Loopio

Director of Software Development

Loopio • $130K — $180K *
Toronto, ON M3C 0E3In-Person
Information Technology
8 - 10 years of experience
Reposted Today
Be an Early Applicant
Job Overview by Ladders

Qualifications

  • 10+ years of experience in software development, with 3-5+ years in leadership roles.
  • Proven success in managing and scaling engineering teams and multiple pods.
  • Experience with document ingestion and processing systems handling complex file formats.
  • Technical fluency in backend system reliability and data quality challenges.
  • Familiarity with AI/ML applications in document understanding.
  • Excellent communication skills to connect technical decisions to business outcomes.
  • Track record of building inclusive and high-trust team environments.

Responsibilities

  • Lead and grow multiple engineering pods while supporting other managers.
  • Drive the architecture evolution of Loopio's document ingestion platform.
  • Collaborate with Data and ML teams for AI-powered integration in the import pipeline.
  • Oversee planning, prioritization, and execution across pods for customer satisfaction.
  • Champion high-quality engineering practices in system observability and optimization.
  • Serve as a key technical voice in strategic planning for the RFX I/O Mission Roadmap.
  • Explore AI/ML techniques to enhance document understanding and automation.

Benefits

  • Flexibility to work remotely with necessary equipment provided.
  • Health and wellness benefits from day one.
  • Professional mastery allowance for ongoing learning support.
  • Supportive culture promoting connections in a remote environment.
  • Participation in townhalls and quarterly celebrations.
  • Opportunities through Employee Resource Groups for connection throughout the year.
Full Job Description
We're looking for a Director of Software Development to lead our RFX I/O Mission Team, which is responsible for the systems that power how customers bring RFPs, RFIs, and other formal procurement documents into the Loopio platform and deliver winning proposals back out. This includes our document ingestion pipelines, portal integrations, AI-assisted import experiences, and the emerging intelligence layer that makes content extraction smarter and faster.

This is a strategic and deeply technical leadership role for someone who has solved hard document processing problems before, parsing complex formats, building reliable ingestion pipelines, and applying AI/ML to improve accuracy and reduce manual effort. You'll lead multiple engineering pods, including other managers, and work closely with Product, Data Science, Infrastructure, and Design to shape how customers interact with proposal documents at scale.

Note: This is an existing vacancy on the team

What You'll Be Doing:

Leadership & Team Development
  • Lead and grow multiple engineering pods, including supporting other managers and technical leads.
  • Foster a high-performing, inclusive engineering culture centered on accountability, autonomy, and craft.
  • Mentor and develop engineering leaders through coaching, clear feedback, and career investment.
  • Attract, retain, and nurture top technical talent.

Technical Direction & Architecture
  • Drive the architecture and evolution of Loopio's document ingestion and processing platform, covering source documents (Word, Excel, PowerPoint, PDF) and customer portal integrations.
  • Partner with Data and ML teams to integrate AI-powered extraction, auto-mapping, conditional logic detection, and document understanding models into the import pipeline.
  • Make technical decisions that balance short-term velocity with long-term scalability, accuracy, and maintainability.
  • Provide hands-on architectural guidance to ensure robust handling of complex, unstructured, and non-standard document formats.

Execution & Delivery
  • Oversee planning, prioritization, and execution across multiple pods, ensuring delivery against a roadmap that directly impacts customer retention and deal conversion.
  • Collaborate with Product and Design partners to translate customer pain points into reliable, intelligent ingestion experiences.
  • Proactively manage technical dependencies, risks, and cross-team coordination - particularly across import, export, and portal integration workstreams.

Operational Excellence
  • Champion high-quality engineering practices including observability, testing, and performance optimization across ingestion and processing systems.
  • Lead incident response and root cause analysis for document processing failures.
  • Continuously refine workflows, tooling, and delivery processes for team efficiency.

Cross-Functional Collaboration
  • Serve as a key technical voice in strategic planning for the RFX I/O Mission Roadmap.
  • Collaborate with Data, Infrastructure, and Platform teams on scalable solutions for document parsing, indexing, and content structuring.
  • Effectively communicate technical decisions and trade-offs to stakeholders across the business, including senior leadership.

Innovation & Emerging Technologies
  • Explore and implement AI/ML techniques to improve document understanding, intelligent field extraction, and automation of repetitive manual tasks in the ingestion process.
  • Keep up with trends in document AI, unstructured data processing, LLM-based extraction, and enterprise portal integrations.
  • Encourage experimentation in how users interact with complex procurement documents, reducing friction throughout the proposal process.


What You'll Bring to the Team:
  • 10+ years of experience in software development, including 3-5+ years in engineering leadership roles.
  • Proven success managing and scaling multiple engineering pods and/or other managers.
  • Experience building and scaling document ingestion and processing systems - handling complex, real-world file formats reliably at scale.
  • Technical fluency in building reliable backend systems, with experience navigating the complexity of real-world document formats and data quality challenges.
  • Familiarity with AI/ML applied to document understanding - such as extraction, classification, layout analysis, or structured data recognition.
  • Excellent communication skills, with the ability to connect technical decisions to business outcomes.
  • Track record of building inclusive, high-trust team environments.
  • Bachelor's or Master's degree in Computer Science or related field - or equivalent industry experience.


Bonus Points for:
  • Experience with structured and unstructured document formats (DOCX, XLSX, PPTX, PDF) and their parsing challenges.
  • Background in ML/AI pipelines applied to document processing, OCR, or NLP-based extraction.
  • Experience with SaaS platforms, especially multi-tenant architectures.
  • Prior work on products where accuracy and user trust in automated processing were critical success metrics.


Where You'll Work
  • Loopio is a remote-first workplace because we recognize the advantages of working flexibly. We are HQ'd in Canada, with established hub regions around the world where we hire from.
  • Our employees (or Loopers, as we call ourselves!) live and work in C🇦 Canada (British Columbia and Ontario), GB London, and I🇳 India (specifically in Gujarat, Maharashtra, and Bengaluru).
  • The majority of our team is based in ON and BC, which means these employees live and work remotely within a 300km radius of Toronto (within Ontario) and Vancouver (Within BC).
  • We offer flexible co-working locations available to Loopers in ON and BC. Those based in ON have the option of working out of our convenient co-working space located in the heart of Downtown Toronto and a 12-minute walk from Union Station. BC Loopers have the option to work centrally in Vancouver. It is whatever works best for you!
  • You'll collaborate with your teams virtually across the UK, India, and North America (we're just a Zoom call and Slack message away!) with core sync hours and focus time for headsdown work 🙇 during the workday
  • We encourage asynchronous collaboration to effectively work as a global #OneTeam!


About Loopio

Loopio is a software company that provides a cloud-based platform for automating the response to requests for proposals (RFPs), requests for information (RFIs), and due diligence questionnaires. The platform streamlines the response process by centralizing content and automating workflows, enabling teams to respond to requests more efficiently and accurately. Loopio serves a variety of industries, including technology, healthcare, finance, and professional services. The company was founded in 2014 and is headquartered in Toronto, Canada.
Learn more about Loopio
Size
200 employees
Industry
Information Technology
Founded
2014
* Ladders Estimates

Similar Jobs

Ad banner background

Get Ready For Your
Next Interview

More Jobs at Loopio

More Information Technology Jobs

Find similar Director of Software Development jobs:

NationwideToronto, ON