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Head Of Operations Jobs in Whitby, ON (NOW HIRING)

Tali AI

Head of Operations

Toronto, ON · On-site

Why this role exists We've reached the stage where "operations" is spread across several leaders and, often, the CEO. We're hiring a full-time Head of Operations to become the operational backbone of ...

LoopX

Head of Operations & Finance

Toronto, ON · On-site

$150 - $200/hr

We are looking for a Head of Operations & Finance to work closely with the CEO in building and scaling LoopX. This person will own core financial planning and internal operations, ensuring the ...

Monograph

Head of Marketing Operations

Toronto, ON · On-site

$250/hr

What you'll do We are looking for a Head of Marketing Operations to lead a critical team to help power Stripe's growth. You will set the direction of marketing operations, solve time-sensitive and ...

Liberty Mutual Canada

Head of Construction

Toronto, ON · On-site +1

Head of Field Underwriting & Distribution and General Manager, North American Construction Company ... Liberty Mutual Canada is the Canadian operation of Liberty Mutual Insurance Company. We offer a ...

Liberty Mutual Canada

Head of Construction

Toronto, ON · On-site

Head of Field Underwriting & Distribution and General Manager, North American Construction Company ... Liberty Mutual Canada is the Canadian operation of Liberty Mutual Insurance Company. We offer a ...

Liberty Mutual Canada

Head of Construction

Toronto, ON · On-site

$200 - $250/hr

Head of Field Underwriting & Distribution and General Manager, North American Construction Company ... Liberty Mutual Canada is the Canadian operation of Liberty Mutual Insurance Company. We offer a ...

GuruLink

Head of Engineering

Toronto, ON · On-site

$150 - $200/hr

Having operated successfully for several years with a lean, highly technical core team, we are scaling our operations and entering a critical phase of organizational growth. Core Mission As the Head ...

Parallelz

Head of Engineering

Toronto, ON · On-site

$125 - $150/hr

... operational platform that will have an impact across the industry. As Head of Engineering, you will lead a small, senior team of graphics, systems, and platform engineers building deeply technical ...

AIG

Head of Multinational - Canada

Toronto, ON · On-site

About the role The Head of Multinational, Canada will provide leadership and strategic direction of ... Demonstrated change agent able to identify and implement operational and process improvements.

Monex

Head of Sales

Toronto, ON · Hybrid

Head of Sales | Toronto Monex is a leading global financial solutions provider, offering a complete set of tools to support business growth and strategic financial operations. We specialize in FX ...

Behavox

Head of Finance

Toronto, ON · Hybrid

About the Role The Head of Finance reports to the Chief Operating Officer and leads the finance ... operations. This is a hybrid position based out in our Toronto office. What You'll Bring

Monex group

Head of Sales

Toronto, ON · On-site

$200 - $250/hr

Head of Sales | Toronto Monex is a leading global financial solutions provider, offering a complete set of tools to support business growth and strategic financial operations. We specialize in FX ...

Cache Ventures

Head of GTM

Toronto, ON · Remote

Now we're installing a Head of GTM to turn founder-driven strategy into repeatable enterprise ... Operational cadence That's Revenue & Ops. You own direction, positioning, and vertical leverage.

Cache Ventures

Head of GTM

Toronto, ON · Remote

Now we're installing a Head of GTM to turn founder-driven strategy into repeatable enterprise ... Operational cadence That's Revenue & Ops. You own direction, positioning, and vertical leverage.

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Head Of Operations information

What does a head of operations do?

A Head of Operations is responsible for overseeing the daily activities and overall efficiency of an organization's operations. This role involves managing teams, optimizing processes, implementing strategic plans, and ensuring that business goals are met. The Head of Operations works closely with other leaders to improve productivity, reduce costs, and maintain high-quality standards across the company. They play a critical role in driving growth and ensuring that the organization's operations align with its long-term objectives.

What are the key skills and qualifications needed to thrive as a head of operations, and why are they important?

To thrive as a Head of Operations, you need strong leadership, strategic planning, and process optimization skills, often supported by a degree in business or management. Familiarity with ERP systems, project management tools, and relevant certifications like PMP or Six Sigma are highly valued. Exceptional communication, problem-solving, and team management abilities help drive operational excellence and foster a high-performing culture. These skills ensure efficient operations, support organizational growth, and enable the successful execution of company objectives.

What are some common challenges faced by a head of operations, and how can they be effectively managed?

A Head of Operations often encounters challenges such as balancing strategic planning with day-to-day operational demands, managing cross-functional teams, and implementing process improvements amid resistance to change. Effective management involves strong communication, the ability to prioritize initiatives, and fostering a culture of collaboration and continuous improvement. Building trust with department leaders and aligning operational goals with the broader company vision are also key to overcoming obstacles in this role.

What is the difference between Head Of Operations vs Operations Manager?

AspectHead Of OperationsOperations Manager
ResponsibilitiesStrategic planning, overseeing multiple departments, setting company-wide operational goalsManaging daily operations, supervising staff, implementing policies at department level
Required CredentialsOften requires extensive experience, bachelor's or master's degree in business or related fieldTypically requires relevant experience, bachelor's degree in business or related field
Work EnvironmentExecutive-level, strategic meetings, cross-department collaborationOperational settings, team management, process optimization

The Head Of Operations focuses on strategic, company-wide oversight and long-term planning, while the Operations Manager handles daily operational activities and team supervision. Both roles require relevant experience and industry knowledge, but the Head Of Operations is more involved in setting overall direction, whereas the Operations Manager executes those strategies on a day-to-day basis.

How much does a Head of Operations get paid?

The salary for a Head of Operations typically ranges from $90,000 to $200,000 annually, depending on the industry, company size, and location. Senior roles often include bonuses, stock options, and other benefits, and strong leadership and strategic skills are essential for this position.

Is head of operations a high position?

The head of operations is a senior leadership role responsible for overseeing daily business activities, strategic planning, and process improvements. It is generally considered a high-level position within an organization, often reporting to executive management and requiring extensive experience and leadership skills.

What are the most commonly searched types of Of Operations jobs in Whitby, ON?

The most popular types of Of Operations jobs in Whitby, ON are:

What are popular job titles related to Head Of Operations jobs in Whitby, ON?

For Head Of Operations jobs in Whitby, ON, the most frequently searched job titles are:

What job categories do people searching Head Of Operations jobs in Whitby, ON look for?

The top searched job categories for Head Of Operations jobs in Whitby, ON are:

What cities near Whitby, ON are hiring for Head Of Operations jobs?

Cities near Whitby, ON with the most Head Of Operations job openings:

Head Of Operations jobs near you
Infographic showing various Head Of Operations job openings in Whitby, ON as of August 2026, with employment types broken down into 88% Full Time, 11% Part Time, and 1% Contract. Highlights an 93% Physical, 3% Hybrid, and 4% Remote job distribution.

Head of Operations

Tali AI

Toronto, ON • On-site

Full-time

Medical, PTO

Re-posted 16 days ago

Job description

Tali AI is on a mission to build industry-leading products that solve real-world problems for clinicians today.
 
How do we do this? Our AI-powered medical assistant empowers clinicians by removing the administrative burden that pulls them away from patients. When clinicians can focus on care, healthcare becomes more accessible, more human, and more sustainable.
 
Tali is transforming the industry, serving thousands of clinicians across Canada and the US, accelerating millions of patient encounters annually, saving clinicians more than 10 hours a week. That time goes back to where it matters most, patient care.

Tali is a Canadian clinical AI platform on a mission to give physicians their time back. We started with an AI scribe that drafts the clinical note while the doctor focuses on the patient, and we're building outward into the system that automates the administrative work around medicine. We hold the largest share of Canadian AI Scribe implementations, integrate deeply with the EMRs Canadian clinicians actually use, and are growing fast at the intersection of healthcare, AI, and data sovereignty.
Why this role exists

We've reached the stage where "operations" is spread across several leaders and, often, the CEO. We're hiring a full-time Head of Operations to become the operational backbone of the company: to consolidate the run-the-business functions into one coherent org, build the systems and cadence that let us scale cleanly, and free the founders to stay on product, growth, and the relationships that move the business.

You'll be the full-time operational anchor alongside a fractional CFO and VP of Sales, and a true partner to the CEO through a pivotal growth chapter. This is a senior leadership-team role with broad ownership and a clear path to grow into a COO mandate.

How you'll build it, AI-native, from first principles

We're an AI company, and we want operations built the way we build our product: not by importing the standard SaaS playbook, but by asking what each function should look like now that AI can do so much of the work.

  • First principles over best practices. Treat the conventional playbook as a data point, not an answer. Start from the real problem and the outcome you want, then design the leanest path to it, even if it looks nothing like how it's "supposed" to be done.

  • AI-native by default. Assume AI and automation are the first tool, not the last resort. The question is rarely "who do we hire to do this?" and more often "how much of this should a human do at all?" Build a team and processes that are small, leveraged, and AI-augmented from day one.

  • Curiosity as a discipline. Meet every operational problem, a clogged funnel, slow onboarding, a compliance burden, with genuine curiosity about why it works the way it does before deciding how to fix it. The good answers usually aren't in the textbook.

What you'll own

The mandate in every domain below is the same: build the AI-native version, not the legacy one.

1. The operating system & cadence

  • Run the company's operating rhythm: annual/quarterly planning, OKRs and goal-setting, and the leadership-meeting and board-prep cycle.

  • Drive cross-functional execution and program management, turning strategy into shipped outcomes across teams.

  • Act as the CEO's force multiplier on special projects, including operational quarterbacking of financing and strategic initiatives alongside the CFO and our advisors.

2. People & Culture

  • Own the People function: hiring velocity (we have several open roles and are scaling), onboarding, and performance and compensation frameworks.

  • Steward culture and team health as headcount grows.

3. Revenue & Business Operations

  • Own RevOps/BizOps, the systems and data beneath the funnel: CRM (HubSpot) hygiene, pipeline and SLA reporting, lead definitions (MQL/PQL), and billing and renewals operations.

  • Make the business measurable and the go-to-market machine efficient; partner closely with Sales, Marketing, and Customer Success.

4. Security, Privacy & Compliance

  • Own the trust backbone of a healthtech company: SOC 2, PHIPA/PIPEDA compliance, data governance, information security, and vendor security reviews.

  • Turn security and privacy into a competitive advantage in enterprise sales and a clean story in any diligence.

5. Legal, Vendor & Corporate Operations

  • Manage contracts, vendors, and procurement (including partner and platform agreements), and coordinate legal and corporate administration.

  • Keep the corporate operating foundation tidy and audit-ready.

What success looks like

  • First 90 days: you've mapped the operational surface area, taken ownership of People and RevOps, established the leadership operating cadence, and stabilised the basics (CRM hygiene, reporting, the financing data room).

  • 6 months: clear OKRs and reporting the leadership team runs on; a People engine keeping pace with hiring; a defined, instrumented funnel (MQL PQL paying); a credible security & compliance roadmap underway.

  • 12 months: operations is a durable, scalable backbone rather than a set of heroics, and the CEO's time has visibly shifted from running the business to growing it.

What we're looking for

Must-haves

  • 8+ years in operations, including senior operational leadership at a startup/scaleup (Series A-C), ideally in B2B SaaS.

  • Hands-on experience standing up and running at least two of: RevOps/BizOps, People/HR, Security/Compliance, IT.

  • A player-coach, equally comfortable setting strategy and doing the work. This is a builder's role, not a delegator's.

  • An AI-native operator, you reach for automation and AI first, and have built (or rebuilt) processes around what AI can now do, not around how things were done before.

  • A first-principles, curious thinker, you treat best practices as inputs, not defaults, and you'd rather take a problem apart and understand it than copy someone else's solution.

  • Strong systems and data instincts; fluency with operational tooling (CRM/RevOps, HRIS, and the like).

  • High trust, low ego, calm under ambiguity, and excellent judgment about what to prioritise and what to let go.

Bonus

  • Healthtech or another regulated industry; familiarity with PHIPA/PIPEDA, SOC 2, or healthcare data.

  • Experience supporting a financing round or other strategic corporate process operationally.

  • Canadian healthcare-system context; HubSpot depth.

 
What this role is not

This is not finance leadership (our CFO owns FP&A and capital), not product or engineering (owned by the CTPO), and not sales leadership (owned by the VP of Sales). The Head of Operations makes all of these run better, owning the operational systems beneath them, rather than owning their outcomes

Team & reporting

Reports to the CEO and sits on the leadership team. Inherits the People & Culture and Revenue & Business Operations functions (each with an existing lead) plus an incoming GTM Ops Engineer, and builds out Security/Compliance and IT.

$170,000 - $220,000 a year
The compensation for this role also includes  Series A equity + benefits.
 
The compensation range listed refers to an annual base salary that may vary depending on a candidate's relevant qualifications, knowledge, competencies and work experience, and other factors including market conditions. Base salary is only one aspect of our total rewards package. Be sure to check out a summary of our benefits below.
More About Tali AI 
 
Perks and Benefits
 
All full-time employees enjoy:
  • Remote and hybrid work options & flexible work hours
  • Comprehensive health and wellness coverage from day one
  • Competitive PTO, including winter shutdown Dec 25 - Jan 1, birthdays and Taliversaries, and 'extra long' long weekends
  • $2000 annually in "Knowledge Dollars" to learn, grow, and level up
  • Quarterly socials & company outings that bring our team together beyond the day-to-day
 
Our Core Values
 
Bold: we embrace ambitious goals, make courageous decisions, and take calculated risks to drive impactful innovation and growth
 
Resourceful: we're self-directed problem solvers; navigating obstacles, learning and acquiring new skills and making sound judgement calls. We consistently deliver on commitments while maintaining a high standard of quality and dependability
 
Candid: Being, honest, transparent, and open in all interactions, fostering a culture of trust and authenticity
 
Caring: Actively supporting and empathizing with our people - customers, patients, and colleagues to help them thrive and achieve their goals
 
 
Why Join Tali
 
Impact at Scale: What you do here matters. You'll influence the Tali experience, fueling a team that's changing how clinicians work and how patients are cared for.
 
Technical Excellence: What you build here sets the bar. You'll work with cutting-edge technology to help shape a truly world-class product.
 
Ownership and Growth: What you take on here truly matters. As an early-stage startup, every team member helps shape our technology, culture, and future. Whether you're a generalist who thrives on variety or a specialist excited to build systems from the ground up, your contributions will be pivotal to what we become.
 
Build with Purpose and Pride: What you contribute here carries real responsibility. You'll help build and support systems that handle highly sensitive medical data with care and integrity, earning the trust of clinicians and safeguarding the safety of patients every day.
 
A Team that Inspires: Collaborate with a talented, driven team that values innovation, humility, and a relentless focus on solving meaningful problems.
 
 
Tali Online
 
Tali is one of Linkedin's Top Startups of 2025
Tali is part of the renowned Digital Supercluster Project
Check out Tali's CEO, Mahshid Yassaei on Cherry Health's Leaders in Healthcare Podcast
 
 
We thank all applicants for their interest; only those candidates selected for an interview will be contacted. Tali is committed to providing a barrier-free recruitment process for all candidates. Should you require accommodations at any point throughout the hiring process, please contact People & Culture at [email protected].
We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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