Clipboard

Strategy & Ops Lead, Applied AI

Canada full-time Mid Salary not listed
full-time Mid level Technology & IT Curated
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About the role

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.

Overview

We are hiring an Applied AI Strategy & Ops Lead to own and evolve our internal tooling ecosystem across Ops. This is a hands-on individual contributor role with real ownership. 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 sit at the intersection of Operations and Engineering, acting as the technical voice of Ops and 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

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

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

Partner with engineers and developers to scope requirements, write technical specs, and prioritize tooling work that matters most to Ops.

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 and debug independently and hold your own in technical conversations with engineers.

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

Interview with Head of Core Services

Interview with Head of Operations

Final Culture Interview with Executive Leadership

Quick Note on Scammers:

Clipboard would never ask you for money or your bank details to participate in our hiring process. Report any scammers impersonating the Clipboard hiring team members here.

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Mid
Technology & IT Operations Remote Collaboration Strategy Ops Applied Mid level

Likely questions

  1. Tell us about work you have done that is close to the Strategy & Ops Lead, Applied AI role.
  2. How would you approach your first 30 days at Clipboard?
  3. Which of Operations, Remote Collaboration and Strategy have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Operations, Remote Collaboration and Strategy.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Strategy & Ops Lead, Applied AI role because I can bring practical experience in Operations, Remote Collaboration and Strategy, learn the team quickly, and contribute to the outcomes Clipboard needs from this hire.

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