Market Expansion Executive

Locations: Toronto, ON (1) | United States – Remote (2)

Vend Park is building the AI-powered digital infrastructure of the built world.

We are transforming how commercial real estate owners manage and monetize parking — using automation, data, and agentic AI to modernize a historically analog industry. What was once manual, fragmented, and operationally heavy is becoming intelligent, software-driven, and revenue-optimized.

In under two years, we’ve expanded to 23 cities and partnered with leading institutional owners including Nuveen, Jamestown, and Federal Realty. We operate as a small, high-ownership team where decisions move quickly, complexity is embraced, and solutions ship with rigor.

We're growing fast, and we're building the team to match. That means hiring elite enterprise sellers who are ready to own a market, close complex deals, and help shape how an entire industry evolves.

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.

• 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.
  

• 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.

• 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.
  

• 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.