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Added 7 mins ago
SL
Program Manager, Canadian Shared Services
Sun Life
Montreal, QC · Sun Life Montreal Metcalfe
- Full-time
What this means: highlights the “right hand to leadership” support – it’s anchored around enabling Canadian Shared Service LT to run the business effectively
Added 7 mins ago
CD
Vice-président(e), Marketing & Billetterie – Spectacles internationaux et Amériques | Vice President Marketing & Ticketing – International & Americas Shows
Cirque du Soleil Entertainment Group
Montreal, QC
- Full-time
Added 22 mins ago
SQ
AVP, Technology Lead - Digital
Sunlife Québec
Montreal, QC
- Full-time
Partner with Chapter, Engineering, Product, and Business leaders on workforce planning, role clarity, succession planning, and capability development.
Added 37 mins ago
C
Customer Success Manager, Public Sector & Defence
Cohere
Ottawa, ON
- $150,000 to $215,000 USD / year
- Full-time
Conduct regular executive business reviews with senior stakeholders, demonstrating ROI, impact, and strategic value
Added 37 mins ago
A
Technology Strategy & Transformation Senior Manager
Accenture
Toronto, ON · Montreal, QC
- Full-time
…technology and innovation as a force to reinvent and improve every business. Our mission is to help client business executives disrupt their industry and utilize technology to capture…
Added 37 mins ago
WK
Sales Programs Manager, FCC Division
Wolters Kluwer
Toronto, ON · CAN - North York
- Full-time
Work closely with Sales Strategy, Revenue Operations, Marketing, Business Development, Enablement, Product Marketing and Customer Success to align programs with broader go-to-market…
Added 1 hour ago
TD
Program Manager
Teifi Digital
Vancouver, BC
- $135,000 to $175,000 CAD / year
Partner with sales and account leadership to identify opportunities for account growth, surfacing new business needs and helping scope subsequent engagements
Added 1 hour ago
D
Chief Solution Architect (Pre-sales, AI + Data Transformation)
Datatonic
Remote, Canada
- Full-time
- Remote
Lead early discovery alongside Sales: understand business pain points, qualify opportunities, and translate ambiguity into structured technical narratives.
Added 1 hour ago
Director, Strategic Partnerships
Clutch Technologies Inc.
Toronto, ON
This is a builder’s role, not a sponsorship or account-management position. You’ll find the opportunity, build the business case, win the partner, negotiate the economics, lead the launch…
Added 1 hour ago
Product Security Lead
SMART Technologies
Calgary, AB
Provide cybersecurity guidance to Product, Engineering, Sales, Customer Success, Legal, and Executive Leadership.
Added 1 hour ago
GT
Communications Specialist
Global Technical Talent, an Inc. 5000 Company
Toronto, ON
- $55 to $60 CAD / hour
- Contract
Contract Duration: 6 months (with possibility of extension and conversion based on business needs and performance)
Added 2 hours ago
GS
Manager, Sales – SmartRock North America
Giatec Scientific Inc.
Ottawa, ON
- Full-time
We’re hiring a Manager, Sales to lead our North American SmartRock team, reporting to the Global Director of Sales, SmartRock. You’ll lead a blended team of Business Development…
Added 2 hours ago
MI
Salesforce Technical Lead
Maarut Inc
Montreal, QC
- Contract
Mastery of Financial Services Cloud, Sales Cloud and Service Cloud
Added 2 hours ago
T
Customer Evolution Manager, SAP AMS
Talan
Toronto, ON · Montreal, Québec
- $140,000 to $200,000 CAD / year
- Full-time
…roadmap. Structure and qualify each opportunity by defining the business problem, expected value, stakeholders, urgency, preliminary scope, and next steps, then collaborate with Sales and…
Added 2 hours ago
JA
Business Development Manager – Substation Services & Lifecycle Solutions
JR Automation
BC · British Columbia, Canada
- Full-time
8+ years of experience in business development, service sales, account management, or power industry sales leadership.
Added 2 hours ago
Senior Business Development Representative - Future Consideration
D2L
Kitchener, ON
Do you have a keen interest in eLearning? Are you looking to start a career in Sales? Good news! You have found the right opportunity to get you started. We are always on the hunt for our…
Added 2 hours ago
Business Development Representative - Future Consideration
D2L
Kitchener, ON
Do you have a keen interest in eLearning? Are you looking to start a career in Sales? Good news! You have found the right opportunity to get you started. We are always on the hunt for our…
Added 3 hours ago
JA
Business Development Manager – Substation Services & Lifecycle Solutions
JR Automation
Stoney Creek, NB
- Full-time
8+ years of experience in business development, service sales, account management, or power industry sales leadership.
Added 3 hours ago
J
Senior Lifecycle Marketing Manager
Jobber
Remote, Canada
- Full-time
- Remote
Through your work with our Business Operations, Marketing, Sales, Success, Product, and Growth teams, you'll create great user experiences at scale and conduct experiments to discover what…
Added 3 hours ago
Q
Account Executive - Hamilton, Ontario (Entry Level)
Quadient
Hamilton, ON
- Full-time
…motivated early-career professionals who want to build valuable business skills, earn competitive compensation, and grow into high-performing sales…
Added 3 hours ago
H
Senior Product Marketing Manager
Hach
Vancouver, BC · London, ON · CAN - Vancouver - Aquatic Informatics ULC
- $125,000 to $150,000 CAD / year
- Full-time
…geographic location, performance, shift, travel requirements, sales or revenue-based metrics, any collective bargaining agreements, and business or organizational…
Added 3 hours ago
BS
Managed Service Director
Bulletproof Solutions Inc
Toronto, ON
- Full-time
Strong communication and executive presence, able to present complex operational details in a clear, business-focused manner.
Added 3 hours ago
KE
Senior Program Manager
Kitchener Executive Consultants Inc
Cambridge, ON
- Full-time
Kitchener Executive Consultants Inc. has partnered with our Client, an established manufacturer of highly engineered, precision components serving demanding and regulated industries, in…
Added 4 hours ago
SL
AVP, Technology Lead - Digital
Sun Life
Toronto, ON · Waterloo, ON · Montreal, QC · Sun Life Toronto One York
- Full-time
Partner with Chapter, Engineering, Product, and Business leaders on workforce planning, role clarity, succession planning, and capability development.
Added 4 hours ago
Sales Account Executive
Aspen Technology
Montreal, QC
The Sales Account Executive is responsible for identifying, developing, and closing business for assigned customer accounts, including consultative upselling of solutions and services at…

Rose Rocket

Mid-Market Account Executive

Remote, Canada

Remote

Full-time

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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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