VP of Sales, Regional (Player-Coach)

Location: Remote, US. Significant travel required.

About Vend Park

Vend Park is a unified technology and operations company transforming how commercial real estate owners manage and monetize parking. By combining agentic AI with a world-class operations team, Vend automates day-to-day management, eliminates inefficiencies, and unlocks revenue trapped in outdated systems and fragmented operating models.

Vend meets each property where it is, replacing the legacy two-vendor model with one integrated solution that unifies technology, operations, and data. The result is streamlined parking operations that increase NOI, lower costs, and deliver a premium experience tenants and guests enjoy.

From office towers and mixed-use properties to healthcare facilities, hotels, universities, event venues, and airports, Vend turns parking into a strategic lever for property value creation, backed by real-time intelligence, seamless automation, and measurable financial impact.

The Role

We're hiring a VP of Sales to bring a significant regional presence for Vend Park. You'll close our largest commercial real estate deals, while building and coaching a sales team for scale. This role involves frequent travel to customer sites, industry events, and team meetings. Our biggest deals are won in person, and you'll be on the road a lot.

This is a true player-coach role. You'll start by going through a full ramp and carrying your own quota, because you can't coach a selling motion you haven't run yourself. Your first six months will be mostly selling. After that, you'll take on a small team of Account Executives and shift progressively toward coaching. You will never fully step out of deals. Our leaders sell.

You'll report to our Head of Revenue and work closely with our CEO. Your region's number, your reps, and your accounts are yours to own. Our go-to-market strategy is already set. This role is about executing it and building a team that can execute it with you.

What You'll Do

• Close enterprise deals. Work and close complex opportunities. You'll keep a book of your own even after you're leading a team.

• Coach a small team of AEs. You'll start with three to four and grow to no more than six. We keep teams small on purpose so the coaching is real. You'll sit in on deals, run debriefs, sharpen discovery, and get reps to where they can navigate a CRE buying process on their own.

• Win institutional accounts. Lead the largest, most complex opportunities. Multi-thread across asset managers, ownership groups, and third-party property managers. Get to the economic buyer early and stay there.

• Structure deals we can deliver profitably. Work with Finance and Operations on revenue share models, capex treatment, management agreements, and pricing. What you sell has to be something we can operate.

• Own your region's number. Forecast it, defend it, and deliver it. Keep pipeline honest and current in HubSpot so the business can plan capital, staffing, and launches around numbers that hold up.

• Help build a modern sales org. Work with our GTM AI Engineer, marketing, and growth teams to use AI and automation where they actually help.

What Success Looks Like

In your first year, you'll close your first enterprise deals and hit your personal quota. You'll bring your AEs up to speed fast and get a growing share of them to quota. Your forecast will be one leadership trusts. You'll win competitive and RFP deals at healthy margins.

What You'll Bring

• You're a high-performing enterprise seller now. You're currently carrying and hitting an individual quota, and you can walk us through deals you closed personally, in detail.

• You have experience with $100K+ ACV deals on sales cycles of four to six months or longer, involving multiple stakeholders and committee decisions.

• You've sold to CRE owners and asset managers. That means asset management and ownership, not only facilities or property management. Experience in CRE services, PropTech, or a related built-world category is strongly preferred.

• You want to lead. You've mentored people informally or developed reps formally. You can name them and tell us what changed in their performance. You want the next step, and you don't want to stop selling to get it.

• You bring a methodology you can teach. Formal training in MEDDPICC or an equivalent, applied in practice.

• You're fluent in deal structuring: revenue share, capex amortization, management agreements, and unit economics.

• You have forecasting discipline. HubSpot experience is a plus.

• You use AI hands-on in your own selling. You have a clear view of where it helps and where it doesn't.

• You're willing to travel frequently. You're comfortable being on the road often to be in front of customers and your team.

Nice to have: existing relationships with institutional owners, asset managers, or third-party property managers; experience selling a combined technology-and-services offering; startup or high-growth experience.

Probably not the right fit: career managers who've spent the last several years away from deals, or lone wolves who'd rather not develop others.

Benefits

• Medical, dental, and vision coverage

• 401(k) with company match

• Unlimited PTO

• Paid parental leave

• Flexible, remote-first work

• Learning and development support, including conferences and certifications

• Retreats and team events

Our Values

Bold: Dream big, take smart risks, and learn from every step.

Empathetic: Be transparent, honest, and human.

Accountable: Deliver on your word and own outcomes.

Self-Starters: Act with initiative.

Team First: We win together.