Account Executive - Chicago (Remote)

Orbital Account Executive

Orbital is the AI platform for real estate legal work. Real estate shapes the world around us: our homes, our workplaces and our cultural landmarks. It's the infrastructure that powers everyday life and is the world's largest asset class. Yet behind every single deal, real estate and legal teams work hard to navigate decades-old complexity; manually connecting documents, hidden obligations, geo-spatial context, and multiple parties into a path forward. We connect the legal and physical record, so that path is clearer than ever before. Our mission is to make real estate transactions faster, clearer, and less manual.

Here, you'll be part of changing how the deals behind the largest asset class get transacted, and will help shape the future of real estate.

We're building at the forefront of AI technology, without losing the deeply human expertise our clients depend on.

Orbital is built with former practising real estate lawyers and 250+ years of combined legal expertise. We're purpose-built for the complexity of real estate: accelerating due diligence, drafting and negotiation, and deal coordination with legal-grade precision.

We've just raised a $60m Series B, led by Brighton Park Capital, to accelerate our global expansion $75m raised to date.

We're trusted by 5,000+ real estate professionals, spanning UK Magic Circle and US Am Law 100 firms, to household names like M&S. Leading firms like BCLP, Orrick, Goodwin, Womble Bond Dickinson and Clifford Chance rely on Orbital to remove the busywork, freeing legal and real estate teams to focus on sharp judgment, standout client service, and closing deals faster.

Working at Orbital means joining a bold, ambitious team, with the trust to take ownership and 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.

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.

Everyone who works with Orbital goes through background screening before they start. It's part of how we keep Orbital secure, for the people who work here and for the client information we're trusted with.