Director of Revenue Operations

Boosted.ai; Toronto; On-site; CAD 120,000 - 160,000; Full time

Job summary

A leading AI-driven finance platform in Toronto is seeking a Senior Revenue Operations member to oversee GTM strategies and drive efficiency across revenue functions. The ideal candidate will have 5+ years in Sales or Revenue Operations, strong analytical skills, and experience with CRM systems like HubSpot. This leadership role focuses on optimizing revenue models, enhancing collaboration across departments, and implementing continuous improvements for operational efficiency.

Benefits

Flexible (Unlimited) Paid Time Off

Medical, Dental, and Vision benefits

Life Insurance and Disability Benefits

Access to a 401(k) retirement savings plan

Paid Parental Leave

Free access to Boosted.ai Alfa™

Qualifications

• At least 5 years of experience in Sales Operations, Revenue Operations, or similar roles.
• Experience working directly with senior leadership and executive teams.
• Proven ability to influence cross-functional teams.

Responsibilities

• Create strategies that drive cohesive teamwork within the GTM organization.
• Optimize existing revenue models and create new revenue streams.
• Collaborate with Finance Leadership for yearly capacity and headcount plans.

Skills

Strategic thinking

Analytical skills

Sales operations

Revenue operations

Communication skills

Project management

Education

Bachelor's degree in Business, Marketing or a related field

MBA

Tools

HubSpot

Salesforce

Outreach

ZoomInfo

Pitchbook

Job description

Job Description

Boosted.ai is building AI purpose-built for finance to help teams do more. Our mission is to optimize investing and boost productivity. We're already trusted by leading enterprises and developers with over $5T under management with Boosted.ai.

From the fastest growing hedge funds to global financial institutions, our tool lets our users stay ahead of the competition with AI that works for them. We believe that modern investment professionals will win the future of finance by using the best tools; a unique competitive edge powered by data, experimentation, and automation.

Boosted.ai is the platform they use to cut through data overload, outpace competitors, and reclaim their time. We're looking for sharp, low-ego people to help teams find their edge.

Why is Boosted.ai the best place to work?

• Customers love the product (adopted by many of the biggest financial institutions and rapidly expanding to more firms)
• We're growing a lot (5x in the last year)
• Incredible culture (our customers keep applying to work here)
• Well-resourced — our lead investors are innovators and disruptors in financial and technology markets, including Spark Capital (Twitter, Slack, Affi…)

As a senior member of the Revenue Operations team, you will strengthen the company's overall go-to-market (GTM) strategy and drive the efficiency and effectiveness of our revenue-generating functions.

You will oversee core aspects of company performance, strategy, and GTM alignment, supporting our revenue teams across Sales, Marketing, and Customer Success. This includes performance management, forecasting, pipeline management, commission planning, quota and territory design, sales tooling, data management, and deal support.

You will also help guide the strategic growth of the GTM organization and ensure that department interactions align with broader company goals set by Executive Leadership. This role requires a strategic thinker with strong analytical skills and a proven track record in revenue operations and enablement.

This is a highly visible and cross-functional leadership role where your work will directly impact company performance and GTM effectiveness. You will help shape how our go-to-market organization operates and scales while working closely with leaders across departments to drive measurable growth.

What You'll Do

Revenue Planning and Execution

Create strategies that drive all teams within the GTM organization to work cohesively and maximize revenue.

• Partner with Executive and Leadership teams to optimize existing revenue models and create new revenue streams using data to guide decisions.
• Collaborate with Finance Leadership to develop yearly capacity and headcount plans.
• Work with Sales and Marketing Leadership to design and implement system improvements, territory planning, and reporting dashboards.

Revenue Operations

Implement and optimize CRM systems (such as HubSpot or Salesforce) to improve productivity and data accuracy.

• Establish key performance indicators (KPIs) for revenue operations and enablement.
• Manage operating rhythms including weekly reviews, sales forecasts, pipeline management, commission planning, KPI reviews, OKRs, quotas, and territory design.
• Analyze sales and marketing data to provide insights and recommendations for leadership.
• Monitor and report on the performance of Sales, Marketing, and Customer Success teams to identify actionable insights.
• Manage Revenue Operations projects and sprints to ensure successful delivery of initiatives.

Revenue Enablement

Develop and execute a comprehensive revenue enablement strategy to support sales effectiveness.

• Provide data management and deal support across the GTM organization.
• Collaborate with Sales Leadership to identify training needs and implement enablement programs.
• Oversee training and onboarding programs for all revenue-driving roles.
• Drive alignment between Sales, Marketing, and Customer Success to enhance overall revenue outcomes.

Process Optimization

Define, document, and improve sales processes to drive operational efficiency and ensure smooth execution of GTM goals.

• Analyze sales processes and workflows to support future GTM motions for each vertical.
• Prepare reports and presentations to communicate findings and recommendations to stakeholders.
• Implement best practices and tools that streamline workflows and improve revenue generation.

Who You Are

• Bachelor's degree in Business, Marketing, or a related field (MBA is a plus).
• At least 5 years of experience in Sales Operations, Revenue Operations, Business Operations, or similar roles in a growth-stage company.
• Experience working directly with senior leadership and executive teams.
• Proven ability to influence cross-functional teams and drive strategic projects without direct authority.
• Strong organizational and communication skills with the ability to bring structure to complex or ambiguous problems.
• Interest in fintech and AI with an understanding of market dynamics and competitive landscapes.
• Demonstrated experience aligning strategic initiatives with overall business objectives.
• Strong knowledge of HubSpot and Salesforce CRM, and familiarity with tools such as Outreach, ZoomInfo, and Pitchbook.
• Prior experience as a senior analyst in Sales, Marketing, or Revenue Operations.
• Proven success in designing and implementing RevOps strategies and process improvements across marketing and sales.
• Excellent collaboration and project management skills.

Our Values

• Collaborative – We value our team and know that success can only come from working together
• Client Centric – Our focus is always on our clients and consistently delivering them value
• Action Oriented – We remove barriers and we seek to improve in measurable ways
• Accountable – We are accountable for ourselves, and we hold each other accountable
• Respectful – We are proud of our work, we are respectful of each other's opinions, and we keep a positive attitude

What We Offer

We want our benefits to reflect our values and offer the following to full-time employees :

• Flexible (Unlimited) Paid Time Off
• Medical, Dental, and Vision benefits for you and your family
• Life Insurance and Disability Benefits
• Access to a 401(k) retirement savings plan (for U.S. employees)
• Paid Parental Leave
• Free access to use Boosted.ai Alfa™ to make money
• We love the energy of in-person collaboration while also offering the flexibility to work from home when needed

These benefits are further detailed in Boosted.ai's policies and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Boosted.ai's equity plans subject to the terms of the applicable plans and policies.

Be You, With Us

We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.