Sales Director
Sales Director, Sentinel by Angel Host
Remote, United States · Reports to the CEO · Full-time · Employed through our US employer of record
Every property manager you know already pays for a dynamic pricing tool, and almost every one is still leaving revenue on the table: weekends sold too early, booking windows missed, discounts nobody needed to give. Not because the tool is broken, but because nobody can watch hundreds of listings across 365 open dates at once.
That is the gap Sentinel closes.
Sentinel is a decision engine, not another dashboard. It watches thousands of signals across a portfolio every day and surfaces one prioritized action at a time: where to act, why, and what it is worth. Explainable every time, never a black box. Dynamic pricing sets rates. Sentinel sets priorities.
We are Angel Host : Montreal-founded, venture-backed, fifty people across eleven countries, and seven years managing revenue for property managers in the Americas and Europe. Sentinel is the tool we built because we needed it ourselves. It went live in May 2026, is already in use in twelve countries, and we plan to grow it more than 30x in two years.
If you have real relationships in the short-term rental world, keep reading.
The position: Sales Director
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.
Let us be blunt about the most important part. What you bring is your network. We can teach you Sentinel. We cannot teach you years of relationships with property managers and industry operators who will take your call. If you have built that in short-term rentals, this role was written for you.
You report directly to the CEO, and there is a real handover waiting: a live pipeline, an established team and a book of clients. Not a cold start.
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. And 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.
Is this job for you?
These are non-negotiable:
- You have a deep, active network in the short-term rental industry. Not "familiarity with hospitality" but actual relationships with property managers, revenue managers and operators who would take your call today. You can name the accounts, and you will be asked to;
- You have 5+ years in B2B sales including at least 2 years leading a quota-carrying team, and you have personally closed complex, multi-stakeholder deals recently;
- You are genuinely comfortable with ongoing travel. In this role conferences are not a perk, they are a channel.
These we would love to see:
- You have sold software, data or r