About HTS Media

HTS Media is Hopper’s advertising and media division, built to help travel brands, destinations, and suppliers connect with travelers at scale. We power advertising placements across Hopper’s app and through our B2B partner network, which includes global brands such as Capital One Travel and TripAdvisor. Our platform gives advertisers measurable results, helping them capture more bookings and earn greater long-term value from their customers, while travelers get relevant offers that make trip planning better.

Our mission is to build the travel industry’s leading retail media network, turning advertising into a major driver of profitability for Hopper and our partners, much like Instacart, Uber, and Amazon have done in their sectors. We’re still in the early stages of our roadmap, yet HTS Media has already become one of Hopper’s fastest-growing and most profitable business units.

Sales is at the core of HTS Media’s growth. Our success depends on building deep partnerships with advertisers who want to reach high-intent travelers at the exact moment they are making booking decisions. The Director of Sales will lead this effort, developing the strategy, team, and execution model that brings new advertisers onto the platform and expands relationships with existing ones.

This role is not just about hitting revenue targets. It is about shaping how the travel industry thinks about retail media, educating the market, and positioning HTS Media as the must-buy platform for performance-driven advertising in travel. The Director of Sales will own the full advertiser-side sales motion, from developing playbooks for consultative selling, to building C-level relationships with major accounts, to creating repeatable success that allows us to scale globally.

What would your day-to-day look like:

• Lead advertiser-side sales for HTS Media, with a focus on DMOs, hotel groups, airlines, and travel brands.

• Develop and execute the go-to-market strategy for driving adoption of our ad products.

• Own and exceed revenue targets through both individual contributions and leadership of a sales team.

• Build, mentor, and scale a high-performing sales team, creating repeatable sales processes and career development paths.

• Establish strong C-level and agency relationships, positioning HTS Media as a key partner for travel advertisers.

• Partner with product and marketing leadership to refine positioning, pricing, and packaging to meet advertiser needs.

• Represent HTS Media at industry events, conferences, and client meetings, acting as a visible leader in the market.

• Provide market feedback to product teams to influence the ad product roadmap and ensure alignment with advertiser demand.

  An ideal candidate has:

• 8+ years in advertising or media sales, with a proven track record of selling to large advertisers and agencies.

• At least 3 years leading sales teams with measurable success in hitting and exceeding revenue targets.

• Strong understanding of advertiser priorities in performance marketing, retail media, or travel advertising.

• Experience selling new products and educating markets, ideally in high-growth or startup environments.

• Ability to recruit, coach, and lead a sales team while also driving individual contributions where needed.

• Skilled in C-level relationship building, negotiation, and closing complex, high-value deals.

• Existing relationships within the travel and advertising ecosystem are a strong plus.

• Entrepreneurial mindset with the ability to thrive in a fast-paced, high-growth environment.

  Perks and benefits of working with us:

• Well-funded and proven startup with large ambitions, competitive salary and upsides of pre-IPO equity packages.

• Hopper covers 100% of the premiums for group insurance plan.

• Hopper offers life, short term and long term disability coverage.

• HSA that covers eligible medical and dental expenses.

• All employees and dependents have access to Dialogue’s telemedicine services, anytime, anywhere.

• All employees have access to an RRSP plan with automatic pre-tax withdrawals per pay.

• Please ask us about our very generous parental leave, much above industry standards!.

• Unlimited PTO.

• Carrot Cash travel stipend.

• Access to co-working space on demand through FlexDesk AND Work-from-home stipend.

• Entrepreneurial culture where pushing limits and taking risks is everyday business.

• Open communication with management and company leadership.

• Small, dynamic teams = massive impact.

  More about Hopper

  At Hopper, we are on a mission to become the leading travel platform globally – powering Hopper’s mobile app, website and our B2B business, HTS (Hopper Technology Solutions). By leveraging massive amounts of data and advanced machine learning algorithms, Hopper combines its world-class travel agency offering with proprietary fintech products to bring transparency, flexibility and savings to travelers globally. We have developed several unique fintech solutions that address everything from pricing volatility to trip disruptions – helping people travel better and save more on their trips.

  The Hopper platform serves hundreds of millions of travelers globally and continues to capture market share around the world. he Hopper app has been downloaded over 120 million times and has become largely popular among younger travelers – with 70% of its users being Gen Z and millennials.

  While everyone knows us as the Gen Z and Millennial travel app, Hopper has evolved to become much more than that. In recent years, we’ve grown into a travel fintech provider, commerce platform, and global travel agency that powers some of the world’s largest brands.

  Through HTS, our B2B division, the company supercharges its partners’ direct channels by integrating our fintech products on their sites or powering end-to-end travel portals. Today, our partners include leading travel brands like Capital One, Nubank, Air Canada, and many more.

  Here are just a few stats that demonstrate the company’s recent growth:

  • Billions of dollars worth of travel and travel fintech are sold through Hopper and HTS’ channels every year.
  • Our fintech products – including Cancel for Any Reason and Flight Disruption Assistance – have exceptionally strong CSAT because the terms are always clear, and customers receive instant, no-questions-asked resolutions.
  • Almost 30% of our app customers purchase at least one fintech product when making a booking; and consumers are 1.6x more likely to repurchase if they add fintech to their booking vs if they booked just travel.

  Given the success of its fintech products, Hopper launched a B2B initiative, HTS (Hopper Technology Solutions), which represents more than 75% of the business.

  Through HTS, any travel provider (airlines, hotels, banks, travel agencies, etc.) can integrate and seamlessly distribute Hopper’s fintech or travel inventory on their direct channels. As its first HTS partnership, the company partnered with Capital One to co-develop Capital One Travel, a new travel portal designed specifically for cardholders. Other HTS partners include Air Canada, Uber, CommBank, Nubank, Flair Airlines and many more.

  Hopper has been named the #1 most innovative company in travel by Fast Company Hopper has been downloaded over 120 million times and continues to have millions of new installs each month. Hopper is now the #3 largest online travel agencies in North America and 70% of our app customers are Gen-Z and millennials travelers.

  Hopper has raised over $750 million USD of private capital and is backed by some of the largest institutional investors and banks in the world. HTS is primed to continue its growth as the leading travel ecommerce provider in a $1 trillion online shopping category. The Hopper app and website will also continue to be the preferred travel provider for Gen Z and Millennials..

  Come take off with us!

  #LI-REMOTE

Compensation Range: CA$30.00 - CA$450,000.00