Head of Operations, Trilogy

3 weeks ago

Canada Crossover Full time

Head of Operations, Trilogy (Remote) Salary: $200,000/year USD (hourly $100). Role at Crossover. Base Pay Range $100.00/hr – $100.00/hr What You Will Be Doing Drive high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions. Architect and deploy automations to replace CRM and task management platforms using Python and LLM APIs. Implement AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and compress cycle times. Own initiatives end-to-end—from initial diagnosis through final deployment—applying proven playbooks and executive judgment. Complete a technical challenge that requires you to design and build AI-first solutions hands-on. What You Won’t Be Doing Build or manage large teams or depend on organizational layers to execute. Participate in prolonged alignment meetings or wait for consensus before taking action. Hand off difficult work to IT departments or third-party vendors—you design and execute the solution directly. Operate in steady-state mode—this role centers on transformation and speed. Key Responsibilities Architect and implement AI-first operational systems that remove manual work, reduce complexity, and enable scalable execution across Trilogy’s global portfolio of software products. Basic Requirements Located in North America (excluding California), South/Central, or Western Europe (UTC -8 to UTC +2). 5+ years leading operations in enterprise software environments. 3+ years in customer-facing functions (Support, Sales, Collections, etc.). Proven capability to develop automation using Python and integrate with LLM APIs. Experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable tools. Track record of moving quickly, thinking independently, and delivering high-impact outcomes without supervision. Nice-to-have Requirements Background leading large-scale organizational changes including M&A integrations or mass offboarding initiatives. Track record designing and launching AI-powered operational systems. Collection of automations you have personally developed and deployed at scale. About Trilogy Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: relentlessly seeking top talent, innovating new technology, and incubating new businesses. Working with Us This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Job Details Seniority level: Director Employment type: Full-time Job function: Management, Engineering, and Strategy/Planning Industry: Software Development, IT Services and IT Consulting, Technology, Information and Internet #J-18808-Ljbffr

  • Head of Operations, Trilogy

    4 weeks ago

    , , Canada Crossover Full time

    Head of Operations, Trilogy (Remote) - $200,000/year USD Join us for the Head of Operations, Trilogy (Remote) - $200,000/year USD role at Crossover. 1 day ago – Be among the first 25 applicants. This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range...

  • Head of Operations, Trilogy

    2 weeks ago

    , , Canada Crossover Full time

    Head of Operations, Trilogy (Remote) - $200,000/year USD Join to apply for the Head of Operations, Trilogy (Remote) - $200,000/year USD role at Crossover This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range $100.00/hr - $100.00/hr This position is designed...

  • Senior Software Engineer, Trilogy

    3 weeks ago

    , , Canada Crossover Full time

    Senior Software Engineer, Trilogy (Remote) - $100,000/year USD Join to apply for the Senior Software Engineer, Trilogy (Remote) role at Crossover. Base pay range $50.00/hr – $50.00/hr Software delivery remains trapped in outdated practices. Backlogs expand endlessly, cycle times stretch into weeks, and "code review" often devolves into perfunctory approval...

  • Head of Risk

    4 weeks ago

    , , Canada Bitfinex Full time

    Join to apply for the Head of Risk - Remote role at Bitfinex 2 days ago Be among the first 25 applicants Join to apply for the Head of Risk - Remote role at Bitfinex The Original Bitcoin ExchangeInspired by Bitcoin's vision of financial freedom, we are committed to empowering individuals to transact and connect seamlessly across the globe. From the early...

  • Head of Operations

    2 weeks ago

    , , Canada CityZeen Full time

    Company Description CityZeen is a pioneer in promoting sustainability through investment in regenerative projects worldwide. Our platform enables individuals to invest in top-tier sustainable initiatives traditionally accessible only to high-net-worth individuals. By providing innovative opportunities, we aim to create positive environmental and social...

  • Chief Financial Officer

    4 weeks ago

    , , Canada Stereotech Inc. Full time

    1 week ago Be among the first 25 applicants Get AI-powered advice on this job and more exclusive features. Stereotech Inc. is a fast-growing Canadian tech company revolutionizing smart living through innovative, energy-efficient smart home products. We also offer a seamless e-commerce experience for a wide range of electronics and tech solutions. By...

  • Operations Head

    1 day ago

    Canada, Singapore, United Kingdom VHR Professional Services Full time

    Operations Head - Electronic Components Lead electronic component manufacturing operations, ensuring efficiency, quality, and cost-effectiveness. Key skills: Lean manufacturing, Supply chain management, Production planning, Quality control.

  • Head of Operations

    4 days ago

    Toronto, Ontario, MAM, Canada Trindent Consulting Full time

    Head of Operations - office based 5 days a weekTrindent Consulting is a global management consulting firm that specializes in technical augmentation in the energy sector, specifically downstream Oil & Gas. We've helped over 100 clients in the United States & Canada achieve significant financial benefits that yield between % return-on-investment within the...

  • AI-Driven Head of Operations

    2 weeks ago

    , , Canada Crossover Full time

    A leading software firm is looking for a Remote Head of Operations to architect AI-first operational frameworks and drive complex change initiatives. With responsibilities including automation development and organization-wide transformations, candidates should possess strong operational leadership experience in enterprise environments. The compensation is...

  • Head of AI-Driven Operations

    3 weeks ago

    , , Canada Crossover Full time

    A leading tech firm is seeking a Head of Operations to lead AI-first operational transformations in the company. The ideal candidate will have over 5 years of experience in operations within enterprise software environments and a strong background in automation using Python and LLM APIs. This full-time role offers a salary of $200,000 per year with a focus...