Head of Customer Success

About Float

Float is on a mission to simplify finance for Canadian businesses, empowering them to eliminate complexity and unlock new opportunities. Through our innovative platform, Float enables businesses to streamline financial operations and optimize cash flow, so they can focus on what matters most: growth. 

As one of Canada’s fastest growing companies and top-rated startups in 2025 , 2024 and 2023 , Float is customer-obsessed, passionate and entrepreneurial, with a team that includes leaders from Uber, Stripe, Shopify, Top Hat, BILL, Ada, Doordash, Snowflake, and Wealthsimple.

At Float, everyone is an owner, bringing their unique perspective to our team and product. Your voice is important, and we take having a culture based on feedback seriously. We openly share our thoughts and differing opinions so we can continue to improve. We do our best to keep our decision-making decentralized so that all team members feel ownership in our success.

Our Product

Float is Canada's complete business finance platform, combining modern financial services and software to help businesses spend, save, and grow. Trusted by 6000+ Canadian companies, Float provides high-limit corporate cards, automated expense management, next-day bill payments, high-yield accounts and fast, friendly support—all built in Canada, for Canada. Float is backed by world-class venture and fintech investors, including Growth Equity at Goldman Sachs Alternatives and OMERS Ventures, partners behind our $70 million Series B raise . 

Our team is a collection of ambitious, collaborative and mission-driven people from all walks of life but with one goal: helping Canadian companies not just survive but thrive. And we’re looking for bold innovators to help shape the future of business finance in Canada.

AI Use in Our Hiring Process

We use technology, including artificial intelligence (AI), to support parts of our hiring process. This may include AI-assisted scheduling and candidate communications, and AI-generated interview notes, guides or summaries to help our team focus on the conversation. All hiring decisions are made by our hiring team.

About the Role

We’re looking for a Head of Customer Success to join Float and be a part of a team building the best corporate card and spend management platform in Canada. As Head of Customer Success, you will be responsible for overseeing our Customer Success strategy to enhance our onboarding processes, increase Total Payment Volume (TPV) from existing customers, and create recurring and predictable post-sale revenue. Your work will be instrumental in building and reshaping our post-sales organization, with a focus on strategy execution, team leadership, customer journey mapping, and playbook development.

As the Customer Success Leader at Float, you will be responsible for:

1. Strategy Execution & Commercial Ownership: Execute and evolve Customer Success strategies that drive Net Revenue Retention through TPV growth , multi-product adoption, and long-term customer retention. Own the post-sale commercial motion , including renewals, expansions, and multi-product attach, in close partnership with Sales and RevOps. Ensure Customer Success directly contributes to revenue outcomes and predictable growth.

2. Customer Growth, Retention & Adoption: Oversee the growth of key customer metrics, including spend penetration, incremental revenue, retention, and expansion . Drive increased adoption of core and emerging products (e.g., Prefunded Cards, Charge Card, USD, Yield Accounts, Reimbursements, and future offerings). Retain and expand key accounts through first-class service, proactive risk management, and strategic value realization.

3. Voice of the Customer & Product Influence: Serve as the voice of the customer across the organization.

   • Systematically collate, analyze, and synthesize customer feedback, requirements, and objections across segments.

   • Translate individual CSM insights into strategic, data-backed themes that inform product prioritization, roadmap decisions, and go-to-market strategy.

   • Partner closely with Product and Engineering to ensure customer needs are clearly articulated, prioritized, and reflected in product evolution.

4. Operational Excellence & Scalable Playbooks: Design, own, and continuously improve post-sale playbooks that support efficient service across high-touch, mid-touch, and low-touch customer segments.

   • Ensure playbooks are maintained, measurable, and usable for onboarding, training, and performance management.

   • Identify and operationalize revenue opportunities for professional services and value-added engagements within Customer Success.

   • Systematize best practices and own functional requirements for CS tools, systems, and workflows to enable scale and consistency.

5. Talent Leadership & Team Development: Recruit, develop, and lead a high-performing Customer Success team . Foster a culture of ownership, urgency, continuous improvement, and measurable business impact. Build strong managers and ICs who can operate strategically with customers while executing consistently at scale.

6. Capacity Planning & Resource Management: Own CS capacity planning in line with customer growth, segmentation, and service expectations. Forecast resource needs, model coverage scenarios, and proactively advocate for additional headcount or tooling where required to maintain customer experience and commercial outcomes.

7. Cross-Functional Leadership & Alignment: Act as a senior cross-functional leader, collaborating with Product, Engineering, Marketing, Sales, and Finance to align on customer insights, product improvements, and growth initiatives. Ensure Customer Success is a proactive partner in shaping company strategy, not just a downstream executor.

About You

Here’s what sets you up for success at Float:

• You Put Customers First, Always. You care deeply about delivering meaningful value. Whether you're building internal systems or customer-facing features, you're always thinking about how to make life better for our users.

• You Act Like an Owner. You take responsibility for outcomes, step up to challenges, and seek solutions proactively—doing what’s best for the business, not just your role.

• You Think Big and Move Fast. You’re energized by building from 0 to 1. You’re not afraid to challenge the status quo, experiment quickly, and learn as you go.

• You Constantly Learn and Grow. You’re hungry to improve your craft and open to feedback. You bring a growth mindset to everything you do.

• You Raise the Bar. You care about doing things well and efficiently. You balance speed with rigor and always look for ways to improve how we work.

• You Win as a Team. You’re a generous collaborator who values communication, context, and shared wins. You lift others up and help make the team stronger.

In addition to living our values...

• You’ve got the experience. To be successful in this role, we’re looking for 7+ years of leadership experience in Customer Success, Account Management, and Implementation within the startup, B2B, and/or fintech sectors. A deep understanding of financial services and accounting platforms is preferred.

• You’re an outstanding leader. You’re an adept leader known for starting from scratch, driving significant process changes, and building highly effective teams.

• Customer Obsession. You have a proven track record of exceeding customer expectations and fostering long-term relationships.

• You’re results-driven: You are known for setting ambitious goals and achieving them, managing priorities and deadlines effectively.

• You’re analytical and data driven. You leverage tools and data to inform strategies, understanding customer needs, market trends, and growth opportunities. You are comfortable preparing your own reports and love analyzing data to find insights.

• You’re proactive and collaborative. You excel in cross-functional environments, driving innovation and improvements through effective collaboration and strategic thinking. Your ability to collaborate effectively across different departments stands out. You bridge the gap between customer success, sales, marketing, and product teams, ensuring a constant feedback loop about what our customers think about our product.

This may not be the role for you if:

• You aren’t ready to be a player-coach

• You aren’t comfortable using data to make decisions

• You don’t have a track record of exceeding your targets

• You haven’t built high-performing teams

• You aren’t resilient

• ​​You don’t love coaching and helping your team grow

• You aren’t comfortable with radical candor

• You aren’t resilient

• You have an ego

• You aren’t super passionate about helping Float build the best financial management platform in Canada

Why You Should Join

• Work at one of Canada's fastest-growing fintech companies

• Make a real impact in a high-autonomy, high-growth role

• Collaborate with an ambitious and supportive team

• Competitive compensation, equity options, and benefits

• Hybrid work model – we are based in Toronto with in-office days for connection and collaboration

• Enjoy catered team lunches every Tuesday, Wednesday and Thursday

• Bring your pup to our dog-friendly office

• Thrive in a high-trust, high-performance culture where your work truly matters

In Short

At Float, you’ll thrive if you’re bold, curious, and eager to make a real impact. We're building something special—and having a lot of fun along the way. If you’re excited to build, grow, and win together, we’d love to meet you.

We’re committed to building a workplace that’s welcoming and accessible for everyone. If you need any accommodations during the hiring process or once you join Float, just let us know! You can reach out to Vic ( View email address on jobs.jobcopilot.com ), and we’ll work with you to make sure you have what you need to succeed.