Solutions Architect - Freight Technology

Location

Chicago, IL (Relocation assistance available for candidates open to moving to Chicago.)

As a Solutions Engineer, you’ll be a technical and business partner supporting sales engagements and helping customers understand how project
44 delivers value. You’ll work closely with Account Executives and senior Solutions Engineers to run technical discovery, map customer requirements to platform capabilities, and deliver compelling demos and evaluations.

This role is hands‑on and growth‑oriented: you’ll build your expertise in supply chain visibility and integrations, contribute to deals in flight, and develop the skills to take on increasingly complex opportunities over time. You are a strong communicator, a practical problem solver, and comfortable working with both technical and business stakeholders.

• Support technical discovery and solution design for a range of opportunities, including enterprise deals, with guidance from senior team members as needed.
• Partner closely with Account Executives to align on customer goals, clarify requirements, and support account strategy execution throughout the sales cycle.
• Translate customer challenges into project
  44 solutions by connecting workflows, integrations, and product capabilities to measurable outcomes.
• Develop domain knowledge in supply chain visibility, transportation management, and digital transformation to effectively support customer conversations.
• Stay current on evolving industry trends (logistics automation, APIs, AI/ML‑driven visibility, IoT) and help customers understand how project
  44 can support innovation and modernization.
• Design and deliver strong product demos and evaluations, including standard demos and moderately customized demonstrations aligned to prospect needs.
• Support proofs of concept and value assessments by helping define scope, validate requirements, coordinate resources, and document outcomes (including benefits/impact where applicable).
• Partner with senior SEs on executive‑ready messaging by contributing technical inputs and supporting materials that help articulate value and ROI.
• Collaborate with Implementation and Customer Success to enable smooth handoffs from sales to delivery and set projects up for success.
• Contribute to enablement and consistency by documenting best practices (demo assets, discovery templates, technical FAQs) and sharing learnings with the broader Solutions Engineering team.
• Share market and customer feedback with Product and Engineering to help improve the platform and inform roadmap discussions.

• 3-5 years of experience in technical pre‑sales, solutions engineering, solutions consulting, implementation, solutions architecture (early‑career), or technical customer‑facing roles within SaaS or enterprise software.
• Interest in and growing knowledge of supply chain, transportation, and logistics processes (direct experience a plus, but not required for all candidates).
• Experience supporting multi‑stakeholder sales cycles, including partnering with Sales and navigating technical/customer IT conversations.
• Working knowledge of APIs, integration fundamentals, and data exchange formats (e.g., JSON, XML).
• Strong communication and presentation skills, with the ability to explain technical concepts clearly to mixed technical and business audiences.

• Familiarity with cloud concepts and common integration patterns (webhooks, SSO basics, data pipelines), or willingness to learn quickly.
• Experience supporting workshops, discovery sessions, and/or POCs/POVs (planning, execution support, documentation).
• Familiarity with programming concepts, SQL, and information security standards.
• Willingness to travel up to approximately 25–40% (depending on customer needs and territory).
• In‑office Commitment: Our office is where ideas spark, connections thrive, and innovation comes alive. We are looking for candidates who are enthusiastic and committed to joining our team on‑site, in our beautiful headquarters four days a week.

We're designing the future of how the world moves and is connected through trade and global supply chains. We can only deliver a truly…