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
Office snacks and monthly catered lunch
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.