rose%20rocket
Mid-Market Account Executive
At a Glance
- Location
- Toronto, Canada
- Employment
- FULL_TIME
- Compensation
- es, targeting accounts in the $25,000–$100,000 ACV range. You’ll navigate mu
- Department
- Rose Rocket
- Posted
- 2026-03-24
Key Requirements
Required Skills
Domain Knowledge
- Engineering
- Legal
- Logistics
- Marketing
- Regulatory
- SaaS
- Supply Chain
Benefits & Perks
at Rose Rocket 🏥 A comprehensive benefits program + health care spending account
Requirements
Five or more years of success in a full-cycle SaaS sales role, with demonstrable experience closing mid-market deals in the $25K–$100K+ ACV range.
Deep expertise in consultative and value-based selling, with experience building ROI models and executive-level business cases.
Proven ability to manage and advance multi-threaded deals involving economic buyers, champions, technical evaluators, and procurement teams simultaneously.
Strong command of a structured sales methodology (e.g., MEDDIC, Challenger) and the discipline to apply it consistently across your pipeline.
Experience driving contract negotiations, including multi-year commitments, custom pricing structures, and procurement or legal review processes.
Curiosity and a desire to deeply understand how our customers’ businesses run.
Compensation & Benefits
🏥 A comprehensive benefits program + health care spending account
🐣 Parental leave top-up
💰 Stock option plan
💻 A Macbook and a sweet tech equipment combo to get you started
🏝 Start with three weeks of vacation (with an option to purchase an additional week every year) + winter holidays office closure and 3 personal days!
💼 Downtown Toronto office complete with an in-house coffee shop, pizza oven, rooftop patio and a few other lifestyle perks that keep our days fun
Responsibilities
Build and manage a robust pipeline of mid-market prospects across the trucking, logistics, and freight brokerage space, with a focus on accounts with $25K–$100K annual contract value.
Lead sophisticated, multi-threaded discovery across economic buyers, technical evaluators, and operational stakeholders to build comprehensive business cases.
Deliver tailored, outcomes-oriented product demonstrations and proof-of-concept engagements that map directly to each customer’s operational priorities.
Navigate complex procurement cycles including RFP responses, security reviews, legal negotiations, and multi-year contract structures.
Develop and execute account plans with clearly defined stakeholder maps, champion strategies, and mutual success timelines.
Construct and present compelling ROI models and business cases that justify investment at the executive level.