Head of Strata Solutions & AI Automation

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.
Strong 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