Remote Director of Software Development

Take your career to new heights with Loopio! ✨

Loopio is a workplace that unleashes learning and growth opportunities for our Loopers. We provide autonomous, challenging work that allows each employee to master their craft. We attract and retain people who are naturally curious, have grit, and are eager to grow their careers. At Loopio, we genuinely support each other—because true success comes from working as #oneteam.

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 Canada (British Columbia and Ontario), London, and 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!

Why You’ll ♥️ Working at Loopio

• Your manager supports your development by providing ongoing feedback and regular 1-on-1s, we leverage Lattice for our 1:1s and performance conversations

• You will have the opportunity to elevate your craft and the opportunity to explore your creativity, with a dedicated professional mastery allowance for more learning support! We encourage experimentation and innovative thinking to drive business impact.

• We offer a wide range of health and wellness benefits to support your physical and mental well-being, starting day 1️⃣ with Loopio.

• We’ll set you up to work remotely with a MacBook laptop , a monthly phone and internet subsidy, and a work-from-home budget to help get your home office all set up.

• You’ll be joining a supportive culture that has thoughtfully built out opportunities for connections in a remote first environment.

• Participate in townhalls, AMA (Ask-Me-Anything), and quarterly celebrations to celebrate the big wins and milestones as #oneteam!

• Our four active Employee Resource Groups offer opportunities for employees to learn and connect year-round. 

• You’ll be a part of an award-winning workplace with an opportunity to make a big impact on the business.

Questioning your qualifications? Read this ‼️ Hi there, we recognize that all too often, potential candidates don’t apply for a position simply because they don’t hit every single criteria included in the job description—particularly members of underrepresented groups. 

Whether or not your experience ✅ checks off all the boxes on a job posting, we still encourage you to apply to ensure that your application receives a review from our team. We understand that a resume can only showcase so much during the applicant stage, so we've created prompts in the application for you to share more about yourself. If you've made a career transition (or a few!), you’re self taught in a new role, or you have skills/experience you’d like to highlight, we want to hear more about what you could bring to the table.

AI in Recruitment ‍ At Loopio, we leverage artificial intelligence (AI) technology to enhance our recruitment process. These tools assist with tasks such as resume screening, drafting preliminary job descriptions, generating initial interview questions, transcription and occasionally sourcing prospective candidates. However, AI is never used to make final hiring decisions; our use of AI serves to support repetitive and administrative tasks in order to streamline our hiring and recruitment workflows. We are committed to the responsible use of AI in our hiring practices, prioritizing both an improved candidate experience and operational efficiency. Our standardized hiring practices remain focused on reducing biases, with all key hiring decisions solely made by our team. We continuously review and refine our hiring practices to align with industry best practices and evolving legal guidelines

AI Usage in Interviews The Loopio interview process is designed to help us better understand your professional experiences, as well as your unique perspective and approach to delivery and collaboration. To ensure a fair and accurate assessment, we expect candidates to refrain from using AI-generated content to produce responses to our interview questions during the live interview, as our goal is to evaluate your own knowledge and problem-solving abilities - not those of an AI assistant. If AI-generated responses are identified during the interview, Loopio reserves the right to disqualify candidates from the interview process.

For specific roles that include a take-home assignment, our AI Interviewee Policy allows the use of AI for initial support; however, the final submission must be a true reflection of your personal insights, skills and decision-making.

Loopio is an equal opportunity employer that is deeply committed to building equitable workplaces that are diverse and inclusive. We actively encourage candidates from all backgrounds and lifestyles to consider us as a future employer. Please contact a member of our Talent Experience team ( View email address on ca.talent.com ) should you require accommodations at any point during our virtual interview processes.