Regional Sales Manager

Ocra • Chicago, IL

4d • Remote

About The Position

Ocra is an AI-powered Revenue Management System and Global Distribution System for hotel parking assets. Its platform helps hotels sell underutilized parking inventory to non-guest customers while protecting parking availability for hotel guests and staff. Ocra partners with more than 50 operators and 25 hotel groups across over 600 North American locations.

The Regional Sales Manager drives new business for Ocra’s hotel parking revenue management software and managed services. This sales-focused role combines customer engagement, strategic selling, relationship-building, and communication to align Ocra’s offerings with customer needs. The successful candidate is collaborative and proactive, has a record of exceeding sales targets, and can engage stakeholders including C-level executives. The role involves frequent travel and collaboration in a startup environment.

Requirements

• At least 3 years of successful sales experience, ideally in enterprise or SaaS software sales.
• Excellent verbal and written communication skills, with the ability to engage and influence decision-makers.
• Proven ability to exceed sales targets and manage a designated territory.
• Strong understanding of the sales cycle and ability to leverage each stage effectively.
• Ability to learn and apply proven sales methodologies.
• Willingness to travel frequently.
• Experience building trusting relationships with executive-level stakeholders.
• Comfort discussing technical and non-technical product aspects with executives.
• Demonstrated urgency, competitiveness, and a positive attitude.
• Strong time management skills and attention to detail.
• High levels of business and financial acumen and emotional intelligence.
• Ability to articulate client strategies and develop valuable solutions.

Nice To Haves

• Experience in technology-driven sales environments.
• Familiarity with HubSpot CRM or similar tools.
• Familiarity with parking industry software.
• Experience selling into the hospitality industry.

Responsibilities

• Win new business for Ocra’s parking technology.
• Secure and lead face-to-face meetings with business leaders and decision-makers.
• Deliver customer presentations and proposals that clearly communicate Ocra’s value proposition.
• Develop, maintain, and grow an ongoing sales pipeline.
• Maintain accurate account status and sales activity information in HubSpot CRM.
• Manage account development and opportunity pursuit using HubSpot CRM.
• Forecast new bookings accurately and develop strategies for securing new accounts.
• Understand and apply Ocra’s consultative and solution-selling process.
• Adapt to a startup environment and collaborate within a small team.

Benefits

• Competitive salary and uncapped commissions.
• Comprehensive benefits.
• Unlimited paid time off.
• Stock option incentive plan.
• Opportunity to work in a dynamic and growing company.
• Collaborative and supportive work environment.
• Opportunity to make a real impact on clients’ businesses.
• Flexible work-from-anywhere policy.
• Company-sponsored 401(k).
• Training and ongoing professional development.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed