Mid-Market Account Executive at Rose%20rocket

Rose Rocket 🚀 is a market leader in Transportation Management Software. We’re 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. 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.  As a Mid-Market Account Executive, you will be a critical driver of Rose Rocket’s growth by owning the full sales cycle for our most complex and high-value opportunities, targeting accounts in the $25,000–$100,000 ACV range. You’ll 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 You’ll 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 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 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 $100,000–$130,000 CAD. 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 You’ll 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. You’ll have the deal complexity to sharpen your skills, the freedom to make decisions, and the satisfaction of seeing your work drive real customer success. 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 + 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 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 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 [Upgrade to PRO to see contact].