Director of Sales
Ocra, Chicago, IL, United States
About Ocra
Ocra is an AI-powered Revenue Management System (RMS) and Global Distribution System (GDS) built for parking assets. Parking owners and operators use Ocra to sell underutilized parking inventory through “parking OTAs” to prepaid reservation customers looking to park near airports, event venues and high-demand transient locations.
Ocra's team of parking revenue management experts drives revenue growth without adding labor or disrupting operations, helping assets increase net operating income (NOI). Ocra partners with 50+ parking operators and 25+ hotel groups at over 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 simplicity to B2B complexity. Ocra is at a true inflection point, with strong and defensible product‑market‑fit, a team of driven AEs already in motion, and strong growing traction across both regional and partnership‑driven sales. This role will inherit a series of AI‑Powered SalesOps agents purpose built at Ocra. This is the engine that is powering our next phase of growth. You’ll step into an actively selling team and have the opportunity to work closely with the CEO and other executives to design systems that scale, define clear rules of engagement, and align 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
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Ocra's team of parking revenue management experts drives revenue growth without adding labor or disrupting operations, helping assets increase net operating income (NOI). Ocra partners with 50+ parking operators and 25+ hotel groups at over 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 simplicity to B2B complexity. Ocra is at a true inflection point, with strong and defensible product‑market‑fit, a team of driven AEs already in motion, and strong growing traction across both regional and partnership‑driven sales. This role will inherit a series of AI‑Powered SalesOps agents purpose built at Ocra. This is the engine that is powering our next phase of growth. You’ll step into an actively selling team and have the opportunity to work closely with the CEO and other executives to design systems that scale, define clear rules of engagement, and align 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
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