Canadian Sales Director Jobs (NOW HIRING)

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.

• 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.

• 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 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.

• 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.

• 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.

• 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, and you know how different that is from running an established team.

• Your presence and tone build trust. Property managers are skeptical of vendors for good reason, and you know how to earn your way past that;
• You want to build something rather than inherit it. We are a few months into monetizing a product that is growing fast, and it is not tidy yet. If that sounds energizing rather than alarming, good;
• You love to laugh and want to be part of an awesome team.

We believe that to attract the best we also have to offer the best, so we have built a package designed to be competitive on cash, meaningful on ownership, and honest about the ramp. As our Sales Director, you will receive:

• 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," our way of giving back.

Seven years of running short-term rental portfolios taught us what to build. Nine months of engineering built it. What happens next is a sales problem, and it is the one we are hiring you to solve.

There are not many people with both a real short-term rental network and a record of building a sales team. If you are one of them, you already know it. Start with the five accounts you would call first.