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Head of Customer Success

Cloudtalk

Toronto, Ontario, Canada Hybrid permanent

Posted: February 25, 2026

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Quick Summary

Highly sought-after position that requires a unique blend of technical expertise and business acumen.

Job Description

🌍 Global SaaS Company | $28M Series B Investment
📍 Barcelona/Toronto | Vibrant International Team
💡1:1 Coaching sessions with our resident coach

About CloudTalk

Powered by a 2024 $28 million Series B investment from top investors like KPN Ventures, Lead Ventures, Point 9, and HenQ, CloudTalk's AI-powered business communication platform helps 4,000+ sales and support teams make customer experience the greatest competitive advantage for driving more revenue.

CloudTalk works seamlessly for businesses of all sizes, from scale-ups like Deel and TIER to big players like Nokia and Rakuten. Modern businesses all around the world can lead meaningful conversations while managing calls and messages from one place.

CloudTalk is on a mission to create a unified ecosystem for sales and customer service teams' communication where every professional can engage in more productive and meaningful conversations.

The Challenge Ahead

We are looking for a metric and results-driven Head of Customer Success to lead our global Customer Success team. This individual will be responsible for managing and guiding a team of 11+ Customer Success Managers with the primary goal of retaining and expanding our managed portfolio, hitting quarterly Net Revenue Retention targets.

This role will report to the CMO.

What’s in it for you:

• Product: Be part of building the 🤖 #1 AI business calling software and have a front-row seat for CloudTalk’s journey to 🚀 $100m ARR!
• Driving Seat: Take the lead in shaping the future of our Customer Success organization at a rapidly growing tech company - and make an immediate impact with direct influence on our growth trajectory.
• Meaningful change: Join the team during scale-time, drive meaningful change and transform the function from a small team to structured organization

What you will work on:

• Playbook: Own post-sale lifecycle: onboarding, adoption and retention. Continuously refine the CloudTalk success playbook and ensure CSMs are coached and supported to execute it effectively. It’s not just about systems, it’s about enabling the team to deliver customer impact with consistency and confidence. Ensure structured handovers, onboardings, QBRs are rigorously executed. Leverage customer health scoring and feedback loops to identify risk and expansion signals.
• Team: Recruit, coach, and engage a team of CSMs who are proactive, consultative, and accountable. Foster a culture of ownership, precision, and CSM excellence. Coach team members not just to deliver, but to raise the bar, uplifting peer performance through feedback, shared standards, and continuous improvement. Build a high-impact team by developing others, not just driving your own initiatives.
• Enablement: Equip CSMs with the enablement they need to consistently deliver high-quality service, including practical training, clear documentation, and performance guidance. Focus on helping the team improve execution and customer value delivery. Use automation and tooling where it clearly supports performance uplift and frees time for higher-impact work.
• Collaboration: Work closely with Product, Sales, and Marketing to close the feedback loop, deliver voice of customer insights, and align around lifecycle stages and revenue expansion

What makes you a great fit:

• Proven experience in high-volume/high-velocity Customer Success or Account Management, with at least 2 years in a leadership role.
• Demonstrated track record of meeting or exceeding customer retention, expansion, and NRR growth targets in a SaaS environment.
• Strong leadership and team management skills, with experience leading teams of 5+ high-performing members. Proven ability to develop CSMs, helping individuals level up in execution, product fluency, and customer impact. You don’t just hit targets; you build teams that do.
• Proficiency in dashboard management and data-driven performance improvement. Passion for continuous improvement and operational efficiency.
• Excellent communication, negotiation, and relationship-building skills.
• Experience with CRM and Customer Success tools (e.g., HubSpot, Salesforce, Custify, Gainsight, ChurnZero).

Why you will love to be a CloudTalker:

Growth:
💡 1-1 Coaching sessions with our resident communications advisor
📚 Leaders Academy & Learning and Development Budget

Flexibility:

🏖 Unlimited Paid Time Off
🎗️ Volunteering Days
⏳ Flexible working hours
🤩 Home office budget
💻 MacBook for work

Well-being:
🏖Recharge Fridays once per quarter
🏋🏼‍♀️Fitness Allowance

Connectedness:
💲 Referral bonuses
👥 Virtual & physical team buildings
👕 Company merchandise

What to expect from our hiring process:

1️⃣ Initial Chat: Interview with our Talent Acquisition team
2️⃣ Role Deep Dive: Meet David, our CMO
3️⃣ Case Interview: Showcase your expertise in a practical task
4️⃣ Culture Bar Raiser Call – Explore your potential to raise the bar in adaptability, ownership, and continuous improvement
🎯 Offer!

By submitting your application, you acknowledge that Cloudtalk will process your personal data based on Cloudtalk’s legitimate interest in finding the most suitable candidate and a pre-contractual relationship with you. For more information on how Cloudtalk processes your personal data, please refer to our Privacy Notice.

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