--- title: 'Strategic Fixer at Clipboard' canonical: 'https://feeny.ai/job/strategic-fixer-clipboard-canada-bdjf8cnrzmdf' type: 'job' last_seen: '2026-11-04' --- # Strategic Fixer at Clipboard - **Company:** Clipboard - **Location:** Canada - **Employment:** full-time - **Work type:** remote - **Posted:** 2026-10-26 - **Last confirmed live:** 2026-11-04 - **Apply:** https://jobs.ashbyhq.com/clipboard/e8de21a4-e6e0-42a6-9b8b-21547feadc3c ## 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](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 Our largest customers run complex operations, and when something isn’t working, the problem rarely sits neatly within one team. A customer may be implementing a new product, dealing with a complicated integration, or facing an operational issue with no obvious owner or solution. That’s where you come in! We’re looking for a Strategic Fixer who wants exposure to a wide range of problems and is ready to own outcomes. You will take ambiguous problems, structure them, dig into the details, align senior stakeholders, and drive execution across teams that don’t report to you. This isn’t a role where you make a recommendation and hand it off. One week you might be diagnosing a failing payroll integration, the next coordinating an engineering fix, and the next working with a customer’s VP of Operations to get an implementation back on track. The problems might vary, but your job stays the same: figure it out, get the right people moving, and own the problem until it’s solved. This role opens doors to a range of growth paths across Clipboard! ## What you'll do - Analyze operational data to spot trends and bottlenecks, and turn your findings into clear recommendations that guide business decisions. - Research and evaluate new tools, including AI, automation, and internal systems, and drive their adoption to make operations more effective. - Design processes, workflows, and operating procedures that improve efficiency, quality, and customer experience - Lead cross-functional projects and strategic initiatives from planning through execution, partnering with Operations, Product, Engineering, Customer Success, and other teams. ## What we're looking for - 2–6 years of experience in a problem-solving role, such as strategy or management consulting, operations, strategy & operations, implementation, customer strategy, or program management. - Experience solving operational problems by improving processes, designing workflows, or building scalable systems, while juggling multiple priorities in ambiguous, fast-moving environments. - Strong analytical skills, with comfort using data (e.g., SQL, Python) to diagnose problems and support decisions. - Clear written and verbal communication, with the ability to explain complex problems simply and align stakeholders across teams, from frontline operators to senior leaders. - A high level of ownership. You don’t stop at the recommendation; you stay with the problem until it’s solved. - A deep curiosity that drives you to reason from first principles and dig until you find the root cause. - A habit of going to the source: testing the feature, listening to the agent call, calling the customer, or running the workflow. Why Join Clipboard? - We are remote-first, giving you the flexibility to work with us from many places. - Fast-paced startup environment. Join a company that values curiosity, independence, and growth. - A hiring process that rewards skills, not just experience. Every applicant gets a fair shot, our selection is based on real-world problem-solving ability, not just credentials. - Opportunity to make a significant impact with our customers on both sides of the marketplace. The Interview Process At Clipboard, we don't believe proxies are a reliable way to measure ability. We prefer to evaluate candidates by having them do work that closely resembles the actual job. We are hiring for several teams through this one posting, so the process also helps us find the team where you’ll fit best. Here is how it works: - Application Review - Case Study - Case Study Interview - Hiring Manager Interview (s) - Offer! 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). ## About Clipboard ## Company Overview - **One-liner**: Clipboard is a remote-first labor marketplace that connects healthcare and dental professionals with workplaces needing to fill shifts. - **Entity Type**: Private (Series C, backed by Sequoia Capital and Y-Combinator) - **Headquarters**: San Francisco, California, United States - **Founded**: 2016 - **Founders**: Wei Deng (Founder and Co-CEO) ## Core Business - **Primary industry**: Healthcare staffing / Labor marketplace / Internet marketplace platforms - **Target customers**: B2B (healthcare facilities, long-term care homes, hospitals, dental clinics, childcare centers) and B2C (healthcare workers, CNAs, nurses, hygienists) - **Mission statement**: "Uplift as many communities as possible" by connecting healthcare professionals with workplaces that need workers, helping people achieve financial stability while providing essential care. ## Products & Services - **Clipboard Marketplace**: An app-based platform where workplaces post open shifts and workers browse and claim them. Covers shift posting, scheduling, worker matching, documentation, and payment. Features include call-off coverage (automatic replacement if a worker cancels), Instant Pay, and worker vetting. - **Built For** (Industry Verticals): Long-Term Care, Hospitals, Home Health & Hospice, Dental Care, Childcare. ## Market Standing - **Valuation**: $1.3 Billion (latest reported valuation) - **Key Metric**: Profitable since 2022 (with heavy reinvestment in growth). Total funding raised: $94.1 million. - **Notable Investors/Partners**: Sequoia Capital, IVP, Y-Combinator. - **Growth Signals**: - Over 9 million shifts covered across healthcare industries. - Serves over 6,500 workplaces and 1 million workers across the U.S. - 6,500 communities served. - 125,000 workers have earned over $1,000 on the platform. - 95% of shifts get staffed when posted a day in advance; 85% are filled by a professional the workplace has worked with before. - Rapidly expanding into Home Health, Hospitals, and other verticals beyond their leadership position in Long-Term Care. - Headcount of 3,606 employees with 2.7% monthly growth and a 34% monthly increase in job postings. ## Competitive Advantages - **Market Leadership**: Dominant player in Long-Term Care staffing in the U.S. - **High Fill Rate & Retention**: 95% fill rate for shifts posted a day in advance and 85% of shifts filled by known workers create a strong network effect and reliability for facilities. - **Profitable Business Model**: Profitable since 2022, indicating a sustainable unit economy while still reinvesting heavily in growth. - **Full Vertical Integration**: Handles the entire workflow from posting and scheduling to payment and compliance, reducing administrative burden for facilities. - **Founder-Market Fit**: Founder Wei Deng got her own CNA certification to deeply understand the customer experience, fostering a culture of extreme customer empathy. ## Strategic Focus - **Vertical Expansion**: Moving beyond its stronghold in Long-Term Care into adjacent high-need verticals like Hospitals, Home Health & Hospice, Dental Care, and Childcare. - **Product & Automation**: Investing in automation to reduce friction for both facilities and workers (e.g., automatic call-off coverage, streamlined scheduling). - **Geographic Growth**: Expanding its network of workers and facilities across more communities in the U.S. - **Talent Acquisition**: Aggressively hiring across engineering, sales, and operations to fuel growth (63 active job postings). ## Why Work Here - **Culture**: Described as "remote first, high trust, and written." The team thrives on autonomy, makes decisions in live documents, and moves fast. Values include "Customer-First Mindset," "Extreme Ownership," "Increasingly High Standards," "Humility," and "Think from First Principles." - **Work Model**: Remote-first with physical offices in Los Angeles, New York City, San Francisco, and Seattle. - **Impact**: Employees directly contribute to solving critical staffing shortages in healthcare, helping workers achieve financial stability and ensuring patients receive care. - **Financial Health**: Profitable and growing, backed by top-tier investors (Sequoia, YC), providing job stability. - **Growth Opportunities**: Rapidly scaling company (3,600+ employees, growing) with a wide range of open roles across the organization. ## Sources 1. [clipboardworks.com](https://www.clipboardworks.com/careers) 2. [clipboardworks.com](https://www.clipboardworks.com/about) 3. [clipboardworks.com](https://www.clipboardworks.com/) 4. [linkedin.com](https://www.linkedin.com/company/clipboard) ## Other roles at Clipboard - [Client Support Specialist (Workplaces - B2B)](https://feeny.ai/job/client-support-specialist-workplaces-b2b-clipboard-central-south-58gemv0wkcqn) — Central & South, United States - [Growth Event Coordinator](https://feeny.ai/job/growth-event-coordinator-clipboard-united-states-qd5pht7ygd90) — United States - [Office and Events Manager](https://feeny.ai/job/office-and-events-manager-clipboard-san-francisco-8h9j6akhm22e) — San Francisco, CA - [Strategic Fixer](https://feeny.ai/job/strategic-fixer-clipboard-united-states-fq9rm191j3x0) — United States - [Technical Support Engineer](https://feeny.ai/job/technical-support-engineer-clipboard-non-u-s-htxjnbsep3v8) — Non-U.S. - [Account Manager](https://feeny.ai/job/account-manager-clipboard-canada-sgkvrfnase16) — Canada - [Field Marketer](https://feeny.ai/job/field-marketer-clipboard-united-states-189n129nqx6a) — United States - [T&S Investigator](https://feeny.ai/job/t-s-investigator-clipboard-canada-qfn6abjq4p3h) — Canada - [T&S Investigator](https://feeny.ai/job/t-s-investigator-clipboard-united-states-ed5s0a01ahac) — United States - [Strategic WFM Analyst](https://feeny.ai/job/strategic-wfm-analyst-clipboard-canada-united-kingdom-europe-wpyh8g58d8x0) — Canada / United Kingdom / Europe