Customer Success Lead (SMB)

2 Berkeley Street, Toronto, Ontario, Canada, M5A 4J6

full-time . January 13, 2026

Description

At Chexy, we’re reshaping the way money moves—making payments smarter, faster, and more rewarding.

We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we’re on a much bigger mission: to build a super app that acts as your co-pilot for all your money—helping you get more value from every dollar you spend.

As a high-growth fintech startup, we’re at the forefront of payments innovation, and we’re looking for hungry, ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we’d love to work with you.

About this role

We’re looking for an experienced, relationship-driven Customer Success Lead (SMB) to own the end-to-end experience for our Small & Medium Business (SMB) customers. In this role you will provide high-touch, high-quality support and success for our SMB customers—primarily via email and Intercom — while building the SMB customer success “program” (playbooks, workflows, and standards) so the experience is consistent as we grow. You will partner closely with our Growth/Sales team to ensure new SMB clients are onboarded smoothly and set up for long-term success.

What You’ll Do

SMB Customer Ownership & Relationship Management

• Own a portfolio of SMB customers as their primary post-sale point of contact.
• Build trusted relationships with SMB decision-makers and operators through proactive communication, check-ins, and thoughtful follow-through.
• Ensure customers have a consistently excellent experience across onboarding, payments/operations, and ongoing support.

SMB Onboarding (Partnering with Growth/Sales)

• Work closely with Growth/Sales to ensure a clean handoff and a strong “first 30 days” experience for every new SMB client.
• Run onboarding kickoffs, collect requirements, align on timelines, and set expectations.
• Coordinate internally to unblock onboarding (product, engineering, operations, risk/fraud, etc.) and drive customers to first value quickly.
• Maintain/iterate an SMB onboarding checklist and standard onboarding communications.

High-Touch SMB Support & Escalations

• Respond to SMB inquiries via email and our CX platform (encouraging fast, high-quality resolutions).
• Troubleshoot issues end-to-end: clarify needs, identify root causes, coordinate fixes, and close the loop.
• Handle escalations with calm urgency—keeping customers informed while mobilizing internal teams.

Build the SMB Customer Success Program (Process + Quality)

• Design and document SMB-specific success workflows and standards (SOPs, macros, templates, SLAs, escalation paths).
• Create/maintain customer-facing and internal documentation: help articles, FAQs, onboarding guides, playbooks.
• Identify recurring SMB issues and drive continuous improvement through better process, automation, and product feedback.
• Improve how our chatbot-first CX operation supports SMBs (e.g., routing rules, escalation triggers, internal handoff protocols).

What We’re Looking For

• 3+ years of experience in Customer Success, Account Management, Implementation, or high-touch Support serving SMB customers (fintech/payments or SaaS experience is a plus).
• Proven ability to manage customer relationships with excellent written communication (email is a core channel for this role).
• Strong troubleshooting and problem-solving skills—you can navigate ambiguity, investigate issues, and coordinate cross-functionally.
• Process-minded and organized: you enjoy building playbooks, improving workflows, and making things repeatable.
• Comfortable working closely with a Growth/Sales team to deliver a great onboarding experience and smooth handoffs (without being responsible for upsells).
• Tech-savvy: comfortable learning tools quickly and working in platforms like Intercom (or similar), Notion, Slack, and Google Suite.
• This role is fully in-office 5 days a week .

Nice to Have

• Experience at an early-stage or fast-growing startup
• Experience at a fintech or a B2C SaaS company
• Familiarity with payment products (card issuing, money transfers, credit, etc.)