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 otherbecause true success comes from working as #oneteam.

Were 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. Youll 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 Youll 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 Loopios 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 Youll Bring to the Team:

• 10 years of experience in software development including 35 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.

• Bachelors or Masters 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 Youll Work

• Loopio is a remote-first workplace because we recognize the advantages of working flexibly. We are HQd 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!

• Youll collaborate with your teams virtually across the UK India and North America (were 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 Youll 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 1 with Loopio.

• Well 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.

• Youll 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.

• Youll 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 dont apply for a position simply because they dont hit every single criteria included in the job descriptionparticularly 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 weve created prompts in the application for you to share more about yourself. If youve made a career transition (or a few!) youre self taught in a new role or you have skills/experience youd 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 () should you require accommodations at any point during our virtual interview processes.

Required Experience:

Director