Revenue Operations & AI Enablement Manager
Location: Toronto, Ontario (remote 4/5 days per week)
Reports To: Director of Revenue Operations
OVERVIEW
At Greenspace, our mission is to empower mental health systems, service providers, and individuals in care with the technology, insights, and expertise they need to meaningfully improve how services are accessed, measured, and delivered.
We are hiring a Revenue Operations & AI Enablement Lead to design, implement, and scale AI-powered workflows across the organization. Roughly 80% of this role will focus on AI enablement across our Go-To-Market function while the remaining will involve partnering with other teams to support practical AI use cases across the company. This is an applied AI operations role focused on building real systems, running experiments, and driving measurable business impact.
ROLE SUMMARY
You will be the primary driver of AI implementation within the revenue organization, while serving as a collaborative AI thought partner to other teams. You will:
- Lead AI workflow implementation within GTM
- Design and refine scalable prompt frameworks and automation systems
- Own AI-driven data acquisition and enrichment pipelines
- Improve automation across our revenue stack
- Partner cross-functionally to support AI use cases beyond revenue
You will work closely with RevOps leadership to translate strategy into practical systems, while collaborating with other functional leaders to support their AI initiatives where appropriate.
KEY RESPONSIBILITIES
1. AI Outbound & GTM Automation Leadership
- Design, implement, and continuously improve AI-powered outbound programs across priority ICP segments.
- Build and refine reusable prompt frameworks for AI SDR workflows, account research, personalization, and prioritization.
- Strengthen targeting logic by integrating and structuring data from multiple internal and external sources.
- Evaluate and iterate on AI-generated outputs using performance metrics such as conversion, pipeline contribution, and engagement.
- Lead quality assurance processes to ensure AI workflows are reliable, scalable, and measurable.
2. AI-Driven Data & Revenue Systems Infrastructure
- Lead the acquisition, structuring, and validation of external data sources to improve ICP modeling and segmentation.
- Build automation flows between tools such as Salesforce, Clay, Salesloft, and others to ensure clean, reliable data movement.
- Improve enrichment logic and prioritization models that support outbound and full lifecycle revenue motions, including expansion and retention within Customer Success.
- Design systems that reduce manual effort while increasing signal quality and operational efficiency.
- Develop reporting frameworks that measure AI impact across the revenue lifecycle, from pipeline creation through renewal and expansion outcomes.
3. Cross-Organizational AI Enablement
- Partner with leaders across Finance, Operations, Customer Success, and other teams to explore and support practical AI and automation use cases.
- Act as a consultative thought partner to help teams identify where AI can remove friction, reduce manual effort, or improve insights.
- Support the implementation and instrumentation of AI-enabled workflows outside of GTM when aligned with organizational priorities.
- Contribute to lightweight AI best practices and responsible usage guidelines across the organization.
- Assist teams in piloting AI solutions and evaluating measurable impact.
QUALIFICATIONS & SKILLS
Mission Alignment: Motivated by improving mental healthcare and aligned with Greenspace’s values.
Experience (3–6+ years): Experience in Revenue Operations, Sales Operations, GTM Automation, Business Operations, or applied AI enablement within a SaaS or technology environment.
Applied AI Experience:
- Demonstrated experience implementing AI-powered workflows in a business setting.
- Experience designing prompt frameworks and improving LLM outputs.
- Experience driving measurable business results through AI-enabled automation.
Systems & Automation Expertise:
- Strong Salesforce experience including objects, reporting, logic, and workflows.
- Experience integrating tools across a technology stack.
- Familiarity with automation platforms such as Zapier, Make, or APIs.
- Comfort working with structured data such as CSV or JSON files and basic querying such as SOQL or SQL.
Analytical & Systems Thinking:
- Ability to structure messy processes into scalable systems.
- Strong understanding of funnel metrics and operational KPIs.
- Ability to evaluate return on investment for automation initiatives.
Ownership & Execution:
- Comfortable operating independently in ambiguous environments.
- Bias toward experimentation and iteration.
- Able to translate high-level strategy into practical implementation.
Communication & Influence:
- Able to explain AI applications clearly to non-technical stakeholders.
- Comfortable partnering cross-functionally to support adoption and implementation.
Good Vibes: You approach challenging times with resilience, optimism, and a solutions-focus. You thrive working both independently and as part of a team.
Nice-to-Haves:
- Exposure to AI-enabled GTM tools (sales engagement, call intelligence, outbound automation).
- Experience with Python, APIs, Zapier, or similar automation tools.
- Experience with Customer Success tools such as Planhat.
- Experience supporting Finance or Operations automation initiatives.
- Experience supporting mid-market or enterprise GTM motions.
- Interest or experience in healthcare, mental health, or regulated industries.
ABOUT GREENSPACE HEALTH
Founded at St. Michael's Hospital in Toronto, Greenspace was created to bridge the gap between the proven benefits of Measurement-Based Care in research and its implementation in practice. Our solutions are designed to empower organizations to leverage data to inform treatment decisions and significantly improve the quality of mental health care across North America.
As a startup, we offer significant responsibility and the opportunity to play a pivotal role in the growth of our company. We are driven by a passion for improving mental health care and the lives of millions of people. We foster a collaborative environment where all ideas are valued, whether they come from the CEO or the newest team member. Learn more about our culture here.
Diversity
Diversity strengthens our organization, and we are committed to being an equal-opportunity employer. We recruit, employ, train, and promote employees regardless of race, religion, color, national origin, gender, age, sexual orientation, gender identity, or disability.
BENEFITS
- Competitive compensation package comprising an annual salary between $100,000 to $120,000 (dependent on experience), equity incentive, and potential for bonus tied to organizational performance.
- Comprehensive benefits program, including paid parental leave.
- Healthy work/life balance - we recognize that building a startup is a marathon, not a sprint.
- Tight-knit collaborative work environment where we work in teams rather than siloed individuals.
- High level of autonomy - we always run with good ideas that are the best use of our time.
- Remote/in-person hybrid work setting. The work location for this position will be in Toronto, Ontario. The team currently works 4 days/week remotely with an expectation to be in office on Wednesdays.
HIRING PROCESS
For hiring, we like to move smart and fast. We also understand that while applying to new roles, there can be added stress when timelines are uncertain. While it is subject to change, applicants should expect the following:
- Overall: approximately a 4-6 week hiring process from application to job offer
- Applications Open: February 18 - March 25
- Initial Screenings: February 25 - March 25
- Live Interviews: March 11 - March 25
- Final Conversations: March 18 - April 1
- Expected Start: April 8, April 15 at the latest
We do our best to ensure every application is responded to, regardless of whether or not the candidate is moving forward in the process (please keep an eye on your email for notifications). However, occasionally timelines and stages above may change. Please do not ask for an update regarding your application status unless you have not heard anything in at least two weeks.
Interesting in Applying?
Think you have what it takes? Please apply with an updated resumé (no cover letter is necessary). The application deadline is 03/11/26. Expected start date is 04/08/26; 04/15/26 at the latest.
