A fractional VP of Sales with 30+ years of complex enterprise sales
The deals, the companies, and the buyers who kept buying.
Seller, regional leader, global sales leader, VP of Sales, and Client Director on Toshiba’s single largest client globally — $100M+ in annual bookings. Retail, brands, manufacturing, and DTC are where a lot of that work happened. The gate is the committee, not the aisle.
Companies I’ve sold for
My inspiration to start Fractional Sales Experts
The situation
Standard AI — an autonomous-checkout company that had to pivot: away from checkout, toward computer-vision behavioral analytics for the physical store, sold to enterprise retail. A small commercial team — no SDR, no sales engineer, no in-house marketing team. I reported to the CEO as VP of Sales and rebuilt the entire go-to-market. Doing all of it as a partner to the CEO is what convinced me a founder doesn’t need a bench to reach the enterprise — they need one person who has done it. That is why this practice exists.
What I helped run
- ICP across five verticals with an eight-persona buyer map
- Positioning built on the Visual Engagement Score — never a point solution, always the connected-store data layer
- A scorecard of the entire vendor field against the IAB/MRC attention-measurement guidelines
- A Big Four consulting alliance taken from kickoff to co-sell
- An exclusive hardware partnership, built from scratch
- An SI co-sell ecosystem, with partners qualified out as well as in
- Roughly fifty playbooks, discovery frameworks and enablement documents
- Signal-based prospecting and a competitive-displacement engine against seven named competitors
- Trade shows and events as a pipeline channel
Milestones
The deals I have worked and sold.
Every step up was the same kind of sale into a bigger, more sophisticated buyer — more stakeholders, more procurement, more at stake. I’ve run that ladder from $300K deals to $100M+ in annual bookings. What changes is not whether you have a process. What changes is whether you can navigate an enterprise that already has one — so you win the very good deals and the very large ones without drowning your own company in theirs.
The way deals get done keeps changing, too. Buying committees keep growing, the technology iterates faster than the buying cycle, and security, privacy and compliance reviews now sit in the middle of the deal instead of at the end. I help you through all of it — including the procurement cycle that decides when, and whether, you get paid.
Enterprise commerce and order management
I’ve been a global seller several times over — running deals across North America, South America, Europe and Asia. The stack I sold: composable commerce, order management, subscriptions, returns, rich media, CX, DX and agentic AI. Kibo was one platform inside that stack, not the whole story.
Full-cycle enterprise pursuits with multi-brand buyers — PLBY Group, Topgolf Callaway Brands and Pura among them — including order management across D2C and B2B, live in under five months. Sophisticated buyers. Emerging technology. The sale is convincing them to trust something they haven’t bought before, while they already own a stack and a committee.
Why it matters to you: the hard part isn’t listing the modules. It’s selling a smaller vendor into a large enterprise, against the incumbents already in the building. I’ve done that globally, more than once. I’ll do it with you, at the size of company you actually are. If you sell into retailers, start with the fractional VP of Sales for retail technology companies page — that sale is written down there.
I have sat on the buyer’s side of the table.
I was Client Director for Kroger, America’s third-largest retailer, badged on-site at Kroger’s Business Technology Center. $100M+ in annual bookings. Toshiba’s single largest client globally. I managed the team inside a support organization of roughly 900 people, meeting weekly with the CIO and daily with the VPs and directors who run the stores’ technology.
Point of sale is mission-critical: when it’s down, the store can’t transact. I ran the relationship at that altitude — the self-checkout program, the 2020 curbside rollout across the chain, the innovation workshop, QBRs with the client and with our vendors, quarterly product reviews in Japan, and deep partnerships with Toshiba’s technology partners and Kroger’s.
Why it matters to you: sitting inside a giant let me watch other sales organizations come in and sell — well and poorly. I know how a large enterprise actually buys, how a deal dies inside the building, and what it takes to be the vendor they keep. That’s the view I bring to your deals: big-company craft, sized for a company that can’t afford to pretend it’s IBM.
The same buyers kept buying from me.
In enterprise sales this is the proof that matters: the relationship outlasted the employer. The number is how many different companies each of them bought from me at.
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The people who vouch for me are running companies, and I protect their time. Tell me who you are and what you’re evaluating, and I’ll open the page to you.
The record, in answers.
What is the largest deal you have closed?
Closed and managed are different ladders. Closed: $1M+ deals at every company I have sold for, $5M enterprise deals into national retailers and global brands, and $10M+ software deals across ERP, eCommerce, analytics, OMS and supply chain, including $30M software deals. Managed: a $100M+ annual book at Kroger as Toshiba’s Client Director. At IBM I closed the largest eCommerce and order-management deal in the company’s history at the time.
Which companies have you sold for?
Amtech Process Systems, JBA Software, ATG, Demandware, Adobe, SAP hybris, IBM, Toshiba Global Commerce Solutions, Kibo and Standard AI. Three of those — Demandware, ATG and hybris — were small companies that went on to be acquired by Salesforce, Oracle and SAP. I was an early seller at each.
Have you sold into retailers and brands?
For most of 30+ years. Kroger, P&G, Luxottica, Abercrombie & Fitch, Bass Pro Shops, Cabela’s, Sherwin-Williams, Callaway, DSW, JTV and Pura from the vendor side, and from inside Kroger’s own technology headquarters as Toshiba’s Client Director. That is why there is a page on being a fractional VP of Sales for retail technology companies.
What did you do at Standard AI?
Rebuilt the go-to-market for a computer-vision company through a product pivot, as VP of Sales reporting to the CEO: ICP across five verticals, an eight-persona buyer map, positioning, a Big Four alliance, an exclusive hardware partnership, an SI co-sell ecosystem, and the playbooks. It is client zero — where the fractional model was proven — and the reason this practice exists.
Can I speak to references?
Yes, on request. References are founders and executives I have sold for and sold to, and they are shared after a first conversation rather than published. Request reference access.
Does the track record translate to a company my size?
That is the whole point of the practice. I have sold with no brand behind me and with IBM and Toshiba on the badge, and the two are different jobs. What transfers is the craft of the committee sale, sized for a company that cannot afford to pretend it is IBM. Who I work with has the fit test.