Director, GTM Engineering & Systems

Ashby Inc.

Job Overview

Location

Remote - US

Job Type

Full-time

Full Job Description

📋 Description

• Lead the GTM Systems & Tools team as part of the Revenue Operations department, architecting and stewarding Ashby’s entire revenue technology stack to support scaling beyond $100M ARR.
• Own the long-term vision, strategy, and roadmap for the GTM tech stack, evaluating, procuring, and implementing tools that resolve current bottlenecks while preparing for future growth.
• Manage and optimize the core revenue technology ecosystem including CRM (HubSpot), marketing automation, sales engagement platforms, analytics tools, and data visualization systems (Omni), ensuring seamless integration and performance.
• Design and maintain scalable data architecture and governance practices to ensure consistency, quality, and flow of data across HubSpot CRM, Sales Engagement, and Customer Success platforms.
• Lead, mentor, and grow a lean team of systems administrators, architects, and GTM developers, setting standards for documentation, UAT testing, and deployment cycles to foster a high-performance culture.
• Act as the primary bridge between Revenue Operations and cross-functional teams including Finance, Data/Analytics, and Engineering to align revenue systems with company-wide data integrity and financial reporting requirements.
• Proactively identify and eliminate technical debt within the revenue stack, streamlining workflows to reduce friction for account executives, growth marketers, and customer success managers.
• Design and automate operational workflows such as lead routing, customer onboarding, and renewals using tools like Chilipiper, LeadIQ, Keyplay, and Accord to minimize manual effort and improve efficiency.
• Maintain deep familiarity with the typical tech stack of a fast-growing SaaS company, including HubSpot, Gong, LinkedIn Sales Nav, Slab, Snowflake, and others — though prior experience with all tools is not required.
• Balance strategic planning with hands-on execution, remaining actively involved in system administration and architecture while managing a team.
• Collaborate on large-scale cross-functional projects with agility and organization, ensuring tools built meet the needs of GTM teams across Marketing, Sales, and Customer Success.
• Stay current on emerging tools and capabilities in the GTM technology landscape, leveraging innovation to enhance system performance and user experience.
• Foster a culture of empathy and clarity by translating complex technical requirements into clear business outcomes for non-technical stakeholders.
• Ensure the revenue tech stack evolves in alignment with Ashby’s growth trajectory, avoiding pitfalls common during rapid scaling from $100M to $300M+ ARR.

🎯 Requirements

• Proven experience leading GTM systems or revenue operations at a fast-growing SaaS company (ideally $100M–$300M ARR)
• Demonstrated ability to architect and manage integrated tech stacks including CRM, marketing automation, sales engagement, and data warehousing tools
• Experience leading and mentoring technical teams in systems administration, data architecture, and automation workflows
• Strong understanding of data governance, integration, and flow across revenue systems
• Proven track record of managing large-scale cross-functional projects with multiple stakeholders
• Hands-on mindset — comfortable both strategizing and executing on system administration and tool configuration

🏖️ Benefits

• 10-year exercise window for stock options with no pressure to purchase upon leaving
• Unlimited PTO with a recommended four weeks per year
• Twelve weeks of fully paid family leave in the US, with plans to expand globally
• Generous equipment, software, and office furniture budget
• $100/month education budget with manager approval for larger expenses like conferences
• Top-notch health insurance for employees and dependents with all premiums covered by Ashby

Skills & Technologies

Remote

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Ashby Inc.

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About Ashby Inc.

Ashby provides recruiting software that combines applicant tracking, candidate relationship management, and analytics in a single platform. It enables recruiting teams to manage pipelines, schedule interviews, communicate with candidates, and generate reports using customizable workflows and automation. The platform integrates with email, calendars, and other recruiting tools to consolidate data and streamline hiring processes. Founded in 2018, Ashby serves high-growth technology companies and enterprises seeking to improve hiring efficiency and make data-driven recruiting decisions.

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