Director Of Sales

About the Company:

Rest is the leading smoke detection platform built exclusively for hotels. Our privacy-safe sensors and cloud-based software help hotels consistently enforce smoke-free policies, protect the guest experience, and maintain healthier room environments. Purpose-built for hotel operations, Rest’s solution is discreet, reliable, and maintenance-free, allowing staff to manage smoking violations with confidence and without disruption. Today, Rest partners with many of the world’s top hotel owners and operators to help them confidently uphold their smoke-free commitment.

About the Job:

The Regional Director of Sales will own a high-value enterprise territory and drive new revenue by selling Rest’s smoke monitoring platform into hotel ownership groups, management companies, and senior operational leaders. This role is built for an experienced enterprise seller who knows how to navigate complex organizational structures, identify the power base, develop champions, and win multi-stakeholder deals.

You will manage the full sales cycle from outbound prospecting through closing, using a disciplined approach to pipeline generation, relationship building, financial modeling, and value-based selling. This is a high-impact role for someone who thrives on autonomy, communicates with clarity and confidence, and brings both executive presence and operational understanding to every interaction.

Responsibilities:

Territory Ownership & Sales Execution

• Own and deliver the annual quota for the assigned territory with disciplined forecasting and proactive pipeline management.
• Build and execute a territory plan that identifies target ownership groups, operational leaders, whitespace potential, and multi-property expansion pathways.
• Use enterprise sales frameworks to map economic buyers, champions, influencers, and blockers across ownership and operational teams.
• Drive a consistent outbound motion, including sequences, personalized outreach, and strategic account penetration.
• Manage every stage of the sales cycle: discovery, pitching, demos, financial justification, proposal development, negotiation, and close.
• Work closely with Rest’s legal and leadership teams to structure terms and advance complex agreements through contracting.

Strategic Stakeholder Engagement

• Build strong relationships across ownership groups and operational leadership, including CFOs, CEOs, VPs of Operations, Regional Operations leaders, and VP-level or regional Asset Managers responsible for financial performance and asset preservation.
• Engage property-level stakeholders such as General Managers as part of demo and evaluation processes, while keeping ownership and executive stakeholders aligned.
• Understand how ownership groups and operational teams collaborate on technology evaluation and decision-making, and adapt your sales strategy accordingly.
• Leverage your hospitality network to create warm introductions, accelerate deal cycles, and uncover portfolio-level opportunities.

Presenting Solutions and Aligning Value

• Lead compelling presentations and on-site demos that resonate with both operational teams and executive decision-makers.
• Clearly articulate Rest’s operational and financial value, including improved consistency, reduced risk, and enhanced guest experience.
• Build and present financial models, ROI analyses, pricing structures, and value comparisons that align with ownership group priorities.
• Tailor messaging and framing based on audience seniority, operational focus, and strategic goals.

Operational Discipline & Internal Collaboration

• Maintain accurate pipeline, weekly forecasting, and activity tracking in Salesforce.
• Collaborate closely with Customer Success, Operations, and Product to ensure smooth onboarding and long-term account health.
• Provide structured market and customer insights that influence product and pricing strategy.

Industry Engagement & Market Expansion

• Represent Rest at conferences, trade shows, association events, and regional hospitality gatherings.
• Stay informed on hotel market trends, ownership group dynamics, and the broader hospitality technology landscape to position Rest effectively.

Experience/Requirements:

• 5+ years of enterprise sales experience with a track record of exceeding quota and closing complex, multi-stakeholder deals.
• Direct experience selling into hotel ownership groups, management companies, or organizations with similar multi-location, portfolio-driven decision structures.
• Strong understanding of how asset managers, operational leaders, and corporate executives evaluate technology.
• Strong financial literacy with the ability to build ROI models, compare pricing structures, and communicate financial outcomes clearly to economic buyers.
• Excellent communicator with strong public speaking skills and the ability to influence CFOs, CEOs, VPs of Operations, and regional leadership teams.
• Proven ability to run disciplined outbound motions, manage long-cycle enterprise sales, and maintain exceptional follow-up.
• Extremely organized, energetic, personable, and comfortable owning an entire territory with minimal oversight.
• Skilled in Salesforce, Excel, Google Workspace, Microsoft Office Suite, and other common sales tools.
• Bachelor’s degree required, preferably in business, finance, or a related field.
• Must have the ability to travel for in-person meetings, onsite demonstrations, and industry events up to approximately 35 percent of the time.

Required Work Location and Home Office Standards:

The candidate must reside in one of the following states to be eligible for this regional role:

Connecticut, Delaware, District of Columbia, Florida, Georgia, Illinois, Indiana, Kentucky, Maine, Maryland, Massachusetts, Michigan, Minnesota, New Hampshire, New Jersey, New York, North Carolina, Ohio, Pennsylvania, Rhode Island, South Carolina, Tennessee, Vermont, Virginia, West Virginia, or Wisconsin.

This is a remote, home-based position

:

Team members are required to work from their designated home office or work space when not traveling for business. A consistent, distraction-free, professional environment is expected during business hours for this client-facing role. The role requires reliable high-speed internet, professional video call setup, and the ability to host polished virtual meetings with executive stakeholders.