Job Overview
Location
Chicago
Job Type
Full-time
Category
Sales
Date Posted
March 24, 2026
Full Job Description
đź“‹ Description
- • As Director of Sales at OCRA, you will lead the strategic development and execution of the sales function during a critical growth phase, directly contributing to the company’s mission of helping hotels monetize underutilized parking inventory through its AI-powered RMS and GDS platform, thereby increasing net operating income without disrupting guest or staff parking access.
- • You will build and run a high-performing sales cadence including pipeline reviews, 1:1s, QBRs, and forecasting; own and optimize HubSpot for clean data, clear stages, and accurate ARR reporting; develop a reliable forecasting framework for leadership decision-making; create scalable systems such as playbooks, SOPs, and onboarding materials; lead and coach regional AEs across multiple territories to elevate performance; provide hands-on deal support across discovery, strategy, objection handling, and closing; set clear performance expectations and drive accountability through data; partner cross-functionally to expand closed deals into long-term revenue; align and streamline collaboration between Sales and Partnerships motions; and partner with the CEO to scale the sales function, bring market insights, and support hiring for growth.
- • OCRA is a fast-growing, early-stage company with a proven product that has gained traction across 600+ locations, 50+ operators, and 25+ hotel groups, backed by $10M in funding including a recent oversubscribed $5M round co-led by Trestle Partners and MCR Hotels; the team consists of driven AEs and parking revenue management experts focused on delivering growth without adding labor or disrupting hotel operations.
- • In this role, you will have the opportunity to build scalable sales infrastructure from the ground up, shape the company’s go-to-market engine, develop leadership and operational expertise in a high-impact SaaS environment, and directly influence OCRA’s next phase of growth by creating systems that enable predictable, repeatable revenue generation.
🎯 Requirements
- • 5–10 years of experience in B2B SaaS sales, including 2–3+ years in a player-coach or leadership role
- • Proven track record of building and scaling sales infrastructure (playbooks, cadences, CRM, forecasting) in early- or growth-stage environments
- • Deep HubSpot expertise with a strong understanding of pipeline hygiene, reporting, and data integrity
- • Experience managing teams across multiple go-to-market motions (e.g., direct + partnerships, SMB + enterprise)
- • Hands-on leader who coaches reps through deal strategy, skill development, and consistent execution
- • Data-driven operator who uses metrics to guide decisions, performance, and accountability
🏖️ Benefits
- • Competitive salary with ancillary earning opportunities
- • Comprehensive benefits: medical, dental, & vision
- • Flexible work-from-anywhere policy
- • Unlimited PTO that supports work-life balance
- • Stock option incentive plan
- • Company-sponsored 401k
- • Opportunity to work in a dynamic and growing company
- • Collaborative and supportive work environment
- • Training and ongoing professional development
Skills & Technologies
About OCRA
OCRA is a leading provider of innovative solutions for the food and beverage industry. The company specializes in developing and implementing advanced technologies that enhance efficiency, quality, and sustainability throughout the food production lifecycle. OCRA's offerings include intelligent automation systems, data analytics platforms, and customized consulting services designed to address the unique challenges faced by food manufacturers and distributors. By leveraging cutting-edge artificial intelligence and machine learning, OCRA empowers its clients to optimize their operations, reduce waste, and ensure compliance with stringent regulatory standards. Their commitment to research and development ensures they remain at the forefront of technological advancements, providing clients with a competitive edge.
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