About the role

Role overview

Join Orbital as a Chicago-based Account Executive on a founding remote sales team. You’ll sell complex, high-value B2B SaaS into the legal and commercial real estate sectors and help shape Orbital’s go-to-market in a new city post-Series B.

What you’ll do

Pipeline and prospecting

Own and build your pipeline via outbound prospecting and inbound leads
Identify, qualify, and develop new business opportunities with law firms and in-house legal teams
Partner with Marketing on ABM and targeted outreach campaigns

Sales execution

Run a disciplined sales cycle from first contact to close
Conduct high-quality discovery calls to uncover pain, quantify impact, and build business cases
Deliver product demos tailored to real estate legal workflows
Manage complex, multi-stakeholder deals (attorneys, IT, and senior leadership)
Maintain deal progression and pipeline hygiene in HubSpot using MEDDPICC (or equivalent)

Collaboration

Partner with Legal Solutions Architects on pre-sales support and technical scoping
Work with Sales Manager on pipeline reviews, forecast accuracy, and deal strategy
Provide customer feedback to Product and Marketing on needs, objections, and competitive dynamics
Contribute to shaping the Chicago sales playbook and go-to-market approach

What we’re looking for

Must-haves

2–5 years of B2B SaaS sales experience with a consistent record of meeting/exceeding quota
Experience running complex, multi-stakeholder sales cycles
Strong discovery and qualification skills (diagnose pain, build business cases, advance deals)
Proactive pipeline building (generate pipeline; don’t rely on inbound only)
Confident communicator (in person, phone, and writing)
Comfortable in a high-growth environment where process is still developing
Based in or willing to relocate to Chicago (role is fully remote)
Ability to learn and credibly articulate complex/technical subject matter in the legal/real estate domain

Nice-to-haves

Experience selling into legal, real estate, or regulated industries
Familiarity with AI or technology products
Exposure to MEDDIC / MEDDPICC (or similar qualification frameworks)

About Orbital

Orbital provides an AI assistant, Orbital Copilot, built for commercial real estate law to accelerate and improve due diligence. The company focuses on automating complex legal document review and workflow coordination for law firms and in-house legal teams, supporting faster, more precise real estate transactions. It is expanding in the US and UK following a recent Series B funding round.

Account Executive - Chicago (Remote)

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