Account Executive - Mid Market

ARE YOU READY TO TAKE YOUR CAREER TO NEW HEIGHTS? ARE YOU SEEKING A NEW CHALLENGE IN A DYNAMIC SECTOR? This is a very exciting and highly innovative time here at Outside. OUR TRUE NORTH:Outside Interactive, Inc., the premier hub for active lifestyle enthusiasts, offers best-in-class content and experiences to more than 70 million of the world’s most passionate outdoor, wellness, and endurance enthusiasts every month. We inspire a broad and diverse audience to do the activities they love with greater enjoyment, inspiration, and knowledge and are dedicated to making real change in the outdoor and fitness industries. About Inntopia & Outside Inntopia is a leading SaaS platform serving the hospitality, destination, and experience industries. We provide enterprise-grade Commerce and Marketing Cloud solutions that help resorts, hotels, attractions, and destination organizations unify their booking experience, streamline operations, and maximize revenue. Our solutions include integrated eCommerce, CRM, CDP, and marketing automation designed to create seamless guest experiences from inspiration through booking and beyond. Inntopia is part of Outside, the world’s leading creator of active lifestyle content, experiences, and technology. Outside reaches millions of highly engaged consumers across adventure, travel, wellness, and outdoor recreation through its portfolio of brands, media properties, and subscription platforms. As part of Outside, Inntopia is uniquely positioned at the intersection of commerce, media, and audience data, giving our partners access to innovative technology and unique opportunities to connect with travelers and outdoor enthusiasts at scale. This combination of powerful SaaS tools and consumer reach makes Inntopia a differentiated partner for hospitality and destination operators looking to modernize their technology stack and accelerate direct bookings. Position Overview We are seeking a highly motivated and results-driven Mid-Market Account Executive to drive new business growth across hospitality, lodging, attractions, and destination verticals. This role will focus on organizations with annual revenues up to approximately $40M and/or multi-location operators with up to four properties. The ideal candidate is consultative, strategic, and experienced in SaaS sales, with a strong ability to navigate complex sales cycles, identify operational pain points, and position technology solutions that deliver measurable ROI. Key Responsibilities • Own the full sales cycle from prospecting through close for net-new mid-market opportunities. • Identify and develop new business opportunities across hotels, resorts, attractions, and destination operators. • Conduct discovery calls to understand client needs around: • Booking engine/eCommerce optimization • Guest data unification (CRM/CDP) • Marketing automation • Call center and reservation workflows • Deliver tailored product demonstrations and solution presentations. • Collaborate with Solutions Consulting, Product, and Onboarding teams to scope integrations and implementation requirements. • Build and maintain a healthy pipeline in Salesforce. • Develop proposals, ROI models, and commercial terms. • Manage multiple stakeholders including marketing, revenue management, operations, and executive leadership. • Maintain accurate forecasting and pipeline visibility. • Represent Inntopia at trade shows, conferences, and industry events. Qualifications • 3–7+ years of SaaS sales experience, preferably in hospitality, travel, martech, or ecommerce. • Proven success closing mid-market deals ($25k–$250k+ ARR). • Experience selling one or more of the following: • CRM platforms • CDP solutions • Booking engines / ecommerce platforms • Marketing automation software • Revenue management systems • Strong consultative selling skills and ability to uncover business pain points. • Experience managing multi-stakeholder sales cycles. • Excellent communication, presentation, and negotiation skills. • Comfortable working cross-functionally with technical and product teams. • Experience with Salesforce or equivalent CRM required. Preferred Experience • Hospitality technology experience (PMS, CRS, booking engines, POS, or distribution). • Knowledge of guest journey marketing and first-party data strategies. • Experience selling into hotels, resorts, tourism boards, or attractions. • Familiarity with integrations across PMS, payment gateways, and third-party reservation systems. What Success Looks Like • Consistently achieve and exceed quota. • Build a strong pipeline of qualified opportunities. • Shorten sales cycles through effective discovery and stakeholder alignment. • Help expand Inntopia’s footprint in the mid-market segment. • Become a trusted advisor to prospects and partners. Compensation & Benefits • Competitive base salary + uncapped commission • Health, dental, and vision benefits • Flexible PTO • Remote-first work environment • Travel opportunities for industry events and client meetings • Career growth within a rapidly evolving SaaS and travel technology company What We Offer: This is a fully remote role, and we welcome applicants based anywhere in the United States or Canada. The disclosure below is provided specifically to satisfy Colorado's pay transparency law for roles that could be performed there, it does not limit who may apply. Entirely remote job that could be performed in Colorado: Employees can expect to be paid a salary of between $70,000-85,000. Additional compensation may include a bonus or commission . Additional benefits include health care, vision, dental, retirement, Flexible Time Away, sick leave, and more. This salary range is merely an estimate and may vary based on an applicant’s location, market data/ranges, an applicant’s skills and prior relevant experience, certain degrees and certifications, and other relevant factors. We are committed to fostering a diverse and inclusive workplace. Outside Inc is an Equal Opportunity Employer. We do not discriminate based on race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other legally protected characteristics. Pursuant to applicable laws, we also make accommodations for qualified individuals with disabilities. We believe a diverse team is a strong team, and we encourage candidates from all backgrounds to apply.