Director of Software Development, Loopio

• 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
• 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

Desirable

• 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
• 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
• 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
• 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
• 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
• 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
• 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