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Head of Software Engineering /Onsite/Chicago/Western Suburbs

Motion Recruitment

Part-time | Contract

Chicago, IL

Job description

Position: Founding Software Developer (AI-Driven Development & Product Build-Out)
Location: Remote-First | Flexible Schedule | Occasional Atlanta Meet-ups
Type: Contract-to-Core Team | High-Growth Startup

Who We Are

Penny Lawns is building more than just landscapes—we’re building a platform to connect customers with skilled, vetted contractors for fast, high-quality, and budget-friendly landscaping solutions.

But behind every great service is world-class technology. That’s where you come in. We're looking for a high-impact, AI-savvy developer to lay the digital groundwork for our entire operation—from building our first apps to reinventing our website to launching customer-facing platforms.

What You’ll Be Building

  • AI-Assisted Development: Use tools like GPT, GitHub Copilot, and automation platforms to streamline code, product testing, and feature rollouts.
  • Penny Lawns V1 App: Our first internal application for job tracking, contractor matching, and project management.
  • Website Overhaul: Redesign PennyLawns.com for maximum speed, conversion rates, and operational efficiency.
  • Customer-Facing Features: Build tools and applications that empower customers to book, track, and manage their landscaping projects easily.
  • Cross-Functional Solutions: Collaborate directly with the CEO to integrate AI-driven, scalable solutions across all areas of the organization.

The Aggressive Offer Package

1. Compensation

  • $750/month startup stipend (during initial build-out phase, ~20-30 hrs/month expected)
  • Milestone Bonuses:
  • Website Redevelopment Live: $500
  • First App Launch: $750
  • Customer Feature Set Phase 1 Live: $1,000

2. Profit Sharing

  • 5% of Net Profits for first-generation employees, kicking in after Year 1 (distributed quarterly)
  • Designed to reward those building the foundation

3. Equity & Stock Offering

  • Up to 4% company equity based on contribution and vesting schedule (4-year standard with 1-year cliff)
  • Early Stock Option Pool Access as company scales
  • Equity protected by standard founder agreements

4. Aggressive Startup Incentives

  • First-Mover Perks: Priority path to CTO or Technical Co-Founder title
  • Freedom of Tech Stack: Choose the tools, frameworks, and AI integrations that set the foundation
  • Direct CEO Access: Work alongside leadership to shape business and product strategy
  • Future Hiring Authority: As we grow, you’ll build and lead the dev team

5. Resources Provided

  • Paid AI tools (OpenAI API, Copilot, automation platforms)
  • Paid productivity tools & web hosting resources
  • $1,000/year professional development fund (courses, conferences, certifications)

Why This Role is a Game-Changer

  • You’re not just writing code—you’re engineering the core product and platform
  • Leverage AI to build faster, smarter, leaner
  • Get in early, own a real stake, and grow with the company
  • Influence product direction, customer experience, and operational systems
  • Escape corporate bureaucracy—move fast, build, iterate, win

The Ideal Candidate

  • Full-stack developer with strong understanding of modern web frameworks
  • Comfortable using AI tools for code, testing, and automation
  • Excited by wearing multiple hats in a fast-paced, early-stage environment
  • Bonus: Experience with payment systems, contractor platforms, or SaaS products
  • Entrepreneurial mindset: You see inefficiencies and can fix them without waiting for permission

The Vision

We’re modernizing the $100B+ landscaping industry, one customer and contractor at a time. The technology you build will help homeowners get quality work done faster—and help small contractors grow their businesses.

How to Apply

Apply Now on this platform!

Job Types: Part-time, Contract

Expected hours: 10 – 15 per week

Compensation Package:

  • Profit sharing
  • Quarterly bonus
  • Stock options

Schedule:

  • Monday to Friday
  • Weekends as needed

Application Question(s):

  • Are you located in the United States?
  • Where are you located?

Work Location: Remote