Head of Customer Success - Canada

CoPilot AI is a Vancouver-based SaaS start-up with a mission: to innovate the way people grow their business by humanizing digital interactions in a scalable way. · We believe in maximizing authentic and mutually beneficial human connections for business growth, which is why CoPi ...

Job description

CoPilot AI is a Vancouver-based SaaS start-up with a mission: to innovate the way people grow their business by humanizing digital interactions in a scalable way.

We believe in maximizing authentic and mutually beneficial human connections for business growth, which is why CoPilot AI automatically targets qualified people on social media, initiates one-to-one conversations, and surfaces timely sales opportunities without requiring any cold calling, events, or expensive advertising. Our goal is to create a place where our customers can have more meaningful conversations at scale.

As we scale into the next phase, we are looking for a Head of Customer Success & Enablement to join our RevOps team

The Role

Join CoPilot AI, a $10M ARR leader in LinkedIn automation. We are evolving into HeyStack, the next generation of Agentic AI for sales.

We are shifting from a passive, self-serve CS model to a high-touch, commercially accountable model. We do not need a visionary to theorize; we need a tactical commander to lift up the team, stabilize an inexperienced team, and build a revenue-protecting enablement engine from the ground up.

What you'll do:

• Kill the Noise: Audit the scattered training materials and build a centralized, sequenced onboarding academy for new CSMs.
• The Coaching Cadence: Implement mandatory, weekly 1:1 shadowing, live call reviews, and mock roleplay scenarios to replace passive reading.
• Shift the Culture: Replace the "figure it out yourself" mentality with extreme ownership. You will teach CSMs how to drive the customer's strategy.
• Drive Expansion: Teach your team how to identify high-health accounts and pitch upgrades based on ROI, pipeline impact, and credit consumption.
• Revenue Accountability Engine: Build the operational playbook that equips "support-minded" CSMs to successfully carry a quota, tying their daily customer interactions directly to the 30% of their comp based on NRR.
• A Culture of Psychological Safety: Rebuild trust with an anxious team through extreme ownership, transparent feedback, and empathetic, side-by-side trench work.

This is a critical role within the company, and our expectations are equally high. Whatever you do should drive growth in the right direction. We will reward the right candidate with career growth, professional development opportunities and perks. Most importantly, you will be part of a success story, joining a team of high-performing professionals committed to excellence.

Who you are:

• Anti-fragile: You thrive when the building is on fire. You don't complain about a lack of process; you write the process.
• A Master Educator: You understand that adults learn through repetition and failure. You prioritize live coaching over sending links to wiki pages.
• Sales-Wired: You have closed deals or carried an expansion quota. You know how to ask uncomfortable questions about money and ROI.
• Low Ego, High Conviction: You lead with empathy but demand excellence. You can repair a damaged team culture without lowering the bar.
• 3–7 Years of Battle-Tested Experience: You have spent at least 3 years in a high-growth SaaS environment, specifically in Customer Success, Account Management, or Sales Enablement. You aren't just quoting books; you've personally navigated the messy middle of scaling a team from $1M to $10M+ ARR.

What's in it for you:

• Competitive Compensation: A competitive annual base salary of $100,000CAD.

• Your annual OTE (On Target Earnings) is $125,000CAD. Variable is tied directly to Net Churn and Expansion ARR.

• Remote-First: At CoPilot AI, we are committed to a culture of trust, autonomy, and high performance. With our Remote-First Policy, we empower you to do your best work from the place you call home. We have an office in downtown Vancouver for team members to use as they wish (completely optional)
• Comprehensive Benefits: We've got you covered with a comprehensive benefits package, including health, dental, and vision insurance.
• Health and Wellness Spending Account: We care about your well-being inside and outside the office. You will receive an additional $200 per month for a health and wellness spending account that accrues upon passing probation - our team uses it for their at-home office setup, electronics, gym memberships, haircuts, and more
• Paid Time Off: We offer a generous paid time off policy as we believe that rest and rejuvenation are key for high performance.
• Stock Options: Upon joining CoPilot AI, you will receive stock options with the expectation of significant value. We're a team of high performers working together on a breakthrough success story, and we want you to share in the value we're creating.

Our Interview Process

One of our operating principles is transparency, so we'd like to share our interview process with you:

• Initial Screen: We value your personality and communication style more than a resume.

To apply, please submit a short (under 2-minute) Loom video:

• Tell us about a specific time you inherited a broken process, a messy knowledge base, or a highly anxious team. Don't give us the whole timeline—just tell us the very first thing you stopped doing, and the very first thing you built to stabilize the situation.
• Include your video link and your CV in your application.
• Viability Screen: A 30-minute call with the People & Culture team. The goal is to align on what this role entails, share context about our team and goals, and learn more about your experience and interest in CoPilot AI.
• Competency & Cultural Add Interview: A 1-hour Zoom call with the hiring manager, the CEO, and the Co-founder at CoPilot AI. The focus of this stage is to know your technical knowledge, ensure deep alignment with our core values and operating principles.
• Offer and Reference Checks: If you've made it this far, the hiring manager will give you a call to share the good news We'll ask for 3 professional references and then send over the formal offer documents. After that, it's simply a countdown until your start date

About CoPilot AI

CoPilot AI has been recognized as a BC Technology Impact Award finalist and lauded by Canadian Business as the winner of the Best Pivot award and one of Canada's Fastest-Growing Companies. Deloitte spotlighted us as a 2021 Canada Companies-to-Watch Winner. Our latest win? Being highlighted by Forbes as one of Canada's best startup employers for 2024

As an equal opportunity employer, CoPilot AI truly stands behind #diversity and are committed to creating an environment of inclusion where hiring decisions are based on merit and business needs and without regard to race, colour, national origin, ancestry, sex, gender, gender identity or expression, sexual orientation, age, genetic information, religion, disability, medical condition, pregnancy, marital status, family status, veteran status, or any other characteristic protected by law. CoPilot AI also makes workplace accommodations for qualified individuals with disabilities as required by applicable law. If you require accommodations during the interview process, please let us know and we will work with you to meet your needs.

Our Values? Glad You Asked

#Innovation: We are passionate about creating, innovating, and pioneering. We constantly strive to challenge the status quo.

#Boldness: We care deeply about our work and the impact we make. We are audacious in our decisions and actions, showcasing our commitment to the success of our customers and our team.

#Authenticity: We pride ourselves on being genuine, transparent, and real in all our interactions. We believe in authenticity, which we exhibit both internally and externally.