Mid-Market Account Executive (Logistics)

TL;DR

Mid-Market Account Executive (Logistics): Managing the full sales cycle for high-value accounts in the transportation industry with an accent on consultative selling and ROI modeling. Focus on navigating multi-stakeholder procurement processes and positioning an AI-native operating system for logistics providers.

Location: Hybrid in Toronto (Office presence required Monday, Tuesday, and Thursday)

Salary: $100,000–$120,000 CAD plus commissions

Company

hirify.global is a venture-backed startup developing the first AI-native operating system designed specifically for the transportation and logistics industry.

What you will do

• Own the full sales cycle for mid-market opportunities with annual contract values ranging from $25,000 to $150,000.
• Lead multi-threaded discovery and strategic conversations with C-suite executives and operational stakeholders.
• Deliver tailored product demonstrations and build comprehensive ROI business cases for potential customers.
• Manage complex procurement cycles, including RFP responses, security reviews, and legal negotiations.
• Collaborate with solutions engineering and implementation teams to ensure a seamless transition from sale to onboarding.
• Oversee a book of business with a focus on long-term account growth, renewals, and expansions.

Requirements

• 3+ years of success in full-cycle software sales with experience closing mid-market deals.
• Expertise in consultative, value-based selling and ROI modeling.
• Strong executive presence and the ability to navigate complex organizations.
• Experience managing multi-year contract negotiations and procurement processes.
• Must be based in or able to work in a hybrid setup in Toronto.

Nice to have

• Track record of meeting or exceeding $750K+ ARR quotas.
• Experience selling TMS, WMS, or other supply chain software to carriers and brokers.
• Proficiency in structured sales methodologies such as MEDDIC or Challenger.
• Experience with HubSpot, Gong, Outreach, or LinkedIn Sales Navigator.
• Prior experience working within a high-growth startup environment.

Culture & Benefits

• Comprehensive benefits program and health care spending account.
• Stock option plan and parental leave top-up.
• Three weeks of vacation, winter office closure, and 3 personal days.
• High-end tech equipment, including a MacBook.
• Modern downtown Toronto office featuring a rooftop patio and in-house coffee shop.