B

Block

Runs Square payments and the Cash App money app

Head of SMB Acquisition

Full-TimeUpdated on 10/23/2026
$175.5k - $263.2k
Expert
Melbourne VIC, Australia
In Person
Sales & Account ManagementAccount Executive

About the job

Requirements
  • 12+ years of experience in high-growth environments leading SMB Sales, Franchise Sales, BDR, Mid-Market Sales, or Account Management organizations, preferably in a fast-moving technology, payments, or financial services company, with experience operating across both high-volume sales motions and complex commercial relationships.
  • Ability to develop talent, motivate high-performing teams, and build strong cross-functional relationships, including a proven track record of coaching and managing frontline managers to results.
  • Experience standing up, scaling, or transforming sales organizations by hiring, onboarding, and developing talent across BDRs, AEs, and frontline managers, and designing the structures and operating rhythms required to support growth.
  • Demonstrated ability to build, operate, and continuously improve playbooks that scale across a large and growing team while preserving the judgment and flexibility required for sophisticated deals.
  • A demonstrated track record of leading teams that consistently drive revenue growth and exceed revenue targets, including experience with sophisticated commercial negotiations and established clients.
  • Proven experience navigating and operating effectively within matrixed global organizations and aligning regional priorities with broader global strategies.
  • Experience working closely with Product and Marketing to drive conversion, including improving merchant acquisition, sign-up, activation, and onboarding journeys, and translating merchant needs into product and go-to-market opportunities.
  • High familiarity and comfort with how product development works, preferably in payments, and credibility with Product and Engineering partners across technical, marketing, product, and commercial disciplines.
  • Demonstrated ability to influence and earn trust with senior internal leaders and external decision makers, including C-suite stakeholders at larger merchant and franchise partners.
  • Ability to set a clear vision, implement robust processes, lead teams through complex relationships, and translate strategy into disciplined execution.
  • Comfort working with analytics and tools that support business performance measurement and management, particularly forecasting, funnel, pipeline, conversion, productivity, and revenue metrics at scale.
  • Ability to seek out relevant data and build compelling business cases and sales narratives that demonstrate the company's value proposition.
  • Ability to alternate between team leadership and hands-on work, including annual planning, pipeline reviews, complex negotiations, and unblocking team members.
Responsibilities
  • Oversee the Australia and New Zealand SMB and Franchise Sales team across BDR, Inbound and Outbound Account Executives, and the Franchise sales motion; build and refine playbooks, processes, and tooling; set segment-wide strategy; and hold the team accountable for OKRs and revenue targets.
  • Develop the sales team and its leaders by building skills, knowledge, and efficacy, fostering performance and continuous improvement, coaching frontline managers, and setting an accountable tone rooted in ownership and empathy.
  • Work with Marketing, Finance, Product, Engineering, Risk, Legal, Account Management, Partnerships, and other cross-functional teams to support revenue generation and build internal relationships across a distributed, global, matrixed stakeholder group.
  • Build and refine repeatable sales approaches across the deal lifecycle, from prospecting, discovery, and qualification through value articulation, solutioning, negotiating, contracting, closing, and onboarding; balance scalable SMB motions with the flexibility required for complex Franchise opportunities.
  • Develop and pitch sales narratives that educate prospective merchants on the company's value proposition; coach the team through sophisticated negotiations; support internal and external advocacy; clear revenue blockers; and communicate with senior decision makers at brands and franchise groups.
  • Implement and maintain best practices in forecasting accuracy, pipeline coverage and health, opportunity progression, and conversion; partner with Finance and Sales Strategy and Operations on rigorous forecasts and understanding risks and upside.
  • Shape and refine ideal customer profiles, priority use cases, and value propositions across SMB and Franchise; use insights, data, and market intelligence to develop sales and growth narratives that inform B2B marketing, product, and go-to-market strategy.
  • Use pipeline and merchant portfolio insights to identify priority industries, franchise networks, growth opportunities, and emerging trends, translating them into segment strategies, scalable acquisition motions, and commercial priorities across Australia and New Zealand.
  • Represent the business to SMB and Franchise merchants as a thought leader in payments and Buy Now Pay Later, demonstrating the product's value as a growth driver and developing relationships with merchant partners, including senior leadership teams where appropriate.
  • Represent merchant feedback and sentiment internally, advocate for merchants while balancing business needs and constraints, and deliver structured insights to influence product, marketing, risk, and commercial priorities.
Desired Qualifications
  • Experience leading SMB Sales, Franchise Sales, BDR, Mid-Market Sales, or Account Management organizations in a fast-moving technology, payments, or financial services company is preferred.
  • Experience with product development in payments is preferred.

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'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

6 month growth

0%

1 year growth

1%

2 year growth

1%
Yahoo Finance
Oct 23rd, 2026
Meta, Barclays, Block cut thousands of jobs as firms shift spending to AI

Companies are cutting jobs and shifting money from staff to artificial intelligence (AI) infrastructure, as the cost of meeting booming AI demand reshapes budgets. Meta will lay off about 8,000 workers, or 10% of its workforce, and leave about 6,000 jobs unfilled. It expects 2026 expenses to reach as much as $169 billion, driven by infrastructure and AI talent. Block is cutting more than 4,000 of its 10,000-plus employees; its shares are up 19% this year. Kroger will lay off 3,000 corporate staff over three years, and Barclays plans to cut 5,000 jobs, about 5% of its workforce. Snap is eliminating about 16% of staff, or 1,000 jobs. Coinbase is cutting about 14%, and Microsoft is offering buyouts to about 8,750 US employees.

Music Business Worldwide
Oct 20th, 2026
Jim Freeman, ex-Amazon Prime Video VP, joins Ticketmaster as CTO to lead 'AI-first' push.

Jim Freeman, ex-Amazon Prime Video VP, joins Ticketmaster as CTO to lead 'AI-first' push. October 20, 2026 Ticketmaster has appointed former Amazon executive Jim Freeman as its Chief Technology Officer. The Live Nation-owned company has also hired Rachel Smith from Block as its first SVP of Data Science and Machine Learning, and ex-Disney executive Chuck Mortimore as SVP of Product. Ticketmaster announced the appointments on Monday (October 19), alongside the addition of the team behind AI startup Ragie. "Reliable, secure and personalized experiences depend on how effectively we use technology and data," said Saumil Mehta, Global President of Ticketmaster. "Jim, Rachel, Chuck and the Ragie.ai team will help us move faster, build better tools and deliver better outcomes for fans, artists, venues and clients." As CTO, Freeman will be responsible for the technology behind Ticketmaster's products for fans and clients, including what the company calls "a new generation of agentic, AI-powered tools." "Jim, Rachel, Chuck and the Ragie.ai team will help us move faster, build better tools and deliver better outcomes for fans, artists, venues and clients." Saumil Mehta, Ticketmaster Freeman will also oversee Ticketmaster's global engineering organization and platform modernization, continue work on its defenses against bots and "bad actors," and lead a push to make "every function AI-first" across the company. Ticketmaster says Freeman has spent more than 30 years running engineering teams at consumer technology businesses. As a VP at Amazon, he helped build and launch Prime Video, then scaled the service to more than 30 million monthly active users worldwide. He also launched Prime Video Direct and Amazon Channels, and expanded the service's device partnerships and distribution. Freeman later served as CTO of European fashion marketplace Zalando, which now connects more than 62 million active customers with 7,000 brands across 29 markets. Most recently, he was a Senior Advisor at Permira. Freeman fills a position that had been vacant since February, according to Variety. Ticketmaster's previous CTO, London-based Carlos Alvarez-Coch, left shortly before the US antitrust trial against Live Nation began on March 2. Smith joins Ticketmaster from Block, where she helped scale the data science teams behind Square, Cash App, and TIDAL. She was responsible for more than 120 data scientists across those businesses. At Ticketmaster, Smith will build what the company calls a "center of excellence for data science," extending its existing analytics work and making data more central to product development and business decisions. Ticketmaster says the move will create its first dedicated data science and machine learning organization, with a focus on fraud detection, bot mitigation, and the fan experience. Mortimore, meanwhile, will lead Ticketmaster's product strategy for identity, access, and trust. His remit covers how fans access and manage their accounts and tickets, as well as protections against "bad actors and unauthorized access," according to Ticketmaster. Mortimore has held product leadership roles at Disney, Stripe, Visa, and Salesforce over more than 20 years, following earlier engineering roles at Netscape and Sun Microsystems. At Disney, his most recent employer, he consolidated identity across the company's global businesses, including its theme parks, Disney+, and Hulu. Ticketmaster said the Ragie team, whose work focuses on AI infrastructure and retrieval technology, will help staff across the business build AI tools and put them to use. Ragie announced on July 27 that it was joining Ticketmaster, a deal Variety reported as an acquisition. Ragie's website still describes the company as a "fully managed RAG-as-a-Service platform," and now carries a banner announcing that "Ragie joins Ticketmaster." RAG, or retrieval-augmented generation, is a technique that lets AI models draw on a company's own documents and data when generating answers. The appointments come almost a year after Mehta joined Ticketmaster as Global President, with a stated aim to "accelerate an AI transformation" at the company. Mehta previously spent more than nine years at Square, where he was most recently Chief Product Officer and Head of Business Org. In May, Ticketmaster cut around 350 jobs, or 8% of its global workforce, primarily in engineering, product, and design, according to Pollstar. "The purpose of [these cuts] is stronger prioritization, especially in engineering product and design," Mehta told Pollstar at the time. "That comes with flattening layers, consolidating ownership, changing how teams are structured and ensuring that we put more energy behind specific initiatives." Ticketmaster's controls on bots and ticket brokers are also the subject of a lawsuit brought against Live Nation and Ticketmaster by the US Federal Trade Commission (FTC) and seven states in September 2025. The complaint alleges that Ticketmaster knowingly allowed brokers to use hundreds or thousands of accounts to exceed artists' ticket limits, and that those tickets were then resold on Ticketmaster's own resale marketplace. In a court filing on October 13, Live Nation and Ticketmaster denied the FTC's claims, calling the lawsuit "misguided." "In 2025, Ticketmaster detected and blocked nearly 260 million attempts daily by bots to access its services, and currently blocks tens of thousands of suspected inauthentic account-creation attempts each day," the filing states. Separately, a federal jury in Manhattan found in April that Live Nation and Ticketmaster had illegally monopolized primary ticketing at major US concert venues, along with the market for large amphitheaters. Live Nation and Ticketmaster have asked the court to throw out the verdict or order a new trial. The coalition of 33 states and the District of Columbia that pressed the case to a verdict, after the DOJ settled its claims a week into the trial, is seeking the divestiture of Ticketmaster. Ticketmaster's revenues rose 15% year-over-year to USD $852 million in Q2 2026, with adjusted operating income up 14% to USD $331 million. The company says it processes more than 600 million tickets annually across more than 35 countries.Music Business Worldwide

Insider Monkey
Oct 19th, 2026
Block (XYZ) grew lending-led gross profit 43%, but are its costs catching up?

Block (XYZ) grew lending-led gross profit 43%, but are its costs catching up? Published October 19, 2026 at 3:40 pm EDT Court filings made public on October 8 revealed that the Federal Trade Commission is investigating whether Block (NYSE:XYZ) left customers with frozen Square and Cash App accounts without enough help. That is an awkward headline for a company whose results have rarely looked better. The surprise in the second quarter was where the growth came from: lending to Cash App customers, not payments or bitcoin. So the question is whether the costs of that lending, and of running after a large staff cut, are starting to catch up with the profit. Square sells card readers, payment processing, and software to restaurants and shops. Cash App lets tens of millions of people send money, spend through a debit card, and borrow small amounts. Growth is strong, and the price looks modest beside it, yet the adjusted profit behind that price leaves out costs that are rising fast. Gross profit rose 25% in the second quarter, with Cash App up 31%. Much of that came from Cash App Borrow, the short-term loan product, which helped lift consumer lending originations 59% to $18.9 billion. Block's Financial Solutions unit, where that lending shows up, grew gross profit 43%, up from 20% a year earlier. Bitcoin moved the other way. Gross profit from the bitcoin business fell 31% because the company cut a trading fee and activity slowed. That business sells a lot of bitcoin but keeps little as profit, so lending now matters far more to the results. Investors who want more stocks like this one can find Block in our recent list of 9 Best Bitcoin Stocks to Buy Now. Square's payments business is speeding up. Square is picking up speed too. Its gross profit grew 13%, helped by a one-time tariff reimbursement, and US payment volume growth reached 10%, the strongest pace since the second quarter of 2023. That ends a slower stretch at the end of 2025. If you're interested in digital payments, we recently compiled a report on 7 Best Fintech Stocks to Buy as Digital Payment Volume Surges. Costs are rising behind the adjusted profit. Bloomberg noted that the FTC's filings point to Block's large workforce cut and its push to use artificial intelligence. They also say customers got little help even after finishing identity checks, so the probe is about how a leaner operation treats the people it serves. Costs already show up in the results. Transaction, loan, and consumer receivable losses rose 99% on a GAAP basis, mostly because Block is making more loans, and legal accruals pushed up administrative expenses. That is why adjusted earnings per share of $1.02 sit far above the GAAP figure of $0.15, and why net margin over the past 12 months was only 1.43%. Management expects growth in loan losses to cool through the rest of 2026, and it says loss rates on its Borrow cohorts remain healthy. If that holds, lending keeps growing without eating the profit. A shareholder is betting on exactly that, while hoping the probe adds little to the legal bill. Investors are pricing in an earnings rebound. Block trades at about 19 times estimated 2026 earnings. This forward P/E divides the share price by the profit per share analysts expect, so a lower number means investors pay less for each dollar of expected earnings. That sits well above the sector median of 10.88 but far below Block's own five-year average of 41.10. It also rests on adjusted earnings, which leave out the legal and restructuring charges above. Growth explains most of the premium to peers. Analysts expect adjusted earnings per share to rise about 71% in 2026, so the multiple is far less demanding against that growth. For investors looking for cheaper growth names, our list of 10 Undervalued Growth Stocks to Buy Now covers more names. Big investors have been adding. Hedge funds holding Block rose to 76 in the second quarter from 63 in the first, so more active funds now back the story. Short sellers, who borrow shares to profit from a drop, hold 3.08% of shares outstanding. That is a small bet against the stock, and it pays off if loan losses or legal costs weigh on the price. So are the costs catching up? In the GAAP results, they are, while adjusted results still show profit pulling ahead. Block's next report, due early next month, will show whether loan losses are cooling as promised and whether legal charges are still climbing.

WhoTakesCoin
Oct 18th, 2026
Revolutionary entry: Block teams up with Sazmining to launch affordable Proto mining hardware!

Revolutionary entry: Block teams up with Sazmining to launch affordable Proto mining hardware! Sunday, October 18, 2026 0 TL;DR: Sazmining is offering individual Proto immersion hashboards at $4,187 each, with financing and managed hosting. The arrangement lowers the upfront hardware purchase but does not remove Bitcoin mining's ongoing costs or profitability risk. Buying into industrial Bitcoin mining usually means dealing with noisy equipment, electricity contracts and cooling infrastructure. A new offering built around Block's Proto hardware takes a different approach: purchase a single hashboard and leave the h Related industries. cryptocurrency

MarketScreener
Oct 16th, 2026
Klaviyo: 85% of Klaviyo code is AI-generated. Here's what changes.

Klaviyo: 85% of Klaviyo code is AI-generated. Here's what changes. Published on 10/16/2026 at 11:33 am EDT On September 23, I joined Stephanie Cohen, Cloudflare's chief strategy officer, and Owen Jennings, Block's head of business, on a panel at The Information's AI Agenda Live in San Francisco. [...] Attachments * Original document * Permalink Disclaimer Klaviyo Inc. published this content on October 16, 2026, and is solely responsible for the information contained herein. Distributed via Public Technologies (PUBT), unedited and unaltered, on October 16, 2026 at 15:32 UTC. (C) Publicnow - 2026