Account Executive - Chicago (Remote)

Orbital•Chicago, IL

3d•Remote

About The Position

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.

Requirements

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

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

Benefits

Base salary of $100,000-$150,000 depending on experience, with uncapped commission and OTE of $200,000-$300,000.
Competitive medical, dental, and vision coverage
Fully remote role
Healthy 401(k) match
Stock options
20 days of paid vacation
11 public holidays
Top-quality gear
$1,200 annual development budget
Ongoing training