Head of Sales

Chatbase; Toronto; On-site; CAD 145,000 - 190,000; Full time

Benefits offered by this job

Equity

Job summary

Chatbase is seeking a senior, player-coach Sales leader in Toronto to own a mid-market/enterprise book and to hire and lead our AE team as it scales. You’ll set the standard for discovery, forecasting, pricing and win strategies while reporting to the Head of GTM.

You’ll drive top-line growth with an equity-forward package, and you’ll work closely with product to ensure the voice of customers informs our roadmap.

Qualifications

• 8+ years in B2B SaaS sales with a track record of beating quota.
• Experience leading AEs and building a sales organization from the ground up.
• You’ve sold to CX, IT or digital leaders at mid-market and enterprise companies.

Responsibilities

• Own your book of mid-market and enterprise deals and close.
• Define and raise the bar for discovery, forecasting, pricing and win rates.
• Hire, coach and scale the AE team as the org grows.
• Provide feedback to product so customer insights shape the roadmap.

Skills

Enterprise sales

Team leadership

Quota beating

Mid-market to enterprise

Job description

More than 10,000 businesses are running AI agents on Chatbase. We started with self-serve, and now we're moving upmarket and building our sales team. Our top AEs have been consistently exceeding quota, and that's given us a lot of confidence in aggressive growth plans for the next year. We're looking for someone who can close, set the bar for the team, and help build it out.

About Chatbase

Chatbase is the AI agent platform that 10,000+ businesses use to talk to their customers, from fast-growing startups to global brands like Dolby, Roche, Pearson, Bridgestone and Chuck E. Cheese. Our agents resolve millions of conversations across support, sales and operations.

We launched in 2023 and we're profitable.

Why now

This is the moment. The product is working, customers keep finding new ways to use it, and we're growing fast. Most of our biggest growth levers haven't been pulled yet. The people who join now will build the teams, playbooks and products that make Chatbase many times bigger than it is today, and they'll share in that upside.

• Top-of-market pay, plus equity. We pay at the top end of the market, and everyone gets equity in a profitable company that’s growing fast.
• Ownership from day one. Small team, huge surface area. You'll own big outcomes and work directly with our CEO.
• Early-stage upside. It's still early enough to get a lot of the upside, in a company that’s already profitable.

The role

This is a player-coach role reporting to Humphrey Su, our Head of GTM. You'll carry your own number from day one, and you'll hire and lead our AE team as it grows.

What you'll own

• Your own book of mid-market and enterprise deals. You lead by closing.
• The bar for the AE team: how we run discovery, forecast, price and win.
• Hiring, coaching and building the sales org as it scales.
• The feedback loop to product, so what you hear in deals shapes what we build.

You might be a fit if

• 8+ years in B2B SaaS sales, with a track record of beating quota and ideally of leading AEs.
• You've sold to support, CX, IT or digital leaders at mid-market and enterprise companies.
• You want to build the sales playbook from the ground up.

How we work

• High ownership, high output. Everyone owns outcomes end to end. We hire people who are precise, fast and great at unblocking themselves.
• Speed is a habit. We decide fast, ship fast and fix fast.
• Critical feedback is a gift. We give it directly and take it without ego. It's how we get better.
• Customer-obsessed. We talk to our customers constantly and relentlessly deliver value to them.

What it takes

We work in person, five days a week, in downtown Toronto. We move fast and hold a high bar. If you want the steepest learning curve of your career and a stake in the outcome, you'll fit right in.

Pay & logistics

• Base salary: CAD $145,000–$190,000.
• Uncapped commission on top. On-target earnings: CAD $290,000–$380,000 (50/50 base and variable).
• Equity.
• Downtown Toronto, in person five days a week.
• We don't use AI to screen, assess or select applicants. A person on our team reviews every application.

How we hire

1. A 30-minute call with Humphrey Su, our Head of GTM.
2. A short take-home based on real work you'd do here.
3. 30 minutes with Yasser Elsaid, our CEO.

A note from Yasser

We've built Chatbase with a small team, and it's working: 10,000+ businesses rely on it, and they keep finding new ways to use it. What we do in the next year decides how big this gets. The people who join now will own a piece of it and be paid well for it. If that's what you've been looking for, I'd love to meet you.

Yasser Elsaid, CEO