Director Client Success Jobs in Saskatchewan (NOW HIRING)

The Seat

You are not here to check in, chase updates, or run sessions by script.

You are here to walk into the most complex, high-stakes client situations in the business - diagnose what is actually broken, reset the relationship, and drive outcomes that protect both the client and the company.

This is a Special Operations seat. That means you get the cases no one else can close, the clients closest to the edge, and the expectation that you figure it out - fast, professionally, and without needing to be managed through it.

In the early weeks you will be close to the ground - understanding the client base, reading the risk signals, and getting a clear picture of what is working and what is not. That proximity is the input. The outcomes you drive from it are the job.

You report into senior leadership. You own your cases. You own the results.
The Company

AI Acquisition is a multi-8-figure business helping founders and operators scale with AI. 3,000+ clients. 200+ mastermind participants. A sales and delivery engine built for speed and scale.

Growth is happening faster than most companies ever see. This seat exists because the client base is scaling, the complexity per account is rising, and we need someone senior enough to operate at the intersection of retention, strategy, and commercial recovery - without hand-holding.

Requirements

What You Actually Do

Own the hardest client situations:

• Take full ownership of complex, escalated, or high-risk client accounts - from first signal through to resolution - applying structured thinking at every stage
• Diagnose the root cause behind every at-risk engagement: is it strategy, execution, expectation misalignment, or delivery failure - and build the right intervention accordingly
• Lead high-stakes conversations at founder and C-suite level - resetting expectations, rebuilding trust, and redirecting momentum toward outcomes
• Maintain meticulous case records that support accountability, continuity, and pattern recognition across the portfolio

Drive retention and commercial recovery:

• Monitor engagement health signals across your assigned accounts and intervene before situations deteriorate into formal escalations
• Develop targeted recovery plans that address root causes - not surface-level complaints - and execute them at pace
• Identify and close expansion opportunities inside at-risk accounts where trust has been rebuilt and appetite exists
• Track and report weekly on case outcomes, revenue protected, churn signals, and patterns requiring broader operational attention

Operate as a senior advisor, not just a handler:

• Lead live advisory sessions with founders - providing direct, implementation-focused guidance across offer, outbound, pipeline, and execution where relevant
• Advise on go-to-market strategy, offer positioning, and 90-day execution priorities when clients need more than just relationship management
• Challenge assumptions, reframe thinking, and reset timelines with the kind of directness that only comes from someone who has seen these situations before
• Act as a signal amplifier between clients and internal delivery teams - translating client reality into structured, actionable feedback

Build what scales:

• Contribute to the development of escalation frameworks, retention playbooks, and client risk systems that work beyond your individual caseload
• Identify patterns across accounts that point to broader delivery or operational gaps requiring intervention at leadership level
• Propose and implement process improvements that reduce escalation volume, resolution time, and repeat risk over time

Requirements

Experience

• 5+ years in client success, account management, consulting, or a senior operational role within a high-growth, agency, or tech-enabled environment
• Proven track record managing complex, escalated, or high-risk client accounts with demonstrable recovery and retention outcomes
• Prior experience operating at or advising founder/C-suite level - not just executing, but influencing decisions under pressure
• Background in at least one of: growth strategy, sales systems, offer development, delivery operations, or scaling advisory
• Direct exposure to cold outbound, go-to-market execution, or B2B sales systems - enough to advise clients credibly, not just manage them

Skills & Competencies

• Strong diagnostic ability - able to rapidly identify root causes across strategy, execution, expectation, and delivery
• Structured thinker with the ability to build and enforce clear action plans, priorities, and accountability frameworks
• Confident communicator with high emotional intelligence - able to reset expectations, manage difficult conversations, and maintain trust under pressure
• Expert-level negotiation and de-escalation - navigates emotionally and commercially charged situations with composure and precision
• Commercially sharp - understands pricing, business models, and the downstream impact of every client decision
• High executive presence - equally effective on a live Zoom with a frustrated founder as in a written case summary to leadership
• Meticulous documentation discipline - maintains thorough records that support continuity, risk management, and process improvement

Mindset & Behavioural Fit

• Senior ownership mentality - operates independently, takes full accountability for outcomes, and doesn't wait to be managed
• Comfortable in ambiguity and fast-moving environments - adapts quickly without losing structure or composure
• Solutions-oriented under pressure - approaches escalations with clarity and a bias toward resolution, not escalation
• AI-native or highly AI-fluent - actively uses AI tools to enhance output quality, response speed, and documentation efficiency
• Discreet, professional, and exercises sound judgment in sensitive, confidential, and commercially significant situations
• Proactive risk detector - spots churn and engagement signals early and acts before situations deteriorate

You Will Probably Not Fit If:

• You need a calm, predictable caseload with clear escalation paths above you
• You are a strong advisor in structured environments but lose composure when clients push back hard
• You measure success by sessions delivered, not by commercial outcomes protected
• You are more comfortable executing a playbook than writing one
• You need significant ramp time before taking ownership of live, high-stakes situations
• You are looking for a traditional CSM or account management role - this is not that

Benefits

What You Get

• Fully Remote
• Full-time, stable role at a profitable bootstrapped company - no runway anxiety, no pivots every quarter
• Direct line to senior leadership that has built and scaled products past $100M in revenue
• Independent Contractor Agreement
• Real growth track - perform in this seat and the scope expands: team lead, broader Special Operations ownership, or a cross-functional senior role