Business Development Representative

About Feathery Feathery is the AI operating system for financial institutions. With hundreds of clients and over $30 million raised, Feathery is the fast-growing leader in financial agentic automation. Industry leaders like Tokio Marine, Sequoia Financial, and Cerity Partners run their client-facing workflows on Feathery, from onboarding and risk assessment to reconciling systems and generating proposals and reports. At the center of it all is Robin, our AI operations assistant. Robin scans client documents, configures and deploys workflows, assists users in their day-to-day work, takes notes during meetings, and supports a growing range of operational tasks across the client lifecycle. We're building a future where financial operations shift from paperwork, manual data entry, and disconnected systems to intelligent, automated workflows that let firms spend their time on clients instead of process. We're proud to be backed by world-class investors who share that vision, including Portage Ventures, Allstate Ventures, and Index Ventures, among others. We're driven by a shared commitment to excellence and velocity. Our values — Own the Problem, Grit Beats Gloss, Say It Straight — shape how we work and grow as a team. Why We’re Hiring As Feathery continues to grow, we’re engaging with more—and larger—organizations looking to modernize their workflows. We’re hiring a Business Development Representative (BDR) to help drive pipeline generation and shape the foundation of our sales motion. This role is ideal for someone who thrives in a fast-paced environment, enjoys building from the ground up, and is excited to play a key role in a high-growth B2B SaaS company. As an early member of the team, you’ll have a direct impact on how we go to market, generate demand, and engage with prospective customers. About the Role This is a high-ownership role that blends: Outbound prospecting and pipeline generation Strategic account research and prospect engagement Experimentation across messaging, channels, and audiences Cross-functional collaboration with sales, marketing, and product You’ll play a key role in building our revenue engine — from developing outbound strategies to helping define how we position Feathery in the market. What You’ll Do Outbound Pipeline Generation & Prospecting Prospect and develop new accounts by educating contacts on how Feathery can automate their workflows Identify and research target accounts and key stakeholders Reach out to prospects via email, LinkedIn, and phone Experiment with different audiences, messaging, and channels to generate enterprise opportunities Qualify prospects and conduct initial discovery conversations to understand customer challenges and goals Take ownership of outbound pipeline generation strategies and continuously improve performance Maintain detailed notes and insights on prospects Customer Engagement & Demos Hold Zoom and in-person meetings with prospective customers Learn the product deeply and deliver tailored demos for different personas Clearly communicate Feathery’s value proposition in a compelling, customer-centric way Sales Motion & Cross-Functional Collaboration Help build and refine outbound playbooks and sales processes Collaborate with marketing, product, and leadership on go-to-market initiatives Contribute insights from prospects to inform product development and positioning Support product launches and new initiatives with customer-facing input About You Strong communication skills with the ability to engage and build trust quickly High level of empathy and ability to tailor messaging to different personas Track record of high achievement in previous roles (academic, professional, or extracurricular) Builder mindset with a desire to help create and refine systems from the ground up Highly motivated, resilient, and comfortable navigating ambiguity Passion for understanding customer problems and helping solve them Enjoy meeting new people and building relationships Excited to be part of a fast-growing startup and help build the revenue function Bonus Experience with outbound prospecting or cold outreach (calls, email, LinkedIn) Experience in a B2B SaaS sales or go-to-market role Familiarity with CRM tools and outbound sales tooling Background in financial services or workflow-heavy industries What We Offer Competitive compensation and equity Health, dental, and vision coverage Unlimited PTO Downtown Toronto office location Stocked office pantry with snacks and ready-to-eat meals A supportive, low-ego team that values ownership and growth Company offsite to connect and recharge Feathery is an equal opportunity employer and does not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other legally protected characteristic. We’re committed to building an inclusive team and provide reasonable accommodations upon request.