Sales Director
About The Position
Sentinel by Angel Host is seeking a Sales Director to own the company's revenue number, lead the sales team, and close key deals. This is a player-coach role where the individual will manage a distributed team of Account Executives and outsourced SDRs, growing the team from its current size. The ideal candidate will leverage their existing network within the short-term rental industry to drive sales. The role reports directly to the CEO and comes with a live pipeline, an established team, and a book of clients. Sentinel is a decision engine designed to optimize revenue for property managers by providing prioritized actions rather than just data. Angel Host, the parent company, is a venture-backed, 50-person organization with seven years of experience in revenue management for property managers in the Americas and Europe. Sentinel, launched in May 2026, is already in use in twelve countries and is projected for significant growth.
Requirements
- Deep, active network in the short-term rental industry with actual relationships with property managers, revenue managers, and operators.
- 5+ years in B2B sales.
- At least 2 years of experience leading a quota-carrying team.
- Proven track record of personally closing complex, multi-stakeholder deals recently.
- Comfortable with ongoing travel for industry conferences.
- Ability to build trust and earn past vendor skepticism.
- Desire to build something new rather than inherit an established structure.
- Ability to maintain HubSpot current for forecasting.
Nice To Haves
- Experience selling software, data, or revenue services into the vacation rental industry (e.g., PMS, dynamic pricing, market data, guest experience, analytics).
- Understanding of revenue management concepts (RevPAR, ADR, occupancy, pickup, booking windows, comp sets, minimum stays).
- Experience as the first or early sales leader at a company scaling from initial customers to $5M+ ARR.
Responsibilities
- Close new ARR quota with property managers (30 to 1,000+ listings), leveraging personal network for initial meetings.
- Manage the full sales cycle: listing performance audit, free trial, and subscription.
- Negotiate deal structures (tiers, modules, commitments) rather than cutting price.
- Lead and grow the sales team, doubling it by mid-2027 through hiring, onboarding, and coaching.
- Set territories, quotas, and compensation plans.
- Conduct weekly pipeline reviews, deal inspections, and call coaching.
- Own a rolling sales forecast for the CEO and board.
- Build the Sentinel sales playbook, including target customer profiles, qualification processes, demo strategies, and pricing.
- Ensure reliable conversion of free trials to paid subscriptions.
- Maintain HubSpot for accurate forecasting.
- Represent Sentinel at industry events (VRMA International, DARM, IMN forums, SCALE, regional meetups).
- Build partner and referral relationships.
- Publish, post, and speak to establish industry recognition.
Benefits
- Base salary of USD $100,000 to $120,000.
- Variable component of USD $70,000 to $90,000 at target.
- On-target earnings of USD $170,000 to $210,000.
- Additional bonuses for exceeding targets.
- Full variable component guaranteed for the first quarter.
- Meaningful stock option grant.
- Budget for industry events.
- 100% of individual medical, dental, and vision premium covered.
- Life and disability insurance.
- 401(k) with employer match.
- Paid vacation.
- All US national holidays paid.
- Freedom to work from home or any location with reliable wifi and a dedicated workspace.
- Up to 3 days of paid time off for volunteering through 'Angels Care'.
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
