Head of Operations

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.