Vacation Rental Sales Consultant
About Guestbook Rewards, Inc.
Our Guiding Principles
Purpose: Help people make the most of life's opportunities to travel.
Mission: Provide the most enriching and financially rewarding travel experiences.
Product Vision: Build the stickiest hotel network for travelers and partners.
Aspirational Future: A world where travelers search less and experience more.
Our Core Values
Focus on possibilities: We have a positive mindset and embrace innovation
Make an impact: We are passionate about delivering meaningful and sustainable outcomes
Be Accountable: We are trustworthy and reliable to travelers, partners, ourselves, and each other
Deliver as a team: We embrace diversity of thought and selfless collaboration to unleash new potential
Invest in each other: We share knowledge and encourage continuous learning to grow together
About the role
As a Vacation Rental Partnerships Consultant at The Guestbook, you’ll act as a trusted advisor to professional vacation rental management companies —helping them better understand their booking mix, guest behavior, and revenue opportunities, and showing how The Guestbook can help grow direct revenue without adding operational complexity.
You’ll work closely with Sales, Partner Success, and Marketing to translate defined sales strategies and partner goals into thoughtful discovery conversations, tailored recommendations, and long-term partnerships. This is not a one-size-fits-all sales role. Instead, you’ll guide partners through the decision-making process by connecting their specific challenges to clear, value-driven solutions.
This role sits within the Sales & Partnerships team and is ideal for an experienced vacation rental professional looking for a flexible, part-time consulting role with meaningful revenue impact.
What you'll do
Sales & Revenue Growth
• Serve as a consultative sales partner to professional vacation rental operators, helping them increase direct bookings and ancillary revenue.
• Proactively engage inbound leads and identify management and ownership groups to target as prospective partners.
• Conduct discovery conversations to understand partner goals and recommend tailored solutions that drive measurable revenue impact.
• Own the sales process end-to-end—from discovery and demos through pricing discussions, contracting, and close.
Partner Insights & Performance
• Use sales data, partner performance metrics, and market trends to inform recommendations and prioritize opportunities.
• Track and report on pipeline activity, conversion rates, and revenue performance using CRM and internal tools.
• Identify performance gaps or anomalies and surface insights to Partner Success and Sales leadership.
• Share feedback from the field to help refine messaging, pricing, and product positioning.
Cross-Functional Collaboration
• Work closely with Partner Success to ensure smooth handoffs and strong post-sale outcomes.
• Partner with Marketing to align on lead quality, campaigns, and sales enablement materials.
• Collaborate with Product and Finance to stay fluent in product capabilities, pricing structures, and value drivers.
• Support evolving sales processes as the business scales.
Sales Operations & Execution
• Maintain accurate and up-to-date CRM records, including notes, forecasts, and deal stages.
• Follow established sales playbooks while continuously refining your approach based on results.
• Assist with sales documentation, FAQs, and internal knowledge sharing.
What you’ll bring to The Guestbook
Required
• Deep understanding of the professional vacation rental management industry from a B2B perspective.
• A strong existing network of contacts within the vacation rental ecosystem.
• Excellent communication skills with the ability to clearly and confidently articulate value.
• Comfort working within defined sales processes while asking thoughtful questions when clarity is needed.
• Ability to translate partner needs into compelling, solution-oriented recommendations.
• High attention to detail, strong follow-through, and a growth mindset.
Nice to Haves
• Familiarity with CRM tools such as HubSpot, Salesforce, or similar platforms.
• Experience selling SaaS, fintech, or revenue-driving tools.
• Comfort using data and dashboards to guide sales conversations.
• Interest in AI-assisted sales tools or automated insights.
Expectations & Working Hours
• This is a part-time role, averaging approximately 10 hours per week to start.
• Hours are flexible within the workweek, with regular availability needed for collaboration, including standups, working sessions, and ad hoc discussions with analytics and business partners.
• Work will typically be planned and prioritized in advance, with occasional shifts based on business needs or reporting deadlines.
• The role is currently scoped as part-time; any future changes to scope or hours would be based on business needs.
Pay
• $55 per billed hour, plus commissionable opportunities.
Apply Now
Apply Now
Our Guiding Principles
Purpose: Help people make the most of life's opportunities to travel.
Mission: Provide the most enriching and financially rewarding travel experiences.
Product Vision: Build the stickiest hotel network for travelers and partners.
Aspirational Future: A world where travelers search less and experience more.
Our Core Values
Focus on possibilities: We have a positive mindset and embrace innovation
Make an impact: We are passionate about delivering meaningful and sustainable outcomes
Be Accountable: We are trustworthy and reliable to travelers, partners, ourselves, and each other
Deliver as a team: We embrace diversity of thought and selfless collaboration to unleash new potential
Invest in each other: We share knowledge and encourage continuous learning to grow together
About the role
As a Vacation Rental Partnerships Consultant at The Guestbook, you’ll act as a trusted advisor to professional vacation rental management companies —helping them better understand their booking mix, guest behavior, and revenue opportunities, and showing how The Guestbook can help grow direct revenue without adding operational complexity.
You’ll work closely with Sales, Partner Success, and Marketing to translate defined sales strategies and partner goals into thoughtful discovery conversations, tailored recommendations, and long-term partnerships. This is not a one-size-fits-all sales role. Instead, you’ll guide partners through the decision-making process by connecting their specific challenges to clear, value-driven solutions.
This role sits within the Sales & Partnerships team and is ideal for an experienced vacation rental professional looking for a flexible, part-time consulting role with meaningful revenue impact.
What you'll do
Sales & Revenue Growth
• Serve as a consultative sales partner to professional vacation rental operators, helping them increase direct bookings and ancillary revenue.
• Proactively engage inbound leads and identify management and ownership groups to target as prospective partners.
• Conduct discovery conversations to understand partner goals and recommend tailored solutions that drive measurable revenue impact.
• Own the sales process end-to-end—from discovery and demos through pricing discussions, contracting, and close.
Partner Insights & Performance
• Use sales data, partner performance metrics, and market trends to inform recommendations and prioritize opportunities.
• Track and report on pipeline activity, conversion rates, and revenue performance using CRM and internal tools.
• Identify performance gaps or anomalies and surface insights to Partner Success and Sales leadership.
• Share feedback from the field to help refine messaging, pricing, and product positioning.
Cross-Functional Collaboration
• Work closely with Partner Success to ensure smooth handoffs and strong post-sale outcomes.
• Partner with Marketing to align on lead quality, campaigns, and sales enablement materials.
• Collaborate with Product and Finance to stay fluent in product capabilities, pricing structures, and value drivers.
• Support evolving sales processes as the business scales.
Sales Operations & Execution
• Maintain accurate and up-to-date CRM records, including notes, forecasts, and deal stages.
• Follow established sales playbooks while continuously refining your approach based on results.
• Assist with sales documentation, FAQs, and internal knowledge sharing.
What you’ll bring to The Guestbook
Required
• Deep understanding of the professional vacation rental management industry from a B2B perspective.
• A strong existing network of contacts within the vacation rental ecosystem.
• Excellent communication skills with the ability to clearly and confidently articulate value.
• Comfort working within defined sales processes while asking thoughtful questions when clarity is needed.
• Ability to translate partner needs into compelling, solution-oriented recommendations.
• High attention to detail, strong follow-through, and a growth mindset.
Nice to Haves
• Familiarity with CRM tools such as HubSpot, Salesforce, or similar platforms.
• Experience selling SaaS, fintech, or revenue-driving tools.
• Comfort using data and dashboards to guide sales conversations.
• Interest in AI-assisted sales tools or automated insights.
Expectations & Working Hours
• This is a part-time role, averaging approximately 10 hours per week to start.
• Hours are flexible within the workweek, with regular availability needed for collaboration, including standups, working sessions, and ad hoc discussions with analytics and business partners.
• Work will typically be planned and prioritized in advance, with occasional shifts based on business needs or reporting deadlines.
• The role is currently scoped as part-time; any future changes to scope or hours would be based on business needs.
Pay
• $55 per billed hour, plus commissionable opportunities.
Apply Now
Apply Now