Company Description

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 former strata manager or senior strata operations leader to serve as our Head of Strata Solutions & AI Automation. In this role, you will work at the intersection of product, operations, and customer success to map complex strata workflows, identify automation opportunities, and drive the adoption of AI-driven solutions across the strata & condo management sector.

This is a hybrid domain solution + product strategy role designed to ensure Howskey solves real strata pain points and is recognized as a strata-native platform.

What You'll Do

- Map end-to-end strata manager and council workflows across financial administration, meeting management, maintenance, and compliance domains.
- Partner with product management to quantify time, cost, and error rates for each workflow to build an ROI-backed automation backlog.
- Identify tasks suitable for AI automation and collaborate with Product and Engineering to translate workflows into AI-driven features (e.g., auto-drafted budgets, meeting packages, vendor RFQs).
- Recruit, onboard,



and lead pilot deployments with strata management firms and self-managed councils, configuring Howskey for their specific workflows.
- Define key success metrics (e.g., hours saved on AGM prep, faster invoice processing) and track operational outcomes.
- Gather structured feedback from pilots to continuously refine workflows, prompts, and system integrations.
- Represent Howskey across the strata community (webinars, panels, industry association meetings) and help shape market-aware messaging and case studies.
- Advise on strategic partnerships with strata management companies and related service providers.

Qualifications

- 5+ years of hands-on experience as a licensed Condo / Strata Manager or senior operations lead managing a portfolio of condo/strata corporations.
- Deep expertise organizing and chairing AGMs, SGMs, and council meetings, including preparing compliant meeting packages and minutes.
- Solid background coordinating maintenance, repairs, emergency responses, and managing contractor service agreements.
- Robust working knowledge advising councils on the Strata Property Act, budgets, bylaws, and related legislation.
- Proven track record of documenting SOPs, improving operational efficiency, or leading process/technology initiatives within a strata management firm.
- Experience evaluating, implementing, or working closely with software tools used in strata or property management.
- Strong communication and stakeholder management skills, with experience resolving conflicts and explaining complex compliance topics to councils, owners, and vendors.
- Excellent written and verbal communication skills with the ability to bridge technical and non-technical discussions.
- Ability to thrive in a fast-paced environment, bringing structure and clarity to complex operational workflows.

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 Strata Solutions & AI Automation (Metro Vancouver)
🏢 howskey
📍 Metro Vancouver