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Free Remote Jobs in Chicago, IL (NOW HIRING)

Orbital

Account Executive - Chicago (Remote)

Chicago, IL · On-site +1

$200K - $300K/yr

We're on a mission to make real estate transactions smarter, faster, and friction-free. Real estate ... The Role We are looking for a Chicago-based Account Executive to join our founding remote sales ...

Symmetry

Remote Sales and Team Builder

Chicago, IL · Remote

$20K - $60K/mo

Remote Sales and Team Builder Must be authorized to work in the US, no work visas offered at this ... and a drug-free workplace. THIS IS A U.S.-BASED POSITION THAT REQUIRES U.S. RESIDENCY. No Work ...

Symmetry

Remote Sales and Team Builder

Chicago, IL · On-site +1

$20K - $60K/mo

Remote Sales and Team Builder Must be authorized to work in the US, no work visas offered at this ... and a drug-free workplace. THIS IS A U.S.-BASED POSITION THAT REQUIRES U.S. RESIDENCY. No Work ...

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Free Remote generally refers to remote job positions that do not require specific credentials and are offered by companies. Freelance Web Developers are independent contractors who work on web development projects, often with specific skills and portfolios. While both work remotely, Free Remote jobs are typically full-time or part-time roles with a single employer, whereas Freelance Web Developers handle multiple clients on a project basis.

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Infographic showing various Free Remote job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 67% Full Time, 20% Part Time, and 12% Contract. Highlights an 93% Physical, 2% Hybrid, and 5% Remote job distribution.

Account Executive - Chicago (Remote)

Orbital

Chicago, IL • On-site, Remote

$200K - $300K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

Re-posted 8 days ago

Job description

We're on a mission to make real estate transactions smarter, faster, and friction-free.
Real estate is the world's largest asset class, yet the legal processes and tools behind it remain slow, manual, and underinvested. Lawyers must review dense documents line by line and piece together information across silos, all while clients demand faster, more transparent due diligence.
That's where we come in. Orbital Copilot is the AI assistant built exclusively for commercial real estate law. Developed with former practicing real estate lawyers, it accelerates complex due diligence by up to 70% while delivering legal-grade precision.
We've just raised a $60m Series B to accelerate our UK/US expansion.
We're trusted by leading firms like Goodwin and BCLP to remove the busywork so legal teams can focus on what they do best: applying sharp legal judgment, delivering standout client service, and getting deals over the line faster.
Working at Orbital means joining a team that's reimagining how real estate transactions get done - moving fast, working collaboratively, and giving people the ownership to make a real impact from day one.
The Role
We are looking for a Chicago-based Account Executive to join our founding remote sales team. This is a role for someone who thrives on selling complex, high-value SaaS solutions, building relationships with sophisticated buyers, and helping shape how we go to market in a new city.
This role reports directly to our Sales Manager and works closely with our Legal Solutions team, Marketing, and Sales Enablement. This is a critical early hire and a genuine opportunity to shape our Chicago presence and contribute to Orbital's US expansion post-Series B.
What You'll Do
Pipeline and Prospecting
  • 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

Sales Execution
  • Run a disciplined, process-driven sales cycle from first contact through to close
  • Conduct high-quality discovery calls to uncover business pain, quantify impact, and build compelling business cases
  • Deliver engaging product demonstrations tailored to the specific 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 (or equivalent qualification framework)

Collaboration
  • Partner with Legal Solutions Architects on pre-sales support and technical scoping
  • Collaborate with the Sales Manager on pipeline reviews, forecast accuracy, and deal strategy
  • Provide field feedback to Product and Marketing on customer needs, objections, and competitive dynamics
  • Help shape our go-to-market approach and playbook as one of our founding Chicago hires

What We're Looking For
Must-Haves
  • 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: able to diagnose pain, build business cases, and advance deals with discipline
  • Proactive pipeline builder: you generate your own pipeline and don't rely on inbound alone
  • Clear, confident communicator: in person, on the phone, and in writing
  • Comfortable operating in a high-growth, scaling environment where process is still being built
  • Based in or willing to relocate to Chicago (this is a fully remote role)
  • Demonstrated ability to learn and credibly articulate complex or technical subject matter: our AEs sell into the legal and real estate market, and must understand the domain well enough to run sharp discovery and handle objections

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
  • Experience at a Series A-C SaaS company

What Success Looks Like
  • 30 days: Understand Orbital's product, market, customers, and sales process. Begin shadowing discovery and demo calls. Start building an outbound pipeline.
  • 60 days: Running your own discovery calls and demos with support. Pipeline building consistently. Delivering accurate forecast inputs.
  • 90 days: Owning the full sales cycle independently. Pipeline at target coverage. Qualified opportunities progressing toward close.

Benefits
  • Compensation: Base salary of $100,000-$150,000 depending on experience, with uncapped commission and OTE of $200,000-$300,000. We share salary ranges upfront to build trust, reduce bias, and support an inclusive process.
  • Comprehensive health benefits: Your well-being is important to us. We provide competitive medical, dental, and vision coverage to help you stay healthy and supported.
  • Flexible Work: This is a fully remote role. We're big on flexibility and trust our people to do great work wherever they are.
  • Preparing for your future: We offer a healthy 401(k) match.
  • Ownership: We give you real ownership in the company through stock options, so you share in our success.
  • Rest and Recharge: You'll receive 20 days of paid vacation, in addition to 11 public holidays. We encourage real breaks so you can show up as your best self.
  • Equipment & Development: We invest in your growth with top-quality gear, a $1,200 annual development budget, and ongoing training to help you build skills and confidence from day one.

Security is everyone's responsibility at Orbital. We ask all team members to follow our security policies, complete regular awareness training, and handle sensitive data with care in line with ISO 27001 standards. Spot something unusual? Reporting risks or incidents quickly helps us maintain the strong culture of security and compliance we all depend on.
At Orbital, we're committed to building a diverse and inclusive team. We especially welcome applications from people who are traditionally underrepresented in tech. Even if you don't meet every single requirement, or if the right role isn't listed yet, we'd still love to hear from you.
This hiring range is a reasonable estimate of the base pay range for this position at the time of posting. Pay is based on several factors, which may include job-related knowledge, skills, experience, and business requirements.

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