Director, Enterprise Sales

Join to apply for the Director, Enterprise Sales role at Sadie About Sadie Sadie is reimagining how hotels engage guests using AI‑driven voice agents. Our platform answers inbound calls 24/7, handles bookings, reservation changes, FAQs, upsells, and seamlessly integrates with PMS, booking engines, channel managers, and other hotel systems. We currently serve hotels across North America and Europe, and are scaling rapidly into new geographies and verticals. Description We are seeking a high‑caliber sales leader with deep relationships in the hotel technology ecosystem to take charge of enterprise sales to major hotel chains, regional groups, and management companies. About the Role The Director, Enterprise Sales – Hotels will own the full sales lifecycle for Sadie’s solution across hotel chains and groups, in North America and Europe (and globally where needed). This is a senior, hands‑on leadership role: you will personally lead major deals, manage complex procurement processes, influence product direction with customer insights, and collaborate closely across your sales, product, engineering, and marketing teams. What You Will Do Directly manage enterprise sales opportunities with hotel chains, owner‑operators, and management companies (large, regional, and strategic accounts). Prospect, engage, nurture, and close complex deals — from discovery and solution design through negotiation, contracting, and rollout. Develop and maintain executive‑level relationships (CRO, CIO, CTO, Director of Ops, Director of Revenue Management, Group Executives) within hotel chains and groups. Collaborate with the product, engineering, and solution teams to design customized offerings, configurations, and integrations that meet chain specifications and technical requirements. Serve as the primary ambassador of Sadie at industry conferences, tradeshows, executive roundtables, and client roadshows. Actively capture market insight and feature feedback from prospects and accounts; drive those back into the product/roadmap process. Lead deal governance: forecasting, pipeline hygiene, risk assessment, contract management, and closing. Provide thought leadership, competitive intelligence, and contribute to the go‑to‑market strategy for the hotel vertical. Mentor and coach more junior sales/account executives (if applicable), helping them scale their pipeline, methodology, and execution. Ensure CRM (HubSpot) is used rigorously for tracking, forecasting, stakeholder alignment, and reporting. What You Bring 8+ years of experience in sales or account management, including significant exposure to enterprise SaaS or hospitality technology. Proven track record of exceeding quotas and closing multi‑property, group, or chain‑level SaaS deals. Deep network and relationships within the hotel ecosystem — ideally across major chains, management companies, and regional groups in North America and Europe. Full‑cycle sales expertise: prospecting, discovery, solution design, negotiation, contracting, and post‑sale handoff. Strong ability to engage stakeholders at all levels (C‑suite, operations, revenue management, IT) and tailor messaging to each audience. Excellent presentation and storytelling skills — confident leading demos and executive‑level discussions. Solid technical fluency to discuss API integrations between hotel systems. Hands‑on experience with CRM tools such as HubSpot (preferred) or equivalent tools for pipeline management, forecasting, and reporting. High emotional intelligence, resilience, and comfort in a fast‑moving, growth‑stage environment. Willingness to travel domestically and internationally as needed. Experience managing or mentoring small teams or senior individual contributors. Why Join Sadie You will lead sales efforts for a cutting‑edge AI voice platform disrupting how hotels interact with guests. You will have autonomy, visibility, and influence over product direction and go‑to‑market strategy in the hotel vertical. You’ll partner with a lean, talented team, at a stage where your efforts and relationships will have outsized impact. Competitive base salary with performance‑based commissions and comprehensive benefits package. Opportunity to attend and represent Sadie at top hospitality conferences and events worldwide. #J-18808-Ljbffr