As a Supply-Side Account Executive, you will sign up real estate owners, asset managers, and property operators to list unused parking inventory on an online monthly-parking marketplace. You will sell into property owners, asset managers, and operators across residential apartment buildings, commercial office buildings, industrial sites, and service-firm offices (law and accounting) with surplus spots. This is a 100% new business development role in Year 1, with leads split 75% self-prospected and 25% warm inbound. Customers include multi-billion-dollar REITs, mid-sized commercial and residential property managers, and individual asset owners. The sales territory covers several assigned cities within the company’s seven to eight highest-traffic North American search markets, including Los Angeles, San Francisco, and other major US metros. This is a newly added position on the supply-development team and reports directly to the Chief Revenue Officer. The base salary is $60,000 – $70,000 CAD (up to $75,000 CAD for an exceptional candidate), plus uncapped commissions.
COMPENSATION & BENEFITS
- $60,000 – $70,000 CAD base salary to start; up to $75,000 CAD for an exceptional candidate
- Standard practice: $5,000 base salary increase at the 3-month mark upon hitting early pipeline metrics
- Year 1 OTE: $75,000 – $110,000 CAD
- Year 2 OTE: $110,000 – $125,000 CAD
- Top-performer OTE: approximately $185,000 CAD
- Uncapped commission — flat fee per parker signed to a contracted property (minimum 12-month engagement), paid monthly
- Stock options
- Partially company-paid extended health and dental coverage
- Wellness program
- 15 vacation days, 10 sick days, 1 personal day
- Catered lunch on Tuesdays and Thursdays
- Casual dress
- Company social events
- Laptop provided
- On-site parking
- Hybrid work arrangement
- Career advancement — Sales Manager track within 2 to 3 years for high performers
THE COMPANY & CULTURE
Our client was founded in approximately 2015, is privately held and employee-owned, and is a member of a larger technology group. The business is in scale-up mode with 25–50% annual revenue growth. Headquartered in Toronto, Ontario, the company operates an online marketplace for monthly parking — signing up real estate owners and operators with unused parking inventory (residential, commercial, and industrial), listing those spots on the platform, and connecting them with monthly parkers searching in those areas. For property partners, idle inventory becomes a new revenue stream with no upfront cost and no operational lift. The company employs 63 people across the business, with 15 based in Toronto. The wider commercial team includes 8 salespeople and 3 sales managers, with approximately 3 dedicated to the supply side. Clients include multi-billion-dollar REITs in major North American markets, mid-sized commercial and residential property managers, and individual asset owners.
The culture is described as chill, merit-based, and free of bureaucracy. Reps are given autonomy and the freedom to try new things. Executive leadership is hands-off but supportive. Onboarding is intentionally light — this is an environment where self-starters thrive and where culture fit alone is not enough; performance must also be present.
OFFICE LOCATION & SALES TERRITORY
- Head Office: Toronto, Ontario, Canada
- Work arrangement: Hybrid — 2 to 3 days per week in the Toronto office, balance from home
- Ideal candidate location: Greater Toronto Area; must be able to commute to the Toronto office 2 to 3 days per week
- Sales territory: Several assigned cities within the company’s seven to eight highest-traffic North American search markets, including Los Angeles, San Francisco, and other major US metros. These priority metros account for 60–80% of all parker search traffic. Specific city assignments are confirmed upon hire.
- Hours: Monday to Friday, 40 hours per week. No regularly scheduled evening or weekend work.
- Overnight travel: Minimal — approximately 2 to 3 trips per year for industry trade shows and in-person meetings with property owners and managers in priority markets
- Driver’s licence: Not required
EXPERIENCE, BACKGROUND & EDUCATION REQUIREMENTS
- 3 to 8 years of B2B sales experience with a demonstrated track record of sustained high-volume outbound cold calling
- Real estate, PropTech, or property management sales experience is strongly preferred — comfort with real estate vocabulary (landlord, asset manager, price per square foot, parking economics) significantly shortens ramp time
- Alternative backgrounds considered: B2B sales reps from any industry whose role required heavy phone-based prospecting into property owners or asset operators — including commercial janitorial services, commercial cleaning, building maintenance, parking technology, facilities services, and similar B2B service categories that cold-call into property managers
- Experience consistently making 50 to 60 outbound calls per day is required — this is a phone-first role
- Self-starter capable of building prospect lists, sourcing asset owner contact information independently, and operating with light onboarding and minimal hand-holding
- HubSpot CRM experience preferred; comfort with a modern CRM is required
- Education: Bachelor’s degree preferred, not required. High school diploma minimum.
- Bilingual: Not required
- Driver’s licence and vehicle: Not required
TECHNICAL SKILLS
- HubSpot CRM — Intermediate preferred
- Microsoft Office (Word, Excel, PowerPoint) — Basic
- Comfort navigating internal data tools, including a search-density heatmap, to identify high-demand zones
THE PRODUCT / SERVICE / SOLUTION
- An online marketplace platform that lists unused parking spots for monthly rent
- Supply-side listing engagement that turns idle parking inventory into a recurring revenue stream for property partners, with no upfront cost or operational lift
- Platform-managed listing, demand generation, and parker onboarding handled by the company on behalf of the property partner
PROSPECTIVE CUSTOMERS / INDUSTRY FOCUS / DECISION MAKER(S)
- Multi-billion-dollar REITs in major North American markets
- Mid-sized commercial and residential property management firms
- Individual asset owners — down to single-driveway listings
- Asset types: residential apartment buildings, commercial office buildings, industrial sites, and service-firm offices (law, accounting) with surplus or underused spots
- Primary decision-makers: property owners, asset managers, building operators, portfolio managers, and senior real estate executives
- Geographic focus: priority North American metros, including Los Angeles, San Francisco, and other major US cities
SALES CYCLE / ORDER VALUE / ACCOUNT SIZE
- This is a marketplace listing engagement, not a transactional sale at the point of contact — the rep is not asking for a credit card or payment
- Each signed property is a minimum 12-month engagement to list inventory on the platform
- Sales cycle varies by property type and decision-maker complexity — individual asset owners can move quickly; multi-billion-dollar REITs and large property management firms typically require a longer consultative engagement
- Revenue per signed account scales as parker inventory fills over time; commission is paid as a flat fee per parker signed to a contracted property
- Three-month pipeline benchmark: 5 to 10 agreements in pipeline; ideally 1st or 2nd building closed by month 3
COMPETITIVE ADVANTAGES
- No upfront cost or operational lift for property partners — idle parking becomes a new revenue stream
- Listing rates that match or sit slightly above the building’s tenant rate, keeping the offer simple to sell
- The company handles listing, demand generation, and parker onboarding on behalf of the property partner
- Established platform with active monthly parker demand across the highest-traffic North American search markets
- Proprietary internal search-density heatmap that identifies the neighbourhoods and intersections with the highest parker demand — reps prospect into validated zones, not cold geographies
- Member of a larger technology group with marketplace infrastructure and demand-generation resources in place
TYPICAL DAY & DUTIES
- 85% New Business Development
- 10% Administrative Duties (CRM logging, list building, pipeline management)
- 5% Customer Service / Partner Onboarding
On a typical day, you will make 50 to 60 outbound cold calls to property and asset owners, managers, and operators in your assigned high-demand metros. You will use the company’s internal search-density heatmap to identify the exact neighbourhoods and intersections with the highest parker demand, then research and build prospect lists of buildings within those zones. You will pursue all asset types where parking surplus exists — residential, commercial, industrial, and service-firm offices. Email follow-up supports phone outreach but does not replace it. Where useful, you may join local real estate associations and industry groups in priority metros to source property manager and owner contact information. You will log all activity, contacts, and pipeline in HubSpot, and onboard signed partners through the platform’s account setup process.
LEADS
- 75% self-prospected outbound / 25% warm inbound
- Outbound benchmark: 50 to 60 cold calls per day, consistently
- Self-prospected pipeline is built using the company’s internal search-density heatmap to identify high-demand zones, then researching buildings and contacts within those zones
- Warm inbound leads come from demand-side requests (parking groups needing inventory in a specific area) routed to the supply rep covering that geography
- Real estate associations, industry groups, and trade shows in priority metros are supplementary sources for contact information
- This is a phone-first role. Reps whose primary channel is email, social, or events will not succeed in this position.
OVERNIGHT TRAVEL
- Less than 5% overnight travel — approximately 2 to 3 trips per year
- Travel is for industry trade shows and in-person meetings with property owners and asset managers in priority markets
- Day-to-day selling is conducted by phone and email from the Toronto office or from home — travel is not part of the regular sales motion
SUPPORT & TRAINING
- Onboarding is intentionally light and designed for self-starters — this is not a hand-holding environment
- Hands-off but supportive leadership style from the Chief Revenue Officer and a sales manager with 3 years managing the team
- HubSpot CRM training and access to the internal search-density heatmap from Day 1
- Product and platform training provided — real estate vocabulary and asset-owner conversations are picked up quickly through coaching and daily activity
- Reps are expected to begin outbound prospecting within their first week
- Early performance bar: 5 to 10 signed agreements in pipeline within the first 3 months; 1st or 2nd building closed by month 3
WHY YOU SHOULD APPLY
- Uncapped commission paid monthly — earnings scale directly with parker volume across signed properties, with top performers earning approximately $185,000 CAD
- Net-new headcount on a rebuilding supply-side team — significant open runway across priority North American metros, not a saturated territory
- Scale-up company with 25–50% annual revenue growth and active investment in supply expansion following a recent executive offsite
- Merit-based, low-bureaucracy culture with real autonomy — reps are trusted to build their own prospect lists, run their own day, and own their results
- Career advancement to Sales Manager track within 2 to 3 years for high performers, plus stock options as part of the total compensation package
Equal Opportunity Employer
Just Sales Jobs and our clients are equal opportunity employers. We do not discriminate. All candidates are evaluated solely on performance merit and organizational fit.
Not the Right Fit? We May Have Other Roles for You.
If this particular role isn’t the right match, we encourage you to browse our other open positions at https://justsalesjobs.ca/jobs-opening/ and apply for any that interest you. Our recruiters review every resume we receive — and if we have another role that could be a great fit for your background, we will reach out to you directly.
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