Subscriptions Sales Enablement Specialist

The Opportunity We’re looking for a highly organized, tech-forward Sales Enablement Specialist to be the operational engine behind Skift's B2B subscriptions sales motion. Sitting squarely in the deal cycle, this role is ideal for a proactive builder who thrives on creating the infrastructure that makes a small team punch above its weight. As part of a forward-thinking group, you will leverage AI tools—including Claude—as a core, non-negotiable part of your daily workflow to accelerate research, draft proposals, and build repeatable processes. This is a fully remote, full-time position. Why This Role Matters As a vital part of the Subscriptions team (covering Skift Pro, Skift Research, Airline Weekly, and Daily Lodging Report), you are the connective tissue between inbound leads and closed revenue. While our Customer Experience team handles post-sale onboarding and retention, you own the pre-sale infrastructure. By taking warm leads and ensuring the sales team has precisely what they need to convert and close—on time, on brand, and on terms—you directly drive Skift's B2B subscription growth and set up future renewals for success. Some of What You’ll Do Deal Strategy & Execution Build and maintain customized pitch decks, pricing proposals, and contract packages for active deals across all Skift subscription properties. Develop and refine tiered pricing frameworks and proposal templates that the sales team can deploy quickly and consistently. Coordinate critical deal logistics, including NDAs, order forms, and contract routing, and ensure a seamless, well-documented post-sale handoff to the Customer Experience team. AI-Powered Workflows & Research Leverage Claude and other AI tools to synthesize account data across HubSpot, Stripe, Beehiiv, and MySkift into actionable pre-call briefs and renewal packages. Build and document repeatable AI-assisted workflows for common sales tasks, such as proposal drafts, pricing comparisons, and renewal summaries. Conduct deep prospect research to brief reps before outreach, and create persona-specific battle cards, objection-handling guides, and product one-pagers. Revenue Operations & CRM Take full ownership of CRM hygiene in HubSpot, maintaining rigorous pipeline data integrity, deal stage tracking, contact records, and activity logging. Proactively identify gaps in the sales process and build the necessary tools and infrastructure to close them. What You’ll Bring 2–4 years of experience in sales enablement, revenue operations, sales coordination, or a related function—ideally within B2B media, SaaS, or subscriptions. Practical AI Expertise: Demonstrated, hands-on use of AI tools (Claude, ChatGPT, or similar) in a professional context for drafting, research, summarization, or workflow automation. CRM Fluency: Deep experience in HubSpot CRM, specifically regarding reports, pipelines, and maintaining strict data integrity. Exceptional Communication: Strong written communication and deck-building skills, coupled with a high attention to detail around contracts and deal documentation. Agility & Organization: The ability to seamlessly manage multiple active deals simultaneously while maintaining a collaborative, shared-success orientation. Bonus: Familiarity with the travel/media industry, experience building prompt libraries, exposure to tiered enterprise pricing models, or experience with platforms like Stripe and Beehiiv is a significant plus. Success Metrics Velocity & Conversion: Rapid, accurate turnaround of customized pitch decks, pricing proposals, and contract packages that actively accelerate the deal cycle. Process Efficiency: The successful creation and implementation of repeatable, AI-assisted workflows that tangibly save the sales team time. Data Integrity: Impeccable CRM hygiene in HubSpot, ensuring accurate pipeline data, precise deal tracking, and consistent activity logging at all times. Seamless Handoffs: Flawless coordination of deal logistics and comprehensive post-sale documentation, setting up the Customer Experience team (and future renewals) for guaranteed success.

What We Offer

Opportunity to grow within a respected and innovative media company. Exposure to the intersection of media, events, and travel intelligence. Collaborative, supportive, and remote-friendly work environment. How We Work Skift's culture is diverse, cohesive, and full of people who love what they do and bring the best of themselves to work. We are remote but very connected and caring about each other. How To Apply If this role sounds like a fit, we’d love to hear from you. PLEASE SEND US A COVER LETTER ALONG WITH YOUR RESUME sharing why you’re interested and how your experience aligns with Skift's mission. Skift is proud to be an Equal Opportunity Employer. We are committed to building a team that reflects the diversity of travelers around the world. We welcome applicants from all life experiences and encourage members of traditionally underrepresented backgrounds to apply. Here’s what you can expect next If selected to interview, a Skift team member will reach out to schedule next steps.