It's been one of the biggest privileges of my career to help the Design team @GustoHQ navigate what it means to be an AI first team, while still holding onto the humanity, taste, judgement, and customer focus that makes us, us.
What a time!
https://t.co/TGPE9ZUjmR
There are lots of good reasons to want in person work but “I can’t personally get anything done when my kids are in the house so I don’t think anyone else can either” is the weakest of arguments.
It's been one of the biggest privileges of my career to help the Design team @GustoHQ navigate what it means to be an AI first team, while still holding onto the humanity, taste, judgement, and customer focus that makes us, us.
What a time!
https://t.co/TGPE9ZUjmR
The @torontolibrary gave me my first job and opened a lot of doors for a kid growing up in Scarborough.
Today, @aratisharma and I are matching donations to @TPL_Foundation 2X up to $100,000 to help fund after-school programs across the city.
Donate 📚➡️ https://t.co/O2grIkC6BA
Gusto just announced Gusto Cofounder, and this is something I'm really excited about. Not just because it's all I've been doing for the last two months, but because I think it's an example of what I've always thought to be the ideal user experience for our customers – almost no user interface, we just do it for you – run payroll via SMS, get weekly reports, set up automatic expense approvals, or anything else on your mind. It's an AI assistant for 500k small businesses, available in their preferred messaging app. Here are a few real conversations I've had with it 👇
Meet Gusto Cofounder: An AI teammate that already knows your business and actually does the work.
Most AI just answers questions. This runs payroll, flags compliance deadlines, handles time-off requests, and works over text or Slack.
Because every founder deserves a cofounder.
Our mission at @GustoHQ is to grow the small business economy with technology and heart. We are deeply grateful to all the work small businesses do every day in communities everywhere, and we are committed to being their partner, taking hats off their head, delivering them peace of mind, and giving them superpowers, so they can progress their business.
@agarfinks from @FortuneMagazine has been following Gusto for a long time, and we recently shared with her some milestones in our journey of building Gusto (including passing $1b of revenue). These are still the early days of what’s possible. We are building Gusto for the long term, and when small businesses succeed, we succeed.
Today is a Gusto Showcase! It’s one of my favorite moments, when we share a summary of how we’re making Gusto better for our 500,000+ small business customers.
At @GustoHQ, we obsess over helping small businesses, and every challenge they face is an opportunity for us to help. Gusto has never been just a tool or technology. We strive to be a partner for small businesses, taking hats off their head, doing work on their behalf, so they can progress in building their business.
With 500,000+ customers, we know we’re still early in the journey. There are millions of small businesses we are eager to serve.
The future of business is small. And that’s big. #GustoShowcase
We’re building such a great team @GustoHQ ! 🚀🚀🚀New head of brand creative, service design, and research — I’m going to learn so much from this brilliant people! https://t.co/mEzBeUseXD
It’s that time of year when being a leader means emerging from hibernation to publish:
• Top 5 Trends
• What’s Dead
• What’s Inevitable
• Predictions for 2026
Love the confidence. But everything is changing at the speed of light and no one knows. Happy holidays!
You’re invited! On Sept 16 we’re hosting our Summer Showcase in San Francisco.
Hear from inspiring entrepreneurs, explore resilience + AI, and get first looks at Gusto’s latest tools.
(Video featuring @edawerd)
I’m excited to share @Guideline401k is joining
@GustoHQ! (pending regulatory approvals)
@kevinbusque + team have helped 1M+ people save for retirement by putting customers first. Together, we’re excited to bring incredible retirement benefits to small businesses!