GTM Engineering and Systems Manager

THE ROLE Ashby is looking for a GTM Engineering Manager to lead our GTM Systems & Tools team within our Revenue Operations department. To scale beyond $100M ARR, our internal infrastructure must be as elegant and high-performing as the product we sell. You will own our entire revenue tech stack, ensuring Marketing, Sales, and Customer Success have the data, automation, and tooling to operate effectively. You will build the AI intelligence layer on top of that foundation: LLM-powered enrichment, predictive scoring, and automated workflows that replace manual audience assembly, sequence selection, and outreach across the full customer lifecycle. CURRENT STATE You won't be starting from zero. Ashby has a complete GTM pipeline: CRM, enrichment, signal detection, orchestration, and delivery all connected and running. What we haven't built is the AI intelligence layer on top of it, or the team to own it. TECH STACK Our current toolkit includes HubSpot (CRM and sequencing), Gong, LinkedIn Sales Nav, Accord, Slab, Chilipiper, LeadIQ, Clay, Cargo, Keyplay, Snowflake, Instantly, and Omni. While we don't require mastery of every tool, we need a "tinkerer’s mindset". You should be comfortable using these as raw materials to build sophisticated, AI-driven automation. WHAT YOU'LL DO Team Leadership. Build and lead a high-impact team. You will define the roles, hire the people, and organize the function to deliver on its responsibilities. Growth Architecture & Strategy. Operate as an internal product team for the GTM org. Define the roadmap, write specs, ship prototypes, and scale winning tactics to shrink iteration cycles from months to hours. Evaluate, procure, and sunset tools as the stack evolves. The GTM Hierarchy of Needs. Own the full stack of revenue engineering: - Data Foundation: Build and maintain the system infrastructure. - Own and evolve the core revenue technology stack (CRM, marketing automation, data warehouse). Ensure data quality, governance, and seamless integration across systems. - Design scalable data architecture that supports every layer above it. You don't just add fields, you build systems. - Data Modeling: Identify and collect unique data points (signals) that predict purchase, expansion, or churn. - Data Activation: Deploy those signals into automated outreach, meeting prep, and expansion nudges. - Agent Development: Design, deploy, and orchestrate AI agents that automate decision-making and execution across Marketing, Sales, Customer Success, and RevOps. GTM Agent Strategy. Define how Ashby uses AI agents across the full customer lifecycle. Identify where agents replace manual decision-making, where they augment human judgment, and where humans stay in the loop. Own the roadmap from first deployment to full orchestration. Cross-Functional Engineering. Partner with Engineering and Data teams to harden winning experiments into production-grade systems. WHO YOU ARE The Empathetic Leader. You build teams that ship and grow. You coach your people, not just manage them. You've spent enough time with sellers and CSMs to understand their workflows from the inside, and you use that knowledge to build systems they actually adopt. You can't automate what you don't understand. The Systems Thinker. You don't just see a single tool; you see an ecosystem. You understand how a change in a marketing automation trigger ripples down to a Customer Success renewal health score. The Hybrid Builder. You are either a commercially minded engineer or a deeply technical operator. You are comfortable writing Python and SQL, designing system integrations, configuring LLM-powered workflows, and evaluating AI agent platforms. You care more about revenue impact than code quality. You have hands-on experience with Clay or similar GTM workflow platforms. The Scaling Veteran. You've built GTM infrastructure at a fast-growing SaaS company (ideally $100M to $300M ARR). You know that every system you build today will need to support new products, new motions, and significantly more volume within a year. You've done this before and know where it breaks. The AI Practitioner. You've designed and deployed AI agents that moved revenue metrics, not just experimented with ChatGPT. You understand prompt engineering, agent orchestration, and the difference between a workflow that runs and a system of agents that thinks. You know where AI replaces human judgment and where it shouldn't. THIS ROLE MAY NOT BE A FIT IF - You've managed revenue systems but haven't built with AI. We need someone who builds new automated systems, not someone who optimizes what's already there. - You've operated in environments where the systems and processes were already established. At Ashby, you will inherit a small team and need to personally prototype solutions in ambiguous situations as you build the function. - You're exceptional at outbound but haven't owned the full customer lifecycle. The biggest opportunities in this role span inbound, expansion, and retention. INTERVIEW PROCESS Our interview process is thorough. We aim to ensure each person joining the team is the right fit for Ashby, and to provide you with enough information to assess if Ashby is the right fit for you. 1. Recruiter Screen with Talent Acquisition Team, 30 minutes 2. Hiring Manager Interview, 60 minutes 3. GTM Challenge Interview, 45 minutes 4. Virtual Onsite, 75 minutes BENEFITS - 10-year exercise window for stock options. You shouldn't feel pressure to purchase stock options if you leave Ashby. Do it when you feel financially comfortable. - Unlimited PTO with four weeks recommended per year. Expect "Vacation?" in our one-on-one agenda until you start taking it. - Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise. - Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! - $100/month education budget with more expensive items (like conferences) covered with manager approval. - If you're in the US, top-notch health insurance for you and your dependents, with all premiums covered by us. Ashby's success hinges on hiring great people and creating an environment where we can be happy, feel challenged, and do our best work. We're being deliberate about building that environment from the ground up. I hope that excites you enough to apply. Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.