[Remote] Director, Marketing AI Transformation

Note: The job is a remote job and is open to candidates in USA. Toast creates technology to help restaurants and local businesses succeed in a digital world. They are seeking a transformation leader to drive AI adoption and workflow redesign across their Marketing organization, focusing on integrating AI into daily work and fostering a culture that embraces this change.

Responsibilities

• Define and implement a comprehensive AI transformation roadmap aligned with marketing leadership's strategic direction and overall business objectives
• Translate strategic bets into sequenced adoption plans that account for team readiness, tool maturity, and infrastructure dependencies
• Identify and prioritize the workflows where AI creates the most leverage and build the playbook for redesigning them
• Build and run programs that drive sustained AI adoption, including practical enablement resources, scalable training programs, and change management approaches that meet teams where they are
• Own the metrics that distinguish real adoption from performative adoption, tracking workflow changes and behavior shifts rather than training completion rates alone
• Champion a culture where marketers see AI as a tool for creativity and efficiency rather than a disruption to manage
• Design and implement the standards, review processes, and decision frameworks that let teams move fast while maintaining brand consistency, quality, and compliance
• Establish how AI generated content gets reviewed before it ships, how parallel agent builds get evaluated and consolidated, and how we define quality when AI is generating at volume
• Navigate the tension between speed and standardization, building systems that enable both
• Partner with marketing leaders to break roles down into workflows and identify which should be automated, redesigned, or augmented with AI
• Build transition plans that move teams from current state to AI augmented operations
• Serve as the bridge between what gets built by the GTM engineering team and what gets adopted by marketing teams
• Recruit, onboard, and support 1 to 2 Champions per marketing team who serve as local AI resources and early adopters
• Give Champions a platform (dedicated Slack channels, demo slots, direct line to the GTM engineering team) and use them as a feedback loop for what is working and what is not
• Scale peer to peer knowledge sharing as the primary mechanism for broad adoption
• Build the measurement framework for AI transformation: adoption rates, workflow efficiency gains, time savings, and output quality
• Design executive facing dashboards that give leadership honest, clear visibility into where AI is delivering value and where it is not
• Partner with HR to factor AI proficiency into performance expectations
• Partner with the GTM Engineering team to receive validated use cases and ensure smooth handoff from build to adoption
• Coordinate with R&D/BTT on foundational data dependencies
• Partner with Sales Operations on Sales-led GTM AI initiatives to ensure we are aligned

Skills

• 8+ years in marketing operations, marketing strategy, or marketing transformation, with experience leading change management or organizational transformation programs at scale
• Demonstrated experience embedding emerging technology (AI or otherwise) into marketing workflows across a large organization (200+ person marketing team preferred)
• Deep understanding of how marketing teams actually work: campaign operations, content production, demand generation, brand, analytics. You know where AI creates genuine leverage versus where it creates noise
• Track record of building programs that drive measurable, sustained behavior change, not just awareness or training completion rates, but actual workflow adoption
• Experience designing governance frameworks for new capabilities at scale
• Strong communication and presentation skills with the ability to present transformation progress to senior leadership with clarity and honesty, including when things are not working
• Comfort with ambiguity. This is a role where the playbook is still being written
• Experience at a company that has gone through a similar AI transformation within marketing
• Familiarity with the B2B SaaS marketing tech stack (MAPs, CRMs, ad platforms, data visualization platforms, etc.) and how AI tools connect to it
• Experience with AI specific tooling ecosystems: Claude/Anthropic, Gemini, agent frameworks, MCP integrations

Benefits

• Cash compensation (overtime, bonus/commissions if eligible)
• Equity
• Benefits
• Hybrid work model that fosters in-person collaboration while valuing individual needs
• Reasonable accommodations for persons with disabilities to enable them to access the hiring process

Company Overview

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