VP of Sales at Hostaway

Job description

Hostaway is the fastest-growing global SaaS start-up in the vacation rental industry. Our products provide the best and most cost-effective solutions for property managers and vacation rental owners. Our major partners include Airbnb, Booking.com, Expedia, and several other leaders in the industry. Currently we have offices in Toronto, Barcelona and in Helsinki.

As the leading property management and vacation rental platform, our mission is simple: To build a cutting-edge product by teaming up with exceptional thinkers and passionate go-getters. We strive to foster the best environment for our team members, to cultivate growth and inspiration and create an exceptional experience on our team.

Work with us. Grow with us. Win with us.

For our Toronto office we are looking for a VP of Sales who will be the driving force behind the growth engine of the company. You must have experience exceeding sales quotas and the aptitude and experience to train and build teams and processes. Your mentorship would help everyone on your team remain on track to achieve goals.


Who you are:

You’ve demonstrated success with leading a distribute and multicultural team to double-digit sales growth month over month.

You are a strategic thinker who can also work tactically, communicate value, think on your feet, and navigate difficult conversations with creativity and confidence. You understand client needs and think creatively to relieve pain points and circumvent obstacles to hit goals.

You are a results-driven leader and a tenacious go-getter who's excited by new challenges and stays positive in the face of adversity — and knows how to translate this motivation to others in the company. You expect yourself to exceed your goals and know how to make it happen.

You are a self-starter who takes charge and is comfortable with ambiguity while delivering results in a fast-paced and rapidly changing environment. You are always looking for ways to optimize and can embrace Hostaway’s mission to get better every day.

You are an expert multitasker who can quickly triage competing priorities and is comfortable balancing long-term goals with short term demands.

You are a confident communicator who understands how to effectively tailor messaging and articulate value, be it in person, on the phone, or over email. You have an affinity for navigating difficult conversations and can hold your ground in negotiations.


  • Create a sales team culture that is positive, motivating and performance-driven
  • Build a successful global and distributed sales team
  • Set and manage sales goals and quotas for the sales team
  • Hire, develop, provide direction to, and retain a team of experienced account executives and sales managers
  • Build, measure and optimize a repeatable sales process to achieve objectives
  • Build repeatable training processes and best practices that enable to effectively prospect, manage, and close opportunities
  • Manage daily & weekly sales activities: pipelines, forecasts, closed deals to ensure above-quota results
  • Collaborate with the engineering/product team to prioritize the product roadmap


  • Extensive knowledge and experience of sales processes, including the effective use of CRM and other sales tools
  • 7-10+ years of progressive sales experience, including direct sales and sales management experience
  • Ideally 5+ years in a SaaS tech startup (Series A-C), rapidly scaling revenue while managing the resource constraints of a startup environment
  • Great people skills – ability to recruit, hire, motivate, manage and coach (help unlock potential)
  • Experience developing scalable processes and analytics skills to optimize processes over time
  • Sales experience in the property management/vacation rental industry is a plus

Who we are:

  • Scandinavian culture that values freedom, flexibility, embraces iteration over perfection, and most of all - success of the individual
  • Super fast-paced team currently growing our international teams and shaping the leaders of tomorrow
  • Critical thinkers who have the courage to take calculated risks and evaluate results on an on-going basis
  • Diverse and open-minded. We don’t care about labels and traditional thinking

    We want to offer you:

    • A beautiful office in downtown Toronto
    • A competitive base salary and stock options in a company you believe in
    • Inclusive learning environment with an international and diverse team
    • Endless growth and career opportunities
    • Opportunities to work remotely from time to time, from any of our remote offices in Barcelona and Helsinki
    • Handpicked team of the best people - we are serial entrepreneurs, guitar players, salsa dancers, top developers, singers, dog-lovers, and all-around the best team spirit

    If this sounds like a team you’d like to be a part of right away - then we can’t wait to hear about you!

    Let’s get in touch and discuss your next big career move.