Senior GTM Systems & AI Lead

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

#LI-SK2

About Us

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. The Diligent One Platform gives practitioners, the C-Suite and the board a consolidated view of their entire GRC practice so they can more effectively manage risk, build greater resilience and make better decisions, faster. 

At Diligent, we're building the future with people who think boldly and move fast.  Whether you're designing systems that leverage large language models or part of a team reimaging workflows with AI, you'll help us unlock entirely new ways of working and thinking.  Curiosity is in our DNA, we look for individuals willing to ask the big questions and experiment fearlessly - those who embrace change not as a challenge, but as an opportunity.  The future belongs to those who keep learning, and we are building it together.  At Diligent, you’re not just building the future - you’re an agent of positive change, joining a global community on a mission to make an impact.

Learn more at diligent.com or follow us on LinkedIn and Facebook

What Diligent Offers You 

• Creativity is ingrained in our culture. We are innovative collaborators by nature. We thrive in exploring how things can be differently both in our internal processes and to help our clients

• We care about our people. Diligent offers a flexible work environment, global days of service, comprehensive health benefits, meeting free days, generous time off policy and wellness programs to name a few

• We have teams all over the world. We may be headquartered in New York City, but we have office hubs in Washington D.C., Vancouver, London, Galway, Budapest, Munich, Bengaluru, Singapore, and Sydney.

• Diversity is important to us. Growing, maintaining and promoting a diverse team is a top priority for us. We foster and encourage diversity through our Employee Resource Groups and provide access to resources and education to support the education of our team, facilitate dialogue, and foster understanding.

Diligent created the modern governance movement. Our world-changing idea is to empower leaders with the technology, insights and connections they need to drive greater impact and accountability – to lead with purpose. Our employees are passionate, smart, and creative people who not only want to help build the software company of the future, but who want to make the world a more sustainable, equitable and better place. 

Headquartered in New York, Diligent has offices in Washington D.C.,  London, Galway, Budapest, Vancouver, Bengaluru, Munich, Singapore and Sydney.   To foster strong collaboration and connection, this role will follow a hybrid work model. If you are within a commuting distance to one of our Diligent office locations, you will be expected to work onsite at least 50% of the time. We believe that in-person engagement helps drive innovation, teamwork, and a strong sense of community.

Diligent is proud to be an equal opportunity employer. We do not discriminate based on race, color, religious creed, sex, national origin, ancestry, citizenship status, pregnancy, childbirth, physical disability, mental disability, age, military status, protected veteran status, marital status, registered domestic partner or civil union status, gender (including sex stereotyping and gender identity or expression), medical condition (including, but not limited to, cancer related or HIV/AIDS related), genetic information, or sexual orientation in accordance with applicable federal, state and local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. See also Diligent's EEO Policy and US EEOC’s Know Your Rights. We are a drug free workplace. 

We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, you may contact us at recruitment@diligent.com. 

To support a fair and consistent hiring process, we use AI and digital automated tools to assist our recruitment team in organizing candidate data, surfacing relevant applications, coordinating interview scheduling and summarizing interview notes. All final screening, evaluation, and hiring decisions are made by humans on our team. To learn more about how we collect, protect, and process your information, please review our Candidate Privacy Policy.  

At Diligent, we recognize the value of a diverse global workforce. Visa sponsorship may be available for select positions based on business needs and specific role requirements. Sponsorship decisions are evaluated on a case-by-case basis, and eligibility should not be assumed for all opportunities. 

Recruitment agencies: Diligent does not accept unsolicited agency resumes. Please do not forward resumes to our jobs alias, Diligent employees or any other organization location. Diligent is not responsible for any fees related to unsolicited resumes