Mid-Market Account Executive
Rose RocketJobsCloseBy Editorial Insights
Rose Rocket is hiring a Mid-Market Account Executive to own the full sales cycle for complex $25,000 to $150,000 ACV deals in trucking, logistics, and freight brokerage, reporting to the CEO in a hybrid Toronto role. The ideal candidate combines three-plus years of full-cycle software sales, executive-level storytelling, ROI modeling, and strong negotiation with the ability to navigate multi-stakeholder procurement and RFPs. Success hinges on disciplined pipeline management, consultative value selling, and partnering with solutions engineering and implementation teams to ensure a seamless post sale handoff. To apply, tailor your ROI case studies to transportation use cases, demonstrate MEDDIC or Challenger usage, and show measurable quota attainment.
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
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.
What You Need to Succeed
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 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.
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.
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
Joining Rose Rocket means becoming part of a pivotal moment: we're developing the first AI-native operating system for the transportation industry, and you'll be at the heart of this journey.
As our Mid-Market AE, you will 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.
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.