AI Deployment Lead

About the company:

Rippling gives businesses one place to run HR, IT, Finance, and global employment. It brings together workforce systems that are normally scattered across a company—like payroll, expenses, benefits, and computers—so businesses can manage and automate every part of the employee lifecycle in a single system, anywhere in the world.

That unified platform provides a powerful foundation for putting AI to work. By connecting live business data, organizational context, and built-in permissions, Rippling AI can answer complex questions and take action across systems while respecting each user’s access and required approvals. Rippling Data Cloud extends this foundation to third-party business data, enabling customers to build AI workflows across their operations. Customers are embracing this approach: Rippling AI generated more ARR in its first two months than any previous Rippling product launch, with revenue growing 121% from July to September.

Based in San Francisco, CA, Rippling has raised $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @Rippling.com addresses.

About the role:

Rippling is standing up a new business line: Rippling AI Solutions. This covers everything from (1) custom applications and AI point solutions sold through Sales (“Build”) to (2) a full turnkey AI consulting and implementation service (“Transform”). We cover the full spectrum, with a focus on G&A and other non R&D orgs.

We will help customers identify, design, build, and ship production AI workflows, while also supporting adoption and change management within the org to tie automations to ROI. We will be an AI thought partner to our customers - though Rippling will be a central part of all solutions we implement, we are model agnostic and insert other 3P AI tools around Rippling as needed.

The ultimate vision is to scale AI Solutions into a large product line that is central to Rippling’s AI strategy of delivering value to its customers and being their “go to” for their AI needs. 

This is a founding role on the AI Solutions team. We are hiring our first AI Deployment Lead to own customer engagements end to end, from discovery through measurable impact. This role combines (1) an AI Transformation Lead, who identifies high-value opportunities, shapes them into a transformation roadmap, owns the client relationship, and drives adoption; and (2) a Forward Deployed Product Manager, who translates customer workflows into product requirements and ships solutions in partnership with our team of Forward Deployed Engineers (FDEs). You will report to the General Manager of AI Solutions and work closely with FDE, Product, and Sales.

What you will do:

1. Own the customer relationship

• Serve as the customer’s day-to-day lead from kickoff through value realization, working with executive sponsors, operators, and end users.
• Align the GM, Sales, FDEs, and the customer on scope, success criteria, and the path to launch.
• Run the operating cadence for each engagement, including status updates, steering committees, risks, decisions, and executive readouts.

2. Run the AI diagnostic and create the AI transformation roadmap

• Diagnose customer workflows and identify the highest-value opportunities for AI-driven operating leverage.
• Create a sequenced, quantified and prioritized AI Transformation Roadmap with baselines, target KPIs, and clear success measures.
• Bring a practical point of view on where Rippling, third-party AI tools, and custom workflows can create the most value.

3. Define and ship AI workflows with FDEs

• In partnership with FDE, translate customer workflows into MVP definitions, requirements, acceptance criteria, and evaluation criteria.
• Product manage the implementation with FDE, from scoping through testing, launch, and iteration.
• Pressure-test solution design with FDE across architecture, integrations, data access, permissions, and edge cases.

4. Drive adoption, ROI, and repeatability

• Lead training, workflow redesign, and change management so shipped workflows are adopted and trusted.
• Measure realized value against the baseline and turn results into case studies, references, and expansion opportunities.
• Codify repeatable patterns into playbooks, templates, ROI models, and product feedback.

5. Build the AI Solutions motion with the GM

• Help refine the nascent AI Solutions playbook across discovery, scoping, delivery, adoption, ROI measurement, and expansion.
• As a founding member of the team, help turn early engagements into a repeatable motion that can scale across customers and future AI Deployment Leads.
• Partner with the GM and FDE leadership on engagement health, staffing needs, delivery capacity, and how the motion should evolve as it scales.

What you will have:

• You have 5 to 10 years of experience as a commercially minded product manager, technically minded consultant, deployment lead, solutions lead, implementation lead, or similar operator in a high-growth environment.
• You have led complex, cross-functional programs from ambiguous problem framing through production launch, adoption, and measurable impact.
• You can communicate clearly with C-level sponsors, operators, end users, product leaders, and engineers.
• You have AI fluency, including enough depth in LLMs, agents, retrieval, evaluations, data, APIs, and integrations to scope solutions, write precise requirements, and earn the trust of technical teams.
• You think in ROI: you can map a workflow, understand where time and money go, quantify the value of changing it, and build a credible business case.
• You are comfortable in zero-to-one environments, where a playbook may not exist and will need to be defined. 
• You are highly customer-facing, structured, and pragmatic, with the judgment to balance ambition, feasibility, and speed.
• You build with AI yourself, through side projects, prototypes, automations, or practical experimentation, and can explain what worked, what failed, and why.

Bonus points:

• Experience at a forward-deployed, applied AI, or technical services organization.
• Experience in HCM, payroll, ERP, finance systems, or G&A workflows.
• Experience serving executive buyers and mid-market customers.
• Ability to prototype or write light code, especially in Python or SQL.
• Experience hiring, coaching, or building a delivery team.
• Founder, early-stage operator, or other entrepreneurial experience.

Additional Information:

Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable accommodation, please email accommodations@rippling.com

Rippling highly values having employees working in-office to foster a collaborative work environment and company culture. For office-based employees (employees who live within a defined radius of a Rippling office), Rippling considers working in the office, at least three days a week under current policy, to be an essential function of the employee's role.

This role will receive a competitive salary + benefits + equity. The salary for US-based employees will be aligned with one of the ranges below based on location; see which tier applies to your location here.

A variety of factors are considered when determining someone’s compensation–including a candidate’s professional background, experience, and location. Final offer amounts may vary from the amounts listed below.