Software Engineer

Caddie is hiring on behalf of Sales Ask, one of Canada’s fastest-growing AI startups transforming the construction and field sales industries.Sales Ask is a cutting-edge speech analytics platform that helps outside sales reps close more deals. By listening, transcribing, and analyzing customer conversations, the software provides actionable insights to increase conversions and revenue.Now, they’re looking for a Software Engineer to join their core team and help build the next generation of AI-powered sales technology.🚀 Why Join Sales AskWork at the intersection of AI, speech recognition, and sales enablement, shaping the future of how outside sales teams sell.Collaborate directly with the CEO and founding team — fast feedback, real impact, zero red tape.Be part of a scrappy, high-performance culture where ownership, speed, and quality matter most.Rapid growth opportunities — as the product and team scale, leadership roles will open fast.🧠 What You’ll DoDesign, build, and deploy scalable backend systems that power Sales Ask’s voice and analytics engine.Collaborate with the AI/ML team to improve transcription accuracy and conversational insights.Work closely with the CEO and product team to ship new features end-to-end — from concept to production.Own key parts of the product architecture, ensuring performance, reliability, and clean code.Move fast: iterate, experiment, and push updates that deliver real value to customers.💡 Who You AreStrong experience in software engineering, ideally full-stack or backend-focused.Skilled in one or more of the following: Python, Node.js, React, TypeScript, or cloud infrastructure (AWS/GCP).Comfortable working in a fast-paced startup — you thrive on ownership and learning by doing.Passionate about AI, voice tech, or sales tools, and eager to build products that real people use every day.A self-starter who takes pride in high-quality code and continuous improvement.🔗 About Sales AskSales Ask is an AI-powered speech analytics platform that helps field sales reps close more deals. By listening, transcribing, and analyzing real customer conversations, Sales Ask provides actionable insights that boost performance, training, and conversion rates.Learn more at salesask.com