Head of Canada Telesales

Since we opened our doors in 2009 the world of commerce has evolved immensely and so has Square. After enabling anyone to take payments and never miss a sale we saw sellers stymied by disparate outmoded products and tools that wouldnt work together. So we expanded into software and started building integrated omnichannel solutions to help sellers sell online manage inventory offer buy now pay later functionality book appointments engage buyers and hire and pay staff. Across it all weve embedded financial services tools at the point of sale so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth enabling sellers to capture the next generation shopper increase order sizes and compete at a larger scale. Today we are a partner to sellers of all sizes large enterprise-scale businesses with complex operations sellers just starting as well as merchants who began selling with Square and have grown larger over time. As our sellers grow so do our solutions. There is a massive opportunity in front of us. Were building a significant meaningful and lasting business and we are helping sellers worldwide do the same. The Role Squares mission is to empower businesses of all sizes to start run and grow. As we continue to strengthen our presence in Canada were seeking an experienced strategic and people-focused sales leader to serve as Head of Canada Sales for our SMB and Mid-Market segments. In this role you will join Squares GlobalSales leadership team shaping how we go to market across Canadas key business segments. Youll collaborate cross-functionally to drive revenue growth expand market share and build a scalable high-performing sales organization that consistently exceeds targets. You will report to the Global Head of Sales for Square. You Will Develop and lead the sales strategy for Canada defining goals operating plans and success metrics across SMB and Mid-Market segments. Oversee and support a multi-layered team of Sales Managers and Account Executives ensuring effective leadership coaching and execution across all levels. Drive consistent performance and accountability ensuring strong pipeline health quota attainment and revenue delivery. Attract develop and retain diverse talent building an inclusive and high-engagement culture grounded in collaboration and shared success. Implement scalable processes and operating rhythms that make performance measurable repeatable and sustainable. Collaborate cross-functionally with Marketing Product Finance Sales Operations and Customer Success to align strategies and remove obstacles to growth. Partner with Sales Operations and Finance to enhance forecasting accuracy compensation design and resource allocation. Refine and expand inbound and outbound sales motions leveraging insights and data to continuously improve productivity and effectiveness. Represent the voice of customers and field teams sharing insights that inform product direction and go-to-market strategy. Model Squares values and culture fostering inclusion transparency and integrity while driving strong business results. You Have 8 years of B2B sales experience within technology or financial services with a strong record of meeting or exceeding targets. 3 years of leadership experience managing multi-layered teams including both Sales Managers and Account Executives. Proven success in developing and executing sales strategies that drive measurable growth and customer impact. Experience building and scaling sales processes that enable consistent execution in dynamic high-growth environments. Strong commercial and analytical skills with the ability to set meaningful KPIs analyze performance and act decisively. Demonstrated cross-functional influence aligning stakeholders across Product Marketing Finance and Operations toward shared outcomes. A balanced leadership style that combines strategic vision operational discipline and empathy. A deep commitment to supporting Canadian SMB and Mid-Market businesses and advancing Squares mission to help them grow. Why Youll Love Working Here Impact : Youll shape the future of Square in one of our most exciting and strategic growth markets directly influencing how we serve Canadian businesses. Growth : Youll operate in a fast-paced high-growth environment with significant opportunity to scale the business develop new sales motions and hone your leadership. Culture : Youll join a diverse inclusive and mission-driven team that values bold ideas transparency and continuous learningwhere your contributions will make a tangible difference to our sellers and our business. Were working to build a more inclusive economy where our customers have equal access to opportunity and we strive to live by these same values in building our workplace. Block is an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We also consider qualified applicants with criminal histories for employment on our team and always assess candidates on an individualized believe in being fair and are committed to an inclusive interview experience including providing reasonable accommodations throughout the recruitment process. If you require an accommodation let your recruiter know. Want to learn more about what were doing to build an inclusive workplace Check out our Inclusion & Diversity page . #J-18808-Ljbffr