Midmarket Software Sales - Founding Team Member for AI Startup

Nestbox AI is on a mission to help midmarket software companies infuse AI across their products and processes—unlocking new value creation and competitive advantage. We’ve built a next-generation AI platform that combines strategic advisory with turnkey execution, delivering custom intelligent solutions for companies in months, not years.

Our intelligent agents don’t just assist—they think, optimize, and execute to transform how businesses operate across sales, operations, finance, and beyond.

Now we’re looking for a founding sales leader who can rapidly bring this capability to their existing network of midmarket software companies quickly.

Why This Role is Unique

Founder-Level Impact: You’ll be the first sales hire, working directly with our technical founders to shape GTM strategy, refine our offering for midmarket software companies, and have a voice in every major decision.
Category-Defining Offering: While others stop at AI strategy slides, we deliver both the roadmap and the working solutions. You’ll sell something software firms actually need.
What You’ll Do

Design and execute Nestbox’s midmarket ICP go-to-market strategy from scratch.
Use your existing network to secure meetings with midmarket C-suite.
Own the full sales cycle—from first conversation to signed engagement.
Identify high-value AI use cases for software companies and position Nestbox as the execution partner of choice.
Partner with our founders to shape product-market fit for the midmarket software segment.
Build sales collateral, playbooks, and repeatable processes for scaling our midmarket vertical.
You Might Be a Fit If…

You already know and can reach senior leaders (CEOs, CIOs, CFOs) at multiple multi-site midmarket software companies.
You’ve sold complex B2B solutions to midmarket software companies—bonus for AI, automation, or transformation projects.
You thrive in a zero-to-one environment and want equity, ownership, and the chance to define a category.
Location

We’re building between Toronto, Chicago, and New York, and want someone who can work in-person to deepen mid-market software relationships in their metro area.

Perks Details

Founding equity potential + base/commission.
Full input into roadmap, messaging, pricing, and positioning.
Access to the most advanced AI agent technology on the market.
Work alongside technical founders with deep AI expertise.
Job Type: Full-time

Pay: $45,000.00 - $140,000.00 per year

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 software C-suites. Please tell us about your network of mid-market software companies and how you built your network.
What do you envision doing in your first 30 days with us to onboard Tier 1 mid-market software companies who want to infuse AI to their products and processes?
Work Location: Hybrid remote in Chicago, IL 60601 Read more