Mid-Market Account Executive

Rose Rocket • Toronto, ON

1d • CA$100,000 - CA$120,000 • Hybrid

About The Position

As a Mid-Market Account Executive, you'll be central to Rose Rocket's growth, owning the full sales cycle for our most complex and high-value opportunities, accounts ranging from $25,000 to $150,000 in annual contract value. You'll navigate multi-stakeholder buying processes, build relationships at the executive level, and position Rose Rocket as a strategic platform investment rather than a point solution. It's a role built for a consultative seller, someone comfortable managing longer, structured sales cycles and focused on delivering real return on investment for customers. You'll report directly to our CEO and play a key role in shaping our go-to-market strategy. Beyond your responsibilities, you'll be part of a team that values both culture and performance. We prioritize curiosity and collaboration just as much as results, and those who have been here will tell you that the relationships built at Rose Rocket last well beyond the job itself.

Requirements

• Three or more years of success in a full-cycle software sales role, with demonstrable experience closing mid-market deals of this size and complexity.
• Deep expertise in consultative and value-based selling, with experience building ROI models and executive-level business cases.
• Executive presence and excellent communication skills: the ability to navigate complex organizations with poise and levity, and lead strategic conversations with senior stakeholders, from champions to C-suite decision-makers.
• Experience driving contract negotiations, including multi-year commitments, custom pricing structures, and procurement or legal review processes.
• High resilience, adaptability, and comfort operating in a rapidly changing environment.
• A team-first mindset, with the ability to work autonomously, take initiative, and contribute across internal teams.
• Genuine curiosity about the most modern tools and methodologies, and a strong desire to deeply understand how our customers' businesses run.

Nice To Haves

• A consistent track record of meeting or exceeding quota, ideally $750K or more in annual recurring revenue, in roles involving complex, multi-stakeholder sales.
• Strong prospecting ability and comfort generating your own pipeline, including outbound motion and strategic account targeting.
• 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 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 procurement processes in mid-market or enterprise environments.
• Familiarity with CRM systems like HubSpot and modern sales enablement tools such as Gong, Outreach, or LinkedIn Sales Navigator.
• Experience working in a startup or high-growth company.

Responsibilities

• Consistently meet and exceed quota while providing exceptional value to customers, maintaining rigorous pipeline hygiene, accurate forecasting, and detailed CRM documentation.
• Build and manage a robust pipeline of mid-market prospects across the trucking, logistics, and freight brokerage space, with a focus on accounts in the $25K–$150K ACV range.
• Sell the first AI-native operating system built for the transportation industry, and operate as an AI-native seller yourself by using modern AI tools and workflows to unlock greater ROI for customers and sharpen your own performance.
• 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.
• Partner closely with solutions engineering, marketing, and our FDS implementation team before close to deliver a seamless, high-caliber buying experience, and after close to ensure a smooth handoff and maintain relationships with key stakeholders through onboarding.
• Manage your book of business, with a focus on renewals, expansion, and long-term account growth.
• Surface market intelligence, customer feedback, and industry trends, including competitive dynamics and regulatory developments, to inform product strategy, competitive positioning, and go-to-market approach.

Benefits

• A comprehensive benefits program and health care spending account.
• Parental leave top-up.
• Stock option plan.
• A MacBook and a sweet tech equipment combo to get you started.
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed