Job Title

Who We Are FlexPay is the first to market and global leader in failed payment recovery. Our outstanding success is built upon a solid foundation of exceptional culture, adherence to our values, and an innovative AI-driven approach to solving this trillion-dollar problem. FlexPay helps subscription businesses accelerate revenue and profit growth by recovering failed payments, which is the single largest cause of customer churn. Were a maturing, institution-backed Fintech SaaS, solving one of the biggest problems faced by merchants. The veteran management team of serial entrepreneurs is supported by a board filled with industry leaders. Our ambition is to redefine payments and in doing so become more than just the next great unicorn, but to become a key element of the infrastructure that makes our worlds economy hum. Were a dynamic, welcoming company that strives to hire the best and brightest people. If you are looking for a place to invest your passion, then keep reading! What The Role Looks Like FlexPay is seeking a seasoned Senior Client Success Manager to own a strategic portfolio of mid-market and enterprise clients. This is a senior-level individual contributor role with direct responsibility for client retention, expansion, and advocacy. Youll serve as the primary driver of long-term client value, deeply integrating into client business strategies and acting as a trusted advisor who brings insights, challenges assumptions, and delivers measurable outcomes. The ideal candidate is an experienced CSM with strong analytical acumen, executive presence, and the ability to manage complex, multi-threaded relationships. Youre as comfortable discussing KPI models and payment recovery strategy with a CFO as you are collaborating with product managers on feature prioritization. Key Responsibilities: Strategic Account Ownership Serve as the strategic owner of a portfolio of high-value accounts across mid-market and enterprise tiers. Lead executive relationships, including with VP, CFO, and CRO stakeholders. Proactively guide clients through payment performance optimization and growth strategies using FlexPay solutions. Drive multi-threaded engagement across technical, financial, and operational personas. Value Reselling & Strategic Alignment Consistently articulate and reinforce FlexPays business value across client touchpoints. Connect product performance to evolving client goals, reframing FlexPays impact as needs shift. Drive alignment on strategic outcomes by continuously mapping FlexPay solutions to client metrics and priorities. Position new features, product enhancements, or modules as solutions to emerging client challenges. Client Growth & Advocacy Identify and pursue opportunities to expand product adoption across all FlexPay products. Translate client successes into advocacy - facilitating testimonials, case studies, references, and event participation. Partner with Marketing and Revenue teams to amplify client stories and build social proof. Risk & Churn Mitigation Leverage health scoring models and behavioral insights to detect early warning signs. Build and execute tailored success plans and retention plays. Lead cross-functional client reviews to ensure alignment, mitigation, and accountability. Insight-Driven Engagement Use internal data (e.g., approval rates, retry patterns, LTV impact) to fuel recommendations and influence client strategy. Contribute to the evolution of FlexPays client health frameworks, segmentation models, and value realization frameworks. Generate reporting and narrative that links FlexPay performance to client KPIs and ROI. Operational Rigor Own the creation and facilitation of business reviews, that are deeply analytical, forward-looking, and outcome oriented. Maintain accurate account documentation and forecasting across CS platforms (Salesforce, PlanHat, etc.). Ensure coordinated success efforts with internal partners (Product, Support, RevOps, Sales Engineering). Voice of Client Leadership Escalate trends in product usage, technical barriers, or unmet needs that impact client outcomes. Collaborate with Product to refine roadmaps and articulate the why behind client requests. Provide input into CS team playbooks, standard methodologies, and client lifecycle programs. What Were Looking For 5-7+ years of experience in a client success, account management, or strategic consulting role, preferably in a B2B SaaS or Fintech environment. Proven success managing a complex book of business with revenue and retention accountability. Strong financial and analytical fluency capable of translating product performance into client ROI. Skilled at navigating multi-stakeholder environments, aligning diverse goals, and driving action. Excellent communication, storytelling, and influence skills across functions and seniority levels. Self-directed with strong time management and prioritization abilities. A mindset of curiosity toward AI, a demonstrated willingness to experiment with it, and an ability to think strategically about how AI can amplify their work Highly collaborative and enjoys a fun, social, and fully remote work environment. Able to travel within Canada and the US. Nice to Have (but not a deal-breaker if you don''''t) Experience with payments, declines, or recurring billing ecosystems. Familiarity with customer success platforms (Planhat, Gainsight) and CRM systems (Salesforce). Experience working with behavioral-driven or machine learning powered products. What We Offer Were a quickly growing global company committed to building a team filled with diverse cultures, viewpoints, and experiences. As they say, variety is the spice of life. No matter how large we become, we will always be connected through our shared sense of community and slightly quirky personalities. Our vibrant culture is filled with talented, creative, deeply curious, high achievers. We believe in and invest in our people because we know they are the secret to our success. We are happy to extend the following benefits to our employees: Unlimited paid time off 100% remote work Flexible hours Comprehensive health benefits package effective from day one Support for continuous learning and development. FlexPay is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, colour, religion, sex, sexual orientation, gender identity, national origin, disability, or any other characteristic protected by law. Accommodation is available upon request for applicants with disabilities.