GTM Readiness Specialist (12 month Fixed-Term Contract)

Here’s a summary of the role:  

We’re hiring a  GTM Readiness Specialist (12 month Fixed Term Contract) to join our team. This is a high-impact role for someone who thrives at the intersection of enablement, operations, execution, and AI-driven innovation. In this role, you will partner closely with GTM Readiness, Commercial, Product Marketing, Product, Sales Leadership, Customer Success, and Operations to help ensure our commercial teams are prepared for key business priorities, including onboarding, product launches, certifications, strategic initiatives, and major company events such as CKO.  

Here’s a breakdown of what you’ll do (not all of it, just the important stuff)’ & ‘These are the essentials you’ll need to get an interview  

This role blends strategic thinking with hands-on execution. You will take business priorities and translate them into structured, scalable readiness programs that improve field preparedness and business performance. From onboarding experiences and certifications to live enablement sessions, operational infrastructure, and AI-powered process improvements, you will play a critical role in driving readiness across the organization.  

A core part of this role is actively exploring how AI can improve the speed, quality, scalability, and consistency of GTM readiness. We are looking for someone who not only executes programs well but also thinks critically about how AI and automation can streamline workflows, improve learner experiences, reduce manual work, and elevate how readiness programs are designed and delivered.  

The ideal candidate is highly organized, operationally strong, proactive, and comfortable managing multiple initiatives simultaneously. You should be able to create structure from ambiguity, continuously improve processes, and assess priorities to ensure work aligns with broader GTM strategy. This is an opportunity for someone who wants to help shape the future of GTM readiness through both operational excellence and modern, AI-enabled ways of working.  

Here’s a breakdown of what  you’ll do (not all of it, just the important stuff):  

• Program execution & ownership: Lead and support end-to-end GTM readiness programs, ensuring alignment to business priorities and consistent execution.  

• GTM session management: Manage live readiness sessions across product launches, Impact Days, and strategic GTM programs, including scheduling, stakeholder coordination, deck development, dry runs, delivery support, and post-session analysis.  

• CKO readiness support: Support this large-scale event through attendee management, pre-work coordination, communications, session registration, grading workflows, and reporting.  

• Cross-functional partnership: Collaborate closely with Product Marketing, Product, Commercial, Leadership, and Operations teams to translate strategic priorities into practical readiness programs.  

• Communications management: Own or support readiness communications through Teams channels, launchpad pages, and stakeholder updates.  

• Measurement & reporting: Track program effectiveness through dashboards, learner progress, certification metrics, surveys, and post-program insights to improve outcomes over time.  

• Content & knowledge governance: Maintain readiness assets, internal knowledge hubs, and source-of-truth resources to ensure teams can easily access current, accurate information.  

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

• 2+ years of experience in sales enablement, GTM readiness, commercial operations, marketing, program management, or a related field in a fast-paced environment  

• Strong project management and operational skills, with the ability to manage multiple concurrent initiatives  

• Experience working cross-functionally with stakeholders across Commercial, Product Marketing, Product, and Leadership  

• Practical familiarity with leveraging AI, automation, and workflow improvements to increase speed, scalability, and consistency.  

• Strong written and verbal communication skills, including executive-facing and broad organizational communications  

• Highly detail-oriented, structured, proactive, and comfortable working in ambiguity  

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

• Demonstrated experience supporting or owning onboarding, certification, product launch, or field readiness programs  

• Hands-on experience with LMS platforms, Airtable, dashboards, or similar operational systems  

Pay Range

$65,000—$81,000 CAD

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 and 

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.

We are a drug free workplace. 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 Know Your Rights . 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 View email address on job-boards.greenhouse.io .

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.

Please find the link to our candidate privacy policy here:  

To all 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.