This is a high-impact role for a builder who combines startup scrappiness with operational discipline,someone who thrives on competition, inspires performance, and transforms promising teams into durable growth engines.

The successful candidate will lead Sales Managers and Territory Account Executives focused on acquiring and expanding small and midsize businesses across key Central markets.

Key responsibilities:

• Scale with purpose: Strengthen and expand the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
• Drive to win: Build a culture grounded in performance, accountability, and competitiveness,where teams are motivated to exceed targets and celebrate excellence.
• Lead from the front: Spend meaningful time in the field,co-selling, coaching, and demonstrating product fluency through action.
• Be a product expert: Master Square's ecosystem end-to-end and ensure teams sell consultatively,connecting product capabilities to seller outcomes.
• Execute with speed and precision: Drive predictable, data-backed growth by managing pipeline health, conversion rates, and sales productivity.
• Think like a builder: Continuously improve systems, tools, and playbooks to help the team sell smarter and scale faster.
• Collaborate to amplify impact: Partner with Marketing, Sales Ops, Partnerships, and Product to align regional execution with national strategy and feedback loops.
• Inspire and develop talent: Attract, retain, and grow high-performing sales professionals who are hungry to win and advance their careers.
• Represent Square locally: Serve as the face of Square's brand and mission across key Central markets,connecting with business leaders, partners, and communities.

Requirements:

• 10+ years of sales experience, including 5+ years leading regional or field sales teams in a high-growth SaaS, fintech, or payments environment.
• Proven success driving overperformance, with a track record of exceeding regional revenue and productivity goals.
• Proven track record of building high-performance teams and creating cultures grounded in coaching, accountability, and excellence.
• Strong product acumen, with the ability to position complex solutions across multiple product lines and use data to guide decisions.
• A builder mindset,move fast, stay resourceful, and operationalize what works at scale.
• Deep operational expertise in forecasting, pipeline management, and KPI tracking.
• Excellent communication and executive presence, with the ability to influence across all levels of the organization.

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Responsibilities:

• Craft and Lead Deal Strategy: Develop sophisticated sales narratives tailored to client business priorities.
• Own the Full Sales Cycle: Manage your pipeline end-to-end with precision.
• Lead Technical, Complex Sales Cycles: Partner with Solutions Engineering to scope platform requirements and API integrations.
• Orchestrate Internal Alignment: Quarterback cross-functional stakeholders across Finance, Legal, Risk, Product, Solutions Engineering, and Account Management.
• Represent Square at the Highest Level: Represent Square in C-suite meetings, on stage at industry conferences, or in working sessions with a prospect's technical team.
• Build Block's Enterprise Network: Represent Square at industry events, trade shows, and networking functions; develop lasting relationships with senior leaders at leading brands and platform partners.
• Be a Multiplier for the Business: Channel the voice of the customer internally to influence product roadmaps and go-to-market strategy.

Requirements:

• 8+ years of enterprise sales experience, with a track record of closing complex, high-value deals with end-to-end ownership.
• Deep experience in technical sales cycles , fluent in conversations involving API integrations, custom development, and platform configuration.
• Proven ability to orchestrate multi-stakeholder deals , internally and externally , with exceptional communication, follow-through, and organizational discipline.
• Executive presence that's equally at home on a conference stage, in a C-suite boardroom, or on a discovery call with a technical champion.
• Experience selling a complex ecosystem of SaaS or fintech products, ideally in payments, commerce, or adjacent verticals.
• Ability to operate independently in a fast-paced, ambiguous environment.
• Talent for translating complexity into clarity.
• BA/BS degree or equivalent professional experience.
• Willingness to travel ~40%

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You will own accounts end-to-end,setting account strategy, generating pipeline, and closing high-value deals across multi-stakeholder buying groups with urgency. You'll partner closely with Solutions Engineering, Product, Partnerships, Legal, and Finance to bring the full Square ecosystem to market.

Responsibilities:

• Own a targeted set of enterprise accounts
• Set clear priorities and be accountable for pipeline quality, deal progression, and closed revenue across your account set
• Define and execute a clear account strategy
• Focus on the highest-impact opportunities and consistently convert pipeline into high-value wins
• Lead complex, multi-stakeholder deals end-to-end
• Navigate executive, technical, and commercial stakeholders to drive alignment, accelerate decisions, and close deals at pace
• Develop strong, insight-led account POVs
• Translate Square's platform into differentiated value that advances deals and improves win rates
• Run a disciplined, detail-oriented sales process
• Maintain momentum across long cycles, qualify rigorously, and increase conversion at each stage of the funnel
• Partner cross-functionally to win
• Work across Solutions Engineering, Product, Partnerships, Legal, and Finance to remove blockers and close complex deals effectively
• Represent Square with credibility at senior levels
• Build trusted relationships with executives that unlock access, influence decisions, and drive long-term partnerships

Requirements:

• 8+ years of enterprise or strategic sales experience, with a consistent track record of exceeding targets and closing complex, high-value deals with full ownership
• Proven ability to build, qualify, and convert pipeline within a focused account set, with strong judgment on where to invest time and why
• Deep experience leading multi-threaded enterprise deals, navigating executive, technical, and procurement stakeholders with clarity and control
• Strong commercial acumen, with the ability to structure and negotiate deals thoughtfully across pricing, scope, and long-term value
• Executive presence and credibility,you communicate with precision, challenge constructively, and earn trust with senior decision-makers
• Experience selling a complex platform, SaaS, fintech, or payments solution into large or operationally sophisticated organisations
• A high standard for execution: you are disciplined, prepared, and follow through consistently, especially in long and ambiguous sales cycles
• A strong sense of ownership,you take responsibility for outcomes, not just activity, and operate effectively without heavy structure
• The ability to simplify complexity and drive clarity, both externally with customers and internally across teams

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You will own accounts end-to-end,setting account strategy, generating pipeline, and closing high-value deals across multi-stakeholder buying groups with urgency. You'll partner closely with Solutions Engineering, Product, Partnerships, Legal, and Finance to bring the full Square ecosystem to market.

Responsibilities:

• Own a targeted set of enterprise accounts
• Set clear priorities and be accountable for pipeline quality, deal progression, and closed revenue across your account set
• Define and execute a clear account strategy
• Lead complex, multi-stakeholder deals end-to-end
• Develop strong, insight-led account POVs
• Run a disciplined, detail-oriented sales process
• Partner cross-functionally to win
• Represent Square with credibility at senior levels

Requirements:

• 8+ years of enterprise or strategic sales experience, with a consistent track record of exceeding targets and closing complex, high-value deals with full ownership
• Proven ability to build, qualify, and convert pipeline within a focused account set, with strong judgment on where to invest time and why
• Deep experience leading multi-threaded enterprise deals, navigating executive, technical, and procurement stakeholders with clarity and control
• Strong commercial acumen, with the ability to structure and negotiate deals thoughtfully across pricing, scope, and long-term value
• Executive presence and credibility,you communicate with precision, challenge constructively, and earn trust with senior decision-makers
• Experience selling a complex platform, SaaS, fintech, or payments solution into large or operationally sophisticated organisations
• A high standard for execution: you are disciplined, prepared, and follow through consistently, especially in long and ambiguous sales cycles
• A strong sense of ownership,you take responsibility for outcomes, not just activity, and operate effectively without heavy structure
• The ability to simplify complexity and drive clarity, both externally with customers and internally across teams

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Responsibilities:

• Monitor and investigate compliance-related alerts generated through transaction monitoring systems and manual reviews.
• Analyze merchant transaction activity, payment flows, customer relationships, and business operations to identify unusual or suspicious behavior.
• Conduct investigations related to anti-money laundering (AML), fraud, sanctions, prohibited activities, financial crime risks, and violations of Square policies.
• Verify merchant information and perform onboarding and ongoing due diligence reviews in accordance with company policies and regulatory requirements.
• Document investigative findings and make risk-based recommendations regarding account actions and escalations.
• Conduct public record research and open-source intelligence reviews to support investigations.
• Interact with merchants in Japanese and English to obtain information, communicate compliance requirements, and support remediation efforts.
• Ensure operational reviews and investigations are completed within established service level agreements (SLAs).
• Communicate with payment network partners, banking partners, and other corporate stakeholders to ensure compliance monitoring activities align with applicable requirements.

Requirements:

• Professional fluency in both Japanese and English (written and verbal).
• Bachelor's degree or equivalent professional experience.
• Minimum 3 years of experience in compliance operations, transaction monitoring, AML investigations, fraud investigations, risk management, or policy implementation within a financial institution, payment service provider, fintech company, or regulated financial services organization.
• Strong understanding of Japanese financial crime compliance requirements.
• Experience conducting customer due diligence (CDD), Know Your Customer (KYC), transaction monitoring, and suspicious activity investigations.
• Knowledge of Japanese payment industry regulations, merchant acquiring requirements, and payment network rules.
• Strong investigative skills, including familiarity with public record research and investigative databases.
• Strong transaction analysis skills that apply across numerous financial products and services in complex scenarios.
• Ability to identify and assess suspicious activity, financial crime risks, and policy violations.
• Strong judgment and ability to make risk-based decisions in complex investigative scenarios.
• Excellent written communication and case documentation skills in both Japanese and English.
• Ability to work in a fast-paced and dynamic environment with a drive to deliver outstanding results.

Nice to Have:

• Experience supporting regulatory examinations, audits, or law enforcement requests in Japan.
• Experience supporting suspicious transaction reporting processes and financial crime investigations.
• Experience working with merchant acquiring, payment processing, fintech, or banking products.
• Familiarity with sanctions screening systems, AML monitoring systems, and fraud detection tools.
• Experience working directly with payment networks, banking partners, regulators, or law enforcement agencies.
• CAMS, CFE, CFCS, or similar compliance certifications.

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About the Role: As a Chargé de Compte PME, you will be responsible for converting high-quality leads into long-term clients, while also generating new opportunities to grow your pipeline.

Responsibilities:

• Manage the entire sales cycle, from initial contact to contract closure, with small and medium-sized businesses across various industries.
• Engage and convert a regular flow of interested leads from marketing, partnerships, or those who have expressed interest in our products.
• Generate a significant portion of your pipeline through prospecting, identifying new opportunities, and creating demand where none existed.
• Act with diligence at every stage, managing time and priorities effectively in a high-volume environment.
• Understand client challenges and propose consultative solutions with measurable impact.
• Collaborate with teams (Integration, Product, Marketing, and Support) to ensure a seamless customer experience and continuous feedback loop.
• Track and forecast your pipeline accurately in Salesforce, using data and metrics to improve performance.
• Consistently meet or exceed monthly and quarterly revenue targets.
• Continuously raise the bar each quarter, improving conversion rates, contract value, and activity.

Requirements:

• 1-2 years of experience in remote sales or contract negotiation, ideally in a SaaS, payment, or SME-focused environment.
• Proven ability to exceed quotas and close deals in a fast-paced sales cycle with high transaction volumes.
• Strong communication skills via phone, video, and email, establishing trust and driving deals forward decisively.
• A true hunter mentality, with a focus on disciplined prospecting and pipeline growth.
• Curiosity and empathy, understanding client needs and proposing suitable solutions.
• Ability to thrive in ambiguity, motivated and eager to learn and grow.
• Proficiency in a CRM (Salesforce or equivalent) and data-driven approach to activity management.
• High expectations for yourself and your team, celebrating victories and sharing best practices.
• Fluency in French and English.

Benefits:

• Competitive salary ($86,000 - $129,000 CAD)
• Remote work options
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning benefits

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You will be joining our Restaurant or Generalist team to help build our Sales Development organization.

As a Business Development Representative, you will work with our Sales team to find new merchants that fit the Square ecosystem.

You will lay the foundation of this sales effort through outbounding to prospective sellers and promoting the value of Square for their business.

You will become an expert in the products and services that enable merchants to grow with the Square ecosystem.

Your responsibilities include:

• Managing a diverse pipeline of businesses and prioritizing outreach to accelerate sales cycles
• Reaching out to businesses in your pipeline at scale through cold calling, emailing, and social selling
• Promoting urgency through a solutions-based sales approach, identifying challenges with businesses and providing targeted value around how Square can help
• Growing your career in sales through frequent developmental opportunities and mentorship from the Account Executive team
• Consistently attaining and exceeding your monthly quotas

Requirements:

• A desire to grow your career in sales
• A BA/BS degree or equivalent practical experience
• Personal leadership, authenticity, team player, energy richness, curiosity
• Enthusiasm for developing sales skills through cold calling
• Comfort with operating in a fast-paced, dynamic environment

Benefits:

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

XML job scraping automation by YubHub

You will be joining our Restaurant or Generalist team to help build our Sales Development organization.

As a Business Development Representative, you will work with our Sales team to find new merchants that fit the Square ecosystem.

You will lay the foundation of this sales effort through outbounding to prospective sellers and promoting the value of Square for their business.

You will become an expert in the products and services that enable merchants to grow with the Square ecosystem.

Your responsibilities include:

• Managing a diverse pipeline of businesses and prioritizing outreach to accelerate sales cycles
• Reaching out to businesses in your pipeline at scale through cold calling, emailing, and social selling
• Promoting urgency through a solutions-based sales approach, identifying challenges with businesses, and providing targeted value around how Square can help
• Growing your career in sales through frequent developmental opportunities and mentorship from the Account Executive team
• Consistently attaining and exceeding your monthly quotas

Requirements:

• A desire to grow your career in sales
• A BA/BS degree or equivalent practical experience
• Personal leadership, authenticity, team player, energy richness, curiosity
• Enthusiasm for developing sales skills through cold calling
• Comfort with operating in a fast-paced, dynamic environment

Benefits:

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

Pay Transparency:

The successful candidate's starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions.

Zone A: $79,768.00 Zone B: $74,152.00 Zone C: $70,018.00 Zone D: $63,700.00

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As a Business Development Representative, you will work with our Sales team to find new merchants that fit the Square ecosystem.

You will:

• Manage a diverse pipeline of businesses and prioritise outreach to accelerate sales cycles
• Reach out to businesses in your pipeline at scale through cold calling, emailing, and social selling
• Promote urgency through a solutions-based sales approach, identifying challenges with businesses and providing targeted value around how Square can help
• Grow your career in sales through frequent developmental opportunities and mentorship from the Account Executive team
• Attain and exceed your monthly quotas

Requirements:

• A desire to grow your career in sales
• A BA/BS degree or equivalent practical experience
• Personal leadership, authenticity, team player, energy richness, curiosity
• Enthusiasm for developing sales skills through cold calling
• Comfort with operating in a fast-paced, dynamic environment

We offer remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning.

XML job scraping automation by YubHub

You will be joining our Restaurant or Generalist team to help build our Sales Development organization.

As a Business Development Representative, you will work with our Sales team to find new merchants that fit the Square ecosystem.

You will lay the foundation of this sales effort through outbounding to prospective sellers and promoting the value of Square for their business.

You will become an expert in the products and services that enable merchants to grow with the Square ecosystem.

Your responsibilities include:

• Managing a diverse pipeline of businesses and prioritizing outreach to accelerate sales cycles
• Reaching out to businesses in your pipeline at scale through cold calling, emailing, and social selling
• Promoting urgency through a solutions-based sales approach, identifying challenges with businesses and providing targeted value around how Square can help
• Growing your career in sales through frequent developmental opportunities and mentorship from the Account Executive team
• Consistently attaining and exceeding your monthly quotas

Requirements:

• Full language proficiency in English and Mandarin
• A desire to grow your career in sales
• A BA/BS degree or equivalent practical experience
• Personal leadership, authenticity, team player, energy richness, curiosity
• Enthusiasm for developing sales skills through cold calling
• Comfort with operating in a fast-paced, dynamic environment

We offer remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning.

XML job scraping automation by YubHub

You will be joining our Restaurant or Generalist team to help build our Sales Development organization.

As a Business Development Representative, you will work with our Sales team to find new merchants that fit the Square ecosystem.

You will lay the foundation of this sales effort through outbounding to prospective sellers and promoting the value of Square for their business.

You will become an expert in the products and services that enable merchants to grow with the Square ecosystem.

Your responsibilities include:

• Managing a diverse pipeline of businesses and prioritizing outreach to accelerate sales cycles
• Reaching out to businesses in your pipeline at scale through cold calling, emailing, and social selling
• Promoting urgency through a solutions-based sales approach, identifying challenges with businesses and providing targeted value around how Square can help
• Growing your career in sales through frequent developmental opportunities and mentorship from the Account Executive team
• Consistently attaining and exceeding your monthly quotas

Requirements:

• Full bilingual language proficiency in Mandarin
• A desire to grow your career in sales
• A BA/BS degree or equivalent practical experience
• Personal leadership, authenticity, team player, energy richness, curiosity
• Enthusiasm for developing sales skills through cold calling
• Comfort with operating in a fast-paced, dynamic environment

Benefits:

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

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The successful candidate will be responsible for shaping and executing the B2B content strategy, working closely with teams across Square to bring those stories to life.

Responsibilities:

• Build and manage an always-on B2B content calendar across priority themes, verticals, campaigns, and moments.
• Execute social-first content formats and original content franchises for co-marketing programs with sellers.
• Create content programs that bring Square's industry POV, customer stories, partner stories, product narratives, and market insights to life.
• Identify opportunities to tell stronger stories across priority verticals, including restaurants, retail, services, and other key business categories.
• Develop thought leadership content that helps Square participate in timely industry and business conversations.
• Support customer storytelling and case study efforts by shaping strong story angles and adapting them into social-first formats.
• Translate business priorities into clear content concepts, briefs, series, and distribution plans.
• Use AI tools and workflows to support content development, including research, ideation, content mapping, repurposing, versioning, briefing, and production planning.
• Build repeatable AI-assisted workflows that help the team move from insight to content more efficiently while maintaining accuracy, brand quality, and human judgment.
• Manage content production workflows from concept through launch, including briefs, timelines, stakeholder inputs, approvals, and delivery.
• Work with internal creative teams, external partners, freelancers, or agencies to produce high-quality content efficiently.
• Track performance across content and social channels, and use insights to refine topics, formats, messaging, and distribution over time.

Requirements:

• 6+ years of experience developing B2B content, social content, integrated campaigns, thought leadership, or content marketing programs.
• A strong understanding of social-first content, especially for LinkedIn and other platforms where business audiences spend time.
• Experience turning complex business topics into clear, compelling content for professional audiences.
• Strong instincts for content formats, storytelling, hooks, pacing, and audience relevance.
• Experience building or managing content calendars, campaigns, series, or always-on programming.
• Experience using AI tools to improve content workflows, speed up content development, or scale content across formats and channels.
• Strong judgment around where AI can add leverage and where human strategy, creativity, taste, and review are essential.
• Strong project management skills, with the ability to move work from idea to brief to execution.
• Experience working cross-functionally with marketing, creative, communications, sales, product, or external partners.
• Good judgment around brand voice, accuracy, approvals, and business context.
• Comfort balancing proactive content development with incoming business needs in a lean, fast-moving environment.

Nice to have:

• Experience in B2B technology, fintech, commerce, SaaS, restaurants, retail, services, or another business-focused category.
• Experience developing executive thought leadership, industry POV content, category campaigns, or recurring content series.
• Experience with customer storytelling, case studies, partner marketing, or sales-supporting content.
• Familiarity with social analytics, content performance reporting, and optimization.
• Experience producing short-form video, event content, interview-based content, or multi-format social campaigns.
• Experience managing agencies, freelancers, creators, or production partners.
• Experience building AI-assisted content systems, prompt libraries, research workflows, repurposing engines, or content operations processes.

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