Rose Rocketis 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 significant 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 RoleRose Rocket is looking for anEnterprise Solutions Deployment Specialistto lead end-to-end deployments for our most complex customer accounts. This is a senior, high-trust 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.You 'll own enterprise relationships from kickoff through go-live, working within an AI-augmented 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 we 're looking for someone who's excited to help shape that intersection over time.What You 'll DoDeployment LeadershipLead the full deployment lifecycle for enterprise accounts from signed contract through stable go-liveFacilitate multi-stakeholder kickoffs, configuration workshops, and UAT sessions with clarity and confidenceManage complex timelines, competing priorities, and executive-level stakeholders while keeping momentumNavigate organizational dynamics and change management challenges common at enterprise scaleServe as the senior point of contact for customers during deployment, building trust through depth and transparencyConfiguration & Technical ArchitectureDesign platform configurations tailored to each customer 's workflows, integrations, roles, and business rules – optimized for long-term stability,



not just immediate requestsDevelop deep fluency across Rose Rocket 's module ecosystem: how fields, automations, integrations, and custom logic interact, and how to sequence configuration for maximum stabilityIdentify and resolve configuration risks before they become deployment blockersContribute reusable configuration patterns and documentation that help the whole team move fasterAI-Augmented Workflow & Team StandardsWork within our AI-enabled deployment process, using audit tooling to assess live environments, identify drift, and generate action plansBuild workflows that extend your output – automations, analysis, documentation, and client-facing materials – and share what 's working with the teamBring structured feedback from enterprise deployments back to Product and Engineering to help inform the roadmapContribute to the evolution of Rose Rocket 's baseline deployment methodology and configuration standardsCross-Functional CollaborationPartner with Account Executives before kickoff to fully understand the customer context built throughout the sales cycleWork with Product, Engineering, and Support to resolve issues that require platform-level knowledgeCollaborate with Revenue Ops and the broader GTM team to ensure customer context is captured, structured, and usable across the lifecycleWhat You Bring5–10 years in enterprise software implementation, solutions deployment, or operations/revenue roles within ERP, TMS, WMS, or similar environmentsDemonstrated experience leading complex, multi-stakeholder deployments from kickoff through go-liveStrong understanding of how enterprise software is configured: field structures, workflow logic, permissions, integrations, and data importsAnalytical mindset and data fluency — comfortable with structured data, configuration exports, and implementation metricsExcellent communication skills: able to run executive meetings, explain technical decisions in plain language, and write documentation people actually useComfort operating in a fast-moving environment where tools are evolving and building new workflows is part of the jobBonus Points ForBackground in Revenue Operations, Customer Experience,



or Implementation leadershipHands-on experience with AI productivity tools in your workflowChange management experience at enterprise accounts involving multi-department deploymentsFamiliarity with transportation, logistics, or freight operations (software or operational)Experience contributing to a deployment methodology, playbook, or base configuration standardThe 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.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 & BenefitsAt Rose RocketA comprehensive benefits program + health care spending accountParental leave top-upStock option planA Macbook and a sweet tech equipment combo to get you startedStart 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 funHybrid structure, where we 're in office together on Monday, Tuesday, and Thursdays, and WFH (optional) on Wednesday and FridaysUse of AI in HiringWe 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 OpportunityRose 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].#J-18808-Ljbffr

📌 Enterprise Solutions Deployment Specialist - C$97,000 - C$121,000 A Year (Toronto)
🏢 Rose Rocket
📍 Toronto