Head of Operations & Customer Success (Toronto, CAN)
- Compensation
- CA$160K–CA$180K (OTE: CA$184K–CA$216K)
- Work mode
- Hybrid/On-site
- Location
- Toronto, ON, Canada
- Industry
- Legal Technology
Your market value for this role
Compared with 27 live mandates (all Head of Function mandates).
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The mandate
We are looking for a Head of Operations & Customer Success with 4-10 years of experience. You're a systems thinker who has seen a fast-growing company go through scaling pains, and you'll bring structure to the organization as we turn into an AI-native legal tech company. We've grown 5x in 6 months, and people ops and customer success haven't kept up. You'll own both areas and build the systems and AI automation we need to grow from 60 to 100+ people.
Key responsibilities
- Build people ops from scratch: an in-house recruiting process for high-volume roles like case managers, pay bands, performance reviews, onboarding, offboarding, payroll and vacation
- Own client satisfaction across all 5 practice areas. Track CSAT and Google reviews, and fix the drivers behind low scores
- Set up a clear system for client complaints and escalations that come in through the portal and email. Trace each escalation to its root cause and cut escalations per 100 files
- Automate workflows with AI tools before adding headcount, and possibly take ownership of Clio data and administration
- Hire and coach a team across talent acquisition, HR and customer success, and set the standard for performance and professionalism
- 4-10 years of experience, including leading operations, people ops or customer success at a fast-growing company (startup experience preferred)
- Strong systems thinker who uses data to find root causes and fix processes, not just symptoms
- Reaches for automation and AI tools before adding headcount
- A culture builder who hires and keeps A players
- Can work hybrid in Toronto, ON (scaling a company from about 20 to 100-200+ people is a strong plus; legal or Clio experience is not required)
What you bring
- 4-10 years of experience, including leading operations, people ops or customer success at a fast-growing company (startup experience preferred)
- Strong systems thinker who uses data to find root causes and fix processes, not just symptoms
- Reaches for automation and AI tools before adding headcount
- A culture builder who hires and keeps A players
- Can work hybrid in Toronto, ON (scaling a company from about 20 to 100-200+ people is a strong plus; legal or Clio experience is not required)
Location & engagement details
Toronto, ON, Canada · Hybrid
C$160K–180K base, depending on experience, plus a target bonus of 15–20% of base. The bonus is tied to outcomes you agree on when you join, like CSAT, escalations per 100 files, Google reviews and people ops metrics. OTE is about C$184K–216K. Also includes flexible vacation and health, dental and wellness coverage.; Visa sponsorship details: Not open to any visas (e.g. US the organization, Green Card holders); Hybrid work policy: About 3 days in-office in Toronto, ON (new office move underway)
About this mandate
This is a live head of function search with direct introductions to the hiring team. The role sits in legal technology and is located in Toronto, ON, Canada on a hybrid/on-site basis, with compensation of CA$160K–CA$180K (OTE: CA$184K–CA$216K).
This is a confidential search. Read the brief above, then apply below for this role. The company name is shared once there's a close match and mutual interest.
Most senior mandates are filled this way — privately, before any listing exists. Read how unadvertised executive roles actually get filled.
- This is a confidential search. The company name and full role details are only discussed on a call with one of our recruiters if there is a close match.
- We use your details — your LinkedIn profile URL and email address — to match you against this mandate and any other closely matched roles.
- A verifiable email address, LinkedIn profile and a recent PDF resume are required. Submissions from bots, spammers or unverifiable profiles are removed.
- There is no call booking at this stage. Calls are scheduled only after we identify a close match.
Who can apply
- C-suite, EVP/SVP, VP and Head of function leaders
- Proven scale-up, venture-backed or enterprise leadership experience
- Track record of building and leading teams in the relevant function
Final hiring decisions rest solely with the hiring company. Outcomes depend on role availability and decisions made by the hiring team.
Apply — Head of Operations & Customer Success (Toronto, CAN)
This application is for this role only. It is reviewed against the brief above, and you will be contacted if there is a close match.
- This is a confidential search. The company name and full role details are only discussed on a call with one of our recruiters if there is a close match.
- We use your details — your LinkedIn profile URL and email address — to match you against this mandate and any other closely matched roles.
- Handled confidentially — your details are never shared without your consent.
- A referral is an introduction, not a guarantee of an interview or an offer.
- Final hiring decisions rest with the hiring company; outcomes depend on role availability and their decisions.