Director of Technology & Systems

About the Role The Director of Technology and Systems will be responsible for building real depth across Finance, GTM, Operations, and People systems, connecting these capabilities into a powerful, AI-integrated backbone. You are a builder-first leader who will blend enterprise architecture with cutting-edge AI automation. Your goal is to eliminate fragmentation and enable every function to move faster by deploying internal AI agents that reduce manual work and surface actionable insights. You will lead the charge in making our internal operations as sophisticated as the external products we build. Key Responsibilities - Enterprise Application Strategy: Own the full lifecycle of our application ecosystem, and specialized AI tools. Ensure these systems converge into a secure, scalable backbone. - AI Agent Deployment: Identify opportunities to replace manual workflows with AI/LLM-powered agents. Build and manage "internal agents" that automate forecasting, revenue capture, and employee self-service. - Cross-Functional Partnership: Serve as the primary technology partner to the leadership team. Align system roadmaps with departmental goals to ensure seamless data flow from production to the back office. - Operational Excellence: Mature our core systems by establishing disciplined change management, clear data governance, and measurable SLAs. Stabilize environments to support audit and regulatory requirements. - Team Leadership: Lead a high-impact team that fosters a culture of curiosity, speed, and user-centricity. Ideally, you have: - 10+ years of experience leading business systems or enterprise applications in a fast-paced, high-growth environment. - Deep familiarity with the enterprise systems landscape across GTM, Finance, and People functions — you understand how these platforms work, where they break down, and how to connect them into a coherent operational backbone. - AI/Automation Mindset: Proven track record of designing and deploying AI/LLM-powered workflows or agentic systems to improve business efficiency. - Architecture Skills: Ability to design scalable data flows and APIs that link disparate SaaS tools into a cohesive ecosystem. - Stakeholder Mastery: Experience influencing C-level executives and translating complex technical needs into business outcomes. - Strong working knowledge of ERP systems and core financial operations — enough to partner credibly with Finance, ask the right questions, and drive system decisions without needing to own every module deeply. - Experience with GTM systems such as, HubSpot, Outreach, Clari, CPQ (e.g., Salesforce CPQ), and similar tools. Compensation packages at Scale for eligible roles include base salary, equity, and benefits. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position and may be inclusive of several career levels at Scale; it will be determined during the interview process based on work location and additional factors, including job-related skills, experience, qualifications, interview performance, and relevant education or training. Scale employees in eligible roles are also granted equity based compensation, subject to Board of Director approval. Your recruiter can share more about the specific salary range for your preferred location during the hiring process, and confirm whether the hired role will be eligible for equity grant. You'll also receive benefits including, but not limited to: comprehensive health, dental and vision coverage, retirement benefits, a learning and development stipend, and generous PTO. Additionally, this role may be eligible for additional benefits such as a commuter stipend. The base salary range for this full-time position in the location of San Francisco is: $235,200—$294,000 USD PLEASE NOTE: Our policy requires a 90-day waiting period before reconsidering candidates for the same role. This allows us to ensure a fair and thorough evaluation of all applicants. About Us: At Scale, our mission is to develop reliable AI systems for the world's most important decisions. Our products provide the high-quality data and full-stack technologies that power the world's leading models, and help enterprises and governments build, deploy, and oversee AI applications that deliver real impact. We work closely with industry leaders like Meta, Ernst & Young, Mayo Clinic, Time Inc., the Government of Qatar, and U.S. government agencies including the Army and Air Force. We are expanding our team to accelerate the development of AI applications. We believe that everyone should be able to bring their whole selves to work, which is why we are proud to be an inclusive and equal opportunity workplace. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability status, gender identity or Veteran status. We are comm