Sales Director - Arryva

Nsight Health

25d•$120,000 - $140,000•Remote

About The Position

Arryva is transforming the short-term rental (STR) industry by providing property owners with a high-tech, low-cost alternative to traditional full-service management. We combine human expertise with AI-powered technology to manage everything from guest communications to dynamic pricing—allowing owners to keep 100% of their data and reviews while paying a fraction of the cost of legacy competitors. Join a fast-growing, mission-driven team that blends hospitality and technology to give property owners true peace of mind. Arryva — Where Technology Meets Hospitality. ---------------------------------------- We are seeking a high-stakes Sales Director to build and own Arryva’s revenue function from the ground up. As we disrupt the multi-billion dollar property management space, we require a "founding operator" who views sales not just as a series of transactions, but as the engine for a repeatable, scalable business model. Reporting directly to the CEO, you will be a "builder-operator": you will design the initial sales playbooks, select the CRM architecture, and serve as a high-performing individual contributor while preparing to scale a team. This is a role for a leader with high "Sales IQ" who can command a room, navigate complex stakeholder maps, and close enterprise-level partnerships with national property management companies. AI Fluency Requirement — Non-Negotiable Arryva is an AI-first organization. Every member of our leadership and operations team is expected to actively use AI tools in their day-to-day work — not as a novelty, but as a core productivity multiplier. This role requires genuine curiosity about AI, comfort experimenting with tools like Claude, ChatGPT, and workflow automation platforms to personalize outreach and automate CRM tasks, and the judgment to know when AI helps and when it doesn't. If AI makes you uncomfortable, this is not the right role.

Requirements

5–10 years of B2B or high-ticket B2C sales experience, with at least 2 years in a senior or director-level leadership role.
Proven Closer: A demonstrated track record of meeting or exceeding quotas in a subscription-based or recurring revenue (MRR) business.
Builder Mindset: Prior experience building or significantly improving a sales process or playbook at an early-stage or growth-stage startup.
AI Fluency: Genuine enthusiasm for and professional experience using AI tools (ChatGPT, Claude, etc.) as a core productivity multiplier for outreach and research.
High Sales IQ: Exceptional ability to lead high-level discovery, navigate complex stakeholder maps, and close enterprise-level deals.

Nice To Haves

Industry Background: Direct experience in Short-Term Rental (STR) management, real estate investment, or PropTech (e.g., Vacasa, Evolve, Guesty).
Personal Credibility: Experience as an STR owner or real estate investor is a significant advantage.
Technical Familiarity: Deep experience with CRM architecture (HubSpot/Salesforce) and sales analytics reporting.
Network: An existing network within the STR investor community or national real estate associations.

Responsibilities

Revenue Generation & Pipeline Ownership: Own the full sales lifecycle from prospecting through contract execution; build and manage a qualified pipeline across individual owners, portfolio investors, and enterprise PM companies.
Sales Strategy & Playbook Development: Design and document Arryva’s formal sales process, including discovery scripts, objection handling, and proposal templates while implementing a CRM to ensure accurate forecasting.
Partnership & Ecosystem Development: Build and maintain high-trust relationships within real estate investment groups, STR communities, and lead commercial negotiations for "White-Label" partnerships and enterprise deals.
AI & Sales Automation: Actively use AI tools (ChatGPT, Claude, etc.) to produce high-quality sales collateral and personalized outreach at scale; identify operational friction points that can be reduced through automation.
Team Leadership & Scaling: Recruit, onboard, and coach the future sales and SDR functions as the company grows; foster a high-performance culture of accountability and data-driven results.