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About the Role
As a Mid-Market Account Executive, you will own the full sales cycle for high-value opportunities, managing accounts with annual contract values from $25,000 to $150,000. This role requires navigating complex buying processes, building executive relationships, and positioning Rose Rocket as a strategic platform investment. It is designed for a consultative seller experienced in managing structured sales cycles and focused on delivering customer ROI.
Responsibilities
- Sell the first AI-native operating system built for the transportation industry, utilizing AI tools to enhance customer ROI and personal performance.
- Meet and exceed quota, provide exceptional customer value, maintain pipeline hygiene, accurate forecasting, and CRM documentation.
- Build and manage a pipeline of mid-market prospects in trucking, logistics, and freight brokerage, targeting accounts in the $25K–$150K ACV range.
- Lead multi-threaded discovery with economic buyers, technical evaluators, and operational stakeholders to build business cases.
- Deliver tailored product demonstrations and proof-of-concept engagements aligned with customer priorities.
- Navigate complex procurement cycles, including RFPs, security reviews, legal negotiations, and multi-year contracts.
- Develop and execute account plans with stakeholder maps, champion strategies, and success timelines.
- Construct and present compelling ROI models and business cases to executives.
- Partner with solutions engineering, marketing, and implementation teams for a seamless buying experience and smooth handoff.
- Manage book of business, focusing on renewals, expansion, and long-term account growth.
- Surface market intelligence, customer feedback, and industry trends to inform product strategy and go-to-market approach.
Requirements
- Executive presence and ability to navigate complex organizations.
- Curiosity about modern tools and methodologies, with a drive to stay ahead.
- Desire to understand customer businesses.
- 3+ years of software sales success, including closing mid-market deals at $25K+.
- Resilience and adaptability in a fast-changing environment.
- Deep expertise in consultative, value-based selling, including building ROI models and executive business cases.
Skills
- AI tools and workflows
- Pipeline management
- Forecasting
- CRM documentation
- Consultative selling
- Value-based selling
- ROI modeling
- Business case development
- Product demonstrations
- Proof-of-concept engagements
- Procurement processes
- RFP responses
- Security reviews
- Legal negotiations
- Contract negotiation
- Account planning
- Stakeholder mapping
- Champion strategy development
- Market intelligence
- Customer feedback analysis
- Industry trend analysis
- Competitive analysis
- Regulatory development analysis
- Prospecting
- Outbound sales
- Strategic account targeting
- Sales methodology application (e.g., MEDDIC, Challenger)
Location
- Downtown Toronto office
Work Type
- Hybrid
- Full-time
Experience Level
- Mid-Market
- 3+ years of software sales experience
- Experience selling complex, multi-stakeholder deals
- Experience in a startup or high-growth company
Salary/Compensations
- $100,000–$120,000 CAD plus eligibility for non-discretionary commission
Benefits
- Comprehensive benefits program and health care spending account
- Parental leave top-up
- Stock option plan
- MacBook and tech equipment
- Three weeks of vacation (with option to purchase an additional week)
- Winter holidays office closure
- 3 personal days
- Downtown Toronto office perks (in-house coffee shop, pizza oven, rooftop patio)
About the Company
- Rose Rocket has built the first AI-native operating system for the transportation industry, helping carriers, brokers, and logistics providers operate more efficiently.
- We are a fast-growing, venture-backed startup targeting the $700+ billion trucking industry.
- Our culture is 'more human, less corporate,' focused on doing meaningful work, teamwork, and celebrating success.
- We are deeply committed to exploring advanced technologies and methodologies while enjoying our community.
- We are the most curious startup, with team members ranking Rose Rocket as one of the greatest places they have worked.
Equal Opportunity
- Rose Rocket does not discriminate in hiring or terms and conditions of employment based on 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.
- We provide accommodation for individuals with accessibility needs.
- Rose Rocket may use artificial intelligence-enabled tools to support recruitment activities such as screening or organizing applications, but all hiring decisions are made by our team.