Front Desk Upselling Trainer

Travel is not just about the destination; it's about every memory made along the way. We are dedicated to shaping the future of travel by partnering with 200+ airline, hospitality, cruise, passenger rail, and financial services companies to create new, meaningful revenue streams through incredible customer experiences. Rooted in our core values of being ambitious, innovative, and collaborative, we are driven to continuously raise the bar, exceed expectations, and bring out the best in everyone, fostering a culture where we believe we are better together, working towards an extraordinary future in travel. Come help us transform everyday travel into extraordinary experiences. ABOUT THE ROLE: As the Front Desk Upselling (FDU) trainer for the Hospitality Upsell team, you will bridge the gap between software and strategy by transforming our upselling tool into a high-performing hotel culture. Your role involves training reception teams to upsell with confidence while empowering senior leadership—across Revenue and Hotel Management—to establish the goals and routines necessary for long-term success. By leveraging your hospitality expertise and coaching skills, you will ensure that every check-in becomes a meaningful opportunity to drive revenue and enhance the guest experience. WHAT YOU WILL BE DOING: Reporting to the VP of Partner Success, you will: Train Front Desk Agents (Selling & Execution) • Teach practical upselling skills for reception: timing, wording, confidence, objection handling, and guest-first recommendations. • Run roleplays and real-life scenarios (arrivals peak, walk-ins, short stays, VIPs, overbooking, complaints, etc.). • Coach agents on converting offers naturally (suggestive selling). • Make FDU easy to use in daily operations (workflow, consistency, speed, and habit building). Enable Managers (Leadership & Performance) • Teach managers how to run FDU as a performance program: targets, routines, accountability, and recognition. • Help set clear goals (team + individual) and define what “good” looks like by shift/property segment. • Train managers on how to coach: observing conversations, giving feedback, and reinforcing behaviors. • Support motivation strategies: contests, scoreboards, incentives, and creating a culture of upselling. Drive Continuous Improvement (Results & Optimization) • Use performance insights (conversion, upgrade mix, ADR uplift, uptake by shift/agent) to shape coaching and retraining. • Recommend actions to improve outcomes: scripts, focus products, offer timing, team routines. • Build and maintain training content: playbooks, scripts, cheat sheets, role-based toolkits, micro-learning modules. • Partner closely with Partner Success to ensure a seamless onboarding-to-activation experience. • Occasionally travel for in-person training at key properties or strategic rollouts. • Curate feedback along with the main FDU Coach to share inputs to the engineering team.  YOU ARE SOMEONE WITH: • Solid hospitality background with real front office exposure (agents, supervisors, duty managers, FO managers, etc.). • Proven training/coaching experience (formal trainer or “go-to” leader who builds team performance). • Strong understanding of reception upselling and guest psychology. • Comfortable training both frontline teams and hotel leadership. • Able to combine empathy + structure: engaging sessions, clear standards, and measurable follow-through. • Data-aware: you don’t need to be an analyst, but you can translate performance data into actions. • Fluent in English (additional languages are a plus). • Willing to travel occasionally. WHAT YOU’LL LOVE ABOUT US: 📅 Flexible Paid Time Off  ✈️ Travel Experience Perk 🧘 Annual Wellness Perk 🚆 Commuter Perk 🌅 Work From Anywhere Program  🍼 Parental Leave Top Up  OUR PROCESS: Plusgrade is an equal-opportunity employer and is committed to providing an accessible recruitment process. We welcome applications from all qualified individuals and are committed to equal employment opportunities regardless of gender identity or expression, race, ethnic origin, creed, place of origin, age, sex, marital status, physical or mental disability, sexual orientation, and any other category protected by law. Upon request, we will provide accommodation for applicants with disabilities.  We believe in diversity and inclusivity and that is why our interview process is designed for a positive candidate experience and to ensure every candidate is evaluated equally. We may utilize technology-assisted/ artificial intelligence tools to help us screen, assess, and select applicants for this position. This job posting is for an existing vacancy. All applications will be reviewed by our Talent Team and the successful candidate(s) will go through the following recruitment process: • Recruiter Phone Interview  • Hiring Manager Interview • Take Home Assignment • ELT Interview  All candidates will be provided with feedback regardless if they pass or didn’t pass any of our interview stages. All your information will be kept confidential.