Position Overview

Diligent is the AI leader in governance, risk and compliance (GRC) SaaS solutions, helping more than 1 million users and 700,000 board members to clarify risk and elevate governance.

Diligent’s GTM Systems and AI team owns the systems, data, integrations, and AI capabilities behind how we go to market. We’re strengthening the foundations of our GTM environment while expanding how we use AI to improve work across Sales, Customer Success, Marketing, and Operations.

As a Senior GTM Systems & AI Lead, you’ll lead complex improvements across our GTM systems. You’ll fix foundational issues such as incomplete or unreliable data, broken integrations, disconnected workflows, and overlapping AI agents. You’ll also identify, build, and scale AI- workflows that make our teams more effective.

This is a senior, hands-on individual contributor role. 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 should be highly technical and comfortable working with APIs, SQL, system integrations, MCP, LLMs, and AI coding tools.

We’re early in building this function, so you’ll have meaningful influence over the roadmap, architecture, standards, and ways of working. You’ll report to the Director, GTM Systems and GTM AI.

This role offers flexible working arrangements, with the option to work on a hybrid or fully remote basis. Applicants must be based in the United States.

Regrettably we are unable to provide visa sponsorship, so you must be eligible to work in the US.

What You'll Be Doing

• Design and build the systems and AI behind how we go to market: connect our GTM systems, automate processes between them, and use AI to make teams faster and data more reliable
• Find manual or inefficient GTM processes and design, build, and scale AI-enabled workflows, agents, and automations to fix them, using GTM systems and AI coding tools with metrics, evals, and guardrails
• Own initiatives end to end, from problem definition through rollout and impact, and build reusable systems and patterns rather than one-off agents
• Work across Sales, Customer Success, Ops, and Marketing as our lead GTM Systems SME: take a problem, shape it into a clear solution, and build the MVP, working with cross-functional teams as needed
• Connect GTM systems through APIs, orchestration platforms, webhooks, MCP, and other integration patterns while keeping system-of-record data accurate and consistent
• Drive adoption of what ships and set the standards for how the team builds
• Identify fragmented or overlapping agents and automations. Consolidate them into maintainable systems with clear ownership, reusable components, appropriate guardrails, and measurable value

Examples of what you might build

• The missing orchestration/MCP layer connecting our dozen+ GTM tools without a bespoke integration project each time
• A self-serve automation marketplace other teams can request and extend without filing a ticket and waiting
• Signal-scoring automation that doubles down on our highest-converting signals and proves ROI on every tool renewal

What success looks like

• Built a clear understanding of our GTM systems, data flows, integrations, automations, and existing AI agents
• Identified and prioritized the foundational issues creating the greatest operational risk or friction
• Improved the reliability of critical data flows and automations while reducing recurring failures
• Established clearer ownership and standards for GTM integrations, agents, and automated workflows.
• Begun shipping AI-enabled solutions that reduce manual work or improve how our GTM teams operate
• Created a practical roadmap that balances foundational systems work with new AI capabilities

These are the essentials you’ll need to get an interview:

• Significant experience working across GTM Systems, Revenue Operations, Business Systems, or a related function, typically gained through five or more years of relevant work
• Hands-on experience building with LLMs and agent frameworks, and fluent with AI coding tools like Claude Code, Codex or any similar tools
• Deep understanding of GTM systems, data, and processes across functions such as Sales, Customer Success, Marketing, and Operations
• Technical fluency with APIs, webhooks, integration and orchestration platforms, data flows, and system architecture

Behavioral Skills:

• Self-starter who can take a business problem from a cross-functional team, define it, and build the AI or automation solution yourself, comfortable in ambiguity
• Strong systems thinking. You can distinguish symptoms from root causes and design solutions that remain reliable as the business and technology stack evolve
• Senior-level influence: leads cross-functional initiatives, raises the bar for how others build, and explains tradeoffs to technical and non-technical leaders up to VP level

It would be great if you had these to, but we’ll support you if you don’t:

• Experience with MCP, RAG, agent evaluation, observability, or governance tooling
• Experience using Python or JavaScript to troubleshoot, extend, or maintain 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 significant organizational change
• Experience measuring adoption, productivity gains, data-quality improvements, or business outcomes from systems and AI initiatives
• Experience of working within a B2B SaaS environment

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