Senior Director, Revenue & Growth Operations

📍 Remote (Canada) │ Hybrid Available – Kitchener, ON 🧑💼 Reports to: Chief Marketing Officer (CMO)

Salary range: $180,000 - 200,000 (CAD)

🏢 About Encircle Encircle is leading the $1.6 trillion property insurance industry out of the dark ages of pen-and-paper processes, into the digital age of transparency and empowerment. Our easy-to-use software platform enables thousands of restoration contractors and insurance professionals around the world to process claims faster. We’re a remote-first company with a collaboration hub in downtown Kitchener—and we’re growing.

📌 About the Role We are looking for a strategic, hands-on operations leader to own Revenue & Growth Operations: the function that brings Revenue Operations and Business Systems together under one leader and aligns Sales, Marketing, Customer Experience, and Finance around predictable, scalable revenue growth. Reporting to the CMO and working as a member of the go-to-market leadership team, you will own the operating rhythm of the revenue engine: the planning, forecasting, process, data, and systems that let every commercial team perform at its best. Encircle is maturing this function to match the next stage of the business, and you will lead that evolution — building a proactive operations capability that runs ahead of the business rather than behind it. The mandate is concrete. Year 1 centers on four builds: a governed data foundation with a single trusted record for every customer account; an enterprise billing and metering capability that supports usage-based and hybrid pricing; a forecasting and commercial intelligence layer leadership can run the business on; and an AI-forward operating model where the commercial team works with AI as a first principle, building on tooling already deployed in the business. The ideal candidate toggles comfortably between strategic planning and hands-on systems work: equally at home designing an annual planning process, pressure-testing a forecast, and reading an integration map to find where it breaks.

🔧 What You’ll Be Doing

GTM strategy and planning

Lead the annual and quarterly GTM planning process: account segmentation, territory design, capacity and coverage modelling, and quota setting in partnership with revenue leadership and Finance. Provide the analytical foundation for compensation design: conversion benchmarks, capacity models, and the data that informs quotas, accelerators, and thresholds. Own target setting and tracking, and produce the quarterly business review materials leadership runs on. Lead our formula for success initiative alongside revenue leadership: defining the leading indicators, activity benchmarks, and milestones for every revenue role, so performance is coachable and measurable across the funnel.

Forecasting, analytics, and insights

Own the forecasting methodology and cadence: a live, data-driven forecast with stage conversion rates, pipeline velocity, and accuracy tracked week over week. Build and maintain the reporting infrastructure for the business: pipeline and funnel health, conversion by segment and source, retention and expansion metrics, and board-level commercial reporting. Establish attribution and ROI models that inform go-to-market strategy and investment decisions. Turn data into decisions: ensure leadership can answer what is converting, where the funnel is leaking, and where the capacity gaps are against plan.

Process and revenue lifecycle

Architect and continuously improve full-funnel processes across Marketing, Sales, and Customer Experience: lifecycle stages, handoff criteria, SLAs, and rules of engagement. Own quote-to-cash process governance, including deal structuring standards, approvals, and renewal and expansion process infrastructure. Identify and remove bottlenecks across the revenue engine, driving measurable improvements in conversion, velocity, and productivity.

Systems and data

Own the go-to-market technology stack end to end (Salesforce, Snowflake, Maxio, our customer success and marketing automation platforms, and the enrichment and intelligence tools around them): architecture, integrations, evaluation, and a formal rationalization so every tool earns its seat as we scale. Drive our data foundation program: a single trusted record for every customer account across CRM, customer success, our product, and warehouse, a governed Snowflake layer architecture, and the customer data platform decision that anchors it. This is the most consequential infrastructure work of Year 1, and it unlocks everything downstream. Oversee the build-out of Maxio into a true enterprise billing and metering system, with a product-to-billing usage data pipeline designed alongside Product and Engineering, and billing data flowing cleanly into commercial reporting. Build the operational backbone for product-led growth: product usage instrumentation, activation milestones, and expansion signals flowing into commercial workflows — a first-order growth motion for us, not a side project.

AI and automation

Own how our commercial organization approaches AI: where it gets applied, how adoption is driven, and how impact is measured. We have role-specific AI tooling already deployed to our commercial teams, and this role sets the standard for what gets built next and evolves it as the data foundation matures. Build toward signal intelligence: turning product usage, engagement, and account data into the right signal for the right person at the right time, so sellers and account managers act on insight rather than intuition. Drive automation across revenue processes so the team scales through capability, not just headcount.

Leadership

Lead, develop, and grow the Revenue & Growth Operations team across its pillars, building a culture of proactive ownership. Operate as a trusted partner to VP and C-level leaders across Sales, Customer Experience, Marketing, Finance, and Product, influencing strategy at the executive level. Communicate clearly what the function is working on, why, and what it is not, making deliberate trade-offs as the business scales.

✅ What You’ll Bring 15+ years in Revenue Operations, GTM Operations, or Commercial Operations in B2B SaaS, with 8+ years in a leadership role with direct reports and executive visibility. A proven track record of building or scaling a RevOps function in a growth-stage company: you have led the shift from reactive to proactive and can describe the before and after. Strong financial and analytical acumen: fluency in SaaS metrics (pipeline coverage, conversion, CAC, NRR, forecast accuracy) and experience translating data into executive decisions. Experience leading GTM planning: segmentation, territory design, capacity modelling, and compensation input alongside Finance. Deep knowledge of Salesforce and the broader GTM systems ecosystem, with the ability to work at an architecture level: schemas, data models, and integration patterns. Working familiarity with a modern data stack (Snowflake or equivalent) and with billing or subscription management platforms; experience with usage-based pricing models is a strong asset. Hands-on experience applying AI within a commercial or operations context, with informed opinions on where it creates real productivity and how to drive adoption. Exceptional communication and leadership skills: comfortable presenting to executives, influencing without authority, and building trust with technical and commercial teams alike. Experience in PE-backed or diligence-ready SaaS environments is a bonus.

🌟 Why This Role This is a build role with real scope. You will have executive sponsorship, a seat at the go-to-market leadership table, and the opportunity to design the function’s operating model rather than inherit one. The work will be visible: the planning, forecasting, data, and systems foundation you build becomes the platform Encircle scales on, and every commercial leader in the business will feel the difference as the function matures. And the timing is real: a newly restructured commercial organization, an expanding AI product suite, and a product-led growth motion all need this foundation now. If you want to build the commercial infrastructure of a scaling vertical SaaS company, and have the support and authority to do it properly, this is the role.

🤝 Why Encircle?

We VALUE our people

⚖️ Balance: Flexible hours, self-managed vacation, and trust to manage your time. 🏠 Remote-first: Work where you’re most productive—with access to our collaboration hub in Kitchener. 🚀 Growth-oriented: We support your learning and career development. 💪 Well-being: We care about the full human—inside and outside of work.

Encircle is an equal opportunity employer committed to building a diverse and inclusive team. We encourage all qualified candidates to apply and will work with applicants to accommodate accessibility needs throughout the hiring process.

A Note on Authenticity: We value genuine interest and authentic interaction. Please be aware that we reserve the right to disqualify candidates if it is determined that application materials or interview responses are excessively generated by AI tools or misrepresent your personal skills and experience.