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Added 7 mins ago
UH
Clinical Nurse Specialist, Cancer Prevention and Interception Clinic
University Health Network
Toronto, ON
- Full-time
Lead intake, assessment, triage, and patient navigation for Cancer Prevention & Interception Clinic referrals, ensuring timely access to appropriate clinical and research pathways
Added 7 mins ago
CM
Senior Regulatory Specialist, AI/ML Projects
Clarius Mobile Health
Toronto, ON
- Temporary
…teams in defining and executing regulatory strategies for AI/ML-enabled medical devices. You'll need deep expertise in the regulatory landscape for AI/ML devices, including AI/ML design and…
Added 21 mins ago
CO
Manager, Digital Solutions
City of Saint John
Saint John, NB
- Full-time
…information management functions. This role ensures that corporate systems - including major enterprise systems and other business applications - are reliable, secure, and aligned with…
Added 21 mins ago
B
Managing Director - Cybersecurity & Core Technology Audit
BMO
Toronto, ON · FCP
- Full-time
…support, operational resilience, physical security, and technology-enabled transformation programs. Operating within the Technology & Operations Audit mandate, the role identifies…
Added 36 mins ago
O
Senior Manager, Data & AI Technology
OLG
Sault Ste. Marie, ON · Toronto, ON · Foster Drive Office
- Full-time
Lead the strategy, operations, support, and lifecycle management of enterprise analytics and customer data technologies, including Power BI, Alteryx, ArcGIS, IBM WatsonX, RecordPoint, the…
Added 37 mins ago
B
Data Integrity Lead
BGIS
Toronto, ON
- Full-time
The Data Integrity Lead is the Quality Assurance (QA) and Data Governance owner for the integrity and assurance of all operational and planning data used across the CIBC Integrated…
Added 1 hour ago
W
Manager, Software (Embedded & Digital Products)
Wabtec
London, ON
- Full-time
As the Manager, Software (Embedded & Digital Products), you will report to the Manager, Engineering & Products and lead a multidisciplinary software organization responsible for embedded…
Added 1 hour ago
B
QA Automation Lead – ATM/POS/DCC Payments
BeachHead
Toronto, ON
- $65 to $70 CAD / hour
- Contract
Are you an experienced QA Test Lead ready to drive automation and lead testing efforts? Apply Now!
Added 1 hour ago
WC
Manager, Software (Embedded & Digital Products)
Wabtec Corporation
London, ON
- Full-time
As the Manager, Software (Embedded & Digital Products), you will report to the Manager, Engineering & Products and lead a multidisciplinary software organization responsible for embedded…
Added 1 hour ago
C
Manager, Machine Learning (Canada)
Clio
Calgary, AB · Vancouver, BC · Toronto, ON
- Full-time
Lead a team of ML engineers to bring state of the art AI to Clio's clients, spanning primarily with agentic systems and LLMs, along with traditional machine learning models.
Added 2 hours ago
RR
Mid-Market Account Executive
Rose Rocket
Remote, Canada
- Full-time
- Remote
Lead sophisticated, multi-threaded discovery across economic buyers, technical evaluators, and operational stakeholders to build comprehensive business cases.
Added 2 hours ago
Senior Transformation Director
D2L
Kitchener, ON · Toronto, ON
…since neither produces a result on its own. Functional teams lead the change in their own areas, supported by the method, patterns, and enablement this role provides, which keeps ownership…
Added 2 hours ago
Manager, Software Engineering
KEV Group
Toronto, ON
…managed, replacing fragmented workflows with secure, modern systems that schools rely on every…
Added 2 hours ago
SQ
Director, Domain Enterprise Architect, Technology Modernization and Cloudification
Sunlife Québec
Montreal, QC
- Full-time
Lead AI-enabled automation projects that accelerate technology discovery, estate analysis, dependency mapping, migration planning, remediation, testing, and architecture documentation.
Added 2 hours ago
FI
Quality Engineer Lead
FP Inc.
Waterloo, ON
- $75 to $90 CAD / hour
- Contract
Experience testing cloud-based APIs, including exposure to AI-enabled or automated test generation tools
Added 2 hours ago
WC
Manager, Software (Embedded & Digital Products)
Wabtec Corporation
London, ON
- Full-time
As the Manager, Software (Embedded & Digital Products), you will report to the Manager, Engineering & Products and lead a multidisciplinary software organization responsible for embedded…
Added 3 hours ago
S
Lead Instructional Designer
SafetyCo
Toronto, ON · Greater Toronto Area, Canada
- Contract
We’re looking for a Lead Instructional Designer to establish the instructional vision for SafetyCoLabs and build the standards that every learning experience will follow. This is not a…
Added 3 hours ago
LP
Administration & Yardi Operations Team Lead (Condominium)
Larlyn Property Management
London, ON
- Full-time
join our growing team as Administration & Yardi Operations Team Lead (Condominium Management). This leadership role is responsible for driving operational excellence, elevating team…
Added 6 hours ago
HT
VP, Accounting & Controllership (Husky)
Husky Technologies
Bolton, ON
- Full-time
At Husky TechnologiesTM, our success is based on your success. Our ability to keep our customers in the lead is based on building the strongest team possible.
Added 6 hours ago
TT
Lead Mechanical CAD Designer
Tetra Tech
Thunder Bay, ON
- Full-time
Tetra Tech is adding a Lead Mechanical CAD Designer to our Mechanical team based in Thunder Bay, ON . This is a new vacant position for which we are actively recruiting.
Added 6 hours ago
OI
Career Services Advisor
Oxford International
Halifax, NS
- $52,000 to $56,000 CAD / year
- Full-time
- Temporary
Lead individual and group career advising sessions focused on résumé development, interview preparation, job-search strategies, workplace professionalism, and networking skills.
Added 6 hours ago
OI
Career Services Advisor
Oxford International Education Group
Halifax, NS
- $52,000 to $56,000 CAD / year
- Full-time
Lead individual and group career advising sessions focused on résumé development, interview preparation, job-search strategies, workplace professionalism, and networking skills.
Added 7 hours ago
WC
Business Development Representative (2026-397-CP)
WoodGreen Community Services
Toronto, ON
- Contract
Using data-driven outreach strategies, market intelligence, and AI-enabled prospecting tools, the BDR converts employer interest into Sales Qualified Leads (SQLs) and hiring activity.…
Added 10 hours ago
AT
Business Systems Analyst
Aarorn Technologies Inc
Toronto, ON
- $60 CAD / hour
- Contract
7+ years of Business Systems Analysis experience in enterprise environments.
Added 11 hours ago
CO
Manager, Digital Solutions
City of Saint John
Saint John, NB
- Full-time
…information management functions. This role ensures that corporate systems - including major enterprise systems and other business applications - are reliable, secure, and aligned with…

Rose Rocket

Mid-Market Account Executive

Remote, Canada

Remote

Full-time

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Applications open in a new tab.

Job details

Job type: Full-time
Workplace: Remote
Posting language: English
Posted: Oct 28, 2026

Original job description

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 careers@roserocket.com.

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.

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More about this job

Responsibilities

Own the full sales cycle for mid-market opportunities, from pipeline development and multi-stakeholder discovery through demonstrations, business cases, procurement, and contract negotiation. Manage account plans and customer relationships, support successful onboarding handoffs, drive renewals and expansion, and share market insights to inform company strategy.

Requirements

Candidates need at least three years of successful software sales experience, including closing mid-market deals of $25,000 or more, and expertise in consultative, value-based selling. They should be resilient and adaptable, comfortable navigating complex organizations, and skilled at building ROI models and executive-level business cases.

Skills

Software Sales
Mid-Market Sales
Consultative Selling
Value-Based Selling
Pipeline Management
Sales Forecasting
CRM Documentation
Executive Relationship Building
Multi-Stakeholder Discovery
Product Demonstrations
Proof-of-Concept Management
ROI Modeling
Business Case Development
Account Planning
Negotiation
Prospecting

Benefits

Health Benefits
Health Care Spending Account
Parental Leave Top-Up
Stock Options
MacBook and Technology Equipment
Three Weeks of Vacation
Option to Purchase an Additional Vacation Week
Winter Holiday Office Closure
Three Personal Days
Hybrid Work Arrangement

Visa sponsorship

Not detected in the job text

Keywords

AI-Native Operating System
Transportation Industry
Trucking
Logistics
Freight Brokerage
Warehouse Management System
Fleet Management
Supply Chain Software
Dispatching
Billing
Compliance
Annual Contract Value
Pipeline Management
Sales Forecasting
CRM
HubSpot
Gong
Outreach
LinkedIn Sales Navigator
MEDDIC
Challenger
RFP
Security Reviews
Procurement
ROI Models
Proof of Concept
Account Planning
Renewals
Expansion

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