Mid-Market Account Executive

Rose Rocket is a market leader in Transportation Management Software. Were a startup going after the $700 billion dollar trucking industry leading the shift to SaaS while revolutionizing the way trucking companies sell service and innovate. We are a more human less corporate culture that is built around doing work that matters winning as a team and celebrating success. Wed 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 well make. Through our process we want you to get to know us and understand how you approach problems learn and what motivates you.

As a Mid-Market Account Executive you will be a critical driver of Rose Rockets growth by owning the full sales cycle for our most complex and high-value opportunities targeting accounts in the $25000$100000 ACV range. Youll navigate multi-stakeholder buying processes build executive-level relationships and position Rose Rocket as a strategic platform investment not just a point solution. This role requires a consultative seller with a track record of managing longer more structured sales cycles and delivering measurable business outcomes for customers.

What Youll Do

• Build and manage a robust pipeline of mid-market prospects across the trucking logistics and freight brokerage space with a focus on accounts with $25K$100K annual contract value.

• 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 customers 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 to deliver a seamless and high-caliber buying experience.

• Work cross functionally with our FDS team post-close to ensure a smooth handoff maintain executive-level relationships through onboarding and identify expansion opportunities within your accounts.

• Manage your book of business with a focus on customer renewals expansion and long-term account growth.

• Consistently meet and exceed quota while maintaining rigorous pipeline hygiene accurate forecasting and detailed CRM documentation.

• Surface market intelligence and customer feedback to inform product strategy competitive positioning and go-to-market approach.

• Stay informed on logistics industry trends emerging technologies competitive dynamics and regulatory developments.

What You Bring

• Five or more years of success in a full-cycle SaaS sales role with demonstrable experience closing mid-market deals in the $25K$100K ACV range.

• 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.

• Deep expertise in consultative and value-based selling with experience building ROI models and executive-level business cases.

• 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.

• Excellent communication skills and the ability to 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 influence without authority across internal teams.

• Curiosity and a desire to deeply understand how our customers businesses run.

Nice to Have

• 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 $100000$130000 CAD commission.

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

Youll be joining a company that is changing how freight moves. The work you do will have a tangible impact on an industry that keeps the economy running. We offer a competitive base salary with an aggressive performance-based structure calibrated for mid-market deal sizes meaningful equity participation and strong opportunities for growth. Youll have the deal complexity to sharpen your skills the freedom to make decisions and the satisfaction of seeing your work drive real customer success.

Dont sweat it if you dont 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 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 were in office together on Monday Tuesday and Thursdays and WFH (optional) on Wednesday and Fridays

Use of AI in Hiring

We may use automated tools or artificial intelligence to support parts of our recruitment process such as resume screening. These tools help streamline the process and assist our team they do not replace human decision-making.

Equal Employment Opportunity

Rose Rocket does not discriminate in hiring or terms and conditions of employment because of an individuals 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

Required Experience:

IC