Head of Data – Remote (USA)

 

MaltingsRetreat

Head of Data – Remote (USA)

last updated March 18, 2026 5:18 UTC

HappyCo

HappyCo

 

HQ: Hybrid

 

OFF: Remote (USA)

Full-Time

Sales and Marketing

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HappyCo is a company where people can grow their careers and work with like minded people, with no egos or politics. HappyCo is values driven and offers a flexible, supportive culture. Join HappyCo and Make Work Happy !

About HappyCo

HappyCo builds modern property management software that helps owners and operators deliver better living experiences at scale. As we continue to evolve our platform, we are entering a period of significant architectural transformation—modernizing legacy systems while expanding into AI-orchestrated, event-driven workflows that will define the next generation of our product.

The Role

The Head of Data will lead the development of HappyCo’s data strategy and infrastructure, with a primary focus on unifying fragmented operational data into a canonical entity model and property graph that powers analytics, benchmarking insights, and AI-enabled product features.

 

This role is both strategic and hands-on. As the company’s most senior data leader, the Head of Data will design the architecture for HappyCo’s data platform while also contributing directly to data modeling, analytics, and machine learning initiatives.

 

Working closely with Product and Engineering, this role will translate product ideas and business questions into reliable data systems that generate meaningful insights and enable intelligent product capabilities.

 

Responsibilities

Data Strategy & Leadership

● Define and execute HappyCo’s overall data strategy aligned with company and product goals

● Establish the roadmap for analytics, machine learning, and data platform evolution

● Collaborate with Product and Engineering leadership to identify high-value opportunities for data-driven insights and AI features

● Build and mentor a small data team including data engineers and analysts

 

Data Unification & Canonical Data Model

● Design and implement a canonical entity model that connects data across operational systems

● Lead the development of HappyCo’s property graph / knowledge layer, linking entities such as businesses, properties, units, inspections, work orders, and maintenance performance

● Develop entity resolution approaches using deterministic rules, fuzzy matching, geospatial matching, and machine learning where appropriate

● Ensure that canonical entities are reliable and usable across analytics, reporting, and product systems

 

Data Platform & Architecture

● Oversee the architecture and evolution of HappyCo’s data platform, including the data warehouse, pipelines, and transformation layers

● Guide development of scalable data ingestion and transformation pipelines using tools such as BigQuery, Databricks,

 

Dataflow, and Pub/Sub

● Establish best practices for data quality, lineage, and governance

● Ensure data infrastructure supports both analytical workloads and product-facing APIs

 

Analytics & Insights

● Enable internal teams with reliable analytics and insights derived from unified data

● Move the organization beyond dashboards toward insight generation and recommendations

● Develop benchmark metrics and analytical models that help customers understand performance and opportunities for improvement

● Support the creation of self-service analytics capabilities across the company

 

Machine Learning & AI Enablement

● Prototype and implement predictive models that leverage unified data sets

● Prepare datasets and feature pipelines for machine learning workflows

● Enable AI product capabilities including agentic workflows and data-driven recommendations

● Ensure the company’s data architecture supports retrieval systems and LLM-powered applications

 

Hands-On Technical Execution

● Contribute directly to data modeling, analytics, and ML development

● Work closely with the Data Engineer to implement pipelines and transformations

● Prototype analytical models and AI-enabled features in collaboration with Product

 

What we’re looking for

Required Experience

● 8+ years of experience working in data science, data engineering, or analytics roles

● Experience designing data architectures and data models for complex operational systems

● Strong experience working with data warehouses and distributed data processing systems

● Hands-on experience building analytical models or machine learning systems

● Demonstrated ability to translate business questions into data-driven solutions

● Experience working cross-functionally with product and engineering teams

Technical Skills

● Strong proficiency in SQL and Python

● Experience with modern data platforms (e.g., BigQuery, Snowflake, Databricks)

● Experience building data pipelines and transformation workflows

● Familiarity with machine learning workflows and model deployment

● Experience with entity resolution, data modeling, or knowledge graph concepts is highly desirable

Leadership Qualities

● Ability to operate effectively as both a strategic leader and hands-on contributor

● Strong communication skills with both technical and non-technical stakeholders

● Experience mentoring and developing data professionals

● Comfort working in a fast-moving startup environment

Why HappyCo

A rare opportunity to shape the technical foundation of a growing SaaS platform during a major architectural transition.

High-impact role with visibility and influence across engineering and product leadership.

Collaborative engineering culture that values clarity, pragmatism, and continuous learning.

Competitive compensation, benefits, and flexible work arrangements.

Success Criteria

First 3 Months

● Develop a clear data strategy and roadmap aligned with product and engineering priorities

● Begin implementation of the canonical entity model and property graph

● Establish reliable mappings across key operational systems

● Identify high-impact analytical opportunities using unified data

First 9 Months

● Deliver the foundational property graph / canonical entity layer

● Enable internal teams with improved analytics and benchmark insights

● Implement initial predictive models or AI-driven features using unified data

● Reduce ad hoc data requests through improved data models and analytics capabilities

Long Term

● Establish HappyCo’s unified data platform as the foundation for product insights and AI capabilities

● Build a high-performing data team including engineers and analysts

● Enable AI-powered workflows and customer-facing insights driven by proprietary data

About HappyCo

Founded in 2011, HappyCo ( https://happy.co) builds mobile and cloud solutions to enable real-time property data. Our flagship product suite ‘Happy Property’ has more than 5 million units on its platform.

We’re everyday people with a shared purpose — improving the lives of others. Our team is made up of thinkers, talkers, planners, makers, builders and everything in between. Together, we’re turning our passions into happier communities!

When customers use our software, their communities get stronger. Our tools empower everyone in multifamily property management to improve their operations and maximize returns, which means they’re building better experiences for their residents. Learn more about our Product Vision here!

Our HappyCo Culture

HappyCo strives to build better communities. So naturally, we are dedicated to making our own community an enjoyable place that allows us do our best work. We’re devoted to building an inclusive, supportive culture that empowers each HappyCo’er to succeed and grow. To learn more about our culture, check out our careers page!

We Offer:

– Work from anywhere supported by a flexible company culture

– Opportunity to work for one of the fastest growing technology companies in the PropTech industry

– Unlimited vacation time

– Generous paid parental leave

– Competitive and equitable pay, including stock options

– Monthly stipends to support Wellness and Home Office expenses