REGISTRATION

WELCOME

B2SMBI Co-Founder & CEO Dave Walker welcomes all attendees with an overview of our agenda’s format and objectives.

BEST2SMB AWARD

2024 BEST2SMB Brand of the Year Winner Announced!

2024 Brand of the Year Finalists:
Google
Alignable
Quickbooks

1 BIG THING

We kick-off all of our events with an exercise brought to us in 2019 by Nicole Wood, co-Founder of Ama a Vida: what’s the 1 big thing you hope to take away from your time at this event? A great ice-breaker as we pair off for what’s always a lively – and loud – exchange!

OUR AGENDA: THE NEW SELL

What we began in Sonoma in May, we continue to examine today. Citing a recent survey from Alignable of over 1500 SMBs, Dave Walker lays down the numbers of AI acceptance and perceived value amongst Small Businesses. We tee-up the substance of our entire agenda: “The New Sell” – and the role of AI – in the $500Bil SMB marketplace.

THE SMB PRODUCTIVITY GAP

Newly appointed Chief Growth & Strategy Officer of B2SMBI – and former global VP/GM for SMB/Mid-Market – Maciek “Magic” Szczesniak introduces a deep-dive into the chasm between large and small enterprise productivity. Citing multiple sources of recent SMB research, we dig into the numbers and the inescapable facts of AI “readiness.”

ASSESSING SMB READINESS

Long-time research contributor to our events, Stephanie Gorski of Accenture continues our insights into SMB AI “readiness.” For those SMBs falling behind, is the problem software? hardware? brainware? We’ll frame the opportunity of a new sell with a single AI-centric value prop: productivity.

SMB PRODUCTIVITY POWER HOUR: KEYNOTE #1

Mathew Goddard leads the Modern Work and Business Applications Solution and Product Growth Marketing team for Microsoft, sitting in the center of AI’s application in the SMB workplace. He recently wrote: “There is no greater opportunity than empowering SMBs to grow their businesses, enhance efficiency, keep staff engaged and productive, and bolster their digital security—especially in the era of AI.” He’ll lay out Microsoft’s AI value-prop, and lessons learned in bringing AI@Work to market.

SMB PRODUCTIVITY POWER HOUR: KEYNOTE #2

2024 Best2SMB Product of the Year Nominee vcita’s CBDO Amir Blich details how AI has become a key piece of the vcita platform. Building on expansive SMB customer feedback surveys, Amir describes what the vcita offering is getting right, and how it is moving forward while bringing a cautious SMB customer forward into the future.

BEST2SMB AWARD

2024 BEST2SMB Product of the Year Winner Announced!

2024 Product of the Year Finalists:
vcita
Asana
Monday.com

SMB PRODUCTIVITY POWER HOUR: KEYNOTE #3

How are AI-driven productivity gains actually manifesting in B2SMB products and services? B2SMB veteran Jared Turner talks AI integration at Boostability – how it’s been conceived, built, delivered and improved within a well-established, widely popular SMB app.

BEST2SMB AWARD

2024 BEST2SMB Hall of Fame Inductees Announced!

2024 Hall of Fame Finalists:
Square
Microsoft
Netsuite
Shopify
Apple
Paypal

THE 2024 BEST2SMB AWARDS & HALL OF FAME LUNCHEON

We’ll take a break over lunch – and enjoy what’s sure to be a beautiful day in a beautiful setting on the Thornhill patio. Buffet served in the Founder’s Room – but take your seat in a wide variety of Arboretum settings.

AFTERNOON STRETCH & RESET

Local Small Business Owner and Fitness Coach/Author Kelsey Dunbar and team help us reset for the work of the afternoon.

GOING TO MARKET WITH AI POWER HOUR: KEYNOTE #1

How is the AI-driven value prop marketed to SMB prospects and customers? How are B2SMB brands presenting the tremendous gains possible with AI enhancements? How are GTM strategies and executions overcoming the very real fear SMBs have of yet another “dark tech,” AI? Sarah Jordan is the first of 3 different B2SMB Leaders to offer her real-world learnings.

GOING TO MARKET WITH AI POWER HOUR: KEYNOTE #2

Time to hear from the Customer! We reprise one of our best sessions of Sonoma: a live panel of SMB owners/decision makers on what it takes to win their business. This highly interactive session allows all of us to hear directly, without filters, what moves a SMB to “Yes.”

GOING TO MARKET WITH AI POWER HOUR: KEYNOTE #3

Aviv Goren is bringing a new AI-Centered offering to SMBs – Roojoom’s “Personal AI” engines drive individual journeys for customer service and for marketing.” Leveraging the high-intelligence/high-touch capabilities of AI, Roojoom’s go-to-market strategy and tactics are lessons worth sharing.

GOING TO MARKET WITH AI BONUS KEYNOTE

Our Sonoma event audience was wowed by Jordan Ritter: Napster founder, serial entrepreneur, and inventor of the “Ear Whisperer” label for great AI. A very compelling update will be offered by Augment Co-Founder, Saurav Pahadia, who updates on the extraordinary progress the AI-based enterprise has made since May. If you want to see a clear vision of the future, you’ll get it here.

PANEL: TEACHING AI TO SMBS

Successful entrepreneurship is now a well-established subject in our best Business Schools. In the course of building curriculums that are impactful to future SMBs, the topic of AI and its application is of course front and center. We’ve assembled a panel of professors from the University of Houston, the University of Washington and other B-schools to describe their coursework in some detail, providing a teachers’ perspective on AI. “Magic” Szczesniak moderates.

INTRODUCTION: THE SMALL BUSINESS PRODUCTIVITY EXPO

B2SMBI’s Dave Walker joins our Business School Guests and Magic Szcesniak to introduce our most significant 2025 initiative – an exclusive partnership with major Business Schools around the US. Planned across 12 different campuses throughout the year, B2SMBI will host live events of between 300-500 SMBs each to offer a serious productivity upgrade. This single day event features a morning of SME keynotes and panels, and an afternoon filled with small-sided workshops delivered by Faculty and B2SMBI-Member leads, and facilitated by B-Schools Graduate Students.

BEST2SMB AWARD

2024 BEST2SMB Executive of the Year Winner Announced!

2024 Executive of the Year Finalists:
Carissa Reiniger
Eric Groves
Kush Shrivastava

BREAKOUT #2: SMALL GROUP WALKABOUTS

Our second breakout of the day allows our attendees to compare notes and share objectives coming out of our “New Sell” agenda. We’ve asked Best2SMB event attendees to lead small groups in a “walkabout” discussion on the content presented across the day. What most impressed you? What was applicable to your challenges? What was unrealistic or downright BS? We’ll invite these Small Group Leaders to then join on stage for a panel discussion engaging our whole audience.

SMB PANEL

Time to hear from the Customer! We reprise one of our best sessions of Sonoma: a live panel of SMB owners/decision makers on what it takes to win their business. This highly interactive session allows all of us to hear directly, without filters, what moves a SMB to “Yes.”

LEADERS' LEAGUE RECEPTION

Step outside for a beautiful view of the Morton Arboretum as we celebrate our Day 1 with drinks and nosh. Then join us for our event dinner!

LEADERS' LEAGUE EVENT DINNER

We cordially invite ALL event attendees to join your peers for an extraordinary dinner at Chicago legend, Meson Sabika. With over 10K 5-star reviews, Meson brings Spain to a restored farmhouse and garden in Naperville. The Tapas menu is served family style, with Sangria flowing freely (as well as an open premium bar), while the warm camaraderie is our network’s super-power. A short and easy 15-minute drive from our Morton Arboretum venue, we hope you join us!

PARTNERSHIPS CIRCLE BRUNCH

A good evening demands a great brunch. Join us for omelettes with feta, spinach and sundried tomato, Amish bacon, and the Arboretum’s famous donuts! Coffee served!

PARTNERING WITH SMB INFLUENCERS

With an SMB following of 3Mil+, Melinda Emerson is an Influencer’s Influence. Her message (and best-selling book) is “Be Your Own Boss,” and she is especially impactful with women entrepreneurs. She’s also worked with a number of Fortune 500 Enterprises who sell at scale to Small Business, assisting in successful marketing, selling and growth initiatives. She gives a primer on how – and why – you should be working with SMB Influencers.

PARTNERSHIP SPOTLIGHT

New B2SMBI Members and Event Attendees will showcase their offerings in 10-minute overviews with special emphasis on their objectives in 2025 and how fellow B2SMB brands might play a valuable role in driving shared success.
UENI
Vensure
Synup
H&R Block

PITCH FOR PARTNERS

Back by popular demand: we’ll invite attendees to stand and introduce their company, their partnership opportunities and what they’re looking for. 3-Minute time limit per Pitch!

WRAP UP & NEXT STEPS

We’ll end Day 2 with summary takeaways and a commitment to meet within 14-days with prospective partners we’ve identified during the time together.

POST-EVENT LUNCH

For those catching late afternoon or evening flights out – and local attendees, too – we’ll gather up for a great deli lunch at Halsted Street Bagel & Deli, just a few minutes from our venue. Join us!