Location: Remote
Employment Type: Full-time

About Us

We're a venture-backed company building an AI-native supply chain operating system for restaurant chains. We automate planning, inventory management, and spend optimization — driving higher sales, lower COGS, and saving operators meaningful time every week. Sightline OS was co-founded by Yusha Hu, who previously led supply chain and procurement teams at Chipotle, sweetgreen, and HelloFresh, and technical cofounders Derrick Staten and Louis Bensard.

The Role

As our founding Account Executive, you'll be the driving force behind our growth, taking us from a highly engaged early customer base to become the category-defining platform in the market. You’ll work side-by-side with our CEO in a high-trust, complex sales motion — running the full deal cycle from prospecting to close, navigating organizational stakeholders, and building the operational muscle (playbooks, pipeline hygiene, forecasting) that we'll use to hire and scale behind you. Our CEO will stay committed to driving founder-led sales, but this is not a hand-it-off role. You'll own your number and you'll own the process.

What You'll Do

• Full-Cycle Enterprise Sales: Own pipeline from first outreach through signed contract. You'll source, qualify, run discovery, deliver demos, build business cases, navigate procurement, and close — with support from our CEO on strategic deals.

• Founder-Led Motion: Work hand-in-hand with our CEO on high-priority accounts. You'll learn to articulate our value prop with the same depth and credibility as an operator, and be able to run deals independently as you ramp.

• MEDDPICC Discipline: Apply structured deal qualification rigorously. You'll know exactly where every deal stands, what the path to close looks like, and what's needed to accelerate.

• Outbound & Prospecting: You'll build and work a target account list, use signal-based outreach, and partner closely with marketing on ABM campaigns to get in front of the right key stakeholders at restaurant chains.

• Playbook Building: You'll document what works — discovery frameworks, objection handling, competitive positioning, business case templates — and be a key contributor to the sales infrastructure we scale behind you.

• Voice of the Customer: You'll bring back what you hear in the field — objections, pain points, competitive intel — and directly shape our marketing, product roadmap, and messaging.

  Requirements

• At least 3 years of enterprise sales experience, with a track record of closing deals with VP and C-suite buyers. You know what a complex deal looks like and you know how to move it.

• Comfortable owning the full cycle. You've sourced your own pipeline, not just worked inbound.

• Structured and rigorous. You use MEDDPICC or an equivalent framework, keep your CRM clean, and can give an accurate forecast. You believe process creates freedom.

• Entrepreneurial mindset and intellectually curious. You're not just running a playbook — you're building one. You care about whether the company wins, not just whether your quota is hit. You are intellectually curious and interested in understanding every aspect of the company. You move fast, don’t like working in silos, and want to contribute to overall company strategy. 

• Clear, compelling communicator. You can distill a complex ROI story into a crisp business case for a CFO and adjust your pitch for a VP of Supply Chain in the same meeting.

• Willing to travel to the NYC office, conferences, customer sites, and other events.

Nice to Have

• Experience selling to restaurant, food & beverage, or retail operators

• Background in supply chain, procurement, or operations software

• Prior experience as an early account executive at a Series A/B startup

What We Offer

• Founding team member equity package

• Market rate OTE with un-capped upside

• The opportunity to build and own the sales function at a high-growth startup, working directly with the CEO

• Be at the forefront of agentic AI solving meaningful, real-world operational problems

If you want to do more than hit quota — if you want to help build a generational company, we want to hear from you.