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

Olive Fintech; Banff; Remote; CAD 60,000 - 85,000; Full time

Job summary

Olive Fintech is looking for a Customer Success Account Manager to oversee and expand key B2B relationships. You will manage client experiences from onboarding through technical support, aiming for high retention and satisfaction. This role requires a balance of technical prowess and client leadership, contributing to the growth and success of both clients and Olive.

Qualifications

• Experience: 3-5 years in Customer Success or Account Management.
• Track record managing B2B accounts valued at $150K+.
• Comfortable understanding APIs and fintech integrations.

Responsibilities

• Own mid-market and enterprise relationships end-to-end.
• Lead successful client onboarding within 30 days.
• Drive adoption of platform features, ensuring client engagement.

Skills

Communication Excellence

Analytical Mindset

Client-Focused Leadership

Strategic Problem-Solving

Technical Expertise

Tools

HubSpot

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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