Remote Chicago Account Executive — AI Real Estate SaaS

Orbital; Chicago (IL); On-site; USD 100,000 - 150,000; Full time

Benefits offered by this job

Health benefits

401(k) match

Remote work

Paid vacation 20 days + 11 holidays

Development budget $1,200 annually

Stock options

Job summary

Orbital is hiring a Chicago-based Account Executive to join our founding remote sales team. You will sell complex, high-value SaaS to sophisticated buyers, shape go-to-market in a new city, and work closely with Legal Solutions, Marketing, and Sales Enablement.

This is a critical early hire reporting to the Sales Manager, with opportunity to influence our Chicago presence and support US expansion post-Series B. The role is fully remote with hub in Chicago.

Qualifications

• 2–5 years of B2B SaaS sales experience with a track record of meeting/exceeding quota.
• Experience running complex, multi-stakeholder sales cycles.
• Strong discovery and qualification skills to diagnose pain and advance deals.
• Proactive pipeline builder who generates own pipeline, not just inbound.
• Clear, confident communicator in person, on the phone, and in writing.
• Willingness to relocate to or be based in Chicago; fully remote role.
• Ability to learn and credibly articulate complex subject matter for legal/real estate markets.

Responsibilities

• Own and build your pipeline through self-sourced outbound and inbound leads.
• Run a disciplined sales cycle from first contact to close; deliver tailored product demonstrations.
• Conduct discovery calls to quantify impact and build business cases.
• Navigate multi-stakeholder deals involving attorneys, IT, and senior leadership.
• Collaborate with Sales Manager, Legal Solutions Architects, Marketing, and Product.

Skills

B2B SaaS sales

Complex multi-stakeholder sales

Discovery & qualification

Pipeline development

Clear communication

Remote/work-from-home adaptability

HubSpot MEDDPICC

Tools

HubSpot

MEDDPICC

Job description

Orbital is hiring a Chicago-based Account Executive to join our founding remote sales team. You will sell complex, high-value SaaS to sophisticated buyers, shape go-to-market in a new city, and work closely with Legal Solutions, Marketing, and Sales Enablement.

This is a critical early hire reporting to the Sales Manager, with opportunity to influence our Chicago presence and support US expansion post-Series B. The role is fully remote with hub in Chicago.