Strategy & Ops Associate, Applied AI

Clipboard; Canada; Hybrid; CAD 90,000 - 120,000; Full time

Job summary

Clipboard is a remote-first company building a healthcare worker marketplace. We are hiring an Applied AI Strategy & Ops Associate to strengthen our internal tooling ecosystem across Operations.

You will work hands-on across support platforms, AI-driven systems, and internal automations to improve day-to-day operations. You will partner with leadership to execute priorities, refine systems, and introduce tooling to scale with the business, ensuring reliable production performance across the

Qualifications

• Strong technical fluency with APIs, integrations and automation tooling.
• Ability to translate defined problems into practical technical solutions.
• Ability to manage multiple priorities with quality and reliability.
• Comfort working across platforms without heavy oversight.

Responsibilities

• Execute high-priority tooling and automation initiatives across the operational stack.
• Build and iterate workflows, integrations, and automations to improve efficiency.
• Support and improve systems across tools, including support platforms and AI-driven solutions.
• Translate defined problems into practical, well-scoped technical solutions.
• Identify gaps or inefficiencies in current tooling and proactively address them.
• Troubleshoot issues, improve reliability, and ensure tools perform in production.
• Contribute to ongoing improvements in how systems connect and operate together.

Skills

Technical fluency

Execution discipline

Systems thinking

Problem solving

Ownership mindset

Tools

Zendesk

AI tools

Job description

About Clipboard

Our mission is to uplift as many communities as possible. We do this through our app-based marketplace that connects healthcare professionals with the workplaces that need amazing workers. This enables hundreds of thousands of people to achieve financial stability for themselves and their families while providing essential care to millions of people across the U.S.

Founded in 2016, we are a remote-first team of over 1,000 people building a top Y-Combinator company and have been profitable since 2022. We’re the leader in Long-Term Care staffing and are rapidly expanding into Home Health, Hospitals, and more, meaning we have more work to do than people to do it, and are growing our team to support millions more people and their communities.

Role Overview

We are hiring an Applied AI Strategy & Ops Associate to support and evolve our internal tooling ecosystem across Ops.

This is a hands-on individual contributor role focused on strengthening the foundation of our operational stack. You’ll work across a range of tools including support platforms, AI-driven systems, and internal automations to improve how our day-to-day operations function.

You’ll partner closely with team leadership to execute against defined priorities, refine existing systems, and introduce new tooling where needed ensuring our stack continues to scale effectively with the business.

What You’ll Do

• Execute against high-priority tooling and automation initiatives across the operational stack

• Build and iterate on workflows, integrations, and automations that improve day-to-day efficiency

• Support and improve systems across multiple tools, including support platforms and AI-driven solutions

• Translate defined problems into practical, well-scoped technical solutions

• Identify gaps or inefficiencies in current tooling and proactively address them

• Troubleshoot issues, improve system reliability, and ensure tools perform effectively in production

• Contribute to ongoing improvements in how our systems connect and operate together

What We’re Looking For

Technical Fluency - You’re comfortable working with APIs, integrations, and automation tooling. You can build, debug, and adapt across different systems without relying on heavy oversight.

Execution Discipline - You take defined problems and drive them through to completion. You manage multiple priorities effectively and maintain a high bar for quality and reliability.

Systems Thinking - You understand how tools, workflows, and dependencies connect. You look for ways to improve how systems operate together, not just individual components.

Problem Solving - You can take loosely defined or scoped problems and translate them into practical, well-structured solutions.

Ownership Mindset - You take responsibility for delivering high-quality work and improving the team’s day-to-day operations through better tooling and processes.

Nice to Have

• Experience working with support platforms such as Zendesk

• Familiarity with AI-driven tools and automation workflows

• Background in Ops, Support, or CX environments

• Experience working with evolving or fragmented tooling stacks

Hiring Process

• Application

• Case Study

• Case Interview with a team member

• Interview with Head of Core Services

• Interview with Head of Operations

• Final Culture Interview with Executive Leadership