GTM Readiness Specialist

We’re hiring a GTM Readiness Specialist to join our team. This role is focused on enablement, operations, execution, and AI‑driven innovation. You will collaborate with GTM Readiness, Commercial, Product Marketing, Product, Sales Leadership, Customer Success, and Operations to ensure our commercial teams are prepared for key business priorities, including onboarding, product launches, certifications, strategic initiatives, and major company events such as CKO.

This role blends strategic thinking with hands‑on execution. You will translate business priorities 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 drive 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 executes programs well and 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.

• 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.

• 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.

• 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

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. 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, please contact us at