Mid-Market Account Executive (AI)

Location: Toronto, Ontario, Canada; hybrid with office attendance on Monday, Tuesday, and Thursday and optional work from home on Wednesday and Friday.

Salary: $100,000–$120,000 CAD annually, plus eligibility for non-discretionary commission.

Company

hirify.global is a venture-backed startup building an AI-native operating system for carriers, brokers, and logistics providers, covering dispatch, billing, customer visibility, and analytics.

What you will do

• Own the full sales cycle for mid-market opportunities with annual contract values of $25,000–$150,000.
• Build and manage a pipeline across trucking, logistics, and freight brokerage accounts while meeting or exceeding quota.
• Lead multi-threaded discovery, tailored demonstrations, proof-of-concept engagements, and executive-level ROI presentations.
• Navigate RFPs, security reviews, legal negotiations, procurement processes, and multi-year contracts.
• Create account plans, stakeholder maps, champion strategies, and mutual success timelines.
• Partner with solutions engineering, marketing, and implementation teams through close, onboarding, renewals, and expansion while sharing market intelligence with product and go-to-market teams.

Requirements

• 3+ years of successful software sales experience, including closing mid-market deals of $25K or more.
• Deep expertise in consultative, value-based selling, including ROI models and executive-level business cases.
• Executive presence and the ability to navigate complex organizations with poise.
• Curiosity about modern tools and methodologies and a desire to understand how customers operate.
• Resilience and adaptability in a fast-changing environment.

Nice to have

• A consistent quota-attainment record, ideally including $750K or more in annual recurring revenue.
• Experience selling to carriers, brokers, or logistics providers, ideally TMS, WMS, fleet management, or adjacent supply chain software.
• Knowledge of transportation workflows such as dispatching, billing, compliance, and fleet management.
• Familiarity with formal mid-market or enterprise procurement processes.
• Experience with HubSpot, Gong, Outreach, or LinkedIn Sales Navigator.
• Startup or high-growth company experience.
• Strong outbound prospecting, strategic account targeting, and self-generated pipeline skills.
• Experience with structured sales methodologies such as MEDDIC or Challenger.

Culture & Benefits

• Hybrid work structure with a downtown Toronto office.
• Comprehensive benefits program, health care spending account, and parental leave top-up.
• Stock option plan, MacBook, and technical equipment.
• Three weeks of vacation at start, optional purchase of an additional week annually, winter holiday office closure, and three personal days.
• Culture focused on curiosity, meaningful work, teamwork, growth, and advanced technologies and methodologies.

Hiring process

• The process is designed to assess problem-solving, learning approach, motivation, and fit with the role.
• Accommodation requests can be included in the application or sent to careers@roserocket.com.