What We’re Looking For

Breezeway is hiring an Account Executive to join our Sales team and play a key role in driving new business growth. The ideal candidate has 2+ years of proven success closing in SaaS sales, thrives in a fast-paced, high-growth environment, and is eager to prospect, build relationships, and close deals with property management companies across the short-term rental and hospitality industry.

You should be comfortable with outbound selling, collaborating closely with SDRs, and willing to travel to key markets and events to get in front of prospects. Experience with field sales or in-market meetings is a plus.

If you’re ambitious, resourceful, and excited to take your SaaS sales career to the next level, we’d love to meet you.

What You’ll Do

• 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.
  
  

What You’ll Bring

• 2+ years of SaaS closing experience with consistent quota attainment and 4+  years of sales experience
  
  
• Strong outbound and prospecting skills — you’re energized by the hunt.
  
  
• Excellent communication, consultative selling, and presentation skills.
  
  
• Willingness to travel for events, conferences, and in-market meetings.
  
  
• A self-starter mindset with curiosity, resilience, and drive to win.

Manager, Revenue Operations

Breezeway is hiring a Manager of Revenue Operations to be responsible for the systems and processes that power our go-to-market engine across Sales, Marketing, Implementation, and Customer Success. This role reports to our CFO and is responsible for building scalable revenue operations foundations, improving funnel performance, and owning the data and reporting that provides the visibility and insights that our leadership team rely on to drive growth. This role owns revenue reporting, pipeline management, GTM analytics, and process design initiatives.  They will partner with cross-functional leaders to improve GTM alignment and operational excellence, including conversion, retention, and expansion motions.

What You’ll Do

• Maintain and optimize our end-to-end GTM processes, ensuring seamless handoffs between Marketing, Sales, Implementation and Customer Success from lead to sales to expansion
• Own and optimize the GTM tech stack (Marketing automation, CRM, Sales outreach, CS tools), ensuring high data quality, strong integrations, and user adoption
• Provide thought leadership and strategy cross-functionally to ensure accurate tracking and reporting on key Revenue drivers and performance metrics
• Partner with Sales and CS Leadership to support forecasting, territory alignment, and capacity planning through consistent operating cadences (e.g. weekly forecasts, pipeline reviews, and quarterly business reviews, etc.)
• Serve as administrator to GTM tech stack and support onboarding and offboarding of employees and provide ongoing support and troubleshooting
• Analyze data across the Sales and Marketing teams and provide valuable insights to management, stakeholders and team members
• Partner with GTM leaders to diagnose bottlenecks and identify opportunities to increase win rates, shorten sales cycles, and improve expansion and renewal outcomes
• In partnership with Marketing, Sales and Finance leadership, develop strategies and processes to accurately report on all steps of the GTM funnel
• Support pricing and packaging decisions and new product or segment launches by providing data and measurement plans
• Establish and enforce data governance standards and documentation for core GTM processes, metrics, and systems
• Introduce automation and leverage AI-enabled tools where appropriate to reduce manual work and improve GTM productivity
• Potential to manage a Revenue Operations team as the company scales

Who You Are

• Able to succeed in a fast-paced, changing, dynamic environment.
• Action-oriented and driven to execute on key objectives.
• Data-driven and analytical.
• Intellectually curious and a continuous learner.
• Adept at cross-functional collaboration.
• Committed to Diversity, Equity, Inclusion, and Belonging (DEIB).

What You'll Bring

• 5–8 years of experience in Revenue Operations, Sales Operations, or GTM operations in a high-velocity SaaS environment (less than 20-day sales cycle length)
• Deep experience with HubSpot, including CRM and Marketing Automation functions.
  • Relevant Hubspot certifications preferred
• Experience with GTM Tools
  • We use Aircall, Intercom, Chilipiper, Arrows, Grain, Appcues, Zapier
• Strong analytical skills with the ability to interpret data and translate it into actionable insights
• Experience partnering with Sales, Marketing, and Customer Success teams
• Strong problem-solving skills with a focus on building improving processes to drive efficiency
• Experience supporting forecasting, pipeline management, and overall funnel performance
• Understanding of core GTM metrics and how to measure and improve performance across the funnel
• Strong communication skills, with the ability to clearly convey insights, recommendations, and updates to a range of stakeholders
• Experience establishing or maintaining data quality and consistency across systems
• Experience and interest in leveraging automation and AI to improve workflows and productivity

What We’re Looking For

Breezeway is hiring a Director of Sales, West to own and scale our West and Central sales organization. You'll be stepping into an established team of 4–5 Account Executives and taking full accountability for revenue performance across the West and Central regions.

This is a hands-on leadership role. The ideal candidate is a high-performing SaaS sales leader ready to step into full ownership of a revenue number — someone equally comfortable coaching reps, running deals, forecasting the business, and building the foundation for the next stage of sales leadership as the team scales. Candidates should be based in the Central or West time zones to align with their team and customers.

What You’ll Do

• Own and deliver West and Central revenue targets, consistently meeting or exceeding monthly, quarterly, and annual goals across a team of 3–5 AEs.
• Lead, coach, and develop Account Executives, setting clear performance expectations, running consistent coaching rhythms, and building repeatable paths to success.
• Stay hands-on in the business, including:
  • Running weekly deal, pipeline, and forecast reviews
  • Partnering with AEs on late-stage deals, pricing, and negotiations
  • Joining customer calls and executive-level conversations as needed
• Drive execution across the full sales cycle, primarily in a high-velocity SMB motion.
• Translate company revenue goals into execution, including territory design, quota allocation, and segment-specific operating plans for West and Central markets.
• Partner closely with Marketing, RevOps, Customer Success, and Product to improve pipeline quality, conversion rates, onboarding readiness, and forecast accuracy.
• Continuously evaluate and improve sales process and pipeline health, using data to identify gaps, course-correct quickly, and drive predictable performance.
• Hire, onboard, and ramp top sales talent, working closely with the People team as the organization scales.
• Build a high-performance sales culture rooted in accountability, trust, clarity, and continuous improvement. 

Who You Are

• 7–10+ years of experience in B2B SaaS sales, with at least 3–5 years in a sales management role 
• A people-first, performance-driven leader who enjoys coaching and developing AEs while holding a clear bar for results.
• Comfortable operating at both the strategic and day-to-day execution levels.
• Experienced supporting multi-stakeholder, higher-ACV SMB deals and helping reps navigate pricing and negotiation conversations.
• Highly organized and data-driven, with strong forecasting discipline.
• Collaborative and effective working cross-functionally.
• Action-oriented, decisive, and focused on outcomes.
• Motivated by growth — both for your team and for your own leadership trajectory.
• Based in the Central or West time zone to support West and Central customers and align with your team's working hours.

We're looking for an insightful, curious Product Marketing Manager to join our growing team. You'll be the connective tissue between product, sales, customer success, and demand gen — translating what we build into messaging that moves the market, enabling every client-facing team to win, and helping us stay ahead of a fast-moving industry.

This is a high-visibility role on a lean, high-output team. You'll own meaningful work from day one. Breezeway sits at the intersection of AI and one of the fastest-growing segments in hospitality, offering a unique opportunity to help shape the future of property operations. You’ll join a fast-moving, execution-oriented team that ships quickly and views marketing as a critical driver of growth. As a remote-first company, we prioritize collaboration, ownership, and building a team that genuinely enjoys working together.

What You'll Do

• Drive GTM for product launches — own positioning, messaging, launch plans, stakeholder management, and enablement assets for new features and capabilities across Breezeway's platform, ensuring sales and customer success teams are equipped to bring them to market
• Enable client-facing teams — build and maintain enablement resources for both sales and CSMs, including battlecards, talk tracks, objection-handling guides, and cross-sell playbooks that help the full revenue team communicate value at every stage of the customer journey.
• Own Breezeway's partner and integration messaging strategy — including joint messaging and co-branded assets with PMS and IoT partners, enablement for partner sales teams, and marketplace/directory listings 
• Drive cross-sell and expansion revenue — partner with Customer Success and Client Marketing to identify expansion opportunities, develop messaging and materials that support upsell motions, and contribute to programs that grow revenue within the existing customer base
• Own competitive intelligence — partner with product to track and analyze the competitive landscape and larger ecosystem, distill insights into actionable materials that help reps and CSMs win and retain business
• Support worldwide demand generation — partner with demand gen to develop campaign messaging, content briefs, and assets that differentiate Breezeway and convert and contribute to pipeline market-specific messaging
• Develop deep customer insights — conduct win/loss analysis, customer interviews, and market research to sharpen our understanding of buyer motivations and inform messaging strategy across the funnel and surface insights for the product team
• Leverage AI-driven insights and tools to enhance go-to-market strategy, messaging, and campaign performance

Who You Are: 

• Able to succeed in a fast-paced, changing, dynamic environment.
• Action-oriented and driven to execute on key objectives.
• Intellectually curious and a continuous learner.
• A strong cross-functional collaborator and communicator; comfortable working across product, sales, CS, and demand gen
• An excellent writer — you sweat the details on copy and know the difference between a feature and a benefit
• Committed to Diversity, Equity, Inclusion, and Belonging (DEIB).

What You’ll Bring 

• 5+ years of product marketing experience in B2B SaaS
• Demonstrated ability to translate technical product capabilities into compelling narratives
• Experience supporting or owning product launches end-to-end
• Proven track record enabling both sales and post-sale teams (CSMs, AMs) with materials that drive adoption, retention, and expansion
• Experience using Hubspot, Jira, and AI tools and data to inform marketing strategy, messaging, and campaign performance.
• Bonus: experience in hospitality tech, proptech, or SMB/mid-market SaaS

What We’re Looking For

Breezeway is hiring a Staff Software Engineer to join our Integrations team, working on third-party API integrations and our public API. This role is ideal for an execution-focused engineer who thrives in a fast-paced environment, delivering high-impact solutions efficiently, and enjoys collaborating on architectural challenges, and scalability problems. If you're product-minded, enjoy tackling technical challenges, and excel at building and maintaining API integrations, we’d love to hear from you.

Who We Are

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.

What You’ll Do

• Develop and maintain 40+ third-party API integrations and our public API,  ensuring reliability and scalability.
• Build REST and SOAP-based integrations, handling rate limits, data integrity, retries, and error management.
• Debug and optimize existing integrations to improve performance, stability, and customer impact.
• Address scalability concerns implementing rapid, but maintainable solutions to enable platform growth while ensuring we continue to meet client SLAs
• Use Flask, Celery, and SQLAlchemy to build and enhance back-end services.
• Monitor releases, troubleshoot integration issues, and leverage Datadog to diagnose and resolves system performance.
• Work with our Product team to refine technical requirements and implement client-first solutions. 
• Own projects from development through deployment, collaborating with the Principal Engineer on architecture.

Who You Are

• Execution-focused engineer who thrives in a high-throughput environment.
• Product-minded, with client empathy that drives rapid problem-solving and delivery.
• Comfortable working heads-down with an emphasis on impact and efficiency.
• Strong problem solver who can analyze and adapt to evolving API behaviors while maintaining system reliability.
• Scalability-Focused Engineer who can help deliver solutions to a growing platform without over-engineering.
• Team player who thrives in a highly collaborative environment, contributing technical expertise and working closely with peers to drive impactful solutions.

What You’ll Bring

• 10+ years of experience in back-end or full-stack development
• Strong Python skills, with experience in performance optimization
• Strong MySQL using SQLAlchemy skills with experience in performance optimization
• Experience integrating with REST, SOAP, and webhook-based APIs
• Proficiency with Celery, and Git in a team environment
• Experience monitoring and debugging APIs using Datadog or similar tools
• Experience working at SaaS or B2C Marketplace 
• Experience with AI development practices
• Familiarity with React and TypeScript