B2b Sales Representation for Ai Agent Startup

20 hours ago

Toronto, Canada Nestbox AI Full time

Nestbox is redefining how modern companies work. We’ve built a next-generation, AI-powered CRM and automation platform that deploys intelligent agents across sales, customer support, operations, finance, and beyond. Our agents do more than assist—they think, optimize, and execute.

Now, we’re looking for a founding GTM and sales leader to help bring this vision to market. You’ll be the first sales hire, joining a technical founding team to define our go-to-market strategy, own the sales process end to end, and help shape the very AI tools you’ll be using daily to drive revenue.

**Why This Role is Unique**
- Sell the OS you live in: You’ll be using the very AI-powered CRM and agent suite that you'll bring to customers. You get to shape the product as you sell it.
- Founder-level impact: This isn’t a standard sales role—this is a founding team position with the opportunity to earn equity, input into company direction, and long-term upside.
- Category-defining tech: Our agents are already automating deep work across sales, support, ops, and marketing. Our platform isn’t just AI-flavored—it’s AI-native.

**What You’ll Do**
- Design and execute Nestbox’s mid-market GTM strategy from scratch
- Own the full sales cycle—from outreach to close
- Identify high-value enterprise use cases for our AI agents
- Partner closely with our technical founders to shape product-market fit
- Build sales collateral, playbooks, and systems

**You Might Be a Fit If**
- You’ve sold complex B2B SaaS (bonus: AI/ML or automation tools)
- You thrive in zero-to-one environments and love figuring things out
- You’ve worked with or sold to enterprise stakeholders (especially CDAOs, CIOs)
- You want equity, autonomy, and ownership—and you’re hungry to build

**Location**
- We’re building this company between Toronto and New York, and are looking for someone based in one of those cities. You will focus on in person sales and relationships in your location.

**Perks & Details**
- Founding equity + base/commission
- Access to the most cutting-edge LLM tools and internal agent tech
- Full input into roadmap, messaging, pricing, and positioning
- Work alongside technical founders who’ve shipped real AI products
- Where are you based?
- Why do you want to join an AI startup as the first sales hire?
- How would you spend your time in your dream work day?
- What’s the most complex B2B deal you’ve closed? Walk us through how you won it.
- What’s your approach to selling a product that isn’t fully defined yet, and where the use cases are still being shaped?
- If you were selling Nestbox tomorrow, what would your first 3 target companies be and why?
- How do you feel about picking up the phone to cold call C-suite decision makers? How do you feel about walking into a C-suite’s office from the street to get their attention?

Pay: $45,000.00-$150,000.00 per year

Application question(s):

- Why do you want to join an AI startup as the first sales hire?
- How would you spend your time in your dream work day?
- What’s the most complex B2B deal you’ve closed? Walk us through how you won it.
- What’s your approach to selling a product that isn’t fully defined yet, and where the use cases are still being shaped?
- If you were selling Nestbox tomorrow, what would your first 3 target companies be and why?
- How do you feel about picking up the phone to cold call C-suite decision makers? How do you feel about walking into a C-suite’s office from the street to get their attention?

Work Location: In person

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