Sales Leader - Digital Native

Sales Leader Opportunity

Join us and help shape the future of AI by defining the narrative around document understanding.

About the Role

We are seeking a Sales Leader to build and lead the team driving our Digital Native revenue motion. In this role, you will player-coach a team of Account Executives and BDRs selling LlamaIndex into high-growth companies, while owning pipeline generation, deal execution, and team development. You will set the operating rhythm, raise the performance bar, and build the systems that turn individual reps into a repeatable revenue engine.

Responsibilities

• Hire, onboard, and develop a team of 6+ mid-market AEs and 3+ BDRs.
• Own team pipeline targets, forecast accuracy, and ARR attainment.
• Run structured deal reviews, coaching reps through discovery, qualification, and close.
• Build and drive a consistent outbound engine leveraging OSS community signals, ICP segmentation, and BDR-AE coordination.
• Lead a weekly operating cadence: pipeline reviews, 1:1s, call coaching, and forecast calls.
• Jump into live deals as a player-coach to unstick opportunities and improve close rates.
• Partner with product and engineering to translate technical differentiation into rep-ready messaging.
• Provide structured market and customer feedback to influence product roadmap and GTM strategy.
• Represent LlamaIndex at industry events and help build our presence in the developer and AI community.

Required Qualifications

• 610 years in sales; 24 years in frontline sales management with a track record of team quota attainment.
• Proven experience managing full-cycle, mid-market AEs.
• Demonstrated success building pipeline from scratch not inheriting it.
• Experience selling technical SaaS products to engineering and technical buyers (AI, developer tools, data infrastructure, or OSS strongly preferred).
• Fluency in deal qualification frameworks (MEDDIC or equivalent) and ability to coach reps to apply them consistently.
• Startup experience: Success operating in high-growth, resource-constrained environments where you built systems rather than inherited them.
• Strong coaching instincts you improve reps through specific behavior change, not motivation.
• AI-first operator: actively uses AI tools for pipeline inspection, account research, call prep, and rep coaching and can teach your team to do the same.

Preferred Qualifications

• Experience building or scaling outbound motion alongside inbound at a developer-first company.
• Familiarity with OSS-led or community-led growth and how to convert it into pipeline.
• Track record of ramping new AEs to productivity within 6090 days.
• Knowledge of technical POC cycles and how to coach reps through build-vs-buy conversations.
• Experience hiring and developing BDRs as a pipeline source.

Why Join Us?

• Impactful Mission: Help companies adopt AI to unlock the value of their unstructured data.
• Collaborative Team: Join a team of experts driving the future of AI.
• Strong AI Brand: Leverage one of the largest open-source AI frameworks and communities, giving us brand recognition in the AI space greater than nearly any company our size.
• Growth Opportunities: Build and own the mid-market motion from the ground up as we scale at the frontier of enterprise AI.

Location: San Francisco, CA.

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

LlamaIndex does not accept unsolicited agency resumes. Please do not forward resumes to our jobs alias, employees, or any other organization location. LlamaIndex is not responsible for any fees related to unsolicited resumes.