---
title: 'Senior AI Engineer at Topline Pro'
canonical: 'https://feeny.ai/job/senior-ai-engineer-topline-pro-boston-jr486v64yjq8'
type: 'job'
last_seen: '2026-11-08'
---

# Senior AI Engineer at Topline Pro

- **Company:** Topline Pro
- **Location:** Boston, MA
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-05-12
- **Last confirmed live:** 2026-11-08
- **Apply:** https://jobs.ashbyhq.com/topline-pro/08241142-2f25-4fcc-b274-e431b385379c

## Job description

## About the Role

We're hiring a Senior AI Engineer to join the team here in Boston. This is an opportunity to have a significant impact on the product. Come help us scale to the next level! You will have the opportunity to make a huge impact on a small yet growing team and culture. In this role, you will work directly on a cross-functional engineering team, reporting to the VP of Engineering.

⚡ What you'll do

- Build AI Agent and Chat Capabilities – Develop AI-powered assistants using cutting-edge technologies and tooling that help our customers run their small businesses
- Deploy & Scale AI Features – Build infrastructure and pipelines to support real-time AI interactions in a production environment
- Experiment & Iterate – Prototype new AI applications, evaluate their performance, and continuously refine them based on user feedback
- Partner with engineering and product leaders – Contribute strategically and play a key role in the product development process

🎯 What we're looking for

- 5+ years of experience in AI, ML, or NLP-related engineering roles
- Proficiency in Python, with preferred experience in Django, React, and PostgreSQL
- Real-world experience with Retrieval Augmented Generation (RAG) and similar practices, including vector embeddings and vector databases
- Hands-on experience with OpenAI and Anthropic APIs
- Familiarity with LLMs and NLP techniques, including prompt engineering, fine-tuning, and evaluation
- Experience with coded agentic frameworks such as Pydantic AI, LangChain/LangGraph, or similar
- Experience with end-to-end MLOps practices: monitoring, deployment, and evaluation
- Experience deploying AI-powered applications in production environments (e.g., cloud-based APIs, real-time processing)
- Experience working on an empowered team with Product and Design as equal counterparts
- Experience in an Agile Scrum environment

## What you bring

- Sharp problem-solving instincts, especially in fast-moving, ambiguous situations
- Confidence to make decisions with best-available rather than perfect information
- A drive to understand why your systems behave the way they do, not just that they work, but how
- Excellent written and verbal communication skills
- A team-first mentality and a love of learning
- Low ego, high energy

🙌 What we offer

- Full Medical, Dental, and Vision Health Coverage
- Computer and workspace enhancements
- 401(k) plan (non-matching)
- Unlimited vacation, 9 company holidays including election day, and 1 personal volunteer day a year
- Company-paid Wellhub membership for fitness and wellness
- Dinner covered with Uber Eats + a stocked kitchen to keep you fuele
- Opportunity to take on significant responsibility and ownership in scaling a product that can change the lives of home service pros

🏠 About Topline Pro We're building an AI-powered Shopify for service businesses. We help service pros (e.g., roofers, landscapers, painters, cleaners) acquire direct business, fast. Up and running within minutes using Gen AI, our digital storefront products help pros get discovered, trusted, and booked repeatedly.

Topline Pro was co-founded by [Nick Ornitz](https://www.linkedin.com/in/nick-ornitz-766935a5/) (CEO) and [Shannon Kay](https://www.linkedin.com/in/shannonekay/) (COO), with an excellent team of 120+ rockstars and plans to expand further in 2026. We serve thousands of local service businesses and were named one of the [top 50 Tech Companies building for SMBs in 2023 and 2024](https://www.prnewswire.com/news-releases/topline-pro-named-to-2023-smbtech-50-301805646.html).

We're YC-backed and well-funded, with several years of runway, and we've experienced rapid growth over the past year. We're in a phenomenal position to scale, with the financial foundation, product-market fit, and momentum to go big. You'll be joining at an inflection point, where the groundwork is laid, and the path to massive impact is clear.

We believe "great candidates" do not come about simply from a check mark next to past experience. We believe in hiring people, not just skills. Even if you do not check every box but find excitement at the prospect of working with us in this capacity, please apply.

Topline Pro is committed to building an inclusive workplace and assembling a team from diverse backgrounds. We ensure that individuals with disabilities receive reasonable accommodation throughout the application and interview process. We strongly encourage applications from underrepresented candidates and those from nontraditional backgrounds.

## About Topline Pro

## Company Overview
- **One-liner**: Topline Pro provides an AI-powered platform that helps home service professionals generate websites, manage marketing, handle sales, and streamline operations to grow their businesses.
- **Entity Type**: Private (Series B)
- **Headquarters**: New York, New York, United States
- **Founded**: 2020
- **Founders**: Nick Ornitz (Co-Founder & CEO), Shannon Kay (Co-Founder & COO)

## Core Business
- Primary industry/industries: Home Services Technology, AI-powered SaaS for SMBs
- Target customers: Home service professionals (roofers, landscapers, electricians, plumbers, etc.), ranging from solo operators to growing teams
- Mission or purpose statement: To empower SMBs with AI that gets work done—helping them win work, do work, and get paid. The company aims to be an “unfair advantage” for pros too busy doing the work to manage their online presence.

## Products & Services
- **Topline Pro Platform (AI Sales Assistant & Marketing Suite)**: An integrated SaaS platform that includes:
    - **AI Website Builder**: Rapidly creates custom, SEO-optimized websites for pros.
    - **Prospect Feed**: Surfaces local jobs as they appear for instant action.
    - **AI Lead Response**: Automatically responds to new inquiries to capture leads.
    - **Review Management**: Collects and shares 5-star reviews to build trust.
    - **Social Media & Content Automation**: Auto-posts content to keep businesses visible.
    - **Invoicing & Payments**: Sends invoices, accepts online payments, and automates reminders.
    - **Customer Hub**: Centralizes all customer details, history, and communication.
    - **Calendar Management**: Provides an organized, conflict-free scheduling system.
    - **Targeted Advertising**: Optimizes ads to put pros in front of ready-to-hire customers.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metrics**:
    - **Total Funding**: $44.13M (including a $27M Series B raised approximately one year ago)
    - **Revenue Booked for Customers**: Over $655M
    - **Positive Reviews Generated**: Over 100M
    - **Small Businesses Powered**: 30K+
    - **States Served**: 30+ U.S. states
- **Notable Investors**: Y Combinator (Winter 2021 batch) and other world-class investors (specific names not fully listed, but the company states it is “supported by world-class investors who believe in our mission”)
- **Growth Signals**: Raised a $27M Series B; reports $655M+ in revenue booked for customers; serves thousands of home service pros across 30+ states; team size has grown significantly (listed as 28 on YC but appears larger based on leadership team structure).

## Competitive Advantages
- **AI-First, Done-for-You Approach**: Unlike DIY website builders, Topline Pro’s AI acts as a “real teammate” that handles website creation, review collection, lead response, and content posting automatically.
- **Vertical Focus**: Solely dedicated to the home services industry, allowing deep specialization in the workflows and needs of pros like roofers and landscapers.
- **Unified Platform**: Replaces the need for pros to piece together disparate tools (website builder, CRM, invoicing, marketing) with a single, integrated solution.
- **Proven Results**: Tangible metrics (over $655M in revenue booked, over 100M reviews generated) demonstrate strong product-market fit and customer value.

## Strategic Focus
- **Scaling the Platform**: Using the $27M Series B to expand product capabilities and market reach.
- **Deepening AI Capabilities**: Continuing to build AI that automates more of the business management workload for pros.
- **Growing the Customer Base**: Expanding from thousands to tens of thousands of small businesses across more U.S. states.

## Why Work Here
- **High-Impact Mission**: The company is “building for builders,” serving a massive, underserved market of home service pros who are skilled at their craft but struggle with business management.
- **Strong Growth Trajectory**: As a well-funded Series B company (raised $27M), Topline Pro is in a high-growth phase, offering opportunities for ownership and impact.
- **Culture & Values**: Emphasizes speed, big thinking, and celebration of wins. Core values include “Be an Owner,” “Think Big, Learn Fast,” and “One Team, One Dream.”
- **Work Environment**: In-person collaboration is valued, with offices in Brooklyn and Boston. The team also has retreats and a “pod culture” with monthly budgets for connection.
- **Benefits**: Comprehensive medical, dental, and vision plans; monthly wellness stipend; 401(k) plan; monthly AI tool stipend; yearly professional development budget; top-tier work equipment.
- **Leadership**: Led by founders Nick Ornitz (CEO) and Shannon Kay (COO), with a strong leadership team including a VP of Engineering, VP of Data, VP of Sales, and Head of Design.

## Sources
1. [toplinepro.com](https://www.toplinepro.com/)
2. [toplinepro.com/careers](https://www.toplinepro.com/careers)
3. [jobs.ashbyhq.com](https://jobs.ashbyhq.com/topline-pro)
4. [cbinsights.com](https://www.cbinsights.com/company/prophone-1)
5. [ycombinator.com](https://www.ycombinator.com/companies/topline-pro)

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