Remote Chicago Account Executive - Complex SaaS

Orbital

Chicago (IL)

Remote

USD 100,000 - 150,000

Full time

14 days+

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Benefits offered by this job

Remote work

Base salary + uncapped commission

Health benefits

Job summary

Orbital Copilot is seeking a Chicago-based Account Executive to join our founding remote sales team. You will sell complex, high-value SaaS solutions to sophisticated buyers and help shape our go-to-market in a new city.

This fully remote role reports to Sales Manager and collaborates with Legal Solutions, Marketing, and Enablement. You will build pipeline, run discovery, deliver demos, and navigate multi-stakeholder deals with MEDDPICC.

Qualifications

2-5 years of B2B SaaS sales experience with a consistent track record of meeting or exceeding quota.
Experience running complex, multi-stakeholder sales cycles.
Strong discovery and qualification skills: diagnose pain, build business cases, and advance deals.
Proactive pipeline builder: generate your own pipeline and don't rely on inbound alone.
Clear, confident communicator: in person, on the phone, and in writing.

Responsibilities

Own and build your pipeline through a combination of self-sourced outbound and inbound leads.
Identify, qualify, and develop new business opportunities within the legal and commercial real estate sectors.
Partner with Marketing on ABM campaigns and targeted outreach to law firms and in-house legal teams.
Run a disciplined, process-driven sales cycle from first contact through to close.
Conduct high-quality discovery calls to uncover pain, quantify impact, and build business cases.
Deliver engaging product demonstrations tailored to workflows of real estate legal teams.
Navigate complex, multi-stakeholder deals involving attorneys, IT, and senior leadership.
Manage deal progression and pipeline hygiene in HubSpot using MEDDPICC.