Fractional VP of Sales for eCommerce and order management software
A commerce deal is a replatform. Nobody replatforms casually.
If you sell a commerce platform, an order management system, search, subscriptions, payments, returns or anything that plugs into the storefront, your buyer is making a three-to-five-year bet with their revenue on the line. I have sold that bet since 2000 — at ATG (acquired by Oracle), Demandware (acquired by Salesforce), hybris (acquired by SAP), Adobe, IBM, commercetools and Kibo. Small vendors that became large ones, and the largest names in the category. This page is how the commerce sale actually works, and what I do inside it as a fractional VP of Sales.
Based in Scottsdale, Arizona. I work in person across Greater Phoenix and remotely with founders across the US.
The VP of eCommerce wants you. Five other people decide.
Digital commerce leaders start these deals. They rarely finish them. A replatform or a new OMS touches every system that takes an order, ships it or reports on it, so the committee is wide and it shows up late.
- The digital leader. VP of eCommerce or Chief Digital Officer. Owns the conversion number and the pain. Owns the budget request, not the signature.
- IT and enterprise architecture. ERP, WMS, POS, PIM, the data platform. Their question is how many integrations you add and who maintains them.
- Operations and fulfillment. Ship-from-store, BOPIS, returns, inventory accuracy. An OMS that adds a step for the stores or the DC dies in the pilot.
- Finance. Total cost over the contract, the GMV-based fee, and the cost of running two platforms during the migration.
- InfoSec and procurement. PCI scope, SOC 2, data residency, the MSA. The checkout is the most audited page the company owns.
- The systems integrator. Often already chosen, often already biased. They know which platforms they can staff and which ones make them money.
Most founders sell the digital leader and lose to the integrator’s preference or the CIO’s integration math. Mapping all six before the demo is the job.
Commerce buys in windows. Miss one and you wait a year.
A retailer or brand changes platforms when a contract ends, a peak season fails or a new leader arrives. Each of those is a trigger you can see coming, if you are watching for it.
The triggers worth tracking
- Contract renewals on the incumbent platform — usually visible 12 to 18 months out.
- A new CDO, VP of eCommerce or CIO in the first 180 days, looking for the project that defines them.
- A bad peak: site outages, oversells, a holiday where the OMS couldn’t keep up.
- An acquisition, a new brand or a move into B2B or marketplace that the current stack can’t carry.
- The holiday code freeze: nothing ships from October to January, so a deal that isn’t signed by late summer usually isn’t live until spring.
Signal-based prospecting beats volume here. Thirty accounts with a live trigger beat three thousand without one.
In commerce, the integrator is half the sale.
Brands rarely buy a commerce platform or an OMS without an implementation partner, and the partner is often in the account before you are. Founders who treat SIs as a referral source get scraps. Founders who treat them as a second sales motion get shortlisted.
- Pick the partners who can staff you. A large SI with no one certified on your product will recommend the platform they can bill against.
- Give them a reason to bring you in. Margin, services scope, a joint win story, and a product that makes their delivery easier, not riskier.
- Sell with them, not through them. Joint account plans on named targets, shared pipeline reviews, and a founder or senior seller in the first meeting.
I have worked alongside the integrators that decide which platforms retailers meet, from the global consultancies to the commerce specialists. The partner motion is part of the sales motion, not a side project.
Twenty-five years inside the commerce category.
I sold eCommerce at ATG and Demandware when the category was young, and joined hybris before SAP bought it. At Adobe I sold the experience and analytics layer around the storefront. At IBM I sold WebSphere Commerce and Sterling Order Management, and closed the then-largest eCommerce and order-management deal in the company’s history, at Kroger.
At commercetools I helped stand up the B2B commerce business. At Kibo I sold composable commerce, order management and subscriptions globally as part of a turnaround. Same buyer, every architecture: on-premise, hosted, SaaS, headless and composable.
That range matters to a founder. I have sold the incumbent and I have sold against it, so I know where the incumbent is strong and where a smaller vendor can win.
Where I sold it from
Fractional VP of Sales for commerce-technology founders.
I help you run the sales motion and bring you in only where the founder is the difference. For an eCommerce or OMS company that usually means:
- An ICP written in the buyer’s terms: GMV band, channel mix, current platform, contract timing, and the trigger that opens the window.
- A committee map for every live deal, with the integration and operations objections answered before the CIO raises them.
- A partner plan: which SIs to recruit, what they need from you, and a joint pipeline you can actually forecast.
- The RFP, security and architecture packets built once, so you look like an enterprise vendor before you are one.
- A pilot or phased rollout with the success measure and the decision date agreed up front.
- A forecast built on what the buyer has done, not on how the demo felt.
eCommerce and OMS, answered.
Do you work with commerce startups that sell to mid-market brands, not just large retailers?
Yes. The gate is a buyer that decides through a committee, not the size of the logo. A mid-market brand replatforming still has IT, operations, finance and an integrator in the room. The motion is the same, just faster.
We keep losing to the incumbent platform. What changes?
Usually the timing and the sponsor. Incumbents win on relationship and perceived risk, not features. You win by finding the account in its window, getting a senior sponsor who will say the smaller vendor is the safer choice, and arriving with the migration risk already answered.
How do you handle the systems integrators?
As a second sales motion. Pick two or three partners who can staff your product, build joint account plans on named targets, and review that pipeline weekly. One good SI relationship is worth more than a dozen logos on a partner page.
Can you help with a headless or composable sale?
Yes. I sold composable commerce at commercetools and Kibo. The composable sale needs more architecture credibility and a clear answer to who owns the integration work. The buyer is buying flexibility and worrying about complexity, and the deal turns on which of those you address first.
Are you a full-time hire in disguise?
No. I am a fractional VP of Sales: senior, part-time, inside your deals for as long as the work needs it, then handed over to a full-time hire, handed back, or kept running as advisory. Services explains the shapes.
Notes from inside these deals.
Why enterprise deals stall after the demo
If a deal dies after the demo, it is rarely because the demo was bad. It is because you never mapped who can actually say yes.
Getting out of founder-led sales without losing the deals
Transitioning away from founder-led sales fails when the founder hands deals to a VP before a motion exists. Here is the sequence that keeps the deals, a 90-day plan, and how to hand off a live deal.
When the founder should show up — and what the fractional VP is doing
Founder and fractional VP of Sales as partners in a complex enterprise deal: three stages that need the founder, three that only feel like they do.
Other industries I work in: Retail technology · AI & computer vision · B2B companies in any industry · B2B SaaS · Point of sale & store technology · Supply chain & logistics technology
Thirty minutes. Bring the commerce deal that is stuck, or the replatform you can’t get shortlisted for.
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