Enablement Trainer, Hostaway
North America
+ Stock options
Vacation rental software for property managers
Job no longer available
Vacation rental software for property managers
201-500 employees
Job no longer available
+ Stock options
201-500 employees
Company mission
To partner with property managers in the growth of their business by providing solutions to achieve their goals.
Role
Who you are
- 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 the job involves
- 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
- 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
Application process
- 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
Our take
Hostaway is an all-in-one vacation rental software solution designed to help property owners streamline and grow their businesses. Hostaway’s product provides property owners a way to present their services to the wider market, making them available on different platforms through the use of its multi-integration software.
What makes Hostaway unique is its comprehensive property management ecosystem. beyond just listings, the platform allows clients to manage their properties across a wide range of platforms, including Airbnb, Booking.com, and HomeAway. it also integrates with other key services like Stripe, Expedia, and Tripadvisor, offering customizable solutions that support the diverse needs of vacation rental hosts.
It also had impressive growth over the past five years, with revenue doubling to tripling each year. Alongside this, it recently raised substantial funding to fuel its expansion across Europe and accelerate product development. With its strong track record and clear vision for the future, the future is one of much excitement for Hostaway.
Freddie
Company Specialist at Welcome to the Jungle
Insights
84% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Dec 2024
$402.9m
GROWTH EQUITY VC
May 2023
$175m
GROWTH EQUITY VC
Total funding: $580.7m
Company benefits
- Company stock options provided to every role
- Career advancement opportunities
- Dynamic international culture
Company HQ
Brickell, Miami, FL
Leadership
Marcus Räder
(Co-Founder & CEO)They have previously served as Product Manager and then Advertising Operations Manager at Kiosked, before moving to be Product Manager at Yousician.
Saber Kordestanchi
(Co-Founder & CSO)They co-founded OrumITC before moving to serve as a Software Engineer at booncon and then Kiosked. They were CTO and COO at Hostaway before becoming CSO.
Ken Weary
(COO)An accomplished international SaaS Executive and Operations Leader specializing in scaling B2B companies to new heights. They joined Hostaway in 2024 as COO.
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