Director, GTM Engineering & Systems

THE ROLE Ashby is looking for a Director to lead our GTM Systems & Tools team, part of our Revenue Operations department. To scale past $100M ARR and beyond, our internal infrastructure must be as elegant and high-performing as the product we sell. You will be the architect and steward of our entire revenue tech stack, ensuring that Marketing, Sales, and Customer Success have the data, automation, and tooling they need to operate efficiently and effectively. You will manage a small, high-impact team of systems administrators, architects and GTM developers, balancing hands-on execution with long-term strategic planning. TECH STACK Our current techstack includes but is not limited to, HubSpot for CRM and email sequencing, Gong for call recording and coaching, Linkedin Sales Nav for recruitment, Accord for mutual action plans, Slab as an internal company wiki, Chilipiper for lead routing, LeadIQ for contact data, Keyplay for account data, Snowflake as our data warehouse, and Omni as our data visualization tool. It is not required that you are familiar with any or all of these specific tools, it is more important that you are familiar generally with the tech stack of a GTM team a fast growing SaaS company. WHAT YOU'LL DO - Systems Strategy & Roadmap: Own the long-term vision for Ashby’s GTM tech stack. You’ll evaluate, procure, and implement tools that solve for today’s bottlenecks while preparing us for the next years of growth. - Systems Architecture & Management: Own and manage the core revenue technology stack, including the CRM, marketing automation platforms, and analytics tools, ensuring they integrate seamlessly. - Data Governance and Architecture: Ensuring data quality and consistency across systems. Design and maintain a seamless flow of data across our ecosystem (HubSpot CRM, Sales Engagement, CS Platforms). You don’t just "add fields"—you build scalable systems and data architecture. - Team Leadership: Lead and mentor a lean team of systems experts. You’ll set the bar for documentation, testing protocols (UAT), and deployment cycles. You create a high performance culture in order to hire and retain top talent. - Cross-Functional Partnership: Act as the primary bridge between RevOps and Finance, Data/Analytics, and Engineering to ensure our revenue systems align with company-wide data integrity and financial reporting. - Optimization: Proactively identify "technical debt" within our revenue stack. You will streamline workflows to reduce friction for our account executives, growth marketers, and CSMs. - Process Optimization: Designing and streamlining operational workflows, such as lead routing, customer onboarding, and renewals, using automation to reduce manual effort. WHO YOU ARE - 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 Scaling Veteran: You have experience at a fast-growing SaaS company (ideally in the $100M–$300M ARR range). You know what good looks like at scale and have seen the pitfalls one can encounter during rapid growth. - The Tools Geek: You love to geek out on the latest technology and stay up to date on the capabilities of tools in your company’s stack. - The Empathetic Leader: You enjoy coaching technical talent and can translate complex technical requirements into business outcomes for stakeholders. - The Builder: You aren't afraid to get your hands dirty. While you are a manager, you still enjoy the "craft" of building systems. THIS ROLE MAY NOT BE A FIT IF: - You don’t like getting your hands dirty. At Ashby we believe managers should be “in the weeds”. You should be equally comfortable architecting and admining a system. - You haven’t operated at meaningful scale. We are looking for someone who can help us scale to 100M+ in ARR. Ideally your previous roles have shown you what good looks at the scale of company we aspire to become. - You aren’