Chief of Staff, GTM

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 https://www.theglobeandmail.com/business/rob-magazine/top-growing-companies/article-ranking-canadas-top-growing-companies-of-2024/ and top-rated startups in 2025 https://www.linkedin.com/posts/floatfinancial_were-proud-to-share-that-float-has-been-activity-7387093684720300032-2DDz/, 2024 https://www.linkedin.com/pulse/linkedin-top-startups-2024-15-canadian-companies-rise-linkedin-news-llihe/ and 2023 https://lnkd.in/TSU23CA, Float is customer-obsessed, passionate and entrepreneurial, with a team that includes leaders from Uber, Stripe, Shopify, Top Hat, 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 intelligent financial operating system, combining modern financial services and software to help businesses spend, save, and grow. Trusted by more than 7,500 Canadian companies, Float provides high-limit corporate cards, automated expense management, next-day bill payments, high-yield accounts, and industry-leading support, all built in Canada, for Canada. Float recently announced our $85 million Series C https://floatfinancial.com/press/float-financial-raises-cad-85-million-series-c, and is backed by world-class investors, including Inovia Capital, Growth Equity at Goldman Sachs Alternatives, OMERS Ventures, and Silicon Valley Bank. 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 hiring a Chief of Staff to work directly with Nina https://www.linkedin.com/in/ninabilimoriaangelo/, Float’s SVP, Go-to-Market, as her closest strategic partner. This is a builder's seat: you'll shape the GTM operating model, the cross-functional handoffs, and the way priorities get set and tracked rather than stepping into an established playbook. You'll move fluidly between big-picture strategy work and hands-on execution, sometimes in the same afternoon: shaping the quarterly GTM narrative for the leadership team one day, driving cross-functional initiatives the next. WHAT YOU'LL BE RESPONSIBLE FOR - Owning the GTM operating rhythm: business reviews, OKR tracking, and leadership/board-ready reporting. - Bridge strategy and execution across Product and GTM, ensuring cross-functional priorities translate into coordinated action and measurable outcomes. - Own and maintain single sources of truth, ensuring key information is accurate, actionable, and surfaced to the right stakeholders at the right cadence. - Turning ambiguous priorities into structured plans with clear owners and timelines. - Driving cross-functional initiatives that span Sales, Marketing, Partnerships, and Customer Success, the ones that don't sit neatly under any one functional leader. - Helping connect strategy and execution between Product & GTM. - Acting as a trusted thought partner and occasional filter, helping the SVP focus time and energy on what matters most. - Representing the SVP in rooms she can't be in, with enough context to make sound calls in real time. - Helping build the GTM org itself as it scales: interview processes, onboarding, team rituals and everything in between. ABOUT YOU In a nutshell, you're an activator. You instinctively know where momentum is needed, bring the right people together, and facilitate the conversations that turn ambiguity into clarity and ideas into execution. You're a trusted thought partner who helps leaders move faster and make better decisions. YOU BRING: - 5+ years of experience, ideally combining management consulting (strategy or operations) with hands-on operating experience in a GTM function such as Sales, Marketing, Revenue Operations, or Business Operations. - Experience at a top-tier technology company or fintech, with a strong understanding of how GTM strategy and execution differ in regulated, trust-driven markets. - Based in Toronto and excited to work closely, in person, with the SVP and leadership team. - Highly analytical and comfortable working with data, but focused on using insights to drive decisions and action, not just build dashboards. - Exceptional at bringing structure to ambiguity, with a proven track record of taking loosely defined problems and translating them into clear plans with measurable outcomes. - An outstanding communicator who can seamlessly shift between writing board-ready narratives, executive briefs, and concise updates that drive alignment. - AI-forward and relentlessly curious. You continuously improve the way you work, leverage AI to accelerate execution, and champion practical AI adoption to help the broader team become more effective. - Thrive in high-growth environments where priorities evolve quickly, and you're energized by solving the company's most important problems, regardless of whether they're inside or outside your formal remit. THIS MAY NOT BE THE ROLE FOR YOU IF: - You want a well-defined lane - this role's scope shifts with whatever the business needs most. - You need heavy structure or precedent to operate. There's no existing Chief of Staff playbook here to inherit. - You're looking for an EA or project-coordinator role, this isn’t it. 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 https://www.linkedin.com/in/victoria-boult-b21b2053/ (victoria@floatfinancial.com), and we’ll work with you to make sure you have what you need to succeed.