Cathy Ferrell

Chief of Staff | Strategic Operator. Trusted #2 | Systems Thinker | Strategic Translator

Greater Toronto Area, Canada

About

I’m the person leaders rely on to bring clarity, alignment, and calm momentum. I operate in the layer between strategy and execution, translating vision into practical next steps, clearing friction, and making sure the system moves in one coordinated direction. Across Zapier and Wave, my roles carried Chief of Staff scope without the formal title. My work lives in patterns, context, and connective tissue, helping executives move from noise to signal so they can focus on what matters most. I’m well equipped to: • Provide steady, proactive support to executives, anticipating needs while surfacing insights and keeping information moving. • Build and maintain the company operating system, including planning cadences, prioritization, and execution rhythms that keep teams coordinated and effective. • Translate vision into actionable plans, OKRs, and roadmaps, keeping teams aligned as priorities evolve. • Align product, design, and engineering on a shared operating model, ensuring what we commit to build is what gets delivered. • Bring clarity through data, AI-informed strategy, and structured decision making. • Create top-to-bottom alignment connecting company goals to day-to-day execution and giving teams the clarity they need to make smart trade-offs and know what comes next. • Cultivate and maintain strong relationships that open new channels of opportunity and collaboration across your company. • Build with intention, using best practices as a starting point and shaping them to fit the company’s context, goals, and stage. • Apply financial fluency to connect operational decisions with budgets, revenue goals, and long-term performance. I’m at my best as a strong number two who makes complexity simple and keeps the whole system pointed in the right direction. Following the elimination of my role during Wave's integration with H&R Block, I'm looking for Chief of Staff and strategic operations roles where I can build durable operating systems, partner closely with senior leadership, and have a long-term mandate to create impact.

Experience

  • Founder at Feral Travel
    Feb 2025 - Present · 1 yr 6 mos

    Founded a curated travel intelligence hub as an independent side venture. I applied intelligence analysis and operating-model design principles to solve information overload in modern travel planning. Built the product to be low-maintenance and useful, with the goal of creating a sustainable, passive income stream alongside long-term leadership work. * Designed the product around a simple promise: reduce search fatigue and give travelers a clear starting point with vetted, reliable content. * Built the underlying systems for content structure, quality standards, and updates, keeping the product lightweight to maintain and easy for users to navigate. * Drew on personal travel experience and user feedback to make decisions about what information mattered most and how to present it clearly. * Created a digital product model that can grow over time without requiring constant upkeep, allowing me to maintain focus on full-time strategic roles.

  • Technology Operations, Office of the CTO at Wave HQ
    Sep 2025 - Jun 2026 · 10 mos

    Member of the Senior Leadership Team Wave Financial (Acquired by H&R Block) Joined as the CTO’s strategic partner and stepped into a broader operating role as Wave entered its integration into H&R Block. Maintained operational continuity and leadership effectiveness through an extended period of ambiguity and organizational change. * Served as the primary interface between engineering leadership and integration stakeholders, representing the technology organization in Wave’s integration with H&R Block. * Partnered directly with the CTO to surface insights, simplify complex issues, and frame recommendations that moved critical decisions forward. * Designed the framework for technology-wide planning on behalf of the CTO, rationalizing the initiative backlog and defining capacity constraints (KTLO vs. investment) to guide leadership prioritization and investment decisions. * Drove alignment across VP and Director-level leadership by structuring planning cycles and leadership forums, establishing a consistent operating cadence as priorities shifted. * Led financial planning and synergy tracking for the technology organization, partnering with Finance on forecasts, budget performance, actuals, and executive reporting while driving technology OKRs.

  • Integrated Strategy and Operations Lead (CoS-Level Function) at Zapier
    Jun 2023 - Nov 2024 · 1 yr 6 mos

    Recognized for delivering strategic impact by expanding the GTM AI program, aligning technical operations, and supporting executive decision-making. Partnered with senior leadership to translate vision into actionable strategy, improve cross-functional coordination, and strengthen operational clarity at scale. • Developed an OKR-based strategic roadmap that addressed org-wide prioritization challenges and helped teams focus. • Identified and resolved systemic pain points in Zapier’s 'default to action' culture, creating lightweight guardrails that protected agility while restoring clarity. • Improved cross-functional alignment by dissolving friction between customer-facing and business teams, creating a more coherent strategy-to-execution ecosystem. • Expanded AI strategy beyond technical implementation to cover UX, change management, and operational readiness, resulting in improved adoption and stronger business outcomes. • Tackled long-standing operational issues overlooked during scale, making it easier for leaders to identify tradeoffs, unblock execution, and design longer-term models. • Supported leaders through major platform transitions (Intercom → Zendesk + Ada), improving cross-functional coordination, on-time delivery, and customer experience.

  • Business Operations & Strategy Consultant at Freelance
    Nov 2017 - May 2023 · 5 yrs 7 mos

    I began consulting after meeting founders and small teams who needed help making sense of growing complexity and turning ideas into clear plans. As my consulting work took hold, I partnered with early-stage and scaling companies to build simple systems, manage work more reliably, and make better decisions as they grew. Selected Engagements: Reason One (Delivery & PMO Strategy) Partnered with the COO after a merger to untangle delivery issues and rebuild operations. Simplified how work moved through the organization, set up clearer processes, and helped teams deliver more reliably while improving client experience. Versafile (Quality & Internal Operations) Worked directly with the CEO to improve service delivery and internal operations. Introduced lightweight automation for reporting, supported EOS and OKR adoption, and improved visibility into the business, leading to better resource use and improved client satisfaction. Frey Labs (Delivery Operations) Partnered with the founder to turn a small design practice into a more scalable design-and-build studio. Set up the operating structure, managed client work, and created the foundational systems the team needed as capabilities expanded.

  • Cofounder | Chief Operating Officer at Yarn
    Nov 2017 - Sep 2018 · 11 mos

    Joined a four-person founding team to build and launch a travel app from concept to App Store release. Established the company's operating foundation across planning, finance, product operations, vendor coordination, and delivery while partnering closely with engineering, design, and go-to-market. • Built the company's initial operating systems across finance, operations, vendor management, and customer support. • Coordinated cross-functional execution across product, engineering, design, and go-to-market to take the product from idea to launch. • Managed day-to-day business operations while supporting product planning, technical support, and launch readiness. • Earned honourable mention in the November 2017 Product Hunt Global Hackathon https://www.producthunt.com/posts/yarn-7 • Launched the product on the App Store and transitioned the business to a new ownership structure.