Founding Account Executive

HRB; Toronto; On-site; CAD 120,000 - 210,000; Full time

Job summary

HRB in Toronto seeks its first Account Executive to own a high-impact revenue stream. You will drive revenue through aggressive outbound activity, managing the full sales cycle from prospecting to close, targeting mid-market and enterprise clients across insurance, software, financial services and logistics with deal sizes from $30K to $300K.

Expect a hunter role with a $1M+ annual quota, frequent collaboration with engineers and product leaders, and close partnership with the CEO to refine

Qualifications

• 3+ years of account executive experience.
• 1+ year of enterprise sales experience.
• Experience selling B2B SaaS products.
• Proficiency in technical products and APIs.
• Hunter mentality with a track record of building pipeline.
• Proactive with clear next steps in mind.
• Strong verbal and written communication skills.
• Willingness to coach and be coached.
• Located in Toronto and able to commute to the office 5X a week.

Responsibilities

• Own and drive at least $1M in annual revenue with quarterly quotas and monthly measurements.
• 90% outbound, 10% inbound—hunter role.
• Own full sales cycle: prospecting, discovery, value-building, closing, and expansion.
• Sell into mid-market and enterprise across insurance, software, financial services and logistics (deal sizes $30K-$300K).
• Build deep relationships with engineers, product leaders and executives (CTO, VP Product, VP Data Science).
• Collaborate with CEO to refine sales strategy, messaging, and systems.
• Provide feedback to engineering to improve product and identify new use cases.
• Maintain sales pipeline and forecasting hygiene with realistic views.

Skills

B2B SaaS

Enterprise sales

Forecasting

Pipeline building

Technical sales

Communication

Coachable

Startup experience

Job description

Since finishing YC, we’ve grown more than 15x and onboarded publicly traded companies—all without a single sales hire or outbound motion. We have more opportunities than we can follow up with. It’s time to bring on our first AE.

Companies building the next generation of insurance products, financial services and software for trucking use our Universal API to access GPS data, speeding data and vehicle stats.

Note: This role is only available to Toronto/GTA-based candidates

Responsibilities

• Own and drive at least $1M in annual revenue, with quotas confirmed quarterly and measured monthly.
• 90% outbound, 10% inbound—this role is for a hunter.
• Own the full sales cycle: prospecting, discovery, value-building, closing, and account expansion.
• Selling into mid-market and enterprise companies across insurance, software, financial services and logistics at deal sizes ranging from $30K to $300K.
• Build deep relationships with engineers, product leaders and executives (e.g. CTOs, VP Product, VP Data Science, etc.)—become a trusted product specialist and subject matter expert to our customers.
• Work directly with our CEO to refine our sales strategy, iterate on messaging, and build upon sales systems, tools and processes.
• Provide structured feedback to engineering to help improve our product and identify opportunities for new use cases that expand our total addressable market.
• Maintain sales pipeline and forecasting hygiene—always providing a realistic view with an understanding of what could accelerate or put key deals at risk

Requirements

• 3+ years of account executive experience
• 1+ year of enterprise sales experience
• Experience selling B2B SaaS products
• Proficiency in technical products and APIs
• A fearless hunter mentality and a track record of quickly building pipeline
• Track record of being extremely proactive and always having next steps in mind
• Strong communication skills–both verbal and written
• Willingness to both coach and be coached
• Previous experience in early-stage startups
• Located in Toronto and able to commute to the office 5X a week

Nice-to-Have

• Previous experience selling to insurance companies or financial institutions