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Senior Implementation Manager

Chicago, IL

About Loop

Loop is a domain-specific AI company specialized in logistics and the physical economy. By leveraging verticalized AI, Loop transforms operational and financial signals within logistics data into structured insights that drive automation, financial transparency, and supply chain optimization at scale. Our solutions support enterprise shippers in modernizing back-office operations and uncovering hidden value within complex logistics networks.

Our investors include J.P. Morgan, Index Ventures, Founders Fund, 8VC, Flexport, and 50 industry-leading angel investors. Our team brings subject matter expertise from companies like Uber, Google, Flexport, Meta, Samsara, Intuit, Rakuten, and long-standing industry leaders like C.H. Robinson.

About the Role

As a Senior Implementation Manager at Loop, you will own end-to-end delivery of our most complex, high-stakes enterprise implementations. You are the strategic hub connecting Sales, Pre-Sales, Engineering, Operations, and Customer Success—responsible for ensuring clients realize measurable value from Loop’s platform from day one through post-launch.

This is a highly autonomous role. You’ll manage multiple large-scale implementations simultaneously, serve as a trusted advisor to senior client stakeholders, and help shape the methodology and standards that elevate the entire implementation practice. You will also mentor and support junior members of the team.

What You'll Own

Enterprise Implementation Delivery

  • Own end-to-end project management for Loop’s largest and most complex enterprise implementations, from kick-off through post-launch hypercare and handoff to Customer Success.
  • Lead deep discovery sessions with client stakeholders to document business and technical requirements, configure Loop’s platform, and ensure the delivered solution precisely addresses client needs.
  • Develop and execute comprehensive implementation plans with clear timelines, milestones, and deliverables—coordinating across engineering, operations, and client teams to ensure on-time delivery.
  • Facilitate kick-off calls, weekly status meetings, executive check-ins, and milestone reviews—both virtually and on-site.
  • Lead process mapping and workflow whiteboarding sessions; produce internal and client-facing documentation for workflows and SOPs.
  • Drive change management conversations with clients, advising on business process transformation and best practices.
  • Ensure clean handoffs to Customer Success, setting up accounts for long-term success and retention.

Strategic & Cross-Functional Influence

  • Partner with Sales and Pre-Sales on scoping and technical discovery for strategic, complex deals—serving as an implementation SME during the sales cycle.
  • Work directly with Loop’s Technical Architect to scope use cases for the product roadmap and advocate for client-driven product enhancements.
  • Proactively identify and communicate implementation risks, escalation points, and opportunities to internal and external stakeholders.
  • Collaborate with Operations to ensure configured products are appropriately supported for ongoing client servicing.
  • Serve as a cross-functional escalation point for complex implementation issues, driving resolution with urgency and clarity.

Team & Practice Development

  • Mentor and support junior Implementation Managers—sharing domain knowledge, reviewing deliverables, and helping them navigate complex situations.
  • Contribute to the development and continuous improvement of implementation playbooks, templates, and methodology standards.
  • Help define and refine best practices for onboarding, configuration, and client communication across the team.

About You

  • 5–8+ years of customer-facing experience in implementation, project/program management, or solutions delivery—preferably in supply chain, logistics, or B2B SaaS.
  • Proven track record delivering complex, enterprise-scale implementations end-to-end with minimal oversight.
  • Deep domain expertise in transportation, logistics, freight audit, or supply chain technology.
  • Experience managing senior to executive-level stakeholders (Director through C-suite) throughout an implementation lifecycle.
  • Highly autonomous—able to prioritize, problem-solve, and drive outcomes across multiple concurrent projects in a fast-paced environment.
  • Strong analytical and data-driven mindset; able to translate implementation data and client outcomes into ROI narratives.
  • Excellent written and verbal communication skills—executive-ready, clear, and concise.
  • Demonstrated ability to lead process mapping and whiteboard complex operational workflows with clients and internal teams.
  • Experience mentoring others or informally leading cross-functional project teams.
  • Proficiency in project management tools (e.g., Monday.com, Linear, Jira, or similar).
  • Ability to travel up to 25%.
  • This is a hybrid role based in Chicago with the expectation of being in the office three days a week.

Benefits & Perks

  • Premium Medical, Dental, and Vision Insurance.
  • 401k plan.
  • Unlimited PTO.
  • Generous professional development budget to feed your curiosity.
  • Physical and mental fitness subsidies for yoga, meditation, gym, etc.

 

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