Location: REMOTE / Toronto, Ontario
This job allows you to work remotely.
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 7-figures in non-dilutive funding and strong ecosystem partnerships, we’re scaling an AI Career Companion already being used by individuals, universities, workforce development organizations, and enterprises.
We’re looking for a Head of Sales to own and scale PathPilot’s revenue engine. You’ll work closely with the founder and leadership team to define our go-to-market strategy, build the sales function from the ground up, and establish PathPilot as the category leader in AI-powered career guidance.
This is a hands-on leadership role for someone who thrives in early-stage environments where you’re just as comfortable closing strategic deals as you are building playbooks, hiring the first reps, and shaping how the market understands our value.
Why join PathPilot?
• Own and build the sales function at a mission-driven AI company
• Work directly with the founder on GTM strategy and revenue decisions
• Sell a product that delivers real, measurable outcomes for people’s careers
• Help define a new category at the intersection of AI, careers, and workforce development
• Build and mentor a team from the ground up
• Operate with autonomy, trust, and flexibility in a remote-friendly environment
• Be backed by strong funding, partnerships, and real customer traction
What are we looking for in a Head of Sales?
You’re a builder, operator, and closer. You know how to design sales strategy—but you also know that early on, nothing matters more than getting in front of customers, learning fast, and closing deals.
You’re deeply comfortable selling complex, consultative solutions to institutions and enterprises. You understand how to navigate long sales cycles, multiple stakeholders, and outcome-driven buying decisions. Most importantly, you’re excited to roll up your sleeves and create something from scratch.
What will you be doing:
• Define and execute PathPilot’s sales and go-to-market strategy
• Own revenue targets and drive consistent pipeline growth
• Close strategic accounts across universities, workforce organizations, and enterprises
• Build, hire, and mentor a high-performing sales team (AEs, SDRs)
• Establish sales processes, playbooks, pricing strategy, and KPIs
• Partner with Marketing to refine positioning, messaging, and lead generation
• Collaborate with Product and Customer Success to ensure strong customer outcomes
• Build forecasting, reporting, and CRM discipline from the ground up
• Represent PathPilot in key sales conversations, partnerships, and market opportunities
How will you spend your time:
• 40% closing deals and managing strategic accounts
• 20% building sales processes, playbooks, and operating rhythm
• 15% hiring, coaching, and developing the sales team
• 15% cross-functional work with Product, Marketing, and Customer Success
• 10% forecasting, reporting, and GTM strategy refinement
In your first 30 days, you will:
• Deeply understand PathPilot’s product, customers, and value proposition
• Close or advance key strategic deals already in the pipeline
• Assess current sales motion, tooling, and gaps
• Align with the founder on revenue targets and GTM priorities
In your first 90 days, you will:
• Own and execute a repeatable sales motion
• Build and document sales playbooks and core messaging
• Hire or begin hiring initial sales team members
• Establish forecasting and reporting cadence
• Close meaningful new institutional or enterprise accounts
In your first 180 days, you will:
• Scale a high-performing sales team and operating rhythm
• Drive predictable revenue growth across multiple segments
• Refine pricing, packaging, and positioning based on market feedback
• Establish PathPilot as a trusted partner in AI-powered career guidance
• Act as a key strategic leader shaping company direction
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:
• Have 8+ years of B2B sales experience, with 3+ years in sales leadership
• Have a proven track record of hitting and exceeding revenue targets
• Have sold SaaS solutions to higher education, government, or enterprise buyers
• Are strong in consultative, solution-based selling
• Are comfortable navigating complex buying committees and long sales cycles
• Take a data-driven approach to pipeline management and forecasting
• Are fluent in modern CRM and sales tech stacks (Salesforce or similar)
• Thrive in ambiguity, autonomy, and early-stage environments
• Care deeply about mission, impact, and building something meaningful
Nice to Have Skills:
Bonus points if you’ve:
• Built a sales team from zero or early stage
• Worked in EdTech, HR tech, or workforce development
• Have existing relationships in higher education or workforce organizations
• Sold products tied to career services, learning, or talent outcomes
