Account Executive - Chicago

About the role

Join Orbital's founding remote sales team in Chicago as an Account Executive. This position offers an exciting opportunity to sell advanced SaaS solutions to sophisticated buyers within the legal and commercial real estate sectors. As a key member of the sales team, you will be responsible for driving new business, managing complex sales cycles, and helping shape Orbital's growth strategy in the US market. You will work closely with cross-functional teams including Legal Solutions, Marketing, and Sales Enablement, contributing to the development of our go-to-market approach. This role is ideal for a motivated sales professional eager to make an impact in a fast-growing company that values innovation, strategic thinking, and customer success.

Key facts

What you'll do

• Generate and nurture your own sales pipeline through outbound prospecting efforts and inbound lead follow-up, ensuring a steady flow of qualified opportunities.
• Identify, qualify, and develop new business opportunities within the legal and commercial real estate sectors, focusing on organizations that can benefit from Orbital's SaaS solutions.
• Partner with the Marketing team to execute targeted account-based marketing campaigns aimed at law firms and in-house legal teams, helping to generate inbound interest and nurture leads.
• Lead the entire sales process from initial outreach and discovery to proposal, negotiation, and closing, ensuring a smooth and professional experience for prospects.
• Conduct detailed discovery calls to understand client needs, pain points, and objectives, and use this information to develop compelling business cases for Orbital's solutions.
• Deliver tailored product demonstrations that highlight the value and capabilities of Orbital's SaaS offerings, specifically designed for real estate legal teams and related stakeholders.
• Manage complex sales cycles that involve multiple stakeholders, including attorneys, IT professionals, and senior executives, ensuring alignment and consensus at each stage.
• Maintain accurate and up-to-date deal pipeline information within HubSpot, tracking progress, next steps, and deal health to facilitate forecasting and strategic planning.
• Collaborate with Legal Solutions Architects to provide pre-sales technical support, scope solutions, and address client-specific requirements.
• Work closely with the Sales Manager on pipeline reviews, forecasting, and developing strategic approaches to close deals efficiently.
• Provide valuable feedback to Product and Marketing teams regarding customer requirements, competitive landscape, and market trends to inform product development and marketing strategies.
• Contribute to the development of Orbital's go-to-market strategy as a founding member of the Chicago sales team, helping to establish best practices and scalable processes.

Requirements

• 2-5 years of B2B SaaS sales experience, with a consistent record of meeting or exceeding sales quotas in a competitive environment.
• Demonstrated ability to manage complex sales cycles involving multiple stakeholders and decision-makers.
• Strong discovery and qualification skills, with the ability to diagnose client needs, create compelling business cases, and advance deals through the sales funnel.
• Proactive approach to building and managing a sales pipeline, not solely relying on inbound leads but actively seeking new opportunities.
• Excellent communication skills, capable of engaging prospects across various formats including calls, emails, and presentations.
• Comfortable working in a rapidly evolving environment where processes and strategies are continuously refined.
• Reside in or be willing to relocate to Chicago to support local client engagement and team collaboration.
• Ability to quickly learn and articulate complex or technical subject matter relevant to legal and real estate markets, demonstrating adaptability and intellectual curiosity.
• Strong organizational skills to manage multiple opportunities and priorities simultaneously.

Nice to have

• Previous sales experience in legal, real estate, or other regulated industries, providing industry-specific insights and relationships.
• Familiarity with AI or related technology products, understanding their applications and benefits within legal and real estate contexts.
• Experience with sales qualification frameworks such as MEDDIC, MEDDPICC, or similar methodologies, to structure and improve sales processes.
• Prior work at a Series A-C SaaS company, with exposure to fast-paced growth environments and scaling sales operations.
• Knowledge of the legal or real estate technology landscape, including common pain points and workflow challenges faced by clients.

Skills & tools

• HubSpot CRM for managing sales pipeline, contacts, and deal tracking.
• MEDDPICC (or equivalent qualification framework) to qualify and advance sales opportunities effectively.
• Strong interpersonal and presentation skills to communicate value propositions convincingly.
• Ability to analyze client needs and translate them into tailored solutions and proposals.
• Basic understanding of SaaS sales cycles, negotiation, and closing techniques.

Practical notes

• This role is fully remote but requires the candidate to be based in Chicago or willing to relocate, as the position involves on-site engagement within the city.
• The company provides a comprehensive benefits package, including health, dental, and vision insurance coverage, to support employee well-being.
• A 401(k) plan with company matching is available to help employees plan for the future.
• Stock options are part of the compensation package, aligning employee interests with company success.
• The role includes 20 days of paid vacation annually, in addition to 11 public holidays recognized by the company.
• An annual development budget of $1,200 is allocated for professional growth, training, and skill enhancement.
• All team members are expected to adhere to security policies and complete awareness training in line with ISO 27001 standards to ensure data protection and compliance.
• The position offers an exciting opportunity to be part of a growing company at the forefront of legal and real estate SaaS solutions, with significant potential for career development and impact.