Demo

Sales Leader - Digital Native at LlamaIndex

Jack & Jill
San Francisco, CA Full Time
POSTED ON 6/21/2026
AVAILABLE BEFORE 7/20/2026
This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Sales Leader - Digital Native

Salary

Not Disclosed

Company Description

LlamaIndex is the leading data framework for building LLM applications, empowering developers to connect custom data sources to large language models. Based in San Francisco, the company is at the forefront of the generative AI revolution, providing essential infrastructure for the next generation of intelligent software.

Job Description

As the Sales Leader for Digital Natives, you will build and scale a high-performing revenue engine at LlamaIndex. You’ll lead a team of mid-market AEs and BDRs, driving outbound strategy and deal execution. This is a player-coach role requiring technical fluency to convert community signals into ARR within the fast-moving AI ecosystem.

Location

San Francisco, USA

Why this role is remarkable

  • Shape the commercial strategy for the industry-standard data framework for LLMs, sitting at the intersection of open-source community and enterprise AI.
  • Join a high-growth startup where you have the autonomy to build sales systems from scratch rather than inheriting legacy processes.
  • Lead a team selling to technical founders and engineering leaders at the world's most innovative high-growth digital native companies.

What You Will Do

  • Hire, onboard, and manage a team of 6 mid-market Account Executives and 3 BDRs to achieve aggressive ARR attainment goals.
  • Architect a consistent outbound engine that leverages open-source community signals and ICP segmentation to drive high-quality pipeline.
  • Directly participate in live deals to coach reps through discovery, qualification using MEDDIC, and complex technical build-vs-buy conversations.

The ideal candidate

  • Possesses 6–10 years of total sales experience, with 2–4 years specifically in frontline management leading mid-market AE teams to quota.
  • Demonstrates deep expertise selling technical products to engineering buyers, ideally within AI, developer tools, or data infrastructure domains.
  • Proven ability to build pipeline and sales systems from the ground up in a resource-constrained, high-velocity startup environment.

Who are Jack & Jill?

Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

How does this work?

  • Jack's an AI agent for job searching and career coaching. He works for you.
  • Jill is the AI recruiter working for the company. She recruits from Jack's network.
  • If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.

Salary.com Estimation for Sales Leader - Digital Native at LlamaIndex in San Francisco, CA
$96,762 to $134,740
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