Head of Revenue Operations

Mortgage Automator • Toronto, ON

7h • Hybrid

About The Position

This role is the strategic thought leader for Revenue Operations at Mortgage Automator. It goes beyond configuring HubSpot: the mandate is to proactively surface where the funnel is leaking, build the systems that make revenue predictable and repeatable, and bring a strong, data-backed point of view to how we grow. You'll build a consolidated view of the business, rooted in our history and tested against forward-looking hypotheses, and use it to align Sales, Customer Success, and Marketing around one version of the truth. You'll also be expected to use AI tools to push both the customer experience and the team's own productivity forward, not just automate what already exists. This is a builder's role. There's no fixed playbook. You'll set the frameworks, the operating rhythms, and the reporting cadence, and you'll be the person leadership and the board turn to for a clear read on where revenue is headed and why.

Requirements

• 4+ years leading a Revenue Operations, Sales Operations, or GTM Operations function in a B2B SaaS environment.
• A track record as a fluent builder: someone who has built forecasting models, funnel reporting, and operational processes from scratch, not just maintained someone else's system.
• Maniacal prioritization. You know how to protect your focus and your team's, even when every department wants a piece of you.
• Strong cross-functional stakeholder management across Sales, Marketing, Customer Success, and Finance.
• Experience presenting to and partnering with a board or executive leadership team on revenue performance and forecasting.
• Deep comfort with CRM systems (HubSpot preferred) and the data architecture behind them, but you think in systems and outcomes, not just fields and workflows.
• A genuinely opinionated approach to data: you don't just report what happened, you tell people what it means and what to do about it.

Nice To Haves

• You think about how the whole funnel connects, not just the piece in front of you.
• You bring a point of view and defend it, but you update it when the data changes your mind.
• You're comfortable being the person who tells Sales, Marketing, or CS leadership something they don't want to hear, backed by data.
• You build for scale, not just for the next fire.
• You use AI as a first instinct, not an afterthought.

Responsibilities

• Own the Funnel; Take end-to-end ownership of the revenue funnel across Marketing, Sales, and Customer Success, from lead creation through renewal and expansion.
• Proactively identify where the funnel is leaking (conversion drop-offs, stalled deals, churn signals) before they show up as missed targets.
• Build and maintain a consolidated, opinionated view of the business that blends historical performance with forward-looking hypotheses.
• Build Forecasting and Reporting Systems; Own forecasting, pipeline management, and revenue performance reporting across the full funnel.
• Establish the operating rhythms and governance (weekly, monthly, quarterly reporting cadences) that give leadership and the board a predictable read on the business.
• Partner directly with the Revenue Leadership Team and executive team on board reporting, re-forecasts, and business reviews.
• Drive Data Strategy and Governance; Set the standards for what data matters, how it's defined, and who owns keeping it clean across HubSpot and other systems.
• Resolve conflicts between systems of record (e.g., CRM vs. Finance) and establish a single source of truth for key metrics.
• Push for proactive, not reactive, data quality: fewer dashboards nobody trusts, more definitions everyone agrees on.
• Use AI to Improve the Customer and Team Experience; Identify where AI can improve the customer experience, deal execution, or team productivity, and build or oversee those tools.
• Bring a point of view on where automation should replace manual work versus where it should augment human judgment.
• Lead Cross-Functional Alignment; Surface insights and recommendations directly to Sales, Customer Success, and Marketing leadership, not just report numbers back to them.
• Build and develop a small, high-leverage Revenue Operations team.
• Act as a trusted partner to the executive team and board on revenue strategy, planning, and performance.
• Other duties as assigned.

Benefits

• Competitive paid vacation to unplug and recharge throughout the year.
• Dedicated personal leave supporting total well-being, including physical recovery or mental health.
• Flexible schedule blending collaborative office time with remote work.
• Monthly team lunches to celebrate wins and connect with colleagues.
• Continuous professional development with internal training and learning opportunities.
• Professional, supportive environment with tools and technology needed to succeed.
• Comprehensive Health Benefits.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed