Sales Leader - Digital Native

LlamaIndex

$130K — $180K *
Enterprise Technology
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in sales, with 3+ in sales management and a proven track record of team quota attainment.
  • Experience in managing full-cycle Account Executives across high-velocity and complex enterprise sales.
  • Background in building pipeline from scratch rather than inheriting it.
  • Strong experience selling technical software to engineering and technical buyers, especially in AI or data infrastructure.
  • Fluency in deal qualification frameworks like MEDDIC, with a focus on coaching reps effectively.
  • Startup experience in high-growth environments, building systems rather than inheriting existing ones.
  • Proficiency in using AI tools for sales processes and pipeline management.

Responsibilities

  • Own pipeline generation, forecast accuracy, and revenue targets across Digital Native and mid-market teams.
  • Hire, onboard, and develop a team of Account Executives and BDRs, prioritizing recruitment and ramp-up.
  • Conduct structured deal reviews, providing coaching on discovery, qualification, and closing techniques.
  • Establish a robust pipeline strategy on a product-led foundation, utilizing product signals for outreach.
  • Lead weekly operational meetings such as pipeline reviews and forecast discussions.
  • Create a framework for team leads to mentor and assist in managing key deals as growth occurs.
  • Engage in complex live deals to resolve obstacles and improve close rates.
  • Deliver structured feedback to influence product roadmap and go-to-market strategies.
  • Represent the company at industry events to enhance visibility in the developer and AI sectors.

Benefits

  • Collaborative team environment focused on professional development.
  • Exposure to cutting-edge technology and potential for career advancement.
  • Opportunity to shape the sales strategy of a growing company in the AI space.
  • Access to AI tools for improving sales efficiency and effectiveness.
Full Job Description
About the Role

We are seeking a Senior Director to build and lead the team driving our Digital Native revenue motion. You will lead a team of Account Executives and BDRs selling into high-growth and AI-native companies across both an enterprise and a mid-market segment, while owning pipeline generation, deal execution, and team development.

This is a builder role. You inherit a small existing team and are immediately tasked with scaling it as we grow. You will set the operating rhythm, raise the performance bar, and build the systems that turn individual reps into a repeatable revenue engine. The scope of the role expands as the team and the business grow.

Responsibilities
  • Own pipeline generation, forecast accuracy, and revenue attainment across the Digital Native and mid-market teams.
  • Hire, onboard, and develop a growing team of Account Executives and BDRs. Recruiting and ramp are core to this role.
  • Run structured deal reviews, coaching reps through discovery, qualification, and close.
  • Build and drive a consistent pipeline motion on a product-led (PLG) foundation, using product-usage and self-serve signals, inbound, and targeted outbound alongside clear ICP segmentation.
  • Lead a weekly operating cadence: pipeline reviews, 1:1s, call coaching, and forecast calls.
  • Develop a team-lead framework so strong individual contributors can mentor and co-run key deals as the team scales.
  • Step into complex live deals to unstick opportunities and improve close rates.
  • Provide structured market and customer feedback to influence product roadmap and GTM strategy.
  • Represent the company at industry events and help build our presence in the developer and AI community.

Required Qualifications
  • 8+ years in sales, with 3+ years in frontline sales management and a track record of team quota attainment.
  • Proven experience managing full-cycle AEs across both high-velocity and more complex enterprise cycles.
  • Demonstrated success building pipeline from scratch, not inheriting it.
  • Experience selling technical software to engineering and technical buyers (AI, developer tools, or data infrastructure), ideally with a product-led growth motion.
  • Fluency in a deal qualification framework (MEDDIC or equivalent) and the ability to coach reps to apply it consistently.
  • Startup experience 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: you actively use 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 an outbound motion alongside a PLG or self-serve motion at a developer-first company.
  • A track record of converting product-led and community signal into pipeline.
  • Experience ramping new AEs to productivity within 60 to 90 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.

Location

San Francisco, CA.

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