Job Description

full stack engineering and AI positions

Wayside

Salary $170K - $185K

Location ::Union Square, New York City, NY

Based in NYC; able to work in- office 4 days/week near Union Square

US work authorization required (no visa sponsorship)

Wayside is a pre-seed AI startup that 18x'd revenue last year and is now hiring a hybrid Software Engineer in New York with a salary range of $170K to $185K.

This role aligns with your focus on full stack engineering and AI positions within the New York market. You will work directly with a team that recently raised $1.5M to automate HR and payroll operations for PEOs.

Ideal companies & backgrounds

Here are a list of companies Wayside likes to see candidates with past work experience from. You can also use these companies and adjacent companies as a place to start sourcing candidates.

("Rippling" OR "Justworks" OR "Gusto" OR "Paychex" OR "ADP" OR "Paylocity" OR "Paycom" OR "MITRE" OR "Deel") - PEO and HR/Payroll tech companies (domain expertise)

( "Microsoft" OR "Google" OR "Amazon" OR "Meta" OR "Apple" OR "Stripe" OR "Databricks" OR "Cloudflare" OR "Datadog") - Big tech companies with strong engineering talent (social proof, systems programming background)

"Switchboard" OR "Poshmark" OR "Ramp" OR "Brex" OR "Mercury" OR "Vanta" OR "Retool" OR "Linear Technology" OR "Vercel" OR "Resend") - High-growth seed to Series B startups (early-stage experience, product engineering mindset)

We are looking for a Software Engineer with 4+ years of experience to join

• You'll own large projects end-to-end-from design and requirements through to delivery building vertical-specific AI workflows that help PEOs scale without scaling headcount.

What will you be doing?

• Building and shipping vertical-specific AI workflows across client support, payroll data entry, and leave management
• Taking large projects from start to finish independently-from design review and requirements to delivered feature
• Defining technical patterns and architecture that will carry the product forward as the company scales
• Contributing to product roadmap decisions and independently designing new features (25% product focus)
• Engaging directly with customers to demo features, collect feedback, and deeply understand their needs

Seniority

• 4 - 7 years of experience in full- stack software engineering (backend- leaning)
• Shipped production features end- to- end as a full- stack or backend- leaning engineer
• Experience at early- stage startups (seed to Series A) in a high- ownership IC role
• Experience building AI/LLM- powered product features deployed in production
• Domain experience in PEO, payroll, or HR tech (e. g. Rippling, Justworks, Gusto, Mitre)

Education

• Top 20 university with CS, CE, or related technical degree

Hard skills

• Backend- leaning full- stack development with web frameworks
• Cloud deployment experience (AWS preferred)
• Experience with low- level languages (C, Java, Rust, C++)

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