Solutions Deployment Specialist

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. 

We are looking for a Solutions Deployment Specialist to support the setup, configuration, and rollout of our platform. This role is focused on helping customers transition from their existing systems, ensuring smooth migrations, and configuring our software to match their business needs.

You’ll work closely with customers and internal teams to guide clients through onboarding, configuration workshops, and day-to-day deployment tasks. This is a hands-on role where you’ll make sure solutions are delivered successfully and customers are set up for long-term success.

Key Responsibilities

Version Ownership

• Contribute to a standardized, repeatable product configuration that can be applied across multiple customers.

• Own the evolution of the base product configuration end to end by leveraging new product releases, updated learnings and customer feedback.

• Create documentation, templates, and guides that speed up future deployments.

• Share feedback with the team on what works well (and what doesn’t) in different customer setups.

Customer Deployments & Migrations

• Support the onboarding process for new customers.

• Assist with reviewing customer legacy systems and helping prepare data for migration.

• Help execute data uploads, testing, and cutovers during deployment projects.

• Document deployment steps and keep project records organized.

Platform Configuration

• Configure the Rose Rocket Platform based on customer workflows, roles, and business rules.

• Set up reporting, permissions, and integrations under the guidance of senior team members.

• Run configuration workshops to capture customer requirements.

• Build repeatable configuration templates and follow best practices.

Project Support & Collaboration

• Partner with Account Executives to keep projects on track and meet deadlines.

• Act as a key point of contact for customers during the deployment phase.

• Escalate technical or product questions to appropriate team members as needed.

• Work closely with Product, Engineering, and Support to resolve issues quickly.

Customer Success Alignment

• Serve as a trusted guide for customers, helping them get the most out of the platform.

• Explain configuration choices and workflows in simple, easy-to-understand language.

• Provide feedback from customer projects to improve our deployment process.

Qualifications

• 1–3 years of experience in transportation, software implementation, or customer onboarding.

• An interest in leveraging technology to improve customer and industry outcomes through software configuration, workflows, or system setup.

• Basic knowledge of data handling (spreadsheets, data imports, or reporting).

• Strong communication and documentation skills.

Preferred Skills

• Experience with SaaS or cloud-based platforms.

• Exposure to ERP, TMS, WMS, or CRM systems (even as an end user).

• Comfortable running customer meetings or workshops.

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 - read about it here

💰 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, music room, library and a few other lifestyle perks that keep our days fun

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 [email protected].