Subscriptions Sales Enablement Specialist

This is a fully remote position, open to applicants in Mexico.

📋 Description

• Create and sustain tailored pitch decks, pricing proposals, and contract packages for ongoing deals across all Skift subscription offerings.

• Design and enhance tiered pricing structures and proposal templates that can be swiftly and consistently utilized by the sales team.

• Manage essential deal logistics, including NDAs, order forms, and contract routing, while ensuring a smooth and well-documented transition to the Customer Experience team after sales.

• Utilize Claude and other AI tools to consolidate account information from HubSpot, Stripe, Beehiiv, and MySkift into actionable pre-call briefs and renewal packages.

• Develop and document repeatable AI-assisted processes for common sales activities, such as creating proposal drafts, comparing pricing, and summarizing renewals.

• Conduct comprehensive prospect research to prepare representatives before outreach, and generate persona-specific battle cards, objection-handling guides, and product one-pagers.

• Assume full responsibility for CRM hygiene in HubSpot, ensuring rigorous data integrity, tracking deal stages, maintaining contact records, and logging activities.

• Proactively identify weaknesses in the sales process and create the tools and infrastructure necessary to address them.

⛳️ Requirements

• 2–4 years of experience in sales enablement, revenue operations, sales coordination, or a related role—preferably within B2B media, SaaS, or subscription services.

• Practical AI Expertise: Proven, hands-on experience with AI tools (Claude, ChatGPT, or similar) in a professional setting for drafting, research, summarizing, or automating workflows.

• CRM Fluency: Extensive experience with HubSpot CRM, particularly in relation to reports, pipelines, and upholding strict data integrity.

• Exceptional Communication: Strong written skills and proficiency in deck-building, along with meticulous attention to detail concerning contracts and deal documentation.

• Agility & Organization: Capability to effectively manage multiple active deals simultaneously while fostering a collaborative, success-oriented environment.

• Bonus: Familiarity with the travel/media sector, experience in developing prompt libraries, knowledge of tiered enterprise pricing models, or experience with platforms like Stripe and Beehiiv is a significant advantage.

🏝️ Benefits

• Opportunity to advance within a reputable and innovative media company.

• Exposure to the convergence of media, events, and travel intelligence.

• Collaborative, supportive, and remote-friendly work environment.