Tax season shouldn’t feel like a panic spiral. Join us live to hear real stories from business owners who’ve been there — and what they’d do differently. You’ll get expert tips from CPA Keila Hill-Trawick, plus a live demo of how to stay tax-ready year-round with Square Banking.
What you'll learn
Real stories from sellers who turned tax-time chaos into year-round confidence
What not to do — the top tax mistakes small business owners make (and how to avoid them, straight from a CPA!)
How to build savings habits before you feel “ready”
How to automate your savings with smart tools that do the work for you (live demo)
Learn how to manage tax season like a pro — and see how Square makes it easy!
THIS WEBINAR WILL BE RECORDED AND SENT TO EVERYONE WHO REGISTERS.
Please RSVP "Yes" to this event at the top right side of this page. That way other Community members and the Square team will know you'll be joining.
Next, use the link below to register for the online event. This will give you the access link for the event.
Register Now
Speakers
Keila Hill-Trawick
Founder & CEO
Little Fish Accounting
Elise Marks
Banking Product Marketing
Square
Jeffrey Kurt
Banking Product Specialist
Square
*Our guest speakers are not employees or consultants of Square. The information provided during this event solely reflects their views and is not endorsed by Square. This event is intended for educational purposes only and does not constitute legal, financial, or tax advice. For specific advice applicable to your business, please contact a professional.
By signing up to attend this event, you acknowledge that you may also receive promotional emails from Square.
Square, the Square logo, Square Financial Services, Square Capital, and others are trademarks of Block, Inc. and/or its subsidiaries. Square Financial Services, Inc. is a wholly owned subsidiary of Square, Inc.
All loans and Savings accounts are issued by Square Financial Services, Inc., a Utah-Chartered Industrial Bank. Member FDIC. Actual fee depends upon payment card processing history, loan amount and other eligibility factors. A minimum payment of 1/18th of the initial loan balance is required every 60 days and full loan repayment is required within 18 months. Loan eligibility is not guaranteed. All loans are subject to credit approval.
Savings accounts are provided by Square Financial Services, Inc. Member FDIC. Accrue annual percentage yield (APY) of 1.00% per folder on folder balances over $10. APY subject to change, current as of 2/18/2025. No minimum deposit is required to open an account. Accounts will not be charged monthly fees. Accounts are FDIC-insured up to $2,500,000. Pending balances are not subject to FDIC insurance.
Square Checking is provided by Sutton Bank, Member FDIC. Square Debit Card is issued by Sutton Bank, Member FDIC, pursuant to a license from Mastercard International Incorporated, and may be used wherever Mastercard is accepted. Accounts are FDIC-insured up to $250,000. Funds generated through Square’s payment processing services are generally available in the Square checking account balance immediately after a payment is processed. Fund availability times may vary due to technical issues.
You're invited
Twice a year, we bring the seller community together to share what we've been building — and this fall, we’re broadcasting live from New York City. Join our livestream as we unveil the newest innovations that will change how you think about running your business: tools designed to handle the complexities behind the scenes so you can focus on your craft, your customers, and your team.
You'll hear directly from Square leadership about what's coming next, plus get a front-row seat to a candid fireside chat between Jack Dorsey (Founder, CEO of Block; Founder of Twitter) and Randy Garutti (former CEO of Shake Shack) — two founders who know what it takes to build something meaningful.
Reserve your virtual seat today — you won’t want to miss it.
What's on the agenda
Fireside chat with two legends: Hear directly from Jack Dorsey and Randy Garutti as they sit down for a candid discussion on building, scaling, and redefining what’s possible.
Exclusive product preview: Be the first to explore Square’s latest tools — built to streamline operations and move your business forward.
Go inside the product: Hear directly from our executive and product teams as they share insights on what’s next.
Register now
Speakers
Jack Dorsey
CEO
Block
Randy Garutti
Former CEO
Shake Shack
Lindsey Irvine
Chief Marketing Officer
Square
Willem Ave
Global Head of Product
Square
Ming Tai Huh
Head of Product, F&B
Square
Miles Suter
Head of Bitcoin
Cash App
Elizabeth Age
VP, Account Mgmt
Square
Brian Grassadonia
Ecosystem Lead
Block
Join us for an exclusive look at the new innovations launching at Square this fall. Each product and feature is designed to help you focus on what matters: your service, your team, your community. You'll hear from the head of product and product experts at Square, plus get hands-on demonstrations of tools that are already transforming businesses like yours.
What to expect:
Opening session: Discover the biggest innovations from this fall’s launch event, including AI-powered business insights, new payment options, and solutions built for your business.
Industry breakout sessions: Choose from deep dives tailored to Food & Beverage, Retail, Services, or Health & Beauty — each featuring tools built for your specific needs.
Q&A: Get your questions answered by Square product developers and specialists.
Whether you're a solo entrepreneur or managing multiple locations, now’s your chance to get an inside look at how Square can help you move from managing the day-to-day to becoming a neighborhood staple.
Can't make it live? Register anyway — we'll send you the recording and resources after the event.
Register now
Speakers
Willem Ave
Global Head of Product
Square
Ming Tai Huh
Head of Product, F&B
Square
Andrea Valdettaro
Sr. PMM, F&B
Square
Matt Kochanowski
Product Marketing Lead
Square
Vicroria Liu
PMM, Retail
Square
Katie Miller
PMM, Health & Beauty
Square
Ian Cornwall
PM, Appointments
Square
Running a busy bar or restaurant means living in the rush — managing orders, staff, and guests all at once. Join us for this live session, where we’ll show you how Square can help you bring calm to the chaos. From faster tabs to smarter shifts, learn how to keep service smooth and your team (and guests) happy.
You’ll learn to:
Uncomplicate every shift with POS tools built for bars and restaurants — learn about tools like bar tabs and Square Handheld with a live demo from a Square Product Specialist.
Simplify staff management and control labor costs with smart scheduling, tip tracking, and team communication tools that help you keep every shift in sync.
Turn guests into regulars by running automated marketing campaigns, sending personalized offers, and leveraging customer insights.
See what’s working (and what's not) with AI-powered reporting in your dashboard to spot key insights instantly.
Grow on your terms with integrated banking, fast access to revenue, and flexible funding options — built specifically for hospitality operators.
Plus, hear real stories from Square sellers on how they run smoother operations and create standout guest experiences.
Register now, we'll see you there!
Running a business shouldn’t feel like a guessing game — which includes preparing for the year ahead. Square polled business owners on the trends they expect to shape 2026, and this webinar dives deep into the signals that matter.
Join us to hear the moves operators across industries are making now — and the shifts they’re preparing for in 2026.
What you’ll learn:
Industry predictions across food and beverage, retail, beauty, and professional services
How business owners are adapting to economic shifts and evolving consumer behavior
How AI, automation, and other tech can help you manage costs, attract customers, and grow
Speakers:
Ryan Cole, CEO/Partner, Hi Neighbor Hospitality Group
René de la Garza, Founder of Brow Down Studio and Brow Down Studio Pro
Matt Kochanowski, Product Marketing Lead, Square
Register now — see you there!
