Enablement Trainer - 100% Remote - North America

NOTE: This is a FULLY remote role, but the candidate must be within the United States to collaborate with their team, peers, and internal customers. You do not have to be in the specific country or city shown in this listing, but please only apply if you are physically based within the United States. Hostaway is a SaaS scale-up that is transforming the vacation rental industry. With innovative solutions and partnerships with giants like Airbnb, VRBO, and Booking, we're taking on the competition and winning. Leveraging our customer-centric core values, we consistently deliver results that encourage growth, learning, and innovation for our team, our customers, and the industry. Profitable, high-growth, and the first short-term rental PMS unicorn . Join us at our most exciting stage yet! Learn more about our recent valuation and story here. About the role We're looking for an experienced and passionate Enablement Trainer to elevate the performance of our Sales team through impactful training and coaching. You'll be instrumental in onboarding new hires, delivering high-impact enablement initiatives, and supporting ongoing skill development for SDRs and Account Executives. As part of the Global Enablement team, you'll work closely with sales leadership and cross-functional partners to drive training consistency, accelerate ramp-up time, and foster a culture of continuous improvement and excellence.

Key Responsibilities

• Deliver engaging virtual and live training, including role-plays, call coaching, and workshops to strengthen sales skills across SDRs, AEs, and global teams.
• Co-own and lead new hire onboarding, ensuring rapid ramp-up on Hostaway's tools, processes, culture, and value propositions.
• Partner with sales leaders to identify performance gaps, reinforce key sales behaviors, and align training priorities.
• Manage and evolve enablement content, playbooks, and resources to stay aligned with product updates and evolving sales strategies.
• Conduct assessments, live listening sessions, and provide actionable feedback to measure retention and improve performance.
• Drive collaboration across sales, marketing, and operations to build scalable learning programs and support pipeline generation.
• Champion a culture of continuous learning, curiosity, and accountability that empowers reps to deliver personalized solutions and exceed targets.
• Proven experience in a training, enablement, sales coaching roles, and/or scaling sales organizations.
• Excellent communication and presentation skills, especially in remote/virtual settings
• Experience delivering onboarding and continuous education in fast-paced environments
• Comfortable managing multiple projects, sessions, and stakeholders

Familiarity with CRM and sales enablement tools like Salesforce, Gong, Chili Piper (or similar)

• A passion for helping others succeed and a mindset of growth, empathy, and impact

What we offer

• Competitive Compensation: We offer competitive pay based on market rates in the country of the applicant.
• 100% Remote: Enjoy the freedom to work from anywhere within your country of residence-be it a co-working space, your home office, or even your dining room table. The choice is yours. Just don't ask to work in our office (we don't have one).
• Equity: Every role in our company comes with valuable stock options in a fast-growing and profitable company. This ensures we all share in the company's success.
• Values-Driven Leadership: Our Core Values are not just words we've written to make us feel good. We leverage them daily when making strategic and tactical decisions.
• Professional Growth: Our rapid growth offers unparalleled learning and development opportunities, along with a multitude of career advancement opportunities.
• Annual Paid Leave: The specific amounts vary by country and are aligned with country and/or contract-specific norms.
• Geographic Specific Benefits: As an international employer, we offer different country-specific benefits such as Health Insurance and Pensions in countries where these perks are customary. The specifics depend on the country of the applicant.
• Dynamic Team Culture: As a global company with team members in over 40 countries, our diverse and international culture fuels our innovation and creativity, providing a key pillar to our success (and making it a lot of fun to work here).

Thank you for your interest. If you apply for this role, you will receive an email from our Talent Acquisition team after your application has been reviewed alongside the qualifications for this role and the qualifications of others who have applied. Apply tot his job Apply To this Job