B

Block

Runs Square payments and the Cash App money app

Head of Mid-Market Sales

Full-Time
$319k - $478.6k
Expert
San Francisco Bay Area, CA, USA
In Person
Sales & Account ManagementAccount Executive

About the job

Requirements
  • 12+ years of experience in high-growth environments leading Mid-Market Sales or Mid-Market Account Management organizations, preferably in a fast-moving technology or financial services company, and experience working with large-scale established clients.
  • Experience navigating and operating effectively within matrixed global organizations.
  • A demonstrated track record of leading teams that consistently drive revenue growth and exceed revenue targets.
  • Leadership skills to develop talent, motivate high-performing teams, and build strong cross-functional relationships; adapt management style to individuals to maximize performance and engagement.
  • Familiarity with how product development works, preferably in payments, and ability to interface credibly with technical, marketing, product, and engineering stakeholders.
  • Executive presence and ability to influence and earn trust with senior leaders, ask effective questions, and apply sound business judgment internally and externally, including at the C-suite level.
  • Operational and strategic mindset, including ability to implement robust processes, lead teams through complex relationships, and set a clear vision.
  • Comfort working with analytics and tools that support business performance measurement and management.
  • Ability to develop sales narratives using relevant data and build business cases to communicate the Cash App and Afterpay value proposition.
  • Willingness to travel.
Responsibilities
  • Oversee the North American Mid-Market Sales team by leading seasoned Mid-Market Account Executives, coaching them through sophisticated deal negotiations, supporting negotiations through internal and external advocacy, and clearing blockers to revenue.
  • Craft a segment-wide strategy, hold the team accountable for delivering on objectives and key results, and execute revenue targets in coordination with the broader Sales and Account Management function at Cash App and Afterpay.
  • Work with Marketing, Finance, Product, Risk, Legal, Account Management, and other cross-functional teams to support revenue generation and build relationships across a distributed, matrixed stakeholder group.
  • Further develop the inherited team's skills, knowledge, effectiveness, and performance-focused culture.
  • Represent Cash App and Afterpay to leading Mid-Market merchants as a thought leader in payments, demonstrate their value as a growth driver, and develop relationships with merchant partners and their leadership teams.
  • Develop and pitch sales narratives that explain the Cash App and Afterpay value proposition to prospective merchants; communicate with senior decision makers at high-growth and established brands across North America; and use insights, data, and market intelligence to improve go-to-market strategy.
  • Use insights across the team's portfolio to centralize and share effective sales and growth narratives that resonate with Mid-Market merchants and inform business-to-business marketing and sales strategy.
  • Represent merchant feedback and sentiment internally, advocate for clients while balancing business needs and constraints, and deliver key insights across the organization in a structured, consistent, and proactive manner.
  • Take responsibility for revenue outcomes across the Mid-Market merchant pipeline in North America.
  • Build and support a strong performance culture, developing others and leading with empathy.
Desired Qualifications
  • Experience in a fast-moving technology or financial services company.
  • Experience with product development in payments.

About the company

Block runs Square, which sells card readers and checkout software to businesses, and Cash App, an app people use to send, save, spend, and borrow money. Its first product, a square card reader that plugged into a phone's headphone jack in 2010, let street vendors and other small sellers accept credit cards. Square earns a fee on each card payment and charges for software, while Cash App makes money from its debit card, short-term loans, Afterpay installment plans, and bitcoin sales. Block also owns the music streaming service TIDAL and builds bitcoin hardware, including the Bitkey wallet and Proto mining rigs. Twitter co-founder Jack Dorsey co-founded the company in 2009, and its main office is in Oakland, California.

Company Size

5,001-10,000

Company Stage

IPO

Headquarters

Oakland, California

Founded

2009

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Simplify Jobs

Simplify's Take

What believers are saying

  • Lending drives growth: Cash App gross profit rose 31% in the June 2026 quarter as consumer loan volume jumped 59%.
  • Stock grants have outperformed PayPal's: Block shares rose 16% from January to early October 2026, while PayPal's fell 6%.
  • Office time is optional: Block has no headquarters, and for most roles staff choose where they work.

What critics are saying

  • Job security is weaker: citing AI tools, Block cut over 4,000 jobs, about 40% of staff, in February 2026.
  • A Justice Department probe hangs over Cash App: Block set aside $526 million by June 2026 to resolve it.
  • Cash App's user base has stalled: 59 million monthly users in June 2026, up just 3% in a year.

What makes Block unique

  • Most profit comes from consumers, not merchants: Cash App made 62% of Block's gross profit in the June 2026 quarter.
  • Engineers work alongside AI agents: agents helped write and review nearly all of Block's live code changes in June 2026.
  • Block owns a bank: Square Financial Services, chartered in Utah, lends to sellers who repay from each card sale.

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Benefits

Remote Work Options

Health Insurance

Flexible Work Hours

Family Planning Benefits

Growth & Insights and Company News

Headcount

6 month growth

-1%

1 year growth

1%

2 year growth

1%
Yahoo Finance
Oct 9th, 2026
Cash App to pay $15M data breach settlement to affected users in October 2026

Block Inc.'s Cash App is set to distribute payments from a $15 million class action settlement this month to users who filed claims before the November 2024 deadline. The settlement resolves a 2022 lawsuit alleging negligence and misrepresentation related to data security incidents in April 2022 and October 2023, as well as unauthorised account withdrawals. The April 2022 incident exposed personal information of 8.2 million Cash App Investing customers. Block denies wrongdoing and admits no legal violations. Eligible claimants could claim up to $2,500 for out-of-pocket losses and compensation for lost time. The court granted final approval in March 2025. Separately, the Federal Trade Commission is investigating whether Block violated consumer protection laws regarding frozen Square accounts.

Banca di Bologna
Oct 8th, 2026
FTC probes Block after consumer complaints over frozen accounts.

FTC probes Block after consumer complaints over frozen accounts. Bloomberg Tech 5 hours ago 53 The Federal Trade Commission is investigating whether Block Inc., the parent of Square and Cash App, violated US consumer protection laws by failing to provide adequate customer service to help with frozen or deactivated accounts amid significant cuts in staffing. BankBit shares this Content always with CC License Screenshot generated in real time with SneakPeek Suite

Bloomberg
Oct 8th, 2026
FTC investigates Block over frozen accounts following consumer complaints and staff cuts

The Federal Trade Commission is investigating Block Inc., parent company of Square and Cash App, over potential violations of US consumer protection laws. The probe centres on whether the company failed to provide adequate customer service for frozen or deactivated accounts following significant staff reductions. The investigation examines Block's handling of consumer complaints regarding account access issues. The FTC is assessing whether the company's customer service capabilities were sufficient to address problems faced by users of its payment platforms.

Radical Compliance
Oct 2nd, 2026
Compliance Jobs Report: Oct. 2.

Compliance Jobs Report: Oct. 2. The Compliance Jobs Report this week has hiring news at Crocs, Chewy, Block, Stryker, Ritz-Carlton Yachts (yes, that's a thing) and a slew of financial firms. Radical Compliance also have promotions to note at McKesson, BNP Paribas, and elsewhere; and job leads in retail, healthcare, and payments. The healthcare salary will make you faint. Radical Compliance gather the Jobs Report news items from LinkedIn, press releases, and wherever else Radical Compliance can find tips - and thank you to everyone who sends them in, you make the Jobs Report possible! If you have any gossip to share (even confidentially) email me at [email protected] or find me on LinkedIn. Compliance Jobs. This week Radical Compliance begin at Crocs, perhaps the world's most well-known maker of ugly but comfortable shoes; the company has hired Anne DeTraglia as vice president of internal audit and enterprise risk. DeTraglia walks into Crocs from Sabre Corp., where she had also been VP of audit and risk until she left the company earlier this year. Gina Bucker is joining Chewy, the online pet food delivery people, as head of internal audit; she starts Oct. 5. Bucker comes to Chewy from JetBlue, where she had been chief audit executive since the start of 2025. Changing of the compliance guard at Swedbank! The Swedish bank says chief compliance officer Britta Hjorth-Larsen is stepping down after four years on the job for personal and family reasons and is moving home to Denmark. Eva Wilhelmsson, deputy CCO and a long-time Swedbank executive, has been appointed acting chief compliance officer until further notice. Payments firm Block has hired Nick DiBari as lead for compliance issues management. DiBari joins the company after seven years at Interactive Brokers, the last five of them as global head of anti-money laundering compliance. (This would be the same Block, by the way, that proudly announced eight months ago that it was cutting 40 percent of its staff to embrace AI. Glad to see at least some humans are still getting hired.) First Citizens Bank has deposited Matt Marteney onto the payroll as vice president of compliance. Marteney joins First Citizen after 28 years at Wells Fargo, where he had most recently been director of financial crimes governance. Wolfgang Rieg has joined British insurance firm Howden as executive compliance business partner. Rieg comes to Howden all the way from New Zealand, where he had been a manager of conduct supervision for the country's Financial Markets Authority. Speaking of executive compliance roles, Judy Lipton just gave up her job at BlackRock as global head of executive compliance; to join asset management firm Millennium ($92 billion assets under management) as compliance chief operating officer. Lipton had been with BlackRock in various compliance roles for 11 years. Nancy Freda-Smith has stepped down from her role as chief audit executive at Ralph Lauren Corp. after 15 years at the company in various audit roles. Next up: Freda-Smith has joined the board of Tempest Therapeutics, where she will serve as audit committee chair. Moment, a fintech that bills itself as "the AI operating system for investment management," has hired Ron Steinfeld as chief compliance officer. Steinfeld joins the firm from MarketAxess, where he had also been chief compliance officer. Jim Back has been hired at Tata Steel in the Netherlands, working as antitrust counsel on the company's ethics and compliance team. Back was last seen at Teva Pharmaceuticals, where he had been senior counsel for EU antitrust issues until last year. David Colford has left Airmar Technology, where he had been a regulatory compliance and sustainability specialist. He's now at Insulet Corp. as a senior product stewardship specialist. Sophie Hibburd has joined Astellas Pharma as ethics and compliance affiliate business partner for Australia. Hibburd had previously been Takeda's head of ethics and compliance for the Oceania region. Merrick Bank, a merchant bank based in Salt Lake City, has hired Brooke Weaver as a level II compliance analyst. Weaver previously worked at Medallion Bank on its compliance testing team. In Omaha, Neb., OrthoNebraska has hired Brayden Walsh as a compliance coordinator. Walsh previously worked at the Developmental Disability Center of Nebraska as director of quality assurance and compliance. Meghan Weaver has been hired as a senior compliance officer at Financial Plus Credit Union in Flint, Mich. Weaver comes to Financial Plus from Comerica Bank, where she had been a retail compliance advisory manager. Amanda Holst has a new gig at Stryker as senior director of compliance, governance, risk, and strategy. Holst comes to the medical equipment maker from United Therapeutics, where she most recently had been senior director of compliance program operations. Chromally, an aerospace manufacturer, just picked up Darie Achstein-Conway as U.S. import compliance manager. Achstein-Conway has previously worked as a trade compliance consultant with Axiom, where Chromally had been one of her clients. Lisa Pepe-Whittaker has taken a job with Fortitude Re as senior vice president of compliance and legal. She previously worked at Deutsche Bank for four years, most recently as global head of requirements, conduct, and reporting. Orion Financial, a credit union based in Memphis, has hired Miles Wolfe as director of IT governance, risk, and compliance. Wolfe comes to Orion from First Horizon Bank, where he had been senior VP and audit senior adviser. And in Miami, Raul Ocampo is the new senior manager for information and security compliance for the Ritz-Carlton Yacht Collection, a group of three luxury yachts that people richer than me can take on vacation. Ocampo sails into this job from Optiv, where he had been head of cybersecurity operations. One hopes he got some free yacht time as part of the package. Regulatory world. Heidi Sorensen has joined the Department of Health & Human Services as deputy associate general counsel for program integrity at the Center for Medicare & Medicaid Services. Sorensen previously spent 19 years at the law firm Alston & Bird. Moving up the ladder. The aptly named Community Bank, which runs community banks from Pennsylvania though New York and northern New England, has promoted Jeff Royer from senior compliance manager to chief compliance officer. Samantha Young has moved up at Wright-Pitt Credit Union in Ohio, from manager of internal audit to vice president of the same. McKesson has promoted Kendra Rester from senior manager of internal audit to senior manager of contracts compliance. BNP Paribas has promoted Alexandra Guerra from senior KYC officer to compliance review control officer. Curry's, a British retailer of personal technology gizmos, has promoted Will Volante from business manager to senior manager for governance, risk, and compliance. Vendors & service providers. Houssam Wazzan has moved out of his role at the World Economic Forum, where he had been lead for the group's Partnering Against Corruption Initiative; now he will head WEF's Civil Society and Responsible Governance program. Open req orders. UCI Health, the hospital system affiliated with the University of California at Irvine, is looking for a chief compliance officer. Job is based in Irvine, Calif., obviously. Salary range is listed at $254,000 to $536,000 but a "well-qualified" candidate "can generally expect $375,000 to $440,000." (The rumbling sound you hear in the distance is the stampede of healthcare compliance professionals rushing to apply.) Tailored Brands, the holding company for men's clothing outlets including Men's Wearhouse, Jos. A Bank, and K&G Fashion, is looking for a director of customs compliance. Job is based in New York City, with a salary range listed at $176,000 to $235,000. Global payments firm Remitly is seeking a head of global transaction monitoring. Job can be based in either Seattle or Arlington, Va., with a salary range of $208,000 to $260,000. Compliance meme of the week. That's all for this week's report. As always, if you have a tip or want to brag about your new job, promotion, career milestone, or anything else, email me at [email protected] or find me on LinkedIn. I'm always happy to give credit to the many hard-working people here in its corner of the business universe.

TechJuice
Sep 26th, 2026
Block brings Bitcoin Lightning payments to x402 for AI agents.

Block brings Bitcoin Lightning payments to x402 for AI agents. By Sabica Tahira | 11 seconds ago | Block has joined the x402 Foundation and added Bitcoin Lightning support to the x402 payment protocol as it expands its efforts to enable payments for artificial intelligence agents. The company said Lightning could support the low-cost, high-volume transactions expected to be required for agentic commerce. Steve Lee, head of Block's Bitcoin development initiative Spiral, said the integration could help make Bitcoin more practical for everyday payments made by people and AI agents acting on their behalf. The x402 protocol is an open payment standard that allows AI agents and web services to autonomously pay for API access, data and digital services. The technology is designed to support automated transactions without requiring users to manually authorize each payment. Block joins major technology companies including Google, Microsoft and Amazon Web Services, as well as crypto companies such as Coinbase and the Solana Foundation, in supporting the x402 Foundation. The foundation was launched in April under the Linux Foundation to advance the payment standard. The move also builds on Block's participation in the Universal Commerce Protocol, which aims to support AI-driven commerce for small businesses. With Lightning now integrated into x402, the initiative adds Bitcoin-based payments to the emerging infrastructure for automated AI commerce.