Director, Enterprise Sales

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October 31

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Aspire Software

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SaaS • Enterprise • B2B

Aspire Software is a company that focuses on acquiring and nurturing businesses with a strong foundation in outstanding products and passionate teams. As part of the Valsef Group, Aspire Software offers resources, knowledge, and a suite of best practices to enhance and expand operations for continuous improvement and sustainable growth. The company emphasizes decentralization to unlock innovation and adaptability within its acquired entities. Aspire Software is dedicated to serving its customers through long-term technology partnerships, leveraging capital and expertise in various verticals to grow both the businesses and individuals involved.

1001 - 5000 employees

☁️ SaaS

🏢 Enterprise

🤝 B2B

📋 Description

• Own the full sales lifecycle for Sadie’s solution across hotel chains and groups, in North America and Europe (and globally where needed). • 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. • Forge relationships with decision-makers in revenue management, operations, technology, and corporate leadership. • Translate technical value propositions into business outcomes and navigate complex buying cycles in enterprise hospitality. • 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.

🎯 Requirements

• 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.