[Hiring] Sales Director @Angel Host

Role Description

You will own Sentinel's number, lead the team that hits it, and personally close the deals only you can close. This is a player-coach role: you take over a distributed team of Account Executives in Canada and Europe, plus outsourced SDRs feeding them pipeline, and grow it from there.

Specifically, we need you to:

• Close:
  • Carry and exceed a personal new-ARR quota with property managers from roughly 30 to 1,000+ listings.
  • Open doors nobody else on the team can open, starting with your own network on day one.
  • Run the full cycle: a listing performance audit, then a free trial, then a paid subscription.
  • Negotiate on structure, meaning tiers, modules and commitments, rather than cutting price.
• Lead:
  • Take over the sales team and double it by mid-2027: hire, onboard, ramp, coach and, when you have to, replace.
  • Set territories, quotas and comp plans people believe in and can actually hit.
  • Run the weekly rhythm of pipeline reviews, deal inspection and call coaching, and own a rolling forecast the CEO and the board can rely on.
• Build:
  • Build the Sentinel sales playbook: who we go after, how we qualify them, how we demo and how we price.
  • Make the free trial convert reliably, not just sometimes.
  • Keep HubSpot current. We forecast off it, so if it is not in there it did not happen.
• Represent:
  • Be Sentinel's face in the industry: VRMA International, DARM, IMN forums, SCALE and the regional meetups where the real conversations happen.
  • Build the partner and referral relationships that bring deals in without a cold call.
  • Publish, post and speak. Be someone the industry recognizes.

Qualifications

• You have a deep, active network in the short-term rental industry.
• You have 5+ years in B2B sales including at least 2 years leading a quota-carrying team.
• You have personally closed complex, multi-stakeholder deals recently.
• You are genuinely comfortable with ongoing travel.

Requirements

• You have sold software, data or revenue services into the vacation rental industry: PMS, dynamic pricing, market data, guest experience, analytics.
• You understand revenue management well enough to hold your own with a revenue manager: RevPAR, ADR, occupancy, pickup, booking windows, comp sets, minimum stays.
• You have been the first or early sales leader at a company scaling from its first paying customers to $5M+ ARR.

Benefits

• A base salary of USD $100,000 to $120,000.
• A variable component of USD $70,000 to $90,000 at target, for on-target earnings of USD $170,000 to $210,000 with additional bonuses if targets are surpassed.
• Your full variable guaranteed for your first quarter.
• A meaningful stock option grant.
• A budget to attend the most important events in our industry.
• 100% of your individual medical, dental and vision premium, plus life and disability insurance and a 401(k) with employer match.
• Paid vacation and all US national holidays.
• Freedom to work from home, or from anywhere you have reliable wifi and a dedicated working space.
• Up to 3 days of paid time off to volunteer with the charity of your choice through "Angels Care."