Director of Sales, AI & Data Cloud

About the role We are looking for a pragmatic, strategic, and technically fluent sales leader to lead Sales for Rippling’s Data Cloud business. Rippling Data Cloud is a foundational part of Rippling’s compound platform, helping companies bring workforce, HR, IT, finance, and operational data together in a unified model that can power reporting, analytics, automation, and AI-native workflows. Instead of forcing teams to reconcile fragmented data across disconnected systems, Rippling Data Cloud gives businesses a trusted way to access, understand, and act on their employee and business data from a single platform. This role is responsible for leading a team of Account Executives & Managers selling Rippling’s Data Cloud products into new customers across SMB, Mid-Market, and Ent segments. The ideal candidate has experience leading high-performing SaaS sales teams in a fast-paced environment, with strong fluency in data, analytics, automation, AI, and platform-oriented selling. This person should be equally comfortable driving operational rigor, coaching technical discovery, improving win rates, inspecting pipeline, and building a repeatable sales motion in a high-growth business. What you will do Lead and scale a high-performing sales team focused on Rippling Data Cloud Own revenue execution across pipeline generation, discovery, technical demos, deal strategy, forecasting, and close Hire, coach, and develop Account Executives and managers who can manage complex sales cycles while navigating technical, analytical, and strategic buying processes Build strong operating rhythms around pipeline inspection, forecast accuracy, deal reviews, rep coaching, and productivity Partner closely with Product, Data, Sales Engineering, Marketing, SDR, RevOps, Enablement, and leadership to ensure the business is delivering against its most important outcomes Develop and reinforce strong positioning for Data Cloud as a platform for unified workforce data, analytics, reporting, automation, and AI-driven decision-making Coach teams on how to connect technical product capabilities to executive-level business outcomes, including data accuracy, operational visibility, workflow automation, and faster decision-making Identify gaps in the sales motion and build repeatable playbooks, talk tracks, enablement, and processes to improve execution Use data to manage key performance metrics across pipeline creation, stage conversion, win rate, sales cycle, ACV, sales efficiency, and quota attainment Build strong cross-functional feedback loops to help Product and GTM teams understand buyer needs, competitive dynamics, packaging opportunities, and repeatable use cases Operate with an entrepreneurial mindset, solving problems cross-functionally and moving quickly as the business scales What you will need 7+ years of B2B SaaS sales experience, with 3+ years managing quota-carrying sales teams Experience selling or leading teams in data, analytics, business intelligence, automation, AI, platform, infrastructure, or complex SaaS products preferred Experience managing managers preferred, or demonstrated ability to scale beyond first-line leadership Proven track record of building teams that consistently meet or exceed quota Ability to coach reps and managers through technical discovery, data-centric use cases, competitive positioning, business case development, and multi-stakeholder sales cycles Strong analytical skills and comfort using data to diagnose performance gaps, improve conversion, and drive sales efficiency Excellent forecast discipline and experience managing pipeline in Salesforce Highly effective communicator with strong executive presence and the ability to build trust across Sales, Product, Data, Marketing, RevOps, Enablement, and leadership Ability to translate technical product capabilities into clear business value for executive, operations, finance, HR, IT, and data stakeholders Hands-on operating style with the ability to inspect details, build process, and move quickly in an ambiguous environment High ownership, strong follow-through, and the courage to challenge the status quo when logic and reason require it Low ego, high integrity, and genuine enthusiasm for building a category-defining company About Rippling Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system. Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365—all within 90 seconds. 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 @ addresses.