Director of Technology & AI

321 the Agency • Orlando, FL

1d • $100,000 • Remote

About The Position

321 is a full-funnel creative agency built for brands that operate in complex, regulated industries — healthcare, insurance, legal services, home services, entertainment, and travel and tourism. We're a remote, AI-first team that combines strategic creative with CRM infrastructure, performance marketing, and paid media to drive real, measurable business outcomes for our clients. Technology isn't a support function at 321 — it's the foundation everything else runs on. Our CRM builds, paid media measurement, AI workflows, and client reporting all depend on systems that are well-architected, secure, and connected. The Director of Technology is the leader who makes that foundation work as one.

As Director of Technology at 321, you will lead the agency's technology function across internal systems, MarTech and CRM infrastructure, data and integrations, AI enablement, and information security. This is a senior leadership role with real strategic authority — you'll own the agency's technology roadmap, set standards for how our platforms are built and governed, and serve as the senior technical voice in client strategy, new business, and agency planning conversations.
The right person for this role thinks in systems, not tools. You understand that a CRM workflow is only as reliable as the integration feeding it, that clean data is the difference between real attribution and guesswork, and that AI only creates leverage when it's built into the way a team actually works. You're as comfortable reviewing a webhook payload or a High Level workflow as you are presenting a technology roadmap to agency leadership — and you lead a team that delivers both.
You'll also work in close coordination with 321 AIM, the agency's proprietary performance marketing platform, ensuring that its technology, data flows, and integrations stay aligned with the systems that power our client programs.

Requirements

• 8+ years of experience in technology, MarTech, or systems roles, with demonstrated depth in CRM architecture, integrations, and data infrastructure — agency experience strongly preferred
• At least 2–3 years in a department leadership, team lead, or senior manager role with direct reports
• Hands-on experience architecting and governing CRM and marketing automation programs in High Level is strongly preferred; Salesforce, Salesforce Marketing Cloud, and/or HubSpot experience also valued
• Deep experience with APIs, webhooks, and middleware (Zapier, Make, n8n, or similar), including troubleshooting integrations across multiple systems
• Strong command of conversion tracking and measurement infrastructure: Google Tag Manager, GA4, server-side tracking, and offline conversion imports
• Working knowledge of data pipelines, data warehousing, and reporting tools (BigQuery, Looker Studio, Power BI, or similar)
• Experience administering cloud-based business systems, identity and access management, and security for a remote team
• Working knowledge of privacy and compliance requirements affecting marketing technology in regulated industries, including HIPAA, TCPA, A2P 10DLC, CAN-SPAM, GDPR, and CCPA
• Practical experience deploying AI tools and LLM-powered workflows, with sound judgment on data privacy and appropriate use
• Scripting or development ability in JavaScript, Python, SQL, or similar is a strong plus
• Excellent communication skills — able to explain technical decisions clearly to clients, agency leadership, and non-technical teammates
• Strong organizational and prioritization skills with the ability to manage department operations across a remote, multi-client environment
• Bachelor's degree in Computer Science, Information Systems, Marketing Technology, or a related field — or equivalent demonstrated experience

Nice To Haves

• Platform certifications (High Level, Salesforce, HubSpot, Google, cloud or security certifications) are a plus

Responsibilities

• Lead, manage, and grow the Technology department, including CRM/MarTech engineers, integration specialists, and systems administration
• Own the agency's technology roadmap, aligning platform investments with client delivery needs, agency growth goals, and operational efficiency
• Set the department's operating model: build standards, QA and testing practices, documentation requirements, change management, and support processes
• Conduct regular 1:1s and performance reviews; provide technical coaching and actively develop team capabilities
• Define role scopes, skill development paths, and staffing recommendations as the department grows to warrant additional headcount
• Serve as the escalation point for system outages, integration failures, data issues, and complex technical questions across the client portfolio
• Own the agency's internal technology stack, including collaboration, project management, identity, file storage, and communication tools
• Manage user access, single sign-on, device policies, and account provisioning and offboarding for a fully remote team
• Establish and enforce information security policies, password and access standards, backup practices, and incident response procedures
• Ensure agency and client systems meet applicable privacy and compliance requirements, including HIPAA, TCPA, A2P 10DLC, CAN-SPAM, GDPR, and CCPA
• Manage technology vendors, licenses, contracts, and costs; evaluate build-versus-buy decisions
• Set architecture and governance standards for client CRM and marketing automation programs built primarily on High Level, with additional work in Salesforce, Salesforce Marketing Cloud, and HubSpot
• Oversee integrations between CRMs, ad platforms, websites, call tracking, payment processors, and third-party systems using APIs, webhooks, and middleware such as Zapier, Make, or n8n
• Standardize snapshots, templates, naming conventions, tagging, and data hygiene practices across client accounts
• Lead technical discovery for new client onboarding and CRM migrations, including data mapping, cleansing, and cutover planning
• Review complex builds for scalability, reliability, and maintainability before launch
• Champion the integration of AI across the agency — from internal operations and reporting to CRM personalization, conversational AI, and workflow automation
• Evaluate, pilot, and roll out AI tools and LLM-powered solutions, with clear standards for data privacy, accuracy, and appropriate use
• Build and maintain internal automations and AI-assisted workflows that reduce manual effort and improve delivery quality
• Stay current on emerging AI and MarTech capabilities and proactively introduce relevant innovations to the agency and its clients
• Own the agency's data and measurement infrastructure, including conversion tracking, Google Tag Manager, GA4, server-side tracking, and offline conversion imports
• Partner with the Director of Digital Marketing to ensure lead source tracking, cost-per-lead reporting, and audience syndication between CRMs and ad platforms work reliably
• Build and maintain data pipelines and reporting infrastructure that feed client dashboards in Looker Studio, Power BI, or similar tools
• Establish data quality standards and monitoring across connected systems
• Serve as the senior technology authority in client strategy sessions, QBRs, and new business pitches — translating technical solutions into clear, business-outcome terms
• Contribute technology recommendations, solution architecture, and implementation estimates to agency proposals and RFP responses
• Partner with 321 AIM on shared clients and platform needs to ensure technology, data flows, and lead infrastructure are coordinated and mutually reinforcing
• Identify opportunities to productize repeatable technology solutions into new agency service offerings

Benefits

• 100% remote work environment
• Flexible scheduling with core collaboration hours
• Paid time off + agency-observed holidays
• Professional development and platform/tool access budget
• Collaborative, AI-forward team culture that values innovation and continuous learning
• Opportunity to build and lead the technology foundation of a high-growth agency operating at the intersection of performance marketing and marketing technology

What This Job Offers

• Job Type: Full-time
• Career Level: Director