The RoleWe 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 DoPipeline 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 ForMust-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.
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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.
