Software Engineer ($160k-$180k + Equity) at Reflow AI Inc. (DBA Wayside)

This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Software Engineer

Salary

$160k-$180k Equity

Company Description

Reflow AI Inc. (DBA Wayside) is a seed-stage NYC startup with $1.3m ARR building AI-powered automation for Professional Employer Organizations (PEOs).

Job Description

Join Reflow AI Inc. (DBA Wayside) as the third software engineer to automate legacy PEO workflows using AI. As a founding team member, you will own features end-to-end using Next.js and TypeScript. You’ll work closely with customers to shape the product roadmap and build AI agents that transform payroll and compliance operations.

Location

New York City, USA

Why this role is remarkable

• Founding-stage opportunity as the 3rd engineer in a high-intensity startup that grew revenue 18x last year to $1.3M ARR.
• Massive individual ownership where you define architectural decisions and the roadmap while working directly with the founding team and customers.
• Build at the cutting edge of AI, deploying production-ready agents to automate complex workflows for multi-billion dollar legacy industries.
  
  

What You Will Do

• Ship backend and user-facing features end-to-end using Next.js and TypeScript, self-hosting on AWS to deliver a world-class product experience.
• Engage directly with customers to demo features, collect feedback, and support users to ensure the product meets real-world operational needs.
• Design and implement AI-enabled workflows for client support and payroll entry, contributing significantly to the core product roadmap and strategy.
  
  

The ideal candidate

• 3 years of professional software development experience with deep proficiency in TypeScript and modern web development frameworks like Next.js.
• Exceptional work ethic and a desire for high-ownership positions in early-stage startups, with the ability to independently manage ambiguous tasks.
• Practical experience with cloud deployment on AWS and a strong interest or experience in building production-grade LLM-enabled systems.
  
  

Who are Jack & Jill?

Ok, I'll go first. I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career. Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

How does this work?

• Jack's an AI agent for job searching and career coaching. He works for you.
• Jill is the AI recruiter working for the company. She recruits from Jack's network.
• If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
  
  

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.