Sales Development Representative

About Feathery Feathery enables companies to automate data intake workflows with a leading form and document AI platform. Customers use Feathery to power workflows ranging from client onboarding to insurance underwriting and beyond. Feathery is the only platform that allows business users to build data-centric user journeys through an all-in-one system of tools. With strong growth and increasing enterprise adoption, we’re scaling our go-to-market team to accelerate pipeline and expand into larger, more complex customer accounts. 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 Sales Development Representative (SDR) 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 Inbound qualification and customer 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 Pipeline Generation & Prospecting Prospect and develop new accounts by educating contacts on how Feathery can automate their workflows Reach out to prospects via email, LinkedIn, and phone Experiment with different audiences, messaging, and channels to generate enterprise opportunities Take ownership of pipeline generation strategies and continuously improve performance Inbound & Qualification Manage inbound interest from prospective customers Qualify leads to determine fit and prioritize opportunities Conduct discovery conversations to understand customer challenges and goals 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.

You will drive pipeline generation through outbound prospecting and inbound lead qualification while managing customer engagement and product demos. Additionally, you will collaborate cross-functionally to refine sales playbooks and contribute to go-to-market strategies.

The ideal candidate possesses strong communication skills, a builder mindset, and a track record of high achievement. Experience in B2B SaaS sales, cold outreach, or financial services is considered a significant bonus.

• Competitive compensation • Equity • Health coverage • Dental coverage • Vision coverage • Unlimited PTO • Office snacks • Monthly catered lunch

• Problem solvingPreferred
• CommunicationPreferred

Identified from the job description. Confirm important requirements above.

• Outbound prospecting
• Pipeline generation
• Lead qualification
• Customer engagement
• Sales demos
• Communication
• Empathy
• B2B SaaS sales
• CRM tools
• Cold outreach
• Strategic planning
• Cross-functional collaboration
• Problem solving
• Relationship building
• Workflow automation

• Sales
• Software
• Technology
• Consulting

Minimum experience

0+ years

Posting language

English

Working hours

40 hours per week

Location requirements

Country, Canada