Howskey is building the AI brain for every property. We started by helping short-term rental hosts turn scattered property information into instant, WhatsApp-based guest answers — and we're now bringing that same idea to condo and strata communities.

Property and community information already exists. It's just buried in bylaws, PDFs, email threads, and someone's memory. When a resident needs an answer, someone on the management team has to stop what they're doing, dig it up, and send it along — over and over, across every building they manage.

Howskey fixes that. We turn a community's own documents into a 24/7 AI Concierge that answers resident questions instantly on WhatsApp, delivers approved documents automatically, and knows when to hand things off to a human. Property managers get their time back. Residents get faster answers. Everybody wins. Learn more at howskey.com/hub

Role Description

We are looking for a high-performing revenue leader and hands-on builder to serve as our Head of Sales. In this role, you will take Howskey from founder-led sales to a repeatable, scalable B2B sales engine targeting property management companies, strata management firms, and residential developer portfolios.

This is a hunter-meets-architect role designed to establish our enterprise go-to-market strategy, own the full sales cycle from cold outreach to multi-building contract execution, and lay the foundation for a world-class sales organization as we expand.

What You'll Do

- Design and execute Howskey’s GTM sales strategy, outbound cadence, and deal structures for property management companies.
- Run targeted outbound campaigns and qualify inbound leads, securing pilot programs and enterprise-wide rollouts.
- Prospect, pitch, deliver compelling product demonstrations, and close multi-property portfolio deals with executives at residential property management companies.




- Collaborate with Product team to feedback market requirements, competitive intelligence, and customer objections to sharpen product-market fit.
- Lead terms negotiations, RFP responses, and contract execution, ensuring seamless handoffs to Customer Success.
- Own pipeline forecasting, quota tracking, and CRM management, defining key metrics (CAC, contract value, conversion rates) to prepare the org for team expansion.
- Represent Howskey at industry conferences, real estate tech expos, and local property management association events to position Howskey as the category leader.

Qualifications

- 5+ years of B2B SaaS sales experience with a proven track record of consistently exceeding quota selling to mid-market or enterprise accounts.
- Experience selling software into Property Management Companies, Real Estate Tech (PropTech), Condo/Strata/HOA management companies.
- Track record scaling revenue in an early-stage startup workplace, comfortable building outbound strategies from scratch.
- Skilled at navigating complex multi-stakeholder deals, pitching to executives, property managers, and council boards alike.
- Deep understanding of ROI-based selling, capable of mapping operational pain points (e.g., ticket volume, admin overhead) to quantifiable financial savings.
- Proficiency with modern sales stacks (HubSpot/Salesforce, Outreach, Apollo, LinkedIn Sales Navigator) and metrics-driven pipeline management.
- Exceptional negotiation, written, and verbal communication skills; comfortable presenting to C-suite leadership and operational teams.
- Highly autonomous, self-directed, and adaptable to fast-moving product updates and market shifts.

Why Join Howskey

- Ground-floor opportunity at a startup solving a real, everyday problem for property managers and residents
- Direct mentorship and access to founders — your work will directly shape how we go to market
- Room to grow into a closing or team-lead role as the company scales
- Remote-friendly, flexible work environment

📌 Head of Sales (Vancouver)
🏢 howskey
📍 Vancouver