If you’ve ever scrambled to buy a birthday gift at the last minute or spent hours setting up an online store only to wonder if shoppers can even find you, you’re not alone. Small and medium business (SMB) owners juggle a hundred things at once, and keeping up with the rapid pace of commerce technology can feel like a full-time job on top of the full-time job you already have. That’s where agentic commerce comes in — and few people know this space better than Kyle Montgomery, Commerce Trailblazer.
Kyle is a commerce lead at Astound Digital, a 15-year veteran of the Salesforce ecosystem, and the co-founder of a gifting startup called Generous. He’s also one of the community leaders behind the Commerce Crew — an online Slack and GitHub community now 10,000 members strong. We sat down with Kyle to talk about how he got here, what agentic commerce actually means for small businesses, and why his advice to anyone just getting started is simply: Lean in.
A Trailblazer is an individual who drives change and uses Salesforce to transform their career, company, and community. They’re passionate about innovation, learning, and helping others, embodying the spirit that anyone can be a Trailblazer.
The Commerce Crew is a thriving community of these pioneers, advocates, and leaders who are experts in commerce technology. This group connects Commerce Trailblazers through an online Slack and GitHub community that is now 10,000+ members strong, dedicated to helping leaders, entrepreneurs, and Trailblazers connect and share ideas.
Kyle didn’t set out to become a commerce expert. His career took him there. Before joining Astound Digital, he was at Accenture, where he got trained on both Salesforce and Demandware — a lucky coincidence that turned into a career-defining advantage.
“Salesforce acquires Demandware and I kind of had a head start,” Kyle says. “It was really serendipitous for me. I was able to educate other people in my firm about Salesforce — what it is, an evolving SaaS platform, helping businesses grow everyday.”
From there, he dove into Trailhead, and he earned certifications across both platforms, and built a career as a cross-cloud practitioner. Today, at a firm of roughly 1,000 people with 500 engineers and consultants, Kyle leads commerce strategy and helps enterprise and growing brands navigate one of the most fast-moving technology shifts in recent memory.
When it comes to skilling up, Kyle is an unabashed Trailhead fan — and not just for the technical content.
“I probably sound like a Salesforce apologist, but I’m just being genuine. I really do use Trailhead,” he says with a laugh. At Astound, he’s created three custom trail mixes for onboarding: One for developers, one for architects, and one for functional analysts and business analysts. Each new team member gets a tailored path from day one.
But what Kyle recommends most enthusiastically isn’t just the hard technical content. “There are Trails on good presentation and interview skills and storytelling in your sales — and I like those. They helped me in my career quite a bit.” His advice to anyone building skills in the Salesforce ecosystem: Don’t skip the soft skills.
Salesforce’s free online learning platform, Trailhead, has modules on everything from managing teams to public speaking, and AI certifications for small business teams are now available to help growing businesses put artificial intelligence (AI) to work across sales, service, marketing, and commerce.
Joi the community of 10,000+ pioneers, advocates, and leaders who are expert in commerce technology to share ideas and build your skills.
Here’s where the conversation gets really useful for any small business owner with a storefront — physical, digital, or both.
Kyle breaks agentic commerce into three clear buckets, a framework he credits to Scott Wingo, a leader in the agentic commerce space: Off-site, on-site, and back office.
“Off-site are the ChatGPTs of the world,” Kyle explains. Consumers are already searching for and buying products through AI-powered answer engines — with or without your participation. “People are finding your products in answer engines and generative engines. So having generative engine optimization (GEO) best practices and answer engine optimization (AEO) best practices — that’s really important.”
For small business owners, this means your product data, brand voice, and loyalty programs need to be structured and accessible to AI agents operating outside your own site. Salesforce supports this through its involvement with the unified commerce protocol (UCP), ensuring retailers still have a voice in off-site commerce. “Making sure that retailers still have a voice in off-site agent commerce — that’s really really incredible that we’re all solving this together,” Kyle says.
Off-site agents are near and dear to Kyle’s heart. His startup, Generous, falls into this category, building an AI agent to help people find great gifts from a variety of brands and merchants.
This is about owning the agentic experience on your own storefront. Salesforce’s Agentforce product helps businesses deploy AI agents that can handle customer service, order inquiries, and even guide shoppers through a purchase — all natively within your site. Kyle points to Salesforce’s recent acquisition of Simulate as another step forward for B2C commerce on this front.
The third bucket is how AI is changing the way businesses build and operate their storefronts behind the scenes. With platforms like Salesforce Commerce Cloud (SFCC), developers and operators can now use AI-assisted “vibe coding” to accelerate site development, reduce costs, and ship faster.
“At Astound, we’re seeing 30% faster implementation times, lower cost to our customers,” Kyle says of their AI software development lifecycle (AI SDLC) approach. “And that’s really exciting.”
His strategic advice to small businesses? Start with off-site. “It’s happening whether you like it or not,” he says. Then build toward on-site and back-office as your comfort with the technology grows. “The future of commerce belongs to businesses that can stay nimble as they grow, and getting a strategy in place early — even a simple one — puts you ahead of the curve.”
One of the most delightful parts of talking to Kyle is hearing about Generous, his AI-first startup. The inspiration? Twenty-three nieces and nephews.
“When I had five, I actually sent them birthday cards, most of the time, I think,” he admits. “As that number grew… it became hard for me to manage. I thought, why isn’t there a tool to help me with this?”
Generous is a Salesforce partner ISV (independent software vendor) currently building an app for the Salesforce AgentExchange. The product uses AI at every layer: You talk to an AI, tell it about the interests of the person you’re gifting — a loved one, a colleague, a prospect — and it recommends a gift. You complete the purchase in a few clicks without leaving the agentic experience. The recipient can even swap the gift before it’s sent, creating a feedback
loop that helps the AI make better recommendations over time.
“It’s AI in the product and then AI in how we built the product as well,” Kyle says. Generous uses tools like Claude (by Anthropic) and cloud-based coding tools to accelerate development — a fully AI-first development approach from day one. For small business founders curious about what it looks like to build with AI, this is a real-world example worth watching.
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One of the most honest moments in the conversation comes when Kyle is asked how he keeps up with AI’s pace of change.
“Who does?” He says. “Six months ago now kind of feels like what five years ago felt a year ago.” The technology is moving so fast that even staying current feels like a sprint. His approach isn’t to try to know everything — it’s to build a culture of shared learning.
“I’m learning as much as I’m teaching. Even though I’m a leader in both my companies, my team is teaching me all the time what they’re innovating with. And they should be empowered to do so.” Leaders, he says, need to create space for teams to experiment, share what works, and bring those learnings back to the group. Community matters too — whether that’s the Commerce Crew’s 10,000-member Slack group or the Trailblazer Community, staying connected to peers who are figuring it out alongside you is one of the best ways to keep pace.
Kyle’s parting advice is straightforward, and it’s the same kind of guidance he’d give his own team.
“Lean in. Just go. Just do it. Just give it a shot.” Whether that means raising your hand for a role at your company, trying a new AI tool within your team’s security guidelines, or launching that storefront you’ve been putting off — the move is to just start.
“Figure out what will work and move the needle for your team. And then go back and share — whether it was successful or not — because you learned, and they can learn from your experience.”
And hey, if you need a little help remembering to send a gift along the way, there’s an app for that.
Whether you’re just launching your first storefront or looking to scale with AI, Salesforce has the tools to help you grow at your own pace.
Start your commerce journey with Salesforce Suites today or activate Foundations to try Agentforce and AI agents to work across your business.
AI supported the writers and editors who created this article.
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