AI Transformation Owner, Marketing

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. Retail is Toast's biggest bet and we are growing rapidly. The opportunity is massive, and the category is ours to define. You'll have the backing of Toast's scale, brand, and resources but you'll be on the team architecting how we operate, scale, and win.  The decisions you make in this role will shape how Toast competes in retail for years to come. Toast is prioritizing AI integration across the enterprise to redefine GTM velocity. As part of this strategy, multiple business units are pursuing specialized AI initiatives tailored to market challenges. This model balances corporate-wide coordination with vertical accountability: teams work in lockstep to scale efficiencies and aggregate impact, while remaining responsible for developing, building, and launching solutions optimized for unique operating environments. The GTM Sales Engineer & AI solutions is the core functional driver of this transformation within the Retail vertical. As an expert in applied AI, you will own the centralized deployment of AI applications to directly improve Productivity Per Rep (PPR). You will drive AI-powered productivity and automation across Retail sales, working with AEs and BDR/SDR teams to accelerate sales and with Onboarding to streamline the path to Customer Go-Live, with the opportunity to grow your impact across other GTM and client-facing teams as the vertical scales. You will be the operational linchpin running the Retail AI GTM Pod, architecting a continuous feedback loop sourcing grassroots ideas from the frontline, filtering them through a business lens, and scaling them into production tools. This is a technical, builder-focused role. You will observe decentralized AI applications working across the organization and partner to accelerate their impact, making them structurally better, integrating them into core systems, and maintaining them long-term. While you will partner with central corporate operations and marketing to advocate for Retail use cases and scale company-wide efficiencies, you will also possess the autonomous engineering capabilities to construct vertical-specific pipelines when distinct merchant workflows require it. This role sits in Revenue Operations, but will also dotted-line report into engineering. A day in the life (Responsibilities)  AI GTM POD GOVERNANCE & SOLUTION SOURCING * Leadership & Facilitation: Stand up the Retail AI GTM Pod to surface, qualify, and scale AI applications across the Retail field. The model could be a working group of AI-forward reps, managers, and leaders organized around defined themes in Sales & Onboarding, contributing domain expertise and frontline signals. The pod functions as an intake mechanism and sounding board, surfacing field experiments, pressure-testing priorities, and keeping your roadmap grounded in what moves the business. * Idea & Solution Sourcing: Serve as the production engine for ideas surfacing through the pod and field. Evaluate what is worth scaling, determine the right build, buy, or borrow path, and take the strongest ideas from experiment to production tool—launching with Enablement to non-technical end-users and maintaining active ownership through adoption tracking, feedback, and iteration. * Build vs. Buy Evaluation: Lead technical discovery to determine the most efficient path for problem statements, assessing whether to build a custom agentic solution, stitch existing APIs, or coordinate with vendors to purchase a scalable product. * Roadmap Prioritization: Translate decisions into a sprint-based roadmap, prioritizing developments based strictly on their potential to drive vertical PPR and eliminate administrative friction. APPLIED ENGINEERING & SYSTEMS INTEGRATION * Agile Sprint Execution: Maintain and execute against a technical scrum board, operating on defined sprint cycles to continuously ship, test, and iterate on AI-powered features. * Industrializing Frontline Wins: Take successful, unscaled local experiments (e.g., territory expansion scoring, contact discovery pipelines, multi-intent category parsers) and harden them with error handling, version control, scalable code, and secure coding practices like input validation, secrets management, and mitigation of LLM risks (e.g., prompt injection). * Systems Integration: Coordinate integration efforts to map vertical AI outputs into core GTM platforms (Salesforce, Snowflake, Taskray), ensuring local applications enhance rather than disrupt foundational enterprise pipelines. * Data Integrity Architecture: Build & monitor data validation frameworks ensuring model inputs are pristine and outputs are entirely auditable and trusted by the field. * Application Security: Design & enforce security controls for Retail AI applications, including authentication/authorization frameworks, secrets management, access controls on model outputs, and mitigations for LLM risks (prompt injection, data exfiltration). Ensure builds meet Toast's security standards given system proximity to payment and customer data workflows. CROSS-FUNCTIONAL PARTNERSHIP & STRATEGIC RADAR * Enterprise Collaboration: Contribute to cross-functional AI coordination cadences connecting Revenue Operations, Marketing AI, and Business Technology teams across Toast. Align on company-wide AI investments, advocate for Retail use cases and merchant requirements in shared roadmaps, and identify where central efforts can be leveraged, adapted, or extended. Serve as Retail's active voice in sequencing these shared initiatives while staying coordinated. * Vertical Personalization: Monitor central enterprise tool developments (e.g., prospecting or enablement agent suites) to identify opportunities to clone, customize, or extend for Retail merchant types. * Bidirectional Knowledge Exchange: Establish a pipeline for sharing locally developed code, architecture patterns, and prompt structures with central teams, ensuring Retail's breakthroughs help elevate Toast's engineering ecosystem. FLUENCY, ENABLEMENT & TRAINING LOOPS * AI Fluency Leadership: Design and execute vertical-wide enablement tracks to build a baseline of confident, independent AI tool usage across sales reps, onboarding consultants, and managers. * Adoption Analytics: Build & monitor adoption tracking mechanisms for deployed AI solutions, ensuring training translates into consistent field usage and measurable reductions in level of effort (LOE). What you'll need to thrive (Requirements) * Applied AI Deployment: 4+ years of experience in a technical, analytical, or GTM operations role, with a track record of owning the full deployment lifecycle of applied AI applications, RAG pipelines, or agentic workflows, including post-launch monitoring, alerting, rollback procedures, and model version management. * Modern AI Toolchain Literacy: Advanced, hands-on proficiency with developer-focused AI tools, specifically the Gemini Suite, Claude Cowork, and Claude Code. * Modern Deployment Stack: Experience deploying and operating AI backend systems in production (API services, model inference pipelines, orchestration layers), with demonstrated ownership through reliability, observability, and incident response. * Application Security Awareness: Familiarity with security best practices for AI-native systems, including authentication/authorization, secrets management, access controls on outputs, and awareness of LLM attack surfaces (prompt injection, data exfiltration). * Agile Operational Fluency: Experience operating within an agile engineering model, including managing technical product backlogs, running sprint cycles, and maintaining scrum boards. * Strategic Diplomacy: Exceptional communication skills with a proven ability to enter central enterprise forums, align stakeholders, advocate for vertical needs, and collaborate across business units. What will help you stand out (Nonessential Skills/Nice to Haves) * Software engineering or computer science background with the ability to write functional code (Python, JavaScript, or equivalent) and construct robust API integrations from scratch. * Direct domain familiarity with B2B SaaS and Retail tech spanning grocery, convenience, or wholesale commerce environments. * Experience building or scaling an AI program for non-technical end-users, including driving literacy, prompt engineering, or tool enablement. * Degree in Computer Science, Engineering, a related technical discipline, or equivalent practical experience as a technical founder or builder.   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. The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy. Zone A $172,000—$275,000 USD Zone B $150,000—$240,000 USD Zone C $135,000—$216,000 USD How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. To learn more: https://careers.toasttab.com/ai-in-hiring Our Approach to Hybrid Working We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

About Us At Cloudflare, we are on a mission to help build a better Internet. Today the company runs one of the world’s largest networks that powers millions of websites and other Internet properties for customers ranging from individual bloggers to SMBs to Fortune 500 companies. Cloudflare protects and accelerates any Internet application online without adding hardware, installing software, or changing a line of code. Internet properties powered by Cloudflare all have web traffic routed through its intelligent global network, which gets smarter with every request. As a result, they see significant improvement in performance and a decrease in spam and other attacks. Cloudflare was named to Entrepreneur Magazine’s Top Company Cultures list and ranked among the World’s Most Innovative Companies by Fast Company.  At Cloudflare, we’re not looking for people who wait for a polished roadmap; we’re looking for the builders who see the cracks in the Internet that everyone else has simply learned to live with. We value candidates who have the instinct to spot a "normalized" problem and the AI-native curiosity to create a solution using the latest tools. Our culture is built on iteration, leveraging AI to ship faster today to make it better tomorrow, while ensuring that every improvement, no matter how small, is shared across the team to lift everyone up. If you’re the type of person who values curiosity over bureaucracy, and that AI is a partner in solving tough problems to keep the Internet moving forward, you’ll fit right in. Available Locations * Remote US About the Role The Global GTM Strategy, Planning and Operations team at Cloudflare supports our high-growth Sales organization through scalable, AI supported GTM planning and operations. We focus on thoughtful planning of sales capacity, segmentation, territory carving, quota setting, and compensation design while ensuring clear rules of engagement for our Sales Team. Our goal is to establish a cohesive, consistent process framework that can support high growth, enable the Company's strategy, and accelerate Cloudflare's leadership in the developer and AI-native business segments. As the Senior Principal, Sales Compensation Design & Strategy, you will design and manage Cloudflare's Sales Compensation Plans across all customer facing teams including Sales, Technical Sales, Partner Sales, and Customer Success & Experience, to ensure they are motivating, aligned with Cloudflare's strategy, and industry leading. This is a high visibility role with significant executive engagement, including leading C-level discussions with our CRO, CFO, CPO, and COO, and serving as the design authority on the Executive Compensation Steering Committee. You will architect new compensation metrics that reflect how Cloudflare monetizes a developer first, AI supportive business - including consumption, adoption, and platform attach - and ensure roles, territories, and quotas align with compensation plans to achieve our GTM objectives. You will establish a governance framework for efficient compensation planning and partner closely with the Compensation Administration and Operations Teams to ensure effective implementation and accurate payouts. A strong understanding of SaaS bookings, monetization approaches, and consumption and adoption models is essential. The scope of executive influence, the architectural work required to support our developer/AI business model, and the AI-native transformation of the compensation design function make this seat fundamental to our GTM execution strategy.  Responsibilities Executive Leadership & Design Authority * Lead the Sales Compensation Design Process with the Executive Steering Committee, including CRO, CFO, and CPO level stakeholders. * Drive C-level discussions on compensation philosophy, pay-for-performance outcomes, and strategic trade-offs; develop recommendation decks and own the narrative through approval. * Architect new metrics that align seller incentives with Cloudflare's developer platform and AI product strategy (e.g., Workers consumption, AI Gateway adoption, platform attach, multi-product penetration). * Create a 3-year roadmap for the Sales Compensation Design function. AI-Native Compensation Design * Build the AI Compensation Design Framework and Application - an internal capability that uses AI to accelerate plan modeling, scenario simulation, payout forecasting, and what-if analysis across thousands of sellers and territories. * Leverage AI to design high-quality SPIFFs and incentive structures, including generating candidate designs, simulating seller behavior, and stress-testing against historical data before launch. * Track ROI of comp plans, SPIFFs, and incentive programs using AI-driven analytics - moving from lagging reporting to predictive measurement of plan effectiveness, seller behavior change, and revenue lift. * Develop AI-powered pay-for-performance reporting that surfaces insights for executives, managers, and sellers in real time, replacing static quarterly reviews with continuous intelligence. Cross-Functional Execution * Collaborate with GTM Strategy, Operations, Finance, HR, IT, and Product to ensure effective deployment of compensation plans and GTM strategy. * Lead compensation enablement and change management for the global Sales team, including AI-assisted communications, FAQ generation, and plan-acceptance workflows. * Design SPIFFs and incentive strategies that balance long-term strategic bets with short-term revenue goals. * Partner with the Compensation Administration and Operations Teams to ensure design intent translates into accurate, auditable payouts. Required Experience & Skills * 15+ years of experience in Sales Compensation Design in a fast-paced tech company or as a management consultant. * Demonstrated fluency with AI tools and AI-augmented workflows - whether through prior comp design work, analytics, or strategic projects. Comfort building or directing the build of AI-powered internal applications is strongly preferred. * Strong analytical skills, including the ability to architect new metrics for emerging business models (consumption, AI monetization). * Exceptional presentation and communication skills, with proven experience presenting to and influencing C-level executives. * Proven experience driving Executive Steering Committee meetings and owning the decision narrative end-to-end. * Experience leading cross-functional initiatives to completion across Finance, HR, IT, Product, and GTM. * Detail-oriented with a strategic mindset. * Bachelor's degree required. Bonus Points The ideal candidate combines a strong background in sales strategy and compensation design with genuine curiosity about applying AI to transform the function. Candidates will have exceptional stakeholder management skills, executive presence, and the confidence to manage evolving strategies in a high-growth company.  Compensation Compensation may be adjusted depending on work location. ● For New York City and Washington based hires: Estimated annual salary of $220,000 - $303,000 ● For Colorado based hires: Estimated annual salary of $200,000 - $275,000 ● For San Francisco Bay Area based hires: Estimated annual salary of $230,000 - $317,000 What Makes Cloudflare Special? We’re not just a highly ambitious, large-scale technology company. We’re a highly ambitious, large-scale technology company with a soul. Fundamental to our mission to help build a better Internet is protecting the free and open Internet. Project Galileo: Since 2014, we've equipped more than 2,400 journalism and civil society organizations in 111 countries with powerful tools to defend themselves against attacks that would otherwise censor their work, technology already used by Cloudflare’s enterprise customers--at no cost. Athenian Project: In 2017, we created the Athenian Project to ensure that state and local governments have the highest level of protection and reliability for free, so that their constituents have access to election information and voter registration. Since the project, we've provided services to more than 425 local government election websites in 33 states. 1.1.1.1: We released 1.1.1.1 to help fix the foundation of the Internet by building a faster, more secure and privacy-centric public DNS resolver. This is available publicly for everyone to use - it is the first consumer-focused service Cloudflare has ever released. Here’s the deal - we don’t store client IP addresses never, ever. We will continue to abide by our privacy commitment and ensure that no user data is sold to advertisers or used to target consumers. Sound like something you’d like to be a part of? We’d love to hear from you! Please note that applicants who progress to the offer stage of the interview process may be asked to attend an in-person interview within one of the Cloudflare Offices or Cloudflare Hubs.  More details about this will be available at that stage of the interview process. This position may require access to information protected under U.S. export control laws, including the U.S. Export Administration Regulations. Please note that any offer of employment may be conditioned on your authorization to receive software or technology controlled under these U.S. export laws without sponsorship for an export license. Cloudflare is proud to be an equal opportunity employer.  We are committed to providing equal employment opportunity for all people and place great value in both diversity and inclusiveness.  All qualified applicants will be considered for employment without regard to their, or any other person's, perceived or actual race, color, religion, sex, gender, gender identity, gender expression, sexual orientation, national origin, ancestry, citizenship, age, physical or mental disability, medical condition, family care status, or any other basis protected by law. We are an AA/Veterans/Disabled Employer. Cloudflare provides reasonable accommodations to qualified individuals with disabilities.  Please tell us if you require a reasonable accommodation to apply for a job. Examples of reasonable accommodations include, but are not limited to, changing the application process, providing documents in an alternate format, using a sign language interpreter, or using specialized equipment.  If you require a reasonable accommodation to apply for a job, please contact us via e-mail at hr@cloudflare.com or via mail at 101 Townsend St. San Francisco, CA 94107.