Head of Sales

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

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