Director of Sales

About Ocra

Ocra is an AI-powered Revenue Management System (RMS) and Global Distribution System (GDS) built for hotel parking assets. Hotels use Ocra to sell underutilized parking inventory through “parking OTAs” to non-guest customers looking to park near airports and event venues.

Ocra's team of parking revenue management experts drives revenue growth without adding labor or disrupting operations, helping hotels increase net operating income (NOI) while never compromising parking for hotel guests and staff.

Ocra partners with 50+ operators and 25+ hotel groups at 600+ locations. The company has raised $10M, most recently an oversubscribed $5M round co-led by Trestle Partners and MCR Hotels.

About the Role

We’re looking for a Director of Sales who loves to build; someone energized by creating structure, unlocking growth, and bringing clarity to complexity. Ocra is at a true inflection point, with a product that’s resonating, a team of driven AEs already in motion, and strong early traction across both regional and partnership-driven sales.

This role is about connecting the dots and building the engine that powers our next phase of growth. You’ll step into an actively selling team and have the opportunity to shape how we operate by bringing structure to our CRM, defining clear rules of engagement, and aligning our two core go-to-market motions (a regional, bottoms-up AE approach and a top-down partnerships and ownership strategy) so they work seamlessly together.

Key Responsibilities

• Build and run a high-performing sales cadence (pipeline reviews, 1:1s, QBRs, forecasting)
• Own and optimize HubSpot - ensuring clean data, clear stages, and accurate ARR reporting
• Develop a forecasting framework that leadership can rely on for decision-making
• Create scalable systems including playbooks, SOPs, and onboarding materials
• Lead and coach regional AEs across multiple territories, elevating performance and execution
• 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 turn closed deals into expanded, long-term revenue
• Align and streamline collaboration between Sales and Partnerships, ensuring efficient lead flow and execution
• Partner with the CEO on scaling the sales function, bringing market insights, and hiring to support growth

What We're Looking For

We're not looking for a head of quota-carrying reps or a VP who needs a large team to be effective. We're looking for someone who gets excited about building the machine, not just running it.

• 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

• Proactive problem-solver who identifies gaps early and brings thoughtful solutions

• Comfortable in fast-paced, ambiguous environments. Able to build structure from the ground up

• Strong cross-functional collaborator, especially with partnerships and leadership teams

• Builder mindset with a focus on creating scalable systems that drive long-term growth

Bonus Points

• Background in hospitality tech, proptech, or selling to hotel operators or ownership groups

• Experience managing an overlay or partnerships motion alongside a direct AE team

• Familiarity with revenue ops concepts; you don't need to be a RevOps engineer, but you know what good looks like

• You've done a consult-to-hire or fractional engagement before and know how to get up to speed fast

Benefits

• Competitive salary w/ 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