sign-off.
Partner Across the Business. Translate operational needs from Marketing, Enrollment, Fulfillment, and Renewals officers into executable automation, data, and tooling roadmaps. Drive change management and adoption so that what gets shipped actually gets used.