Customer Success / Account Manager (Mid-Market & Enterprise)

Olive Fintech; Regina; Remote; CAD 70,000 - 100,000; Full time

Job summary

A fast-growing fintech startup seeks a Customer Success Account Manager to manage mid-market and enterprise relationships. In this role, you'll drive client success through onboarding, engagement, and technical support, ensuring a high retention rate for key accounts. If you thrive in a dynamic environment and excel in building client relationships, this is your opportunity to shape customer loyalty in the fintech sector.

Qualifications

• 3-5 years in Customer Success, Account Management, or related client-facing roles.
• Experience managing B2B accounts valued at $150K+ annually.

Responsibilities

• Manage and expand a portfolio of $150K - $300K ARR B2B accounts.
• Lead successful client onboarding and ensure smooth product implementation.

Skills

Analytical Mindset

Client-Focused Leadership

Communication Excellence

Strategic Problem-Solving

Technical Expertise

Tools

CRM tools (HubSpot)

Project Management tools (Jira, Slack)

Job description

At Olive, we believe everyday spending should build deeper, more meaningful relationships between businesses and their customers. Our white-label platform powers rewards, charitable rounding, and card-linked offers that feel both personal and purposeful - enabling financial institutions, fintechs, and retailers to create loyalty experiences within their own ecosystems.

As a fast-growing startup, we move quickly, iterate often, and value progress over perfection. We’re building a team of people who thrive in ambiguity, take ownership, and care deeply about making an impact. We operate remotely, with a culture rooted in flexibility, feedback, and a shared commitment to excellence.

The Customer Success (Account Manager) role is core to our growth. You’ll own mid-market and enterprise relationships end-to-end - from onboarding and adoption to long-term success. Acting as a strategic partner, technical translator, and client advocate, your work will directly influence how Olive delivers measurable outcomes for some of our most valuable clients.

What Success Looks Like at Olive :

• Manage and expand a portfolio of $150K - $300K ARR B2B accounts, achieving a retention rate of 90% or higher.
• Lead successful client onboarding and ensure smooth product implementation within 30 days of contract execution.
• Confidently translate client needs into platform capabilities, troubleshooting and resolving technical issues in partnership within the product and engineering teams.
• Drive adoption of key platform features, ensuring at least 80% of clients actively engage with the full suite of offerings.
• Identify and capture expansion opportunities , increasing the average customer value by 10-15% across the portfolio.
• Provide actionable insights to the product and development teams based on client feedback, contributing to the continuous improvement of the Olive platform,
• Experience : 3-5 years in Customer Success, Account Management, or related client-facting roles, with a proven track record of managing B2B accounts valued at $150K+ annually.
• Technical Expertise : You have the ability to understand the Olive platform deeply, onboard clients effectively, and troubleshoot technical challenges that arise. You should feel comfortable working with APIs, card-linked reward systems, and other fintech integrations.
• Client-Focused Leadership : You’re able to balance client priorities with business goals, acting as a trusted advisor while driving business outcomes
• Analytical Mindset : Ability to analyze usage patterns and data to make informed decisions and improve client performance
• Strategic Problem-Solving : You excel at identifying client pain points and translating them into actionable solutions that drive both short-term and long-term success.
• Communication Excellence : You possess exceptional written and verbal communication skills, with the ability to influence stakeholders at all levels, including executives
• Operational Expertise : Comfortable using CRM and project management tools such as HubSpot, Jira, and Slack to manage client interactions and internal workflows.
• Bonus : Experience in fintech, loyalty programs, payments, or regulated environments is a plus

Ready to leverage your technical expertise and customer service experience to help shape the future of customer loyalty? Apply now and build with us.

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