Head of Customer Success & Support

Jobgether; Canada; Remote; CAD 150,000 - 210,000; Full time

Benefits offered by this job

Fully remote opportunity

Long-term contractor-informed growth

Job summary

Jobgether is seeking a hands-on Head of Customer Success & Support based in Canada to build and scale post-sale relationships for a growing B2B SaaS marketplace. You will lead a small team, own key enterprise relationships, and manage escalations while collaborating with Sales, Product, and Engineering to drive adoption, retention, and revenue growth.

In this role you will establish playbooks, SLAs, and metrics, lead quarterly reviews, and champion customer-centric improvements.

Qualifications

• 6+ years in CS or Account Management, including 3+ years with enterprise accounts.
• Proven in leading a team while managing strategic relationships.
• Experience building/scaling CS or Support in startups.
• Comfort communicating with C-suite and senior leaders.
• Experience handling complex escalations across departments.
• Familiarity with vendor risk, procurement, and renewal cycles.
• Commercial acumen for renewals and expansions.
• Data-driven approach using account health indicators.
• Proven ability to balance strategy with day-to-day needs.
• Availability for full-time with overlap with US Eastern hours.

Responsibilities

• Manage strategic accounts across enterprise organizations, financial institutions, and vendor partners.
• Lead and develop a small CS and Support team while owning key relationships.
• Build onboarding playbooks, SLAs, escalation paths, and ticketing workflows.
• Establish account health scoring and reporting for adoption and renewal risk.
• Collaborate with Sales on renewals, pricing, and expansion opportunities.
• Lead quarterly business reviews and impact reviews.
• Conduct vendor performance reviews to strengthen marketplace participation.
• Own customer escalations and coordinate cross-team resolutions.
• Support customers through security reviews, procurement, and contracts.
• Provide feedback to Product/Engineering for platform improvements.
• Utilize CRM and support platforms, plus AI tools to scale operations.
• Define success measures and standard operating processes within 90 days.
• Drive first-year outcomes including net revenue retention targets.

Skills

Executive communication

Team leadership

Customer success

Renewals & expansions

Vendor management

Data-driven decisions

Cross-functional collaboration

Tools

Attio

Intercom

Job description

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Head of Customer Success & Support based in Canada.

We are seeking a hands-on customer success leader to build and scale the customer relationships and support operations behind a growing B2B SaaS marketplace. In this role, you will oversee the full post-sale customer journey, managing strategic relationships across enterprise organizations, financial institutions, and vendor partners. You will lead a small team while remaining directly involved in key accounts, escalations, and commercial discussions. You will establish the processes, service standards, and account health metrics that drive adoption, customer satisfaction, and long-term retention. Working closely with leadership, Sales, Product, and Engineering, you will help turn customer insights into measurable business improvements. This is a long-term opportunity to shape a growing function, take ownership, and develop alongside the business.

Accountabilities

• Personally manage strategic accounts across enterprise organizations, financial institutions, and vendor partners, building trusted relationships with senior stakeholders.

• Lead, hire, coach, and develop a small Customer Success and Support team while maintaining direct ownership of key customer relationships.

• Build and improve customer success and support operations, including onboarding playbooks, service level agreements, escalation paths, and ticketing workflows.

• Establish account health scoring and reporting to monitor adoption, engagement, customer value, and renewal risk.

• Identify renewal risks at least 120 days in advance and coordinate proactive mitigation plans with Sales.

• Partner with Sales on renewals, pricing discussions, and account expansion opportunities.

• Lead quarterly business reviews and impact reviews, demonstrating the value delivered to community partners.

• Conduct vendor performance reviews to assess outcomes and strengthen marketplace participation.

• Own customer escalations and coordinate timely, effective resolutions across internal teams.

• Support customers through enterprise security reviews, vendor risk assessments, procurement requirements, and contract cycles.

• Bring actionable customer and vendor feedback to Product and Engineering to inform platform improvements.

• Use CRM systems, support platforms, and AI tools to improve service consistency, operational efficiency, and the team's ability to scale.

• Establish clear success measures and operating processes, with core customer success workflows and service level agreements in place within the first 90 days.

• Drive first-year outcomes including account health scoring across the customer base, achievement of agreed net revenue retention targets, and early identification of strategic account and vendor risks.

Requirements:

• At least 6 years of experience in Customer Success or Account Management, including a minimum of 3 years managing enterprise accounts.

• Demonstrated experience leading a team while personally managing strategic customer relationships.

• Proven track record of building, improving, or scaling a Customer Success or Support function in a startup environment.

• Confidence communicating with C-suite executives, managing directors, and other senior decision-makers.

• Strong experience managing complex customer escalations and coordinating solutions across multiple departments.

• Familiarity with enterprise security reviews, vendor risk assessments, procurement processes, and contract and renewal cycles.

• Commercial acumen and experience contributing to renewal, pricing, and expansion conversations.

• Ability to use customer data and account health indicators to identify risks, prioritize action, and improve retention.

• Proficiency with CRM and customer support platforms such as Attio and Intercom, as well as practical experience using AI to scale support operations.

• Strong leadership, communication, relationship management, and problem-solving skills.

• A hands-on, structured approach, with the ability to balance strategic planning, team development, and day-to-day customer needs.

• Availability for a full-time commitment with substantial overlap with US Eastern business hours.

• Nice to have: Experience in financial services or fintech, supporting banks or investment firms, managing enterprise partner programs, or working with marketplaces serving both community partners and vendors.

• Additional advantage: An established network within the venture capital or private equity ecosystem.

Benefits:

• Fully remote opportunity, open to candidates anywhere in the United States or Canada.

• Long-term, full-time growth opportunity structured through a contractor agreement.

• Direct collaboration with company leadership and cross-functional teams, including Sales, Product, and Engineering.

• Ownership of strategic customer relationships and the overall Customer Success and Support operating model.

• Opportunity to lead, develop, and grow a small team.

• Significant influence over customer onboarding, support processes, account health measurement, renewals, and expansion strategy.

• Opportunity to grow with a scaling SaaS business and make a measurable impact on customer retention and revenue.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Data Privacy Notice:

By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

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