Posted 11 days ago
Head of Sales
@ Chatbase
Toronto, Ontario
Overview
Chatbase, an AI agent platform, is hiring a Head of Sales who will carry a personal quota of mid-market and enterprise deals and build the AE team. The role is a full-time, in-person player-coach position in downtown Toronto, five days a week. The pay is CAD $145,000–$190,000 base plus uncapped commission, with on-target earnings of CAD $290,000–$380,000 and equity.
Pay:
$290,000–$380,000 a year
Responsibilities:
- Carry a personal book of mid-market and enterprise deals
- Set the sales bar for discovery, forecasting, pricing and winning
- Hire, coach and build the AE team as it scales
- Feed customer insights from deals back to product
Requirements summary:
- 8+ years in B2B SaaS sales
- Track record of beating quota
- Experience leading AEs preferred
- Experience selling to support, CX, IT or digital leaders
Tools & skills
Source and dates
Employer career site / ATS feed · ashby
- Employer posting date
- 2026-10-27
- First seen by our source
- 2026-10-27
- Source record updated
- 2026-10-28
These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.
Job details
| Seniority | Lead |
| Department | Sales |
| Experience | 8+ years |
| Manages people | Yes |
| Hours per week | 40 (estimated) |
| Work setting | Office |
| Position | Mostly sitting |
| Physical demands | physical low · computer high |
| Perks mentioned | Performance bonus, Stock or equity |
Summary and details written by AI from the posting; the employer’s posting is the authority.
Chatbase
Saved company profile
Historical company information from a saved The Jobs API profile (LinkedIn/Crunchbase fields). It is not live-verified; figures may have changed. Missing values remain unknown.
AI Agents for magical customer experiences.
Full company description
Chatbase is the AI customer support platform for companies that take service seriously. Our platform enables businesses to build and deploy AI agents that don't just simply answer questions, but take action to resolve them. By connecting to your CRM, helpdesk, payment processors, and other tools, Chatbase agents take real action: updating subscriptions, checking order status, processing requests, and escalating intelligently when a human touch is needed. Chatbase is trusted by 10K+ global teams ranging from boutique retail and fitness brands to massive telecoms and infrastructure companies. Our platform is designed for teams that want the power of enterprise-grade AI without the complexity. What sets us apart: - AI agents trained on your business and data, not generic responses - Omnichannel deployment: web, whatsapp, slack, email & more - Seamless live agent handoff with full context preserved - 80+ languages with automatic detection - SOC 2 and GDPR compliant, enterprise-grade security Support doesn't have to be a cost center. With Chatbase, it can beome a competitive advantage.
- LinkedIn followers
- 31,396
- People associated on LinkedIn
- 64
- Reported office locations
- San Francisco, US
- Business categories
- Agentic AI
- Other recorded names
- Chatbase
- Profile identifies a recruitment agency
- No
- Reported total investment
- 0
Currency and observation date were not supplied; this is not a current valuation or a funding round.
Chatbase is the AI customer support platform for companies that take service seriously. Our platform enables businesses to build and deploy AI agents that don't just simply answer questions, but take action to resolve them. By connecting to your CRM, helpdesk, payment processors, and other tools, Chatbase agents take real action: updating subscriptions, checking order status, processing requests, and escalating…
| Field | Value |
|---|---|
| Industry | Software Development |
| Company size | 11-50 employees |
| Headquarters | San Francisco |
| Organization type | Privately Held |
| Year founded | 2023 |
| Open jobs on Jobsy | 10 |
| View page |
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
We move fast.
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
Journal
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