Loopio Inc. logo

Director of Software Development

Job Overview

Location

Toronto, ON Hub

Job Type

Full-time

Category

Software Engineering

Date Posted

March 25, 2026

Full Job Description

đź“‹ Description

  • • As the Director of Software Development at Loopio Inc., you will be instrumental in leading the RFX I/O Mission Team, a critical group responsible for the sophisticated systems that manage how customers import formal procurement documents like RFPs and RFIs into the Loopio platform, and subsequently export winning proposals. This leadership role is pivotal in shaping the future of document ingestion, portal integrations, AI-driven import enhancements, and the development of an intelligent layer designed to make content extraction more efficient and accurate. You will be at the forefront of solving complex document processing challenges, focusing on parsing intricate formats, building robust and reliable ingestion pipelines, and leveraging Artificial Intelligence and Machine Learning to significantly improve accuracy and minimize manual effort for our users.
  • • Your day-to-day responsibilities will encompass a broad spectrum of leadership, technical direction, and execution. You will lead and nurture multiple engineering pods, providing mentorship and support to other managers and technical leads, fostering an environment of high performance, inclusivity, and accountability. A key aspect of your role will be to drive the architectural vision and ongoing evolution of Loopio's document ingestion and processing platform. This includes overseeing the systems that handle diverse source documents such as Word, Excel, PowerPoint, and PDF, as well as managing integrations with customer portals. You will collaborate closely with Data and ML teams to seamlessly integrate AI-powered features, including intelligent extraction, auto-mapping, conditional logic detection, and advanced document understanding models directly into the import pipeline. Your technical decisions will be crucial in balancing the need for rapid development with the imperative of long-term scalability, accuracy, and maintainability, ensuring that the platform can reliably handle complex, unstructured, and non-standard document formats.
  • • Furthermore, you will be responsible for overseeing the planning, prioritization, and execution of projects across your multiple pods, ensuring that the team delivers against a roadmap that directly influences customer retention and deal conversion rates. This involves close collaboration with Product and Design partners to translate customer pain points into intuitive and intelligent ingestion experiences. You will proactively identify and manage technical dependencies, mitigate risks, and ensure seamless cross-team coordination, particularly between import, export, and portal integration workstreams. Championing high-quality engineering practices such as robust testing, comprehensive observability, and performance optimization across all ingestion and processing systems will be paramount. You will also lead incident response efforts and conduct thorough root cause analyses for any document processing failures, continuously refining workflows, tooling, and delivery processes to enhance team efficiency and operational excellence.
  • • You will serve as a key technical authority in strategic planning for the RFX I/O Mission Roadmap, working closely with Data, Infrastructure, and Platform teams to architect scalable solutions for document parsing, indexing, and content structuring. Effective communication of technical decisions, including the rationale behind trade-offs, to a diverse range of stakeholders, including senior leadership, will be a critical function. A significant part of your role will involve exploring and implementing cutting-edge AI/ML techniques to enhance document understanding, automate repetitive manual tasks within the ingestion process, and drive innovation in how users interact with complex procurement documents, ultimately reducing friction and improving the overall proposal process. You will stay abreast of the latest trends in document AI, unstructured data processing, Large Language Model (LLM)-based extraction, and enterprise portal integrations, encouraging experimentation and fostering a culture of continuous learning and improvement within your teams.
  • • About the team and company: Loopio is dedicated to fostering a workplace that champions learning and growth, providing autonomous and challenging work that empowers employees to master their skills. The company attracts and retains curious, resilient individuals eager to advance their careers, all while operating under a philosophy of mutual support, embodying the spirit of #oneteam. This role is an exciting opportunity to join an existing, high-impact team within a company that values innovation and employee development.
  • • In this role, you will have the unparalleled opportunity to elevate your technical craft and explore your creative potential. You will be empowered to drive significant business impact through innovative solutions in document processing and AI integration. This position offers a unique chance to mentor and develop engineering leaders, shape the technical direction of a core product area, and contribute to a product that is critical for customer success. You will gain deep expertise in document AI, large-scale data processing, and building resilient, intelligent systems, all within a supportive and forward-thinking organization.

Skills & Technologies

Remote
Degree Required

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Loopio Inc.
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About Loopio Inc.

Loopio provides cloud-based RFP, RFx, and security questionnaire response software for enterprise sales, security, and proposal teams. Its platform centralizes content, automates workflows, and offers AI-driven suggestions to accelerate response creation, ensure consistency, and maintain compliance. Core features include a searchable knowledge library, collaboration tools, customizable templates, and analytics dashboards. Serving technology, financial services, and professional services firms, Loopio integrates with Salesforce, HubSpot, and Slack to embed response management into existing sales processes and reduce turnaround times.

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