Chief Technology Officer

ABOUT 321 THE AGENCY

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.

ABOUT THE ROLE

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.

WHAT YOU'LL DO

Executive Leadership & Technology Vision

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

Technology Organization & Talent

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

Proprietary Platforms & Product Strategy

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

AI Strategy & Innovation

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

Enterprise Architecture, Security & Risk

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

Data Strategy & Measurement

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

Client, Partner & Agency Growth

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

WHAT YOU HAVE

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

REPORTING STRUCTURE

The Chief Technology Officer reports directly to the CEO and is a member of the agency's executive leadership team. This role leads the full technology organization, including the Director of Technology and teams spanning CRM/MarTech, integrations, data,