Head of Data Cloud & AI Sales

Rippling (Netherlands); New York (NY); On-site; USD 180,000 - 260,000; Full time

Job summary

Rippling is seeking a pragmatic, strategic sales leader to head Sales for Rippling’s Data Cloud business. You will lead a team of Account Executives and Managers selling into SMB, Mid-Market, and Enterprise segments, guiding revenue generation and shaping the go-to-market motion.

You will mentor reps, build repeatable playbooks, and partner with Product, Data, Sales Engineering, Marketing, RevOps and Enablement to drive data-driven outcomes, forecasting, and faster decision-making.

Qualifications

• 7+ years of B2B SaaS sales experience, with 3+ years managing quota-carrying sales teams.
• Experience selling or leading teams in data, analytics, 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.

Responsibilities

• 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.

Skills

B2B SaaS sales

Quota-carrying leadership

Data analytics

AI and analytics fluency

Platform selling

Forecasting in Salesforce

Team management

Tools

Salesforce

Job description

Rippling is seeking a pragmatic, strategic sales leader to head Sales for Rippling’s Data Cloud business. You will lead a team of Account Executives and Managers selling into SMB, Mid-Market, and Enterprise segments, guiding revenue generation and shaping the go-to-market motion.

You will mentor reps, build repeatable playbooks, and partner with Product, Data, Sales Engineering, Marketing, RevOps and Enablement to drive data-driven outcomes, forecasting, and faster decision-making.