Job Title

Rose Rocket is a market leader in Transportation Management Software, focusing on the trucking industry and driving the transition to SaaS. We are a more human, less corporate culture built around doing meaningful work, winning as a team, and celebrating success. About the Role Rose Rocket is looking for an Enterprise Solutions Deployment Specialist to lead end-to-end deployments for our most complex customer accounts. This is a senior, hightrust role suited to someone with deep experience in enterprise software implementation ideally within ERP, TMS, or operations software who thrives on solving hard configuration problems alongside customers navigating real operational change. Youll own enterprise relationships from kickoff through golive, working within an AIaugmented deployment process where configuration recommendations, customer context, and audit tooling are already in motion before you begin. Your job is to critically evaluate those outputs, build on them, and bring your own judgment to the table not start from scratch. When you spot a gap in how we work, we want you to help close it: through a new workflow, an automated process, or a raised standard. This role sits at the intersection of software configuration, operations consulting, and emerging AI tooling and were looking for someone whos excited to help shape that intersection over time. What Youll Do Deployment Leadership - Lead the full deployment lifecycle for enterprise accounts from signed contract through stable golive - Facilitate multistakeholder kickoffs, configuration workshops, and UAT sessions with clarity and confidence - Manage complex timelines, competing priorities, and executivelevel stakeholders while keeping momentum - Navigate organizational dynamics and changemanagement challenges common at enterprise scale - Serve as the senior point of contact for customers during deployment, building trust through depth and transparency Configuration & Technical Architecture - Design platform configurations tailored to each customers workflows, integrations, roles, and business rules optimized for longterm stability, not just immediate requests - Develop deep fluency across Rose Rockets module ecosystem: how fields, automations, integrations, and custom logic interact, and how to sequence configuration for maximum stability - Identify and resolve configuration risks before they become deployment blockers - Contribute reusable configuration patterns and documentation that help the whole team move faster AIAugmented Workflow & Team Standards - Work within our AIenabled deployment process, using audit tooling to assess live environments, identify drift, and generate action plans - Build workflows that extend your output automations, analysis, documentation, and clientfacing materials and share whats working with the team - Bring structured feedback from enterprise deployments back to Product and Engineering to help inform the roadmap - Contribute to the evolution of Rose Rockets baseline deployment methodology and configuration standards CrossFunctional Collaboration - Partner with Account Executives before kickoff to fully understand the customer context built throughout the sales cycle - Work with Product, Engineering, and Support to resolve issues that require platformlevel knowledge - Collaborate with Revenue Ops and the broader GTM team to ensure customer context is captured, structured, and usable across the lifecycle What You Bring - 510 years in enterprise software implementation, solutions deployment, or operations/revenue roles within ERP, TMS, WMS, or similar environments - Demonstrated experience leading complex, multistakeholder deployments from kickoff through golive - Strong understanding of how enterprise software is configured: field structures, workflow logic, permissions, integrations, and data imports - Analytical mindset and data fluency comfortable with structured data, configuration exports, and implementation metrics - Excellent communication skills: able to run executive meetings, explain technical decisions in plain language, and write documentation people actually use - Comfort operating in a fastmoving environment where tools are evolving and building new workflows is part of the job Bonus Points For - Background in Revenue Operations, Customer Experience, or Implementation leadership - Handson experience with AI productivity tools in your workflow - Change management experience at enterprise accounts involving multidepartment deployments - Familiarity with transportation, logistics, or freight operations (software or operational) - Experience contributing to a deployment methodology, playbook, or base configuration standard The expected salary range for this role is $97,000$121,000 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. 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, we want to hear from you! Perks & Benefits at Rose Rocket - A comprehensive benefits program + health care spending account - Parental leave topup - 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 inhouse coffee shop, pizza oven, rooftop patio and a few other lifestyle perks that keep our days fun - Hybrid structure: we are 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 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 accessibilityrelated assistance, requests for information in accessible alternative formats or to report any accessibility problems, please share in your application or email [email protected]. #J-18808-Ljbffr