Nestbox is on a mission to bring no errors to the future of 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 to create pipelines with no errors.
Now, we’re looking for a founding GTM and midmarket 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 to midmarket clients (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, Chicago, and New York, and are looking for someone based in the Chicago metro area. 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
Job Type: Full-time
Pay: $40,000.00 - $105,100.55 per year
Benefits:
• Paid training
Schedule:
• No nights
Application Question(s):
• What is your current situation? What do you dream of doing 5 years from today?
• We are looking for a founding B2B sales leader with an existing network of midmarket C-suite decision makers (200-5,000 employees). Tell us in depth about the midmarket decision makers you have sold to: what roles you sold to, industry, company size; what you sold them, your role in the deals?
• What do you envision doing in your first 30 days with us to onboard Tier 1 midmarket clients to the solution?
Work Location: In person
