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Remote Relocate Jobs in Chicago, IL (NOW HIRING)

Orbital

Account Executive - Chicago (Remote)

Chicago, IL · On-site +1

$200K - $300K/yr

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 ...

e2E

Director of Tax (Remote)

Chicago, IL · Remote

$105K - $120K/yr

... remote and hybrid work arrangements ... Applicants should either currently reside in the Kansas City Metro area or plan to relocate to ...

J.R. Simplot Company

Credit Manager - Midwest

Chicago, IL · Remote

$85K - $100K/yr

Although the role is remote, it is preferred that eligible candidates must be residing within the ... Relocation Assistance Program (where applicable) * Education Assistance Benefits details available ...

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Remote Relocate information

What is a remote relocate?

A Remote Relocate job refers to a position where employees work remotely but may be required or offered the opportunity to relocate to a different city, state, or country. These roles are often designed for workers who prefer the flexibility of remote work but are open to moving for company needs, team integration, or long-term assignments. Employers may provide relocation assistance or incentives to help with the transition. The specific requirements and relocation policies vary by employer and job type, so it's important to clarify details before accepting a position.

What is the difference between Remote Relocate vs Remote Customer Support?

AspectRemote RelocateRemote Customer Support
Required CredentialsVaries by industry, often includes relevant experience or certificationsCustomer service skills, communication skills, sometimes certifications in support tools
Work EnvironmentInitially remote, with potential relocation to company office or client sitePrimarily remote, often from home or support centers
Employer & Industry UsageUsed across industries for roles requiring physical presence later in the processCommon in retail, tech, and service industries for remote support roles
Search & Comparison IntentPeople looking for roles that start remotely but may require relocation laterPeople seeking fully remote customer support jobs

The main difference is that Remote Relocate involves starting remotely with the possibility of relocating to a physical office or site later, while Remote Customer Support is typically a fully remote role without relocation requirements. Understanding these distinctions helps job seekers find roles aligned with their preferences for remote work or relocation opportunities.

What are some common challenges faced by employees in a remote role that requires occasional relocation, and how can they be managed?

Employees working remotely with occasional requirements to relocate may face challenges such as adapting to new time zones, managing work-life balance during transitions, and staying connected with their teams. It's important to establish clear communication channels and make use of collaboration tools to remain engaged. Proactively planning relocation logistics and setting routines can help maintain productivity and minimize disruption. Many organizations also provide relocation support and resources, so it's beneficial to inquire about these before starting.

What are the key skills and qualifications needed to thrive as a remote relocate?

To thrive as a Remote Relocation Specialist, you need strong organizational skills, knowledge of relocation processes, and often a background in HR, real estate, or global mobility. Familiarity with relocation management software, HRIS systems, and global compliance regulations is typically required. Excellent communication, problem-solving abilities, and cultural sensitivity are standout soft skills in this role. These capabilities ensure smooth transitions for relocating employees and contribute to client satisfaction and operational efficiency.
What are the most commonly searched types of Relocate jobs in Chicago, IL? The most popular types of Relocate jobs in Chicago, IL are:
What are popular job titles related to Remote Relocate jobs in Chicago, IL? For Remote Relocate jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Relocate jobs in Chicago, IL look for? The top searched job categories for Remote Relocate jobs in Chicago, IL are:
Remote Relocate jobs near you

Account Executive - Chicago (Remote)

Orbital

Chicago, IL • On-site, Remote

$200K - $300K/yr

Full-time

Medical, Dental, Vision, Retirement, PTO

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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