[All remote jobs](https://jobicy.com/jobs.md)[![Clipboard logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2026/11/cbfb643f01fb-221.webp)](https://jobicy.com/company/clipboard.md)[Clipboard](https://jobicy.com/company/clipboard.md) # Strategy & Ops Lead, Applied AI AI Summary Clipboard is seeking an individual contributor to lead operational tooling strategy and execution for applied AI initiatives. The role owns workflows, integrations, automations, and reliability improvements across support and operations systems. This person will translate operational needs into technical specifications and partner closely with engineering and operations leadership. Success requires strong API and automation fluency, practical troubleshooting ability, and systems thinking across a scaling tool ecosystem. Experience with Zendesk, AI-enabled tools, and CX or support environments is beneficial.[Apply for this job](#job-application)[View company](https://jobicy.com/company/clipboard.md)ShareRemote from[Canada](https://jobicy.com/job-region/canada.md), [Europe](https://jobicy.com/job-region/europe.md)SalaryUSD 120k–140k / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceDirectorPublished9 Nov 2026Apply before9 Dec 2026Listing views54Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. ### About [Clipboard](https://jobicy.com/company/clipboard.md) 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](https://www.ycombinator.com/topcompanies/) 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](https://forms.gle/SyGaxHFbon7Hg9fW6). Show more [Apply now >](https://jobicy.com/jobs/160213-strategy-ops-lead-applied-ai.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 4/5IndependentCollaborative AI insightThe role combines technical implementation, operational strategy, and cross-functional prioritization across multiple interconnected systems. It requires independent execution while translating ambiguous operational problems into reliable technical solutions. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$130,000US market range (per year)$115k–$155k0$170.50k AI insightThe employer discloses a base salary range of $120,000–$140,000 USD per year through ATS compensation data. The estimated market range for a senior applied AI operations and tooling lead is $115,000–$155,000 USD per year; this is an AI estimate rather than verified salary research. ## Core skills Skills and capabilities most closely associated with this opportunity. [Operational strategy](https://jobicy.com/jobs?search_keywords=Operational%20strategy.md)[Applied AI](https://jobicy.com/jobs?search_keywords=Applied%20AI.md)[Workflow automation](https://jobicy.com/jobs?search_keywords=Workflow%20automation.md)[API integrations](https://jobicy.com/jobs?search_keywords=API%20integrations.md)[Technical specifications](https://jobicy.com/jobs?search_keywords=Technical%20specifications.md)[Systems thinking](https://jobicy.com/jobs?search_keywords=Systems%20thinking.md)[Process improvement](https://jobicy.com/jobs?search_keywords=Process%20improvement.md)[Tooling strategy](https://jobicy.com/jobs?search_keywords=Tooling%20strategy.md)[Production troubleshooting](https://jobicy.com/jobs?search_keywords=Production%20troubleshooting.md)[System reliability](https://jobicy.com/jobs?search_keywords=System%20reliability.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Zendesk](https://jobicy.com/jobs?search_keywords=Zendesk.md)[Support operations](https://jobicy.com/jobs?search_keywords=Support%20operations.md)[Requirements prioritization](https://jobicy.com/jobs?search_keywords=Requirements%20prioritization.md) Sample interview questionsHow would you approach improving an operations workflow that involves several disconnected tools?I would first map the current process, users, handoffs, data sources, failure points, and measurable outcomes. I would prioritize the highest-impact bottleneck, define a lightweight technical specification, validate integration options, and implement the solution with monitoring and a clear rollback path. Describe how you translate an operational problem into a technical requirement for engineering partners. I frame the business problem, affected users, desired outcome, constraints, and success metrics before proposing a solution. I document data inputs and outputs, workflow logic, edge cases, dependencies, and priority so engineers can estimate and build with minimal ambiguity. What would you monitor after launching an AI-driven support automation? I would monitor adoption, automation completion rate, escalation rate, error patterns, response quality, latency, and downstream operational impact. I would also establish regular human review for high-risk cases and iterate based on user feedback and performance data. How do you prioritize multiple tooling requests from different operations teams? I assess requests by customer and business impact, urgency, operational effort saved, risk reduction, technical complexity, and dependencies. I make trade-offs transparent, align priorities with leadership objectives, and communicate expected sequencing and rationale to stakeholders. How would you troubleshoot an unreliable integration between a support platform and an internal system? I would reproduce the issue, inspect logs and payloads, verify authentication and rate limits, compare expected and actual data mappings, and isolate whether the failure is upstream, downstream, or in the automation layer. After fixing the immediate defect, I would add alerts, retries where appropriate, and documentation to reduce recurrence. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. 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