Title:  Founding Engineer (Tech Lead)

Location: New York City (Hybrid)

Reporting Structure: This role reports to the Co-Founder

Company Description

Our client is an early-stage startup that helps professional employer organizations (PEOs) scale their client operations without scaling headcount, using our AI-powered analytics and automation platform.

We’ve 13x’d our revenue this year and are looking to bring on a founding engineering lead to help us ensure we deliver a world-class product experience for our customers. In this role you will be joining the founding team alongside co-founders.

Quick facts:

• Raised $1.4M in early-stage capital to accelerate product and engineering growth.
• 16xd revenue growth in the past year
• Working with leading PEOs and tech-forward HR organizations that are replacing legacy systems like Salesforce and HubSpot with Wayside’s AI-native platform.

Responsibilities:

As full-time employee #4 you can expect to work on a large variety of things, but our core areas of need are:

• Development: You will ship both backend and user-facing features in the Wayside platform.
• Customer Success: You will engage with our customers to demo features, collect feedback, offer support, and deeply understand the needs of who we serve.
• Product: You will help manage our product roadmap, independently design features, and make decisions about the surfaces in which our users spend time.
• Management: You’ll lead a team of 2-3 engineers to help deliver features for our customer-base

Is this you?

• You’re a builder at heart — hands-on, technical, and excited to work directly with founders in an early-stage environment.
• You have 3+ years of experience developing web applications, ideally with TypeScript and modern frameworks.
• You’re comfortable working across the stack and enjoy making architectural decisions that balance speed and scalability.
• You’re customer-driven — you care about understanding user pain points and turning feedback into elegant solutions.
• You communicate clearly, write well, and thrive in environments that value autonomy, ownership, and clarity over bureaucracy.
• You’ve led or mentored small engineering teams and are eager to grow into a broader leadership role (Head of Eng / CTO).
• Bonus points if you’ve built or integrated AI-enabled systems in production or have startup experience where you’ve worn multiple hats.

Preferred Qualifications

• Experience working on LLM-enabled systems deployed in production.
• Proficiency in Python.
• Experience working professionally with low-level languages (C, Java, Rust, C++).
• Experience with high-ownership positions in startups.
• Exceptional work ethic, an interest in the grind of early-stage startups, and the ability to independently manage ambiguous tasks.
• 3+ years working as a professional software developer.
• Basic proficiency with cloud deployment practices.
• Professional experience with web development frameworks.
• Competency in Typescript.

#Perks

• Up to $200K Annual Salary
• Favorable Equity
• Health Insurance
• Full Autonomy in a high-growth Startup