Director, GTM Engineering & Systems

About the role

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’t exceptional at leading large scale cross-functional projects. This role must collaborate with most teams and people at Ashby. Your tools are the backbone of the GTM team’s success. In order to build and maintain tools that meet the needs of the GTM org you will need to manage large cross functional projects with organization and agility.

INTERVIEW PROCESS

Our interview process is thorough — we aim to ensure each person joining the team is the right fit for Ashby and will provide ample information to assess if Ashby is the right fit for you. The process for this role is as follows:

• Recruiter Screen with Talent Acquisition Team - 30 minutes

• Hiring Manager Interview - 60 minutes

• Challenge Interview - 45 minutes

• Virtual Onsite - 75 min

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.

Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position.

Covesight rechecks every listing nightly. Last confirmed live: 2026-07-16.