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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 ranging 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

Consistently meet and exceed quota while providing exceptional value to customers.
Maintain rigorous pipeline hygiene, accurate forecasting, and detailed CRM documentation.
Build and manage a robust pipeline of mid-market prospects in the trucking, logistics, and freight brokerage space.
Sell the first AI-native operating system built for the transportation industry.
Operate as an AI-native seller using modern AI tools and workflows.
Lead sophisticated, multi-threaded discovery across economic buyers, technical evaluators, and operational stakeholders.
Build comprehensive business cases.
Deliver tailored, outcomes-oriented product demonstrations and proof-of-concept engagements.
Navigate complex procurement cycles, including RFP responses, security reviews, and legal negotiations.
Develop and execute account plans with clearly defined stakeholder maps and champion strategies.
Construct and present compelling ROI models and business cases to executives.
Partner closely with solutions engineering, marketing, and implementation teams before and after close.
Manage your 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

Three or more years of success in a full-cycle software sales role.
Demonstrable experience closing mid-market deals of significant size and complexity.
Deep expertise in consultative and value-based selling.
Experience building ROI models and executive-level business cases.
Executive presence and excellent communication skills.
Ability to navigate complex organizations and lead strategic conversations with senior stakeholders.
Experience driving contract negotiations, including multi-year commitments and procurement processes.
High resilience, adaptability, and comfort operating in a rapidly changing environment.
A team-first mindset with the ability to work autonomously and take initiative.
Genuine curiosity about modern tools and methodologies.
Strong desire to deeply understand customer businesses.

Skills

Consultative selling
Value-based selling
ROI modeling
Executive-level business case development
Contract negotiation
Pipeline management
Forecasting
CRM documentation
Prospecting
Account planning
Stakeholder mapping
AI tools and workflows
Modern sales enablement tools (e.g., Gong, Outreach, LinkedIn Sales Navigator)
CRM systems (e.g., HubSpot)

Location

Downtown Toronto

Work Type

Hybrid

Experience Level

Mid-Market
Senior

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.
We help carriers, brokers, and logistics providers run their business more efficiently.
We are a fast-growing, venture-backed startup.
We are taking on the $700+ billion dollar trucking industry.
We have a 'more human, less corporate' culture built around doing work that matters, winning as a team, and celebrating success.

Equal 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.
Rose Rocket may use artificial intelligence–enabled tools as part of our recruitment and hiring process to support activities such as screening or organizing applications. All hiring decisions are made by our team.