Chief Technology Officer

Workshop Venture Partners; Boston (MA); Remote; USD 120,000 - 180,000; Full time

Job summary

An innovative firm is seeking a hands-on CTO to lead the development of an AI-driven platform for small businesses. This role combines deep engineering skills with product intuition, allowing you to shape the future of office management through technology. You will work closely with founders to build and scale systems that enhance workflows, drive product improvements, and foster a high-performing team. Join a mission-driven company where your contributions will have a significant impact on local HVAC businesses and the environment. If you are passionate about leveraging AI to solve real-world challenges, this is the perfect opportunity for you.

Benefits

Competitive salary

Meaningful equity

Full benefits

Flexible work environment

Autonomy to build your team

Qualifications

• 10+ years of software development experience with a focus on AI/ML.
• Experience managing high-performing teams and product development.

Responsibilities

• Lead the development of AI-powered workflows and scalable systems.
• Recruit and mentor a high-performing engineering team.

Skills

Software Development

AI/ML Experience

Team Leadership

Full-stack Proficiency

Strong Communication Skills

Problem Solving

Tools

TypeScript

React

KoaJS

MongoDB Atlas

AWS

Terraform

Firebase

AI Tools (Anthropic, OpenAI, Gemini, Deepgram)

Job description

WorkHero is building the AI-powered back office for the skilled trades.

Tens of thousands of small HVAC businesses across the U.S. are overwhelmed by administrative work. WorkHero pairs experienced office managers with custom-built AI tools to reduce administrative burden and help owners grow thriving businesses.

Why it matters:

• We are helping local HVAC owners stay independent—growing their businesses and building meaningful wealth for themselves and their families.

• We are accelerating climate goals by expanding the capacity of small HVAC companies who are responsible for installing the millions of heat pumps our planet needs.

• We are proving that you can blend human expertise and AI to create exciting roles for our employees and exceptional results for customers.

WorkHero is an early-stage company with exciting traction and strong support from angel investors and Workshop Ventures. Our advisors include Chad Laurans (founder of SimpliSafe, the $1B+ home security company) and Gerald Chertavian (founder of Year Up, a $200M per year non-profit).

The Role:

We’re hiring a hands-on CTO to lead the development of our AI-first platform. You’ll work directly with the founders to turn service insights into scalable systems—building tools that supercharge human workflows and transform small business operations. This role blends product intuition, deep engineering skill, and the drive to build an enduring company and high performing team.

What You'll Do:

In your first 6–12 months, you’ll be deep in the code—building core systems, shipping features, and shaping the product alongside the founders. As we grow, your role will evolve into technical leadership, strategy, and team development. You’ll also play a key role in the product development cycle, partnering closely with the Product team on day-to-day decisions and roadmap planning.

You will:

• Build AI-powered workflows using the latest in LLMs to amplify our office management team

• Architect scalable, event-driven systems to support rapid growth

• Pair with Product and Service teams to turn user feedback into actionable, tactical product improvements

• Contribute to roadmap planning and help prioritize features that deliver real impact

• Own the technical strategy and make high-leverage architecture decisions

• Recruit, mentor, and lead a high-performing engineering team

• Stay current with AI advancements and integrate them when they drive real-world value

What We’re Looking For:

We’re looking for a rare hybrid: someone who can ship code today, lead a team tomorrow, and shape the AI-driven tools of the future.

You have:

• At least 10 years of software development experience

• Experience managing and hiring for high performing teams

• Experience with AI/ML, particularly in applying AI & ML to product development

• Experience building products at a startup or as a founder

• Full-stack proficiency, with deep expertise in at least one area

• Strong communication and collaboration skills

• Comfortable making decisions in uncertain environments

• Passion for solving real-world problems for small businesses

Nice-to-haves:

• Experience managing offshore or distributed teams

• Experience with Event Driven Systems

• Experience blending human and AI workflows

• Knowledge of the HVAC industry or similar trades

Our Tech Stack:

Here’s a glimpse of our current technology stack and what you can expect to work with on day one.

• Full Stack TypeScript

  • React Frontends

  • KoaJS Backend

  • CRXJS + TypeScript Browser Extension

  • React Native Mobile App

• NX Monorepo with shared typing & libraries

• MongoDB Atlas

• AWS - Docker in ECS, S3, Hosted RabbitMQ

• IAC Managed in Terraform

• Firebase & GCP services

• AI Tools: Anthropic, OpenAI, Gemini, Deepgram

Why Join Us:

• Shape the future of a high-growth, venture-backed company as a core member of the leadership team

• Be at the forefront of Human-AI systems, building transformative tech that scales small business support in ways previously unattainable

• Build tech that makes life easier for thousands of small business owners

• Competitive salary, meaningful equity, and full benefits

• Flexible, remote-first work environment with autonomy to build your team

• A mission-driven team that values impact and integrity

We are committed to creating a diverse and inclusive work environment. We welcome applicants from all backgrounds and experiences.