Proven track record of building and scaling sales organizations Deeply data-driven and detail-oriented Experience designing sales processes, playbooks, and operating models from the ground up Comfortable in strategy conversations and live deals Understand GTM across multiple channels and buyer types Skilled at coaching, training, and elevating sales talent Respected as both a leader and a partner Thrive in fast-moving, ambiguous environments Scrappy, resourceful, and execution-focused What Great Looks Like in This Role A clear, repeatable, and scalable sales process exists across the organization The pipeline is healthy, predictable, and aligned to revenue goals Sales velocity, conversion, and deal quality improve consistently The sales team is coached, confident, and accountable Marketing and Sales operate as true partners Product and other teams have strong feedback loops from the market Revenue becomes a function of system strength, not individual heroics Why This Role Matters This is a defining role in building Chegg Skills' growth engine. This is a strategic, operational, and hands-on leader who can design systems, drive performance, coach teams, and close meaningful deals while navigating ambiguity.