Head of Customer Success & Enablement

CoPilot AI

11d • $100,000 - $125,000 • Remote

About The Position

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!
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.
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.

Requirements

• 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.

Responsibilities

• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed