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 Manager of Customer Success & Enablement to join our RevOps team!

The Role

We are a $10M ARR B2B SaaS company evolving into HeyStack, the next generation of Agentic AI for sales. Our previous self-serve CS model broke at scale, doubling our monthly net churn from 6% to 12%. We are shifting from a passive, self-serve CS model to a high-touch, commercially accountable model. We need a hands-on Manager of CS & Enablement to align our team with this new commercial motion, modernize our operational processes, and construct a revenue-protecting enablement engine from the ground up. This is a high-visibility, process-driven transformation.

What You Will Build:

• The Enablement Academy: Transform scattered documentation into a linear, highly structured onboarding path, prioritizing critical skills in their required sequence: Onboarding first, then Churn Saves, then Expansion.

• The Coaching Engine: Replace passive wiki-reading with a rigorous, supportive cadence of live weekly 1:1 shadowing, call reviews, and mock roleplay scenarios.

• The Commercial Playbook: Build the operational framework that upskills CSMs to own an expansion quota, tying daily customer interactions directly to commercial outcomes and net churn reduction.

• A Culture of High Trust & High Performance: Build team morale through extreme ownership, transparent feedback, and empathetic, side-by-side mentorship to ensure the team feels supported and equipped to succeed during this transition.

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:

• The Commercial Coach: You have sales or marketing DNA and have carried a quota. You prioritize live coaching and roleplay over sending links, teaching teams how to drive strategy and ask hard questions about money and ROI.

• The Process Architect: You thrive at startup speed. You can take messy, scattered knowledge and build a structured, scalable enablement process from scratch with high operational execution.

• The Empathic Leader: You engage the team through extreme ownership and high emotional intelligence, building trust without lowering the bar for performance.

• The Stabilizing Anchor: You project calm clarity. When the team is navigating market shifts, complex process overhauls, or startup ambiguity, you absorb the chaos and provide methodical, step-by-step direction to steady the ship.

• The Systems Thinker: You don’t just put out fires; you fix the underlying machinery. You proactively brainstorm with the team to continuously optimize workflows, refine commercial playbooks, and execute strategic initiatives like limited-time offers to drive urgency and expansion.

• The Change Champion: Startup life means constant iteration. You know how to execute exceptional change management—translating rapid pivots into clear, motivating objectives that get the team on track without burning them out.

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:

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

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

   1. 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.

   2. Include your video link and your CV in your application.

2. 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.

3. 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.

4. 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.