Group Subscriptions Renewals Specialist

The Opportunity We’re looking for a proactive, results-driven Group Subscriptions Renewals Specialist to join Skift and take ownership of the retention and expansion of our B2B account base. As the frontline of subscriber revenue, you will ensure the accounts we've won stay, grow, and deepen their relationship with our platform. You will manage a dynamic book of group subscription accounts across Skift Pro, Skift Research, Airline Weekly, and Daily Lodging Report. Crucially, you will leverage AI tools—including Claude—as a core, non-negotiable part of your daily workflow to research accounts, prep for conversations, and build efficient processes that maximize your impact. This is a fully remote, full-time position. Why This Role Matters Sitting strategically between our Customer Experience team (who handles onboarding and daily support) and our Sales Managers (who hunt for new business), this role is the engine protecting and growing our existing book of business. You are focused entirely on the health and expansion of our subscriber base—protecting Annual Recurring Revenue (ARR), finding opportunities to grow it, and ensuring no renewal falls through the cracks. Your work guarantees that our B2B clients continue to extract maximum value from Skift’s intelligence products, directly fueling our subscription-first business model. Some of What You’ll Do Renewal Strategy & Revenue Growth Own the full renewal cycle for a portfolio of B2B group subscription accounts—from forecasting and initial outreach to strategic negotiation and close. Actively identify and aggressively pursue upsell and expansion opportunities, including seat additions, tier upgrades, and cross-product sales. Collaborate with the Director of Subscriptions on pricing strategy, renewal terms, and tiered packaging. AI-Powered Workflow & Execution Use Claude and other AI tools to prepare comprehensive account briefs, draft highly personalized renewal proposals, and scale your outreach efficiently. Partner seamlessly with the Sales Enablement Specialist to develop tailored pricing proposals and compelling renewal packages. Relationship Management & Retention Build and maintain strong, consultative relationships with key contacts at subscriber organizations, focusing on demonstrating ongoing value between renewal windows. Flag at-risk accounts early, collaborating cross-functionally with Customer Experience to proactively address issues before they result in churn. Data Integrity & Reporting Maintain precise pipeline and account data in HubSpot, carefully tracking renewal dates, contact records, deal stages, and notes. Track and report on critical performance metrics like renewal rate, net revenue retention, and expansion. What You’ll Bring 2–4 years of experience in a B2B renewals, account management, or subscription sales role—preferably within media, SaaS, or data/intelligence products. Practical AI Expertise: Demonstrated, hands-on use of AI tools (Claude, ChatGPT, or similar) in a professional context for account research, outreach drafting, or workflow automation. CRM Fluency: Deep experience in HubSpot or a comparable CRM, with a strong grasp of pipeline management, renewal tracking, and activity logging. Consultative Communication: Strong written and verbal communication skills, allowing you to run renewal and pricing conversations that feel strategic and consultative, not just transactional. Agility & Organization: A proactive, highly organized approach to managing your own book of business, ensuring nothing slips through the cracks while comfortably navigating multi-stakeholder negotiations. Bonus: Familiarity with the travel industry, experience managing a high-volume book (100+ accounts), exposure to tiered/seat-based pricing, or a background in cross-selling within a multi-product portfolio is a significant plus. Success Metrics Retention & ARR: Maintaining exceptionally high renewal rates and protecting Annual Recurring Revenue (ARR) across your assigned portfolio. Revenue Expansion: Consistent success in identifying and closing upsell, cross-sell, and seat expansion opportunities within the existing account base. Process Efficiency: Effective utilization of AI tools to scale outreach and prepare account briefs, allowing you to cover more ground without sacrificing personalization or quality. Cross-Functional Collaboration: Seamless partnership with Sales Enablement and Customer Experience to proactively mitigate churn and deliver tailored renewal packages. 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.