Strategic Customer Success Director – Enterprise AI
NOTE: We can only hire you if you live in any of these Canada Provinces:
****Ontario, British Columbia, Alberta, Nova Scotia, Quebec****
NOTE: if you do not live in any of these places above we can not hire you and you will not be contacted.
Travel: Approximately 20-30% (US / Canada)
Working Timezone (EST)
Compensation (CAD): $196K-245K CAD + 10% bonus
Must have experience in SAAS, AI Native OR Agentic EXP, High Touch Exp, 7+ years exp.
The Opportunity
Our client is an enterprise AI company helping some of the world’s largest organizations transform customer experience through AI.
We are looking for a Strategic Customer Success Director – Enterprise AI (IC ROLE) to own a select portfolio of highly strategic Fortune 50 and large enterprise customers.
This is not a traditional Customer Success role focused on onboarding, support tickets, or technical implementation.
You will effectively operate as the CEO of a small portfolio of major enterprise accounts - building executive relationships, understanding each customer's business and AI strategy, driving measurable value, protecting the relationship, identifying risk, and uncovering opportunities to expand how customers use the platform.
You will work with sophisticated organizations that are evaluating how AI can reduce human workload while maintaining - or improving - the customer experience.
Your objective is simple: Keep the logo. Deliver value. Expand the relationship. Grow the account.
What You’ll Do
- You will own highly strategic enterprise accounts, developing a deep understanding of their business, customer experience strategy, AI priorities, current use cases, and future opportunities.
- You will build trusted relationships across the organization, from operational teams to senior executives, including leaders across Customer Experience, Operations, Digital Transformation, Technology, AI, and the C-suite.
- You will regularly be onsite with customers - sitting in the room with their teams, understanding what is happening firsthand, and helping leadership answer questions such as:
Where can AI remove unnecessary human workload?
Which customer interactions should be automated next?
Where are the largest opportunities for deflection?
Which AI use cases can improve the customer experience?
Where should humans remain involved?
What should the customer's next phase of AI adoption look like?
- You will lead QBRs, EBRs, executive strategy sessions, success planning, value reviews, and account planning, ensuring customers clearly understand the value they are receiving from the platform.
- You will identify customer risk well before renewal and coordinate the appropriate internal resources to address it.
- You will understand customer contracts, commitments, renewal dates, and commercial objectives. While you will not personally negotiate pricing, you will play an important role in ensuring customers are positioned to renew successfully.
- You will continuously identify opportunities to expand the relationship through additional AI use cases, business units, customer journeys, channels, or geographies and partner with Account Management to convert those opportunities into commercial growth.
- Internally, you will act as the customer's quarterback, working cross-functionally with Product, Engineering, Field Engineering, Delivery, Support, Sales, and Account Management.
- When technical challenges arise, you will be able to understand the business impact, frame the problem clearly, and bring the appropriate technical teams into the conversation.
What This Role Is NOT
- This is not an implementation or delivery role.
- You will not personally build integrations, configure APIs, troubleshoot production systems, or own technical implementation.
- You will not be responsible for onboarding every new customer.
- You will not be the primary support contact resolving individual tickets.
- You will not be responsible for negotiating pricing or closing expansion opportunities.
Instead, you own the WHY and WHAT:
- What does the customer need? Why does it matter? What business outcome are they trying to achieve? Where is value being created? What is at risk? Where can the relationship grow? What needs to happen next?
- Technical and delivery teams own the HOW, while Account Management owns the commercial negotiation and close.
What We’re Looking For
- We are looking for a mature, highly credible enterprise customer leader who can walk into a room with executives from a Fortune 50 company and immediately command trust.
- You should bring approximately 8–10+ years of experience across Enterprise Customer Success, Strategic Accounts, Client Partnerships, Enterprise SaaS, AI, CX technology, CCaaS, cloud software, or another complex technology environment.
- You must have experience managing a small portfolio of very large, sophisticated enterprise customers in a high-touch environment.
- You should be able to clearly discuss:
- The number and size of strategic accounts you have managed
- ARR or commercial value of your portfolio
- Major enterprise renewals
- GRR and NRR
- Customer retention and churn risk
- Executive stakeholder management
- QBRs and EBRs
- Adoption and consumption
- Expansion opportunities you have identified
- Complex customer escalations you have successfully navigated
- You should understand how enterprise customers evaluate and adopt AI, generative AI, LLMs, APIs, integrations, automation, and agentic AI.
NOTE AND READ: You do not need to be an engineer.
However, you must be technically knowledgeable enough to have credible AI conversations with customers, understand how the technology fits into their environment, identify relevant use cases, and translate business problems into clear requirements for technical teams.
The Ideal Profile
- The strongest candidates will have worked with major organizations where customer relationships are complex, executive visibility is high, and the cost of losing an account is significant.
- You are comfortable walking into a customer's office, meeting the operational team, sitting down with senior leadership, understanding what is and is not working, and developing a clear plan for what happens next.
- You are commercially minded without being a salesperson.
- You understand that successful Customer Success is ultimately about value, retention, adoption, relationships, and growth.
- You don't wait until a renewal is 60 days away to discover there is a problem. You understand the health of the relationship months in advance and proactively mobilize the right people to protect it.
- You can operate independently and jump in immediately with minimal training or hand-holding.
What Success Looks Like
Success in this role means your customers:
Stay. Adopt. Expand. Advocate.
- You will know your accounts deeply enough to understand where each relationship stands, what executives care about, what value is being delivered, where risk exists, and where the next growth opportunity will come from.
- You will help some of the world's largest companies determine how AI should responsibly transform their customer experience - while ensuring the technology delivers measurable business value.
- Seniority Level
- Mid-Senior level
- Employment Type
- Full-time
