Mid-Market Account Executive

About Rose Rocket

Rose Rocket 🚀 has built the first AI-native operating system for the transportation industry, helping carriers, brokers, and logistics providers run their business more efficiently, from dispatch and billing to customer visibility and analytics. We're a fast-growing, venture-backed startup taking on the $700+ billion dollar trucking industry, with a 'more human, less corporate' culture built around doing work that matters, winning as a team, and celebrating success. We'd love to hear from you if you want to build this with us.

We understand that joining a team is one of the most important decisions you make ❤️, and adding a team member is one of the most important decisions we'll make. Through our process, we want you to get to know us and understand how you approach problems, learn, and what motivates you.

About the Role

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.

What You'll Do

• 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.

• 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.

• 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.

What You Bring

• Executive presence and the poise to navigate complex organizations with grace and levity.

• A genuine curiosity about modern tools and methodologies, and a drive to stay ahead of them.

• A real desire to understand how our customers' businesses actually run.

• 3+ years of software sales success, including a track record of closing mid-market deals at $25K+.

• Resilience and adaptability, with comfort operating in a fast-changing environment.

• Deep expertise in consultative, value-based selling, including building ROI models and executive-level business cases.

Nice to Have

• A consistent track record of meeting or exceeding quota, ideally $750K or more in annual recurring revenue, in roles involving complex, multi-stakeholder sales.

• 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.

• Strong prospecting ability and comfort generating your own pipeline, including outbound motion and strategic account targeting.

• Strong command of a structured sales methodology (e.g., MEDDIC, Challenger) and the discipline to apply it consistently across your pipeline.

The expected salary range for this role is $100,000–$120,000 CAD plus eligibility for non-discretionary commission under our sales compensation plan.

This range reflects the scope of the role, relevant experience, and opportunities for growth. Most new hires join between the minimum and midpoint of the range, with the upper end typically reserved for team members who demonstrate sustained high performance and impact over time.

Final compensation will be determined based on experience, skills, and overall fit for the role.

Why Join Rose Rocket

Simply put, Rose Rocket is an intriguing balance of culture and performance. We are deeply committed to exploring the most advanced technologies and methodologies while enjoying the community we have crafted together. We are not the biggest nor the richest start-up around, but we are the most curious by far. Ask any of our current or former team mates, they would rank Rose Rocket as among the greatest places they have ever worked, forming bonds that last far far beyond our tenureship together.

Don’t sweat it if you don’t have everything listed above. We believe in growth and curiosity. If you have some of these qualities and are excited about this opportunity, then we want to hear from you!

Perks & Benefits at Rose Rocket

🏥 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.

🏝 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.

☕️ Hybrid structure, where we're in office together on Monday, Tuesday, and Thursdays, and WFH (optional) on Wednesday and Fridays.

Equal Employment Opportunity

Rose Rocket does not discriminate in hiring or terms and conditions of employment because of an individual’s race, ancestry, colour, place of origin, religion, gender, gender identity, national origin, citizenship, age, disability, sexual orientation, family status or marital status, or any other protected category recognized by provincial or federal laws.

Should you require any accommodation, please inform us and we will work with you to meet your accessibility needs. For any accessibility-related assistance, requests for information in accessible alternative formats or to report any accessibility problems, please share in your application or email [email protected].

Artificial Intelligence in Hiring

Rose Rocket may use artificial intelligence–enabled tools as part of our recruitment and hiring process. These tools are used to support our team with activities such as screening or organizing applications and do not replace human decision-making. All hiring decisions are made by our team, with care and consideration for each candidate.