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Oscar

Head of Sales (Founding GTM)

Oscar, San Francisco

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Head of Sales - YC-Backed, On-Site (San Francisco)

Location: San Francisco, CA (On-site only)
Type: Full-time
Compensation:

  • Base Salary : $160,000 - $200,000

  • On-Target Earnings (OTE) : $280,000 - $350,000

  • Equity : Competitive, meaningful equity in a fast-growing YC-backed company

About the Company

We're working with a Y Combinator-backed software startup based in San Francisco , building next-generation tools for data infrastructure and observability . Backed by top-tier investors and technical founders, this startup is solving critical pain points for modern engineering teams dealing with growing data complexity, broken pipelines, and visibility gaps.

They're now hiring a founding Head of Sales to lead their GTM motion from the ground up.

This is a unique opportunity to take on a player-coach role, selling directly into engineering leadership (CTOs, VPs, Heads of Data) at mid-market and enterprise companies, and later helping shape the sales team, process, and playbooks that follow.

What You'll Do
  • Serve as the first full-time sales hire , owning the entire sales cycle : from prospecting to closing

  • Sell to technical and executive stakeholders in engineering and data driven organizations

  • Refine the ideal customer profile (ICP) , messaging, and outbound strategy in partnership with the founders

  • Build and maintain a healthy pipeline through outbound, networking, and partner channels

  • Represent the company at in person meetings, demos, and events in SF and beyond

  • Provide real time customer feedback to influence product direction

  • Help define the future GTM org structure , including hiring and onboarding future AEs

Who We're Looking For

We're looking for a senior level Account Executive or Director with proven startup success, technical sales acumen, and a relentless bias toward execution.
Prior experience in a startup environment is required.

Must Have Experience

  • 5-10+ years of full-cycle SaaS sales experience

  • Strong background selling into technical buyers, especially Heads of Engineering, CTOs, or CEOs

  • Experience in data infrastructure, observability, dev tools, or enterprise SaaS

  • Clear history of meeting or exceeding quota in mid-market or enterprise deals

  • Able to operate independently , thrive in ambiguity, and build from zero

  • Excellent communicator, both in technical and business conversations

  • Strong working knowledge of SFDC, sales playbooks, outbound tooling, and deal strategy

  • Must be based in or willing to relocate to San Francisco, this is an on site role

Bonus Points For

  • Prior experience at a Y Combinator backed startup

  • Prior experience as a founding AE, sales lead, or early-stage GTM builder

  • Technical literacy in modern data stacks: Snowflake, dbt, Airflow, etc.

Why This Role Is Special
  • You'll be selling a product with strong founder market fit , early traction, and technical validation

  • You'll help shape the sales culture and motion for a company just hitting its growth stride

  • You'll be in the room with decision makers, directly influencing GTM, product, and company strategy

  • You'll work onsite in San Francisco with a high-output, collaborative team of builders and operators

  • Competitive base, strong upside on OTE, and equity in a YC-backed rocketship

Oscar Associates Limited (US) is acting as an Employment Agency in relation to this vacancy.

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