<p>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 wouldn’t work together.<br><br>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 loyal buyers, and hire and pay staff. Across it all, we’ve 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.<br><br>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. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.</p>
<h4><strong>The Role</strong></h4>
<p>At Square, we’re re-imagining how mid-market businesses grow. As a <strong>Senior Sales Account Executive</strong> on our Mid-Market Team, you’ll bring Square’s ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You’ll run sophisticated, multi-product deals from the first touch to final close — blending hunter instincts, consultative depth, and strategic execution.</p>
<p>If you’re an experienced closer who thrives in outbound environments, loves solving meaningful business challenges, and consistently delivers against ambitious targets — this is your role.</p>
<h4><strong>You Will</strong></h4>
<ul>
<li><strong>Own the full outbound sales cycle</strong> — from prospecting to negotiation to close — with mid-market merchants.</li>
<li><strong>Build and manage a high-quality pipeline</strong> through cold outreach, social selling, targeted campaigns, and creative outbound strategies.</li>
<li><strong>Develop multi-product solutions</strong> across Square’s ecosystem and tailor them to each merchant’s unique needs.</li>
<li><strong>Partner with Business Development</strong> on lead flow while independently driving net-new logo acquisition.</li>
<li><strong>Conduct high-impact discovery, demos, and negotiations</strong> with decisiveness across multi-stakeholder deals.</li>
<li><strong>Act as a consultant and trusted advisor</strong> — seamlessly flexing across BDR, AE, and AM responsibilities when needed.</li>
<li><strong>Collaborate cross-functionally</strong> with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.</li>
<li><strong>Maintain disciplined pipeline management</strong> and forecasting accuracy in Salesforce.</li>
<li><strong>Consistently hit and exceed revenue goals</strong> — monthly and quarterly.<br><br></li>
</ul>
<h4><strong>You Have</strong></h4>
<ul>
<li><strong>5+ years of full-cycle B2B sales experience</strong> with consistent quota achievement.</li>
<li><strong>Proven success in outbound prospecting</strong> and net-new business creation (SaaS or fintech preferred).</li>
<li><strong>Experience closing complex, multi-threaded deals</strong> with longer sales cycles.</li>
<li><strong>Ability to build pipeline from scratch</strong> using targeted, strategic outreach.</li>
<li><strong>Exceptional communication, presentation, and negotiation skills</strong> across phone, video, and written channels.</li>
<li><strong>Strong consultative selling skills</strong> — diagnose business challenges and map tailored solutions.</li>
<li><strong>A hunter’s mindset</strong> — resilient, creative, and driven to win.</li>
<li><strong>Ability to work independently</strong> while contributing to a team-first environment.</li>
<li><strong>Advanced proficiency with Salesforce</strong> and modern sales tools.</li>
<li><strong>BA/BS degree or equivalent experience</strong></li>
</ul>
<p>&nbsp;</p>
<p class="p2">We're 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 will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances.</p>
<p class="p2">We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible.&nbsp;<strong>Want to learn more about what we're doing to build a workplace that is fair and square? Check out our</strong>&nbsp;<a href="https://block.xyz/news/inclusion"><span class="s1">I+D page</span></a>.</p><div class="content-pay-transparency"><div class="pay-input"><div class="description"><p>&nbsp;</p>
<p><span data-sheets-root="1" data-sheets-value="{&quot;1&quot;:2,&quot;2&quot;:&quot;Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.\n\nZone A: CAD $125,900 - CAD $188,900\nZone B: CAD $121,500 - CAD $182,300&quot;}" data-sheets-userformat="{&quot;2&quot;:448,&quot;9&quot;:0,&quot;10&quot;:1,&quot;11&quot;:4}" data-sheets-formula="=TO_TEXT(iferror(index(Calculator!R10C3:R11C3,match(&quot;This One&quot;,Calculator!R10C1:R11C1,0))&amp;CHAR(10)&amp;CHAR(10)&amp;index(Calculator!R14C3:R20C3,match(&quot;This One&quot;,Calculator!R14C1:R20C1,0))&amp;if(Calculator!R6C3=&quot;Yes&quot;,CHAR(10)&amp;CHAR(10)&amp;Calculator!R22C3,&quot;&quot;),&quot;No output found. Please review inputs.&quot;))">Block takes a market-based approach to pay, and pay may vary depending on your location. Canada locations are categorized into one of two zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.<br><br></span></p></div><div class="title">Zone A: </div><div class="pay-range"><span>$116,064</span><span class="divider">&mdash;</span><span>$174,096 CAD</span></div></div><div class="pay-input"><div class="title">Zone B: </div><div class="pay-range"><span>$116,064</span><span class="divider">&mdash;</span><span>$174,096 CAD</span></div></div></div><div class="content-conclusion"><p><strong>Application Guidelines</strong></p>
<p>Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.</p>
<p><strong>Use of AI in Our Hiring Process</strong></p>
<p>We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.&nbsp;</p>
<p>Contact us <a href="https://privacy.block.xyz/privacyportal/form">here</a>&nbsp;with hiring practice or data usage questions.</p>
<p><em data-stringify-type="italic">Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.&nbsp;</em><em data-stringify-type="italic"><a class="c-link c-link--underline" href="https://block.xyz/employee-benefits" target="_blank" data-stringify-link="https://block.xyz/documents/benefits.pdf" data-sk="tooltip_parent">Check out our other benefits at Block.</a></em></p>
<p><em>Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people.&nbsp;<strong data-stringify-type="bold">Square</strong>&nbsp;makes commerce and financial services accessible to sellers.&nbsp;<strong data-stringify-type="bold">Cash App</strong>&nbsp;is the easy way to spend, send, and store money.&nbsp;<strong data-stringify-type="bold">Afterpay</strong>&nbsp;is transforming the way customers manage their spending over time.&nbsp;<strong data-stringify-type="bold">TIDAL</strong>&nbsp;is a music platform that empowers artists to thrive as entrepreneurs.&nbsp;<strong data-stringify-type="bold">Bitkey</strong>&nbsp;is a simple self-custody wallet built for bitcoin.&nbsp;<strong data-stringify-type="bold">Proto</strong>&nbsp;is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.</em></p>
<p><a href="https://block.xyz/en/legal/applicant-privacy-notice" target="_blank">Privacy Policy</a></p></div>

Senior Account Executive, Mid-Market

<div class="content-intro"><p><strong>About Pinterest:</strong></p>
<p>Millions of people around the world come to our platform to find creative ideas, dream about new possibilities and plan for memories that will last a lifetime. At Pinterest, we’re on a mission to bring everyone the inspiration to create a life they love, and that starts with the people behind the product.</p>
<p>Discover a career where you ignite innovation for millions, transform passion into growth opportunities, celebrate each other’s unique experiences and embrace the&nbsp;<a href="https://www.pinterestcareers.com/our-life/pinflex/">flexibility</a> to do your best work. Creating a career you love? It’s Possible.</p>
<p>At Pinterest, AI isn't just a feature, it's a powerful partner that augments our creativity and amplifies our impact, and we’re looking for candidates who are excited to be a part of that. To get a complete picture of your experience and abilities, we’ll explore your foundational skills and how you collaborate with AI.</p>
<p>Through our interview process, what matters most is that you can always explain your approach, showing us not just what you know, but how you think. You can read more about our AI interview philosophy and how we use AI in our recruiting process <a href="https://www.pinterestcareers.com/our-philosophy-on-ai-in-hiring/">here</a>.</p></div><p>Pinterest’s Canada business is a scaled, high-potential market spanning Emerging, CPG, and Retail, with more than 60 employees across 10+ sales pods and $150M+ in L4Q revenue. Canada has strong momentum and meaningful upside, but also requires renewed market leadership, sharper operating rigor, and a more unified country strategy. This Managing Director role is Pinterest’s senior sales leader in Canada, accountable for revenue growth, organizational productivity, customer relationships, and the health of the Canada sales organization.</p>
<p>This role requires a leader who can operate at both the market and organizational level: setting a clear commercial strategy, building trusted relationships with major Canadian advertisers and agencies, and leading through a period of transformation as Emerging, CPG, and Retail come together under one country model. The right candidate will bring deep knowledge of the Canadian advertising ecosystem, strong sales leadership judgment, and the ability to unify teams, improve productivity, and rebuild a strong Canada identity and culture.</p>
<p>&nbsp;</p>
<p><strong>What You'll Do:</strong></p>
<ul>
<li>Serve as the senior sales leader for Canada across Emerging, CPG, and Retail, setting and executing the country strategy and translating regional priorities into clear annual and quarterly growth plans</li>
<li>Own revenue performance across the Canada business, including forecasting, pipeline management, account prioritization, and recovery or acceleration plans to deliver sustained growth across multiple quarters</li>
<li>Lead five direct reports and a 60+ person organization across 10+ sales pods, creating clarity on priorities, decision-making, and accountability while strengthening leadership bench and succession</li>
<li>Unify Emerging, CPG, and Retail under one Canada operating model, establishing a consistent cadence across forecasting, pipeline reviews, account planning, and performance management</li>
<li>Direct resources, coverage, and leadership attention toward the highest-growth opportunities, improving productivity, account ownership, and vertical alignment while protecting customer continuity</li>
<li>Build and maintain trusted C-level relationships with priority advertisers, agencies, and holding companies across the Canadian market</li>
<li>Resolve complex customer and business escalations with strong judgment, balancing short-term business needs with long-term partnership health</li>
<li>Increase adoption of Pinterest’s full-funnel solutions across brand, performance, creative, and measurement offerings</li>
<li>Partner closely with GBO on business planning, forecasting, resource allocation, organizational design, and performance management</li>
<li>Partner with GTM on market strategy, opportunity sizing, sales motions, advertiser positioning, agency planning, and product adoption</li>
<li>Partner with EPD on product priorities, advertiser feedback, measurement needs, market opportunities, and customer escalations relevant to Canada</li>
<li>Represent the Canada business with North America and global leadership, ensuring the market has strong voice, visibility, and advocacy in broader business and product decisions</li>
<li>Lead through change with clarity and resilience, helping rebuild a healthy, inclusive, high-performing culture where employees feel valued, connected, and empowered to perform</li>
<li>Use data, AI, and automation to improve planning and execution while maintaining strong standards for accuracy, privacy, and accountability</li>
</ul>
<h2>&nbsp;</h2>
<p><strong>What We're Looking For:</strong></p>
<ul>
<li>10+ years of experience in advertising sales, media, digital platforms, marketing technology, or a related commercial field</li>
<li>Experience leading a country, market, business unit, or multi-segment sales organization with significant revenue accountability</li>
<li>Proven ability to develop sales strategy and deliver sustained year-over-year growth, not just isolated strong quarters</li>
<li>Deep knowledge of the Canadian advertiser and agency ecosystem, including strong relationships and credibility in-market</li>
<li>Strong understanding of digital advertising, full-funnel marketing, measurement, and go-to-market strategy</li>
<li>Experience leading leaders and managing a scaled organization through change, with a track record of building clarity, alignment, and momentum</li>
<li>Strong operating discipline across forecasting, pipeline management, account planning, resource allocation, and performance management</li>
<li>Demonstrated ability to improve productivity by directing resources and organizational focus toward the strongest growth opportunities</li>
<li>Strong talent judgment, including experience coaching leaders, managing performance, strengthening succession, and developing inclusive teams</li>
<li>C-level executive presence and experience building senior customer relationships while navigating complex escalations</li>
<li>Strong judgment, resilience, and decision-making in fast-moving, high-visibility commercial environments</li>
<li>Demonstrated ability to influence cross-functional partners, including product and business stakeholders, in a matrixed organization</li>
<li>Bachelor’s degree in business, advertising, marketing, a related field or equivalent experience.</li>
</ul>
<p>&nbsp;</p>
<p><strong>Relocation Statement:</strong>&nbsp;</p>
<ul>
<li>This position is eligible for relocation assistance. Visit our <a href="https://www.pinterestcareers.com/pinflex/">PinFlex</a> page to learn more about our working model.</li>
</ul>
<p>&nbsp;</p>
<p><strong>In-Office Requirement Statement:</strong></p>
<ul>
<li>We let the type of work you do guide the collaboration style. That means we're not always working in an office, but we continue to gather for key moments of collaboration and connection.</li>
<li>This role will need to be in the office for in-person collaboration at least once a week and therefore needs to be in a commutable distance from our Pinterest office in Toronto.</li>
</ul>
<p>&nbsp;</p>
<p>#LI-ONSITE</p>
<p>#LI-AM9</p><div class="content-conclusion"><p><strong>Our Commitment to Inclusion:</strong></p>
<div>Pinterest is an equal opportunity employer and makes employment decisions on the basis of merit. We want to have the best qualified people in every job. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, religion or religious creed, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, age, marital status, status as a protected veteran, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member) or any other consideration made unlawful by applicable federal, state or local laws. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. If you require a medical or religious accommodation during the job application process, please complete&nbsp;<a href="https://forms.gle/sS24D4WboEKUZMQK6">this form</a> for support.</div>
<div>&nbsp;</div>
<div><em>By submitting this application, I certify that all information submitted in my application and throughout the hiring process is true, accurate, and complete to the best of my knowledge. I understand that any false statement, omission, or misrepresentation may disqualify me from employment consideration or result in termination if discovered after hire.</em></div></div>

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