Founding Account Executive
REMOTE /
Toronto, Ontario, Canada
- Permanent
This job allows you to work remotely
Job Description
PathPilot is building the next generation of AI-powered infrastructure for workforce development and career navigation.
With seven figures in non-dilutive funding and strong ecosystem partnerships, we are scaling an AI platform already being used by individuals, universities, workforce development organizations, and enterprises to help people better navigate the rapidly changing world of work.
Career services teams, workforce organizations, and employers are facing unprecedented pressure. Demand for career guidance, up-skilling, and job matching continues to grow, while resources remain limited.
PathPilot addresses this challenge by embedding AI directly into the workforce ecosystem, enabling organizations to deliver personalized career guidance, skills pathways, and job navigation support at scale.
We are now expanding our early customer base and are looking for a Founding Account Executive to help bring this platform to organizations across Canada and beyond.
About the Role
This is a foundational go-to-market role.
As PathPilot’s Founding Account Executive, you will work directly with the founder to build pipeline, close early partners, and help shape how we bring this platform to market.
You will lead consultative sales conversations with leaders across universities, workforce development organizations, and enterprises who are looking for new ways to support people navigating their careers in an AI-driven economy.
This role is ideal for someone who thrives in early-stage environments where you are equally comfortable:
• opening new doors
• running complex sales conversations
• closing strategic partnerships
• helping refine the company’s go-to-market playbook
You should also be excited about AI and emerging technologies, and comfortable learning how AI platforms work and explaining their value to non-technical stakeholders.
Why Join PathPilot
• Help build a category-defining platform at the intersection of AI, workforce development, and career navigation
• Join a company with strong funding, ecosystem partnerships, and real early traction
• Work directly with the founder on go-to-market strategy and major deals
• Sell a product with meaningful social and economic impact
• Play a foundational role in shaping how the company scales
What You’ll Be Responsible For
• Generate and manage pipeline across universities, workforce organizations, and enterprise partners
• Lead consultative sales conversations with institutional stakeholders
• Close pilot partnerships and convert successful pilots into long-term commercial relationships
• Help organizations understand how AI can expand their career development capacity
• Work closely with the founder to refine messaging, pricing, and sales strategy
• Contribute to building early sales playbooks and outreach strategies
• Represent PathPilot in ecosystem events, conferences, and strategic meetings
• Maintain strong CRM and pipeline discipline
What Your Time Will Look Like
• 50% meeting with prospective partners and closing deals
• 20% pipeline development and outreach
• 15% supporting pilot programs and partner success
• 10% refining sales messaging and GTM strategy
• 5% CRM, reporting, and forecasting
In Your First 30 Days
• Develop a deep understanding of PathPilot’s platform and market
• Meet with existing pilot partners and key prospects
• Build a prioritized target account list
• Begin outbound outreach and discovery conversations
In Your First 90 Days
• Close several new pilot partnerships
• Establish a consistent pipeline generation motion
• Build relationships with key organizations in the workforce development ecosystem
• Help refine PathPilot’s positioning based on real market conversations
In Your First 6 Months
• Help establish PathPilot as a recognized solution within the workforce and career services ecosystem
• Convert early pilots into long-term commercial partnerships
• Build a strong pipeline across multiple market segments
• Play a meaningful role in shaping the company’s long-term go-to-market strategy
Our hiring process:
• Intro Call – Align on mission, values, and expectations
• Sales Strategy Exercise – Walk us through how you’d sell PathPilot
• Leadership Interview – Deep dive into your experience and approach
• Final Conversation – Alignment with the founder on vision and culture
• Offer – We move quickly and collaboratively
Must Have Skills:
You might be the person we’re looking for if you:
• 5–10+ years of experience in B2B sales, partnerships, or business development
• Experience selling SaaS, technology, or AI-enabled products
• Strong consultative selling skills and ability to navigate complex organizations
• Curiosity and enthusiasm for AI and emerging technologies
• Entrepreneurial mindset and comfort operating in an early-stage company
• Excellent communication and relationship-building skills
Nice to Have Skills:
Bonus points if you’ve:
• Experience selling into universities, workforce organizations, or government
• Experience in HR tech, EdTech, or workforce technology
• Experience working in a startup or high-growth environment
Special Perks:
Compensation
Competitive base salary with performance incentives tied to pilot acquisition and commercial partnerships.