GTM AI Engineer

About the Role This is the first role of its kind at AppWork, and the mandate is bigger than fixing what's broken. We want every person on our Sales and Marketing teams to have real AI-powered support solving the specific problems that slow them down every day. Not a chatbot bolted onto a workflow. Actual tools and agents built around how our team really works. You'll spend real time understanding each function's process and the bottlenecks that come with it, then build the tools, automations, and agents to solve for them, sometimes by connecting what we already have, sometimes by building something that doesn't exist yet. You'll approach it strategically so everything ties together as one system, while still leaving room to experiment fast and throw out what doesn't work. Your First Two Months Month one is learning. You'll sit with reps and marketing to understand our processes end to end, and figure out where the real friction lives, not just where it looks like it lives from the outside. Month two is building. You'll start turning what you learned into working prototypes, testing them with the people who'll actually use them, and refining fast based on what sticks. From there, you're building the org's AI infrastructure for the long haul: new tools where nothing exists yet, integrations where they do, and the training and rollout that makes sure people actually adopt what you build. What You'll Own Work directly with reps and marketing to map their day-to-day process and pinpoint the bottlenecks worth solving. Design and build new AI tools and agents from scratch where no off-the-shelf solution solves the problem, not just wire together existing software. Connect and automate across our existing stack (HubSpot, ClickUp, Slack, and others) wherever that's genuinely the right solution. Balance a strategic view of how everything should connect with a willingness to prototype fast, test small, and iterate based on real usage. Lead the organization through the change that comes with new tooling: training the team, driving adoption, and being the person people go to when something doesn't click. Track adoption and impact on everything you ship, and use that data to decide what to double down on and what to kill. Serve as AppWork's subject matter expert on applied AI for GTM, staying ahead of what's possible and translating it into what's actually useful here. What You Bring This role calls for someone genuinely versatile: comfortable moving between strategy and hands-on building, between technical work and leading people through change. We're less focused on a specific background and more on how you think and operate. A builder's mindset. You'd rather prototype something and learn from it than write a plan and wait for permission. Strong technical ability, with real experience building things, whether that's custom AI agents and automations, scripts, or integrations, not just configuring templates. Comfort working across no-code and low-code tools (Zapier, Clay, HubSpot workflows) as well as code (Python, JavaScript, or similar) when the problem calls for it. A track record of figuring things out in ambiguity, without a playbook to follow, and getting to a working answer anyway. Experience leading change with non-technical teams: training people, driving adoption, and sticking with a rollout until it actually takes hold. Sharp instincts for translating a business pain point into a technical solution, and explaining that solution back in plain language. Genuine curiosity about AI systems and agents, and strong opinions on where they create real value versus where they're just noise. Nice to Have, not required: Prior experience building AI agents or applied AI tools in a business setting. Background in revenue operations, sales, or marketing. Experience in multifamily, proptech, or another vertical SaaS business. This role can be based out of our St. Petersburg, FL office or fully remote. Why this Seat You won't inherit a system, you'll build one. You'll have a direct line to the CRO, real autonomy over how you approach the problem, and the chance to define what an AI-first GTM org looks like at AppWork from the ground up. If you like being handed a hard, undefined problem and figuring out the answer yourself, this is that job. Compensation & Benefits Competitive salary Equity Unlimited PTO Medical, dental, and vision coverage