[Hiring] Market Expansion Executive @Vend Park

Role Description

This is a senior individual contributor role reporting directly to the Head of Revenue. As a Market Expansion Executive, you will be responsible for driving new business across your territory — from first contact to signed contract and beyond. You'll own the full sales cycle, navigating complex, multi-stakeholder deals with commercial real estate owners, asset managers, and property operators.

We are hiring three Market Expansion Executives: one based in Toronto, ON and two based anywhere in the United States. All three roles are greenfield territory opportunities with significant upside.

This is not a role for someone looking to manage a playbook someone else wrote. We want hunters — disciplined, process-driven enterprise closers who thrive in a high-growth environment and know how to win.

What You'll Do

• Own end-to-end pipeline development and management across your territory, from prospecting through close.
• Identify, engage, and build relationships with key decision-makers at commercial real estate firms — including owners, asset managers, and property management executives.
• Execute a rigorous, structured sales process (MEDPICC or equivalent framework) to qualify opportunities, manage complex buying committees, and drive deals to close.
• Develop and execute territory go-to-market plans with a clear view on target accounts, entry strategies, and competitive positioning.
• Partner closely with Revenue, Marketing, and Customer Success to align on pipeline health, account intelligence, and expansion opportunities.
• Accurately forecast your pipeline and maintain meticulous CRM hygiene — your numbers should never be a surprise.
• Represent Vend at key industry events, conferences, and in-person meetings with prospects and partners (up to 25% travel expected).
• Serve as a voice of the customer, feeding market insights back to the product and leadership teams.

Qualifications

• 7+ years of B2B enterprise sales experience, with a consistent track record of closing six-figure deals (ACV $100K+).
• Demonstrated experience selling into commercial real estate — whether in proptech, CRE SaaS, property management software, or adjacent industries.
• Deep familiarity with structured sales methodologies — MEDPICC, MEDDIC, Challenger, or equivalent. You don't just know the acronym; you live it.
• Proven ability to manage complex, multi-stakeholder sales cycles of 6+ months from qualification through execution.
• A sharp prospector — comfortable with outbound, cold outreach, and building pipeline from scratch in a greenfield territory.
• Exceptional communicator who can translate technical solutions into business value for both operational and C-suite audiences.
• High degree of autonomy, accountability, and ownership — you set your own agenda and hit your numbers.

Preferred

• Prior experience at a high-growth SaaS startup — you know how to operate with limited resources and still win.
• Existing network within commercial real estate ownership, asset management, or property management is a strong differentiator.
• Familiarity with parking, mobility, or building operations technology.
• Experience opening net-new markets — not just inheriting a warm book of business.

Benefits

• Greenfield territory with real upside — you're not fighting over someone else's accounts.
• Competitive base salary + uncapped commission structure built for high performers.
• Direct line to leadership — your wins and your insights matter here.
• A category-defining product in a market ready for disruption.
• A clear path to leadership — we're hiring ICs who we expect to grow into player-coaches and ultimately own their territories as market leaders. If you want to build something, not just sell something, this is that opportunity.
• A culture worth showing up for — we work hard and we celebrate harder. Vend Park hosts multiple company offsites per year to destinations like Costa Rica and Belize. Fair warning: if your passport is expired, now would be a great time to renew it.
• A tight-knit, high-performance team that moves fast and backs its people.