Build the AI technician for the real world.

The role

As a Founding AI Engineer, you will build the agents at the heart of Squash and own their path from early experiment to reliable production system. You may spend one week improving how an agent investigates an unfamiliar IT issue, the next designing evaluations that expose where it fails, and the next building the tools and infrastructure it needs to act safely across customer systems. You will work directly with customers, help decide what to build, write production code, and operate what you ship. You will also help define how AI gets used across the MSP industry: which work agents should own, where people stay in control, how decisions are explained, and what a great technician experience looks like. The standards for AI-native service delivery are still being written, and you will have a meaningful hand in shaping them. This will remain a hands-on building position.

What you’ll do

• Build and improve AI agents that investigate IT issues, maintain context, use tools across customer systems, follow policies, request approval, and recover when things do not go as planned.
• Design evaluation systems that measure agent quality, expose failure modes, and turn production traces and customer feedback into improvements.
• Experiment with models, prompts, retrieval approaches, tool design, and agent architectures, then turn the best ideas into dependable production systems.
• Build the integrations and backend infrastructure that let agents operate securely, reliably, and observably across long-running customer workflows.
• Work directly with customers to understand their problems, ship end-to-end product improvements, and help establish our engineering practices and culture as Squash grows.

Who you are

• You have built and shipped production software using modern AI models, ideally including agents or other tool-using systems.
• You are an AI-native software engineer who experiments quickly with new models and techniques and turns promising prototypes into reliable production systems.
• You know how to evaluate nondeterministic systems, investigate failures, and balance speed with quality, safety, and customer trust.
• You take ownership, use AI deeply in your work, have strong product instincts, and work comfortably with customers to turn ambiguous problems into working products.

The role

As a Founding GTM Associate, you will work directly with the founders across sales, marketing, customer success, and revenue operations. You will help create pipeline, support active deals, turn customer learning into better marketing, help new customers get value, and build the systems that keep all of it moving. The scope is intentionally broad and will evolve as the company grows. One week you may be running a targeted outbound campaign, the next helping a customer through onboarding, and the next cleaning up our CRM or turning a customer win into a case study. You will see and influence almost every part of how an early-stage AI company finds customers, earns trust, and builds a repeatable growth engine. This is a strong fit for someone who may want to start a company one day or build a career in software sales, growth, customer success, or operations. As Squash grows, the role can develop around what you are great at and where you want to grow.

What you’ll do

• Research target accounts, build pipeline through thoughtful outreach, and support the sales process from the first conversation through demos, follow-up, proposals, and close.
• Create content, customer stories, campaigns, and event programs that make Squash easier to understand and give prospects a reason to engage.
• Help onboard customers, stay close to their experience, solve problems, and bring clear feedback back to the product and engineering team.
• Own the operating details behind growth, including CRM hygiene, pipeline tracking, reporting, follow-up, and simple automations.
• Run experiments across the customer journey, learn what works, and help turn those lessons into a repeatable GTM playbook.

Who you are

• Experience in sales, marketing, customer success, or operations is helpful, but we care more about evidence that you learn quickly, communicate well, and get things done.
• You communicate clearly, enjoy talking with customers and prospects, and are willing to make a cold call or send the first message.
• You are organized, pay attention to details, and follow through without needing someone to remind you.
• You use AI and modern tools to move faster and are comfortable learning new systems as you go.
• You care more about outcomes than job boundaries. You are ambitious, low ego, and ready to switch between creative, analytical, and operational work as your responsibility grows.