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Diligent is the AI leader in governance, risk and compliance (GRC) SaaS solutions, serving over 1 million users and 700,000 board members. The GTM Systems and AI team owns the systems, data, integrations, and AI capabilities that power go-to-market execution across Sales, Customer Success, Marketing, and Operations.
As a Senior GTM Systems & AI Lead, you will own complex improvements across the GTM systems landscape. You'll address foundational issues including incomplete or unreliable data, broken integrations, disconnected workflows, and overlapping AI agents. You'll identify, build, and scale AI-enabled workflows that make GTM teams more effective.
This is a senior, hands-on individual contributor role reporting to the Director of GTM Systems and GTM AI. You'll investigate problems, recommend priorities, design solutions, and lead initiatives from definition through rollout and measurable impact. You won't need to be a traditional software engineer, but you must be highly technical and comfortable with APIs, SQL, system integrations, MCP, LLMs, and AI coding tools.
Key responsibilities include:
- Design and build systems and AI infrastructure connecting GTM tools, automating processes, and using AI to improve team velocity and data reliability
- Find manual or inefficient GTM processes and design, build, and scale AI-enabled workflows, agents, and automations with metrics, evals, and guardrails
- Own initiatives end-to-end from problem definition through rollout and impact, building reusable systems and patterns rather than one-off solutions
- Work across Sales, Customer Success, Ops, and Marketing as the lead GTM Systems subject matter expert
- Connect GTM systems through APIs, orchestration platforms, webhooks, MCP, and other integration patterns while maintaining data accuracy and consistency
- Drive adoption of shipped solutions and establish standards for how the team builds
- Identify fragmented or overlapping agents and automations, consolidating them into maintainable systems with clear ownership, reusable components, appropriate guardrails, and measurable value
Examples of potential projects include building an orchestration/MCP layer connecting multiple GTM tools without bespoke integration projects, creating a self-serve automation marketplace for other teams, and developing signal-scoring automation that improves tool ROI.
Success metrics include building a clear understanding of GTM systems and data flows, identifying and prioritizing foundational issues, improving reliability of critical data flows and automations, establishing clearer ownership and standards for integrations and workflows, shipping AI-enabled solutions that reduce manual work, and creating a practical roadmap balancing foundational work with new capabilities.
The role offers flexible working arrangements with the option to work hybrid or fully remote, though applicants must be based in the United States. If within commuting distance of a Diligent office, hybrid roles typically require 50% onsite presence.
REQUIREMENTS:
- Significant experience working across GTM Systems, Revenue Operations, Business Systems, or related function (typically 5+ years)
- Hands-on experience building with LLMs and agent frameworks; fluency with AI coding tools like Claude Code or Codex
- Deep understanding of GTM systems, data, and processes across Sales, Customer Success, Marketing, and Operations
- Technical fluency with APIs, webhooks, integration and orchestration platforms, data flows, and system architecture
- Self-starter who can take business problems from cross-functional teams, define them, and build AI or automation solutions independently, comfortable with ambiguity
- Strong systems thinking; ability to distinguish symptoms from root causes and design reliable solutions
- Senior-level influence: leads cross-functional initiatives, raises the bar for how others build, explains tradeoffs to technical and non-technical leaders up to VP level
Nice-to-have skills:
- Experience with MCP, RAG, agent evaluation, observability, or governance tooling
- Python or JavaScript experience for troubleshooting, extending, or maintaining automations and integrations
- Experience rationalizing overlapping agents, automations, integrations, or GTM tools
- Experience establishing standards and reusable patterns for AI-enabled workflows
- Experience improving systems and data through M&A, rapid growth, or organizational change
- Experience measuring adoption, productivity gains, data-quality improvements, or business outcomes from systems and AI initiatives
- B2B SaaS environment experience
