Account Executive - Chicago (Remote)

About the role

We are seeking an Account Executive to join our founding remote sales team in Chicago. This role is critical for shaping our presence in the city and contributing to our US expansion post-Series B. The ideal candidate will have 2-5 years of B2B SaaS sales experience, strong discovery and qualification skills, and the ability to navigate complex, multi-stakeholder deals.

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 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)
• 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

Requirements

• Must-have: 2-5 years of B2B SaaS sales experience with a consistent track record of meeting or exceeding quota, strong discovery and qualification skills, proactive pipeline builder, clear and confident communicator, comfortable operating in a high-growth, scaling environment, willingness to relocate to Chicago
• 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

Qualifications

• Must-have: Demonstrated ability to learn and credibly articulate complex or technical subject matter, understanding of Orbital's product, market, customers, and sales process
• 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

Skills

• Must-have: Strong sales and communication skills, ability to build and manage a pipeline, ability to conduct discovery calls and demos, ability to navigate complex deals, ability to manage deal progression and pipeline hygiene
• Nice-to-haves: Familiarity with MEDDIC, MEDDPICC, or similar qualification frameworks, experience at a Series A-C SaaS company

Benefits

• Compensation: Base salary of $100,000-$150,000 depending on experience, with uncapped commission and OTE of $200,000-$300,000
• Comprehensive health benefits: Medical, dental, and vision coverage
• Flexible work: Fully remote role
• Preparing for your future: Healthy 401(k) match
• Ownership: Stock options
• Rest and recharge: 20 days of paid vacation, 11 public holidays
• Equipment & Development: Top-quality gear, $1,200 annual development budget, ongoing training
• Security: ISO 27001 standards