Director, Marketing AI Transformation

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

We are seeking a transformation leader to drive AI adoption and workflow redesign across Toast's 200+ person Marketing organization. This role will be instrumental in turning AI capability into AI fluency by leading the change management, governance, and enablement programs that make adoption real, measurable, and durable. You will be the central point of expertise for how marketing teams integrate AI into their daily work, partnering with our GTM Engineering team (which builds the tools and workflows) and marketing leaders (who own the strategy and outcomes). This role focuses on the human side of the transformation: how teams learn, how workflows change, how adoption is measured, and how culture shifts.

A day in the life (Responsibilities) 

Develop and Execute AI Transformation Strategy:

• 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.

Drive Change Management and Adoption:

• 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.

Build AI Governance Frameworks:

• 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.

Design Workflow Transformation:

• 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.

Operationalize the AI Champions Network:

• 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.

Measure and Report on Transformation Progress:

• 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.

Cross-Functional Collaboration:

• 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

What you'll need to thrive (Requirements)

• 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.

Nice to haves

• 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.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.

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