Sales Development Representative
REMOTE /
Toronto, Ontario, Canada
- Permanent
This job allows you to work remotely
Job Description
PathPilot is on a mission to help millions of people unlock their potential by navigating and optimizing their careers through the power of AI. With strong funding, growing traction, and partnerships across education and workforce ecosystems, we’re building an AI Career Companion that helps institutions and enterprises deliver better career outcomes at scale.
We’re looking for a Sales Development Representative (SDR) to be the first touchpoint for organizations discovering PathPilot. You’ll play a critical role in introducing our mission, qualifying opportunities, and laying the foundation for long-term partnerships with universities, workforce development organizations, and enterprises.
This role is ideal for someone early in their sales career who wants to learn fast, make a real impact, and grow into a high-performing Account Executive or broader GTM leader over time.
Why join PathPilot?
• Be an early GTM hire at a fast-growing, mission-driven AI company
• Learn modern SaaS selling from the ground up in a real-world environment
• Work closely with senior sales leadership and the founder
• Sell a product that genuinely helps people navigate their careers
• Gain exposure to enterprise, institutional, and public-sector buyers
• Build a strong foundation for a long-term career in sales or partnerships
• Enjoy flexibility, autonomy, and a remote-friendly work culture
What are we looking for in an SDR?
You’re curious, driven, and comfortable starting conversations with new people. You care about understanding customer problems and communicating value clearly. You take ownership of your work, handle rejection with resilience, and are motivated by growth and learning.
You don’t need to be a polished closer yet but you’re eager to build the skills, habits, and mindset that great salespeople share.
What will you be doing:
• Research and identify potential customers across higher education, workforce development, and enterprise markets
• Conduct outbound prospecting via email, phone, LinkedIn, and other channels
• Qualify inbound leads and book discovery calls and demos for Account Executives
• Learn and articulate PathPilot’s value proposition and competitive positioning
• Build relationships with key stakeholders at target organizations
• Maintain clean, accurate records in CRM systems (Salesforce or similar)
• Partner with Marketing to provide feedback on lead quality and campaign performance
• Consistently meet or exceed activity, pipeline, and qualification targets
How will you spend your time:
• 40% outbound prospecting and lead generation
• 20% qualifying inbound leads and discovery conversations
• 15% research, account planning, and personalization
• 15% collaboration with Sales, Marketing, and GTM leadership
• 10% learning, coaching, and skill development
In your first 30 days, you will:
• Learn PathPilot’s product, market, and ideal customer profiles
• Shadow sales calls and understand the full sales cycle
• Begin outbound prospecting with coaching and support
• Build confidence in messaging and qualification frameworks
In your first 90 days, you will:
• Consistently generate qualified pipeline for Account Executives
• Own your outbound motion and personalization strategy
• Provide feedback to Marketing on lead quality and messaging
• Hit or exceed monthly activity and pipeline targets
In your first 180 days, you will:
• Become a trusted front-line representative of PathPilot
• Contribute meaningfully to revenue growth and market expansion
• Refine your sales skills across discovery, qualification, and positioning
• Position yourself for growth into an Account Executive or advanced GTM role
Our hiring process:
• Intro Call – Learn about PathPilot and the SDR role
• Role Play or Outreach Exercise – Show us how you approach prospects
• Interview – Discuss mindset, coachability, and growth goals
• Final Conversation – Alignment on values and trajectory
• Offer – We move quickly and transparently
Must Have Skills:
You might be the person we’re looking for if you:
• Have 1–3 years of experience in sales, business development, or a customer-facing role
• Are an excellent written and verbal communicator
• Are self-motivated, resilient, and comfortable with outreach and follow-up
• Have a strong growth mindset and are highly coachable
• Are organized and detail-oriented when managing leads and CRM data
• Are excited about AI, EdTech, and workforce development
• Want to build a long-term career in sales, partnerships, or GTM leadership
Nice to Have Skills:
Bonus points if you’ve:
• Sold to higher education, government, or institutional buyers
• Worked in career services, recruiting, or workforce-focused roles
• Used sales engagement tools like Outreach, Salesloft, or Apollo
• Completed a bachelor’s degree or have equivalent practical experience