AI Revenue Enablement Specialist
Justworks
Who We Are
At Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people.
We’re helping businesses get off the ground by enabling them to focus on running their business. We solve HR issues. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you.
We're united by shared goals and shared motivations at Justworks. These are best summed up in our company values, which are reflected in our product and in our team.
If this sounds like you, you’ll fit right in.
About GTM Readiness at Justworks
In the era of AI, automation, and accelerated go-to-market cycles, Justworks is transforming how we prepare our customer-facing teams. The GTM Readiness organization exists to ensure every revenue-generating team member — across Sales Development, Sales, Partnerships, Onboarding, Customer Support, and Customer Success — is equipped with the skills, tools, and confidence to represent the Justworks brand with precision and empathy.
Our vision is to become a performance-focused, AI-enabled function that accelerates time-to-productivity, improves execution of strategic GTM plays, and drives measurable revenue outcomes — all while preserving the white-glove customer experience that defines our brand.
We are replacing static content and reactive support with scalable infrastructure, generative AI, and embedded field readiness. The AI Revenue Enablement Specialist will play a critical role in operationalizing this future.
Who You Are
As an AI Revenue Enablement Specialist, you will own the design, automation, and distribution of scalable, AI-generated content and training across our go-to-market organization. This role sits within the Enablement Infrastructure & Content Operations pillar — the team responsible for building the operational backbone of GTM Readiness, including our LMS/CMS systems, content governance model, and performance analytics infrastructure.
You will partner closely with GTM Enablement leads, Product Marketing, Revenue Operations, and frontline managers to ensure learning is embedded at the point of need — not just in a classroom. The ideal candidate brings a strong operational mindset, deep familiarity with AI tools, and a bias for automation and speed.
Key Responsibilities
- AI Content Development & Repurposing
- Use generative AI platforms (e.g., ChatGPT, Cassidy.ai, Synthesia, Spekit, Second Nature) to generate and repackage enablement content into multi-format assets (tooltips, emails, videos, LMS modules, simulations).
- Manage AI prompt design and testing to ensure contextual accuracy, tone alignment, and audience relevance.
- Training Automation & Delivery Workflows
- Build automated workflows that push just-in-time learning to reps via Slack, LMS, Salesforce, and email.
- Ensure content is dynamically tailored to user role, lifecycle stage (e.g., onboarding, launch), and GTM motion.
- Enablement Infrastructure & Tooling
- Maintain and optimize our enablement systems stack (e.g., Highspot, Wisetail, Second Nature, etc.).
- Work with Revenue Ops and BI to surface real-time insights on rep engagement and content effectiveness.
- Content Governance & Version Control
- Ensure enablement content adheres to our taxonomy, tagging standards, brand guidelines, and is regularly updated in collaboration with SMEs.
- Performance & Impact Measurement
- Develop dashboards or reports to track content usage, engagement, and correlation to commercial outcomes like time-to-productivity and play adoption.
Qualifications
- 3–5 years of experience in Revenue Enablement, Sales Readiness, or GTM Operations, with a strong focus on content automation and AI tooling.
- Proven hands-on experience with AI platforms for content creation (e.g., ChatGPT, Synthesia, Cassidy.ai, Spekit, Second Nature).
- Strong project management and stakeholder communication skills — able to translate field needs into scalable tech-driven solutions.
- Deep familiarity with enablement infrastructure, including CMS/LMS systems and content distribution strategies.
- Analytical mindset with experience measuring enablement impact on rep performance or GTM execution.
- Creative, curious, and adaptable — excited to build in an evolving, AI-powered environment.
- Bonus: experience working in a high-growth SaaS company and collaborating with Product Marketing or Sales Enablement teams.
The base wage range for this position based in our New York City office is targeted at $122,000 - $134,200 per year. Final offers may vary from those listed.
#LI-Hybrid #LI-KO1
Actual compensation is based on multiple factors that are unique to each candidate, including and not limited to skill set, level of relevant experience, and specific work location. Salary ranges for positions based in other locations may differ based on the cost of labor in that location.
For more information about Justworks’ Total Reward Philosophy, including all of the perks and benefits we are proud to offer our team members, please visit Total Rewards @ Justworks.
Diversity At Justworks
Justworks is committed to maintaining a workplace where diversity of identity, culture, and life experience is the norm and is celebrated authentically and respected consistently. Diversity in our work, our people, and our product drives creativity and innovation, entrepreneurial leadership and integrity, competitiveness, and collaboration throughout our business and in the market. We depend on our differences to make our team stronger, our workplace more dynamic, and our product accessible to all of our customers.
We’re proud to be an equal opportunity employer open to all qualified applicants regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital or familial status, disability, pregnancy, gender identity or expression, veteran status, genetic information, or any other legally protected status. Justworks is fully dedicated to providing necessary support to candidates with disabilities who may require reasonable accommodations. We also provide reasonable accommodations to employees based on their sincerely held religious beliefs, as well as for other covered reasons consistent with applicable federal, state, and local laws. If you're in need of a reasonable accommodation, please reach out to us at accommodations@justworks.com. Your comfort and success matter to us, and we're here to ensure an inclusive experience.