Chief Technology Officer

321 the Agency • Orlando, FL

4d • 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 is central to how 321 competes and grows. From our CRM and automation programs to 321 AIM, our proprietary performance marketing platform, the systems we build are a core part of the value we deliver. The Chief Technology Officer is the executive who sets the vision for that technology and turns it into a lasting competitive advantage. As Chief Technology Officer at 321, you will own the agency's technology vision, strategy, and execution at the executive level. This is a C-suite role with company-wide authority — you'll shape how 321 builds, buys, secures, and monetizes technology, lead the technology organization, and help define the agency's direction as a member of the executive leadership team. The right person for this role thinks in platforms and business models, not just systems. You understand that the right architecture decisions compound over years, that proprietary technology and data can become defensible products, and that AI is reshaping what an agency can deliver and how it should be priced. You're as comfortable advising on a High Level or Salesforce architecture as you are presenting a multi-year technology strategy to ownership, investors, or enterprise clients — and you build the organization that executes it. You'll provide executive technology leadership in partnership with 321 AIM, guiding platform architecture, scalability, and roadmap decisions so that our proprietary technology and client service delivery grow together.

Requirements

• 12+ years of experience in technology leadership, with demonstrated depth in MarTech, CRM architecture, data infrastructure, and platform or product development — agency, MarTech, or SaaS experience strongly preferred
• At least 5 years in an executive or senior technology leadership role (CTO, VP of Technology or Engineering, or Director overseeing multiple teams), including building and scaling technology organizations
• Proven track record of setting technology strategy and delivering measurable business results, including revenue growth, margin improvement, or new product lines
• Experience leading the development of proprietary platforms or software products, from architecture and roadmap through launch and scale
• Deep understanding of CRM and marketing automation ecosystems — High Level strongly preferred; Salesforce, Salesforce Marketing Cloud, and HubSpot also valued
• Strong command of enterprise architecture, cloud infrastructure (AWS, Google Cloud, or Azure), APIs, integrations, and data platforms
• Experience leading security and compliance programs in regulated industries, including HIPAA; SOC 2 or similar framework experience strongly preferred
• Demonstrated leadership in AI strategy and adoption, including LLM-powered products or workflows, with sound judgment on governance and responsible use
• Experience owning technology budgets, vendor strategy, and build-versus-buy decisions
• Executive-level communication skills — able to present technology strategy to ownership, investors, boards, and enterprise clients with clarity and credibility
• Comfort operating in a fast-growing, remote, multi-client environment with competing priorities
• Bachelor's degree in Computer Science, Engineering, Information Systems, or a related field — or equivalent demonstrated experience; advanced degree a plus

Responsibilities

• Define and own the agency's multi-year technology vision and strategy, aligned with company growth goals, service offerings, and market positioning
• Serve as a member of the executive leadership team, contributing to company strategy, annual planning, and major business decisions
• Own the technology budget, including platform, licensing, infrastructure, and headcount investments, with clear return-on-investment expectations
• Lead build-versus-buy-versus-partner decisions for major platforms and capabilities
• Report on technology performance, risk, and investment outcomes to ownership and, where applicable, investors or a board
• Build, lead, and scale the technology organization, including the Director of Technology and teams spanning CRM/MarTech, integrations, data, AI, and systems administration
• Design the organizational structure, leadership roles, and hiring plan needed to support the agency's growth
• Set the culture, engineering standards, and operating principles for how technology is built, shipped, and supported across the agency
• Develop leaders within the technology organization through coaching, succession planning, and clear career paths
• Provide executive technology leadership for 321 AIM in partnership with its leadership, guiding platform architecture, scalability, reliability, and roadmap priorities
• Identify opportunities to turn repeatable agency solutions, data assets, and automations into proprietary products, platforms, or productized services
• Oversee product development practices, including requirements, release management, quality assurance, and technical documentation
• Protect and grow the agency's technology intellectual property
• Set the company-wide AI strategy, positioning 321 as a leader in AI-powered marketing, CRM, and performance services
• Govern responsible AI use, including data privacy, model selection, accuracy standards, and client disclosure practices
• Lead the evaluation and adoption of emerging technologies that create new service lines, improve margins, or strengthen client outcomes
• Partner with department leaders to embed AI into creative, paid media, CRM, reporting, and agency operations
• Own the agency's enterprise architecture across internal systems, client platforms, data infrastructure, and integrations
• Lead the information security program, including policies, access management, vendor risk, incident response, and business continuity
• Ensure agency and client technology meets regulatory and contractual requirements in healthcare, insurance, legal, and other regulated industries, including HIPAA, business associate agreements, TCPA, GDPR, and CCPA
• Guide the agency toward formal security and compliance frameworks such as SOC 2 as client and growth needs require
• Define the agency's data strategy, including how client, campaign, and performance data is collected, governed, stored, and used
• Oversee the measurement and attribution infrastructure that connects marketing activity to closed revenue for clients
• Build the data foundation needed to support performance-based pricing, benchmarking, and predictive insights across the client portfolio
• Serve as the agency's senior technology executive with clients, partners, and prospects — including CMO, CIO, and ownership-level audiences
• Lead the technology narrative in new business pitches, RFP responses, and strategic client relationships
• Build and manage strategic technology partnerships with platforms such as High Level, Salesforce, HubSpot, Google, and Meta
• Lead technical due diligence for partnerships, acquisitions, or major client engagements as the agency grows

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 shape the technology strategy and proprietary platforms 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: Executive