Breezeway

Role Description Breezeway’s award-winning property operations and experience platform helps coordinate, communicate, and verify detailed work at properties. Powering over 55M property care tasks, Breezeway helps thousands of short-term rental managers and hospitality operators increase operational efficiency and boost service revenue while eliminating manual work and elevating the experience at each property. As a Client Onboarding & Success Manager for the Italian Market, you'll own the full client journey — from onboarding new customers through to long-term retention and growth. What You'll Do - Onboarding: - Collaborate with Sales and CX to ensure efficient onboarding of new Italian-market accounts, with clear handoffs and cross-functional alignment. - Run training sessions that educate clients on Breezeway best practices and how to get the most out of the platform for their specific operations. - Actively monitor onboarding health — tracking timelines, milestones, and early adoption signals across your book. - Troubleshoot client issues to resolution or escalate to the right internal resource quickly. - Build and iterate on onboarding materials, processes, and documentation in Italian as a foundation for the market. - Collaborate cross-functionally with Sales and Product to translate client feedback into practical improvements. - Client Success: - Maintain continuous engagement with clients post-onboarding to drive adoption, build confidence, and increase platform value. - Identify churn risks early and develop action plans to address them before they escalate. - Develop engagement and success strategies informed by data and client feedback; identify upsell and cross-sell opportunities. - Serve as the primary Italian-speaking point of contact — a trusted partner, not just a support resource. - Represent the voice of the client internally, bringing feedback that enables continuous improvement in how we serve this market. - Apply a solutions-oriented approach to client needs and escalate issues quickly when needed. Qualifications - Driven to understand client needs, empower them with best practices, and build genuine trust. - A self-starter who thrives in fast-paced, ambiguous environments. - A clear, confident communicator who can adapt your style across a property manager in the field and an executive in a QBR. - Operationally minded — you think in systems, sweat the details, and enjoy building processes from scratch. - A creative problem-solver with a proven track record of finding practical solutions for clients. - Committed to a collaborative, inclusive team environment built on customer empathy. Requirements - 2–4 years of experience in implementation, client success, or account management — ideally in a SaaS environment. - Fluency in Italian and English (written and spoken). - Strong project management and prioritization skills; proven ability to juggle multiple clients and competing priorities. - Experience with CRM software and web-based tools; comfortable navigating Google Suite, Zoom, and Slack. - Solid Excel skills — conditional formatting, VLOOKUP, formula functions, sorting and filtering. - Experience in the short-term rental or property management industry is a strong plus. - Startup or early-stage company experience is a bonus. Benefits - Breezeway is an equal opportunity employer and prohibits discrimination based on race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status. - We embrace diversity and are committed to creating an inclusive workplace. - We believe that respect fosters open-mindedness and curiosity, enabling us to gain valuable perspectives from our teammates, the market, and our clients. - All qualified applicants will receive consideration for employment without regard to these factors. - If you need accommodation during the application process, please let us know.

• Identify and qualify new sales opportunities through inbound lead follow-up and proactive outbound prospecting. • Research prospective clients, identify key players, and generate interest. • Collaborate closely with the Sales team to develop and implement lead strategies and plans. • Schedule and conduct online product demonstrations and webinars. • Work with channel and distribution partners to leverage leads and build pipeline and awareness.

Role Description Breezeway is hiring a Sales Development Representative to join our Sales team and have an immediate impact on our exponential growth. The successful candidate will thrive in a fast-paced environment, conduct consistent outreach to generate interest in our products and qualify prospects, and contribute to our team’s evolution. This is a great opportunity for a smart, energetic, self-motivated person to grow into the next stage of their career. If you are hard-working, driven, and ambitious, and want to bring your previous sales success to the next level, we’d love to chat with you. What You’ll Do - Identify and qualify new sales opportunities through inbound lead follow-up and proactive outbound prospecting. - Research prospective clients, identify key players, and generate interest. - Collaborate closely with the Sales team to develop and implement lead strategies and plans. - Schedule and conduct online product demonstrations and webinars. - Work with channel and distribution partners to leverage leads and build pipeline and awareness. Who You Are - Excellent communication skills that enable you to motivate and inspire prospects. - Desire to meet and exceed measurable performance goals. - Able to operate autonomously as an empowered contributor to the team. - Tons of positive energy, passion, humor, and enthusiasm. - Committed to Diversity, Equity, Inclusion, and Belonging (DEIB). What You’ll Bring - 1+ years prior successful sales experience or demonstrated success in a high-energy role and drive to pursue sales. - Strong time management and prioritization. - Proven ability to juggle multiple projects while maintaining sharp attention to detail. - Proficient with CRM applications, MS Office, and Google Apps. - Experience working in a startup environment is a plus. Company Description Breezeway is an equal opportunity employer and prohibits discrimination based on race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status. We embrace diversity and are committed to creating an inclusive workplace. We believe that respect fosters open-mindedness and curiosity, enabling us to gain valuable perspectives from our teammates, the market, and our clients. All qualified applicants will receive consideration for employment without regard to these factors. If you need accommodation during the application process, please let us know. We're a remote-first company with team members across the U.S. and globe, but we currently hire only in the following states and countries. - Countries: US and Spain - United States: Arizona, Arkansas, California, Connecticut, Florida, Georgia, Idaho, Illinois, Maine, Massachusetts, Michigan, Missouri, Nevada, New Hampshire, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Utah, Vermont, Virginia, Washington, and Wisconsin.

• Identify, prospect, and qualify new sales opportunities through a mix of outbound efforts and collaboration with SDRs • Manage the full sales cycle from initial discovery through close • Build relationships with key stakeholders across enterprise accounts • Conduct tailored product demos and virtual or in-person presentations • Partner cross-functionally with Marketing, Implementation, and Success to ensure seamless client onboarding • Maintain accurate pipeline data and forecasting within HubSpot • Consistently meet and exceed activity, pipeline, and revenue goals

• Build and ship full-stack product features across a Python/Flask backend and React frontend. • Design and evolve REST and GraphQL APIs, working closely with product and other engineering teams to define clean, durable interfaces. • Work with SQLAlchemy ORM and relational data models to build reliable, performant backend services. • Contribute to our growing LLM-powered feature set - building integrations with AI models, designing prompts and pipelines, and thinking carefully about quality and reliability in AI-assisted workflows. • Communicate trade-offs and provide feedback on code and implementation decisions to peers as part of everyday development • Collaborate with design, product, and other engineers to deliver high-quality work end-to-end.

• Build and ship full-stack product features across a Python/Flask backend and React frontend. • Design and evolve REST and GraphQL APIs, working closely with product and other engineering teams to define clean, durable interfaces. • Work with SQLAlchemy ORM and relational data models to build reliable, performant backend services. • Contribute to our growing LLM-powered feature set - building integrations with AI models, designing prompts and pipelines, and thinking carefully about quality and reliability in AI-assisted workflows. • Communicate trade-offs and provide feedback on code and implementation decisions to peers as part of everyday development • Collaborate with design, product, and other engineers to deliver high-quality work end-to-end.

• Define and lead Breezeway’s end-to-end post-sale strategy across onboarding, adoption, retention, and support • Establish clear KPIs and performance frameworks tied to retention, efficiency, and customer outcomes • Serve as the executive voice of the customer and bring customer insights into leadership discussions and company priorities • Ensure a consistent, high-quality customer experience across all touchpoints • Lead and develop a multi-layered CX organization, including senior leaders across Customer Success, Implementation, and Support • Evolve organizational structure, roles, and coverage models to support scale and profitability • Drive a high-performance culture grounded in accountability, clarity, and continuous improvement • Own net revenue retention (NRR), gross retention, and overall customer health metrics • Build and scale programs that drive adoption, engagement, and long-term value realization • Partner closely with Sales to ensure seamless handoffs and aligned expectations across the customer lifecycle • Engage directly with strategic accounts and high-impact customer situations • Optimize onboarding processes to reduce time-to-value and improve activation rates • Standardize and scale implementation while maintaining flexibility across customer segments • Improve predictability and efficiency in onboarding delivery • Oversee global support operations with a focus on responsiveness, quality, and cost efficiency • Implement scalable support models, including tiering, self-service, and escalation management • Leverage AI, automation, and tooling to improve support outcomes and team productivity • Ensure Assist functions are well-integrated and delivering measurable customer value • Act as a core partner to Product, Sales, Marketing, and Finance to align on company priorities and execution • Partner with Product to incorporate customer insights into roadmap and prioritization • Collaborate with Sales and Marketing to ensure alignment across the full customer lifecycle • Work with Finance on forecasting, capacity planning, and improving overall unit economics • Build scalable processes, systems, and reporting across the CX organization • Drive efficiency improvements across onboarding, support, and customer success delivery • Establish capacity models and resource planning aligned with growth and margin targets • Leverage data, systems (including HubSpot), and AI to increase visibility and improve decision-making.

• Ensure the client has the best understanding of our platform, technical capabilities, and know how to enable their success, while learning about their unique business needs and how they align with future product development at Breezeway. • Accelerate new user adoption through functional and conceptual instruction and provide ongoing education on new features. • Maintain continuous engagement with clients to increase value and build confidence in the product. • Drive further adoption and identify upsell opportunities. • Identify business churn risks early, and create action plans to circumvent them. • Develop strategies for engagement, adoption, and success planning, by analyzing data and client feedback. Further drive value by identifying additional upsell and cross-sell opportunities. • Represent the voice of the client internally, and provide feedback that enables continuous development and improvement of how we do business. • Apply a solution-oriented approach to meeting client needs, and escalate client issues quickly.

• Ensure the client has the best understanding of our platform, technical capabilities, and know how to enable their success, while learning about their unique business needs and how they align with future product development at Breezeway. • Accelerate new user adoption through functional and conceptual instruction and provide ongoing education on new features. • Maintain continuous engagement with clients to • Increase value and build confidence in the product by providing ongoing education on new features and products. • Drive further adoption. • Identify upsell opportunities. • Identify business churn risks early, and create action plans to circumvent them. • Develop strategies for engagement, adoption, and success planning, by analyzing data and client feedback. Further drive value by identifying additional upsell and cross sell opportunities. • Represent the voice of the client internally, and provide feedback that enables continuous development and improvement of how we do business. • Apply a solution-oriented approach to meeting client needs, and escalate client issues quickly.

• Identify, prospect, and qualify new sales opportunities through a mix of outbound efforts and collaboration with SDRs. • Manage the full sales cycle from initial discovery through close. • Conduct tailored product demos and virtual or in-person presentations. • Partner cross-functionally with Marketing, Implementation, and Success to ensure seamless client onboarding. • Maintain accurate pipeline data and forecasting within HubSpot. • Consistently meet and exceed activity, pipeline, and revenue goals.