From Evangelizing to Executing with Jason Greenwood

The B2B eCommerce industry has reached a turning point.

For years, digital leaders have been explaining why manufacturers and distributors need digital commerce. Now, the conversation has shifted. The market understands the value. The real challenge is execution, what to do first, how to prioritize, and how to generate real return without forcing customers to change how they work.

That shift was at the center of a recent conversation with Jason Greenwood, founder of Greenwood Consulting and one of the most respected independent voices in global B2B commerce.

Their discussion covered entrepreneurship, personal brand, digital adoption, and the next phase of B2B commerce, especially how AI and conversational channels are reshaping the way buyers and sellers interact.

What emerged was a clear message:
The future of B2B eCommerce isn’t about forcing behavior change. It’s about meeting customers where they already are.

From Evangelism to Execution: How the B2B Market Has Changed

Jason Greenwood has spent more than two decades working across retail, manufacturing, and distribution, first in B2C, then increasingly in B2B. When he went independent nearly five years ago, much of his work involved persuading companies that digital commerce even mattered.

That’s no longer the case.

According to Greenwood, the industry crossed an important threshold around 2024. Research on B2B buying behavior, particularly the rise of millennial and Gen Z buyers, made it impossible to ignore the mismatch between traditional sales models and how modern buyers want to work.

Today, most manufacturers and distributors no longer ask whether they need digital commerce. Instead, they ask:

• What should we prioritize first?
• How do we sequence initiatives?
• How do we generate value quickly?
• How do we avoid disrupting our sales teams?

This shift has fundamentally changed Greenwood’s role. He now spends less time convincing leaders of the value of B2B eCommerce and more time helping them build practical roadmaps that align technology, people, and process.

Why B2B Customers Shouldn’t Be Forced to Change Their Behavior

One of the most important themes in the conversation was customer behavior, and why trying to change it often fails.

Many B2B buyers have deeply ingrained habits:

• emailing purchase orders
• texting or messaging account managers
• sending photos from job sites
• calling in last-minute availability checks
• requesting delivery updates through familiar channels

Historically, digital commerce projects tried to move these buyers into portals and dashboards. Adoption suffered, not because the technology was poor, but because the behavior change required was too high.

Greenwood outlined a more effective approach: use digital systems to intercept existing behavior instead of replacing it.

With modern conversational and multimodal AI, communication channels like email, messaging apps, and collaboration tools can now function as digital commerce interfaces. Purchase orders can be read, validated, and routed automatically. Inventory checks, pricing requests, and order status updates can be handled digitally, without forcing customers to log into anything new.

This approach allows companies to generate meaningful ROI from their commerce platforms while respecting how customers already operate.

The Untapped Opportunity: Eliminating Sales Admin Work

Another critical insight from the discussion was how much time B2B sales teams spend on administrative tasks.

Greenwood shared that, based on his client research, 20% to 60% of a sales representative’s time is often consumed by:

• entering orders into ERP systems
• pulling spec sheets
• checking inventory and pricing
• tracking shipments
• responding to routine customer questions

None of this increases commission. None of it deepens customer relationships.

Digital commerce, when implemented correctly, can automate most of this work. The result isn’t fewer salespeople, it’s more effective ones. Sales reps gain capacity to focus on consultative selling, problem solving, and account growth.

This shift is one reason Greenwood often encounters resistance early in projects. Sales teams fear replacement. Once they see the goal is to remove the work they dislike most, that resistance tends to disappear quickly.

Entrepreneurship, Personal Brand, and the Reality of Independence

The conversation also explored Greenwood’s entrepreneurial journey, and the realities many aspiring consultants underestimate.

According to Greenwood, the hardest part of independence isn’t delivering work. It’s maintaining pipeline.

Many professionals assume that being good at their craft is enough. In reality, independent work requires consistent visibility, trust, and reputation, long before monetization is needed.

Greenwood began building his personal brand years before going independent, publishing content consistently across LinkedIn, YouTube, and podcasting. That investment created inbound opportunity, partnerships, and credibility, reducing reliance on outbound selling.

A recurring theme in the discussion was intent. Greenwood emphasized that audiences quickly recognize when content exists only to sell. The most effective personal brands focus on sharing expertise, helping peers, and contributing to the industry, with monetization emerging as a byproduct, not the goal.

Why Discovery and Questions Matter More Than Answers

When asked what differentiates his consulting work, Greenwood didn’t point to frameworks or platforms. He pointed to questions.

His discovery process includes more than 150 structured questions designed to uncover how a business truly operates, not how leaders think it operates. In many engagements, these conversations surface process changes and inefficiencies that executives were unaware of.

This ability to surface hidden complexity is especially valuable in B2B organizations that have grown through acquisition, operate multiple ERP systems, or rely on undocumented tribal knowledge.

For Greenwood, asking better questions leads to better outcomes, not only for digital commerce projects, but for organizational alignment as a whole.

AI, Conversational Commerce, and the Next Phase of B2B eCommerce

Looking ahead, Greenwood expressed particular interest in how AI is reshaping B2B commerce, not as a replacement for platforms, but as an interface layer.

Conversational AI allows companies to:

• process emailed or messaged purchase orders
• answer customer questions in natural language
• integrate commerce actions into communication tools
• reduce friction without redesigning buyer workflows

This creates a new category of “behavior-neutral” digital transformation, where value is captured without forcing customers to adopt new habits.

Importantly, Greenwood noted that many B2B organizations have already completed the hardest part of this journey: modernizing their back-office systems. Cloud ERP, PIM, and CRM investments now provide the foundation needed to support these next-generation experiences.

The State of B2B eCommerce Today

The conversation between with Jason Greenwood highlights a clear reality:

• B2B eCommerce is no longer about proving value
• The market understands the need
• The focus has shifted to prioritization, sequencing, and execution
• Customer experience must adapt to existing behavior, not fight it
• Digital commerce must serve internal teams as much as external buyers

For manufacturers and distributors, the opportunity is no longer theoretical. The tools exist. The buying behavior has changed. The expectations are clear.

The companies that succeed next won’t be the ones with the most features, they’ll be the ones that remove friction, respect customer workflows, and give their teams better ways to work.

That is the real future of B2B eCommerce.

Contact Jason Greenwood

Jason Greenwood