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