Chief Marketing Officer, then Chief Strategy Officer (2018 to 2020); Board of Advisors (2014 to 2016)
The first time I walked into Elastic Path’s Vancouver office, in January 2014, I was the guy on the other side of the table: Adobe’s commerce strategy and marketing lead, there to kick off a year of partner planning. Four years later I joined as Chief Marketing Officer. In between I sat on their advisory board, and before any of that I had tried to figure out how Adobe could buy them. I kept finding reasons to be in the room with this company, and by the time I finally worked there I had seen it from four different seats: partner, would-be acquirer, advisor, operator. This chapter is the story of what those seats added up to: a financing round that nearly died weeks after I arrived, a demand engine that did everything we asked of it, and the harder, more interesting question of what a leader owes the truth when the engine works and the business still stalls.
The long way in
The relationship started with an idea I was chasing at Adobe. We kept building beautiful marketing experiences that ended at a cliff: the customer fell out of the brand moment and into a clunky e-commerce site to actually buy. I thought that was backwards. Brands spend enormous energy creating products and services people love, and then relegate them to thumbnails in rows and columns on a web store. The work I led at Adobe, which we called experience-driven commerce, was about closing that gap: let the transaction happen wherever the customer already is, inside the content, inside the app, inside the moment. We proved it on Adobe’s own business, moving the buying experience into the product itself, so going from a free trial to a paid license was a button inside Photoshop rather than a trip to a web page. I even tried to get Amazon to license us 1-Click. They politely declined.
Chasing that idea meant evaluating every commerce engine on the market for what was, at the time, a very unusual requirement: we did not want their storefront, we wanted their APIs. One company stood out. Elastic Path had effectively ripped the head off its own platform, building an API layer called Cortex after working with customers like Symantec who needed commerce embedded in a software download flow, not another website. They were unapologetically API first when everyone else’s API was an afterthought. That evaluation shaped Adobe’s whole approach to content and commerce, and it put Elastic Path permanently on my radar.
It also put me on other people’s radar. While I was still working this space, a well-known Chicago private equity firm called me cold. They had a thesis that commerce technology was ripe for consolidation, they had been shopping it around the industry, and several people had pointed them to me. My honest first reaction was that it was Publishers Clearing House calling. It was not. I spent real time developing the roll-up thesis with them, and Elastic Path was one of the pieces I wanted, partly for the technology and partly because it had leaders I trusted to build around. The effort ended when I asked them whether I could hire a CEO to run it. Their model was that I would be the CEO, and when it became clear I was not ready to make that jump, they moved on. I was naive, and I have thought about that conversation many times since. A few years later a roll-up appeared on the market that looked a lot like the thesis. Ideas you pitch in hotel lobbies have a way of finding other owners.
Elastic Path and I made it official in 2014: a seat on their advisory board, which came with the small comedy of needing formal sign-off from Intel, my employer at the time, before I could say yes. I did not treat it as a quarterly phone call. At their advisory day in early 2015 I showed up with my own slides: a segmentation framework for their partner program, which the company adopted, and a challenge I was uniquely qualified to deliver. Elastic Path had built its go-to-market almost entirely around Adobe, and I told them, as the former Adobe guy, that their best friend had become their ceiling. What about the customer who just wants a store? My favorite assignment, though, was playing the prospect from hell in their sales dry runs: where was the discovery, why was I ninety minutes into a meeting without seeing a demo, why did the pitch mention Adobe more than it mentioned me, the customer. The advisory seat ended formally in 2016, when I took responsibility for IBM WebSphere Commerce, an obvious competitor. But Harry Chemko, Elastic Path’s founder and CEO, and I stayed in touch, talking about the industry the way other people talk about their favorite sports teams. At one of those dinners, in early 2018, I told him I had decided to leave IBM. My read was that commerce no longer sat anywhere near the center of IBM’s future, whatever the products did, and my purpose was no longer the priority. (That December, IBM announced the portfolio’s sale to HCL.) Harry read me in on the funding round he was closing and asked if I would consider running marketing. After years spent rebuilding a giant’s commerce platform toward services, here was the smallest company I knew that had made the API layer the point from the beginning.
Saving the round I was hired to spend
Harry’s pitch was that it was time for me to pick up a hockey stick. The product was in a good place. The market needed an alternative to the giant, tired commerce suites. He needed someone to tell their story, and he was closing a growth round to fund the push.
There was a second reason I said yes. I had spent more than a decade marketing to CMOs, building products for them at Adobe and IBM, studying them as my buyer. Here was a chance to sit in that chair myself, in an industry I knew deeply enough to de-risk the move. I wanted to know if I could actually do the job I had been selling to.
Then, weeks after I started, Adobe announced it was acquiring Magento, and our financing nearly died on the table. Part of the round’s logic had been that Adobe might one day buy Elastic Path; now the lead investor was staring at a world where the most strategic acquirer had just bought our competitor. What I knew, and what a financial investor could not be expected to know, is how intimate the e-commerce industry is. Sales and commerce leaders rotate between companies their whole careers; everyone has worked with everyone at some point. So we worked that intimacy deliberately. I flew to Vancouver, sat down with Harry and the team, and we built what I can only describe as a surround strategy: calls lined up with Adobe’s own partners and sales leaders, who knew they would keep winning with Elastic Path long before Magento could serve enterprise needs; prospects I knew from my IBM years who wanted off their platforms; the analysts who had watched this market for decades. The picture we painted for the investor was specific. If you were a telco or a manufacturer running hundreds of millions through your commerce platform, you were not betting it on Magento, and the entire industry had watched this movie before: ATG to Oracle, hybris to SAP, Demandware to Salesforce. Independent platforms with real enterprise chops get bought, and we were next in line. The round closed in June 2018: CAD $43 million, about USD $32 million at the time, led by Sageview Capital, with participation from existing investors Yaletown Partners and BDC.
Sitting in the chair
The marketing organization I inherited was generating huge volumes of leads and almost nothing else. Nearly half the spend went to events that produced stacks of badge scans, chased by exactly one business development rep. We could see leads and we could see opportunities, and the machinery between them was a mystery: well under one percent of leads ever became a real conversation.
I had written a 30-60-90 plan as a candidate, and I am still a little proud of how literally we executed it. We instrumented the funnel end to end with marketing automation, lead scoring, and attribution, so that within two quarters the board was looking at a real demand waterfall instead of a leads number. We introduced qualification discipline. We rebuilt the team deliberately around demand generation expertise, including a trade I would make again ten times over: I recruited a marketer who had ridden the hybris rocket all the way to its SAP acquisition, gave her the product marketing leadership she wanted, and stacked the bench behind her with specialists. And we got surgical about where the money went, leaning into account-based marketing while it was still early. At our most precise, we ran a true one-to-one program against a single senior commerce executive at a Fortune 100 heavy-equipment maker: low-cost mobile and social inventory geofenced to the account’s footprint, audiences built small enough that we knew he was in them, all with the platforms’ standard tooling, plus a clever inversion of the usual economics, running cheap experiments on Facebook to qualify an audience we could then buy on LinkedIn for a fraction of what named targeting costs. The goal I gave the team was that he would call us and surrender. Months later I met him at an event in Chicago. It worked.
The numbers told the story I had been hired to produce. Marketing-qualified leads tripled across the fiscal year. Sales-qualified leads doubled year over year on roughly twelve percent more spend. On events, the biggest line in the budget, our cost per lead ran a quarter under the published industry benchmark. And in a market where we held under one percent share, our share of voice approached fifteen percent, which is the whole game for a challenger brand: sound several sizes bigger than you are, so you are in the room when the shortlist gets made.
The chair itself taught me things no amount of marketing to CMOs had. It was my first time leading a team of genuinely senior leaders, and it requires a different style than managing managers. I was lucky to have people on that team who were as good at coaching me as I was at coaching them. That sentence is not modesty. It is the operating model I have used for every executive team since.
The category we made everyone argue about
The brand work rode on top of something bigger that I still consider career-defining: we took an architectural idea and made it the vocabulary of an industry. “Headless commerce,” the separation of the buying experience from the commerce engine behind it, was the productized version of everything I had been chasing since the Photoshop days. As CMO I bet the company’s positioning on it.
The claim is better when it is precise, so here is the precise version. The public record credits Dirk Hoerig, the founder of our sharpest competitor, with putting the name “headless commerce” on the idea in 2013, and I tip my cap; it was the right name, and naming a thing well is its own kind of talent. What the record also shows is that Elastic Path had already built the thing being named. The company launched its API-first commerce engine in early 2012, an architecture born from running the official store of the 2010 Vancouver Olympics and from customers like Symantec who needed commerce inside a software download, not another website. By October of 2013 the term was already appearing in SAP hybris’s printed datasheets as ordinary vocabulary, which tells you how fast a good name spreads when the architecture underneath it is already real. So my claim is narrower and, I think, more interesting: Elastic Path pioneered the architecture, a rival named it beautifully, and then, as CMO, I helped popularize it. We evangelized the idea relentlessly, until Forrester’s 2018 Wave formally described a group of “headless commerce vendors” containing exactly two companies, and we were one of them. That same evaluation scored our product vision a perfect five out of five and wrote that “commerce anywhere is Elastic Path’s strength.” A year later, a Forrester analyst told us his clients’ most common question had become “why is everyone saying they’re headless?”, and the competitive attacks against us had shifted to arguing about whether our headless was the real headless. When your competitors are fighting in vocabulary you spent two years amplifying, the category work is done. I tell that fuller history, primary sources and all, in its own piece: The DCAPItator.
When the engine worked and the deals still did not close
By early 2019 I was watching two charts move in opposite directions. Demand was compounding every quarter. Bookings were not. A company’s first answer to that picture is almost always sales, because sales is the biggest surface: leadership, process, enablement, targeting all get inspected before anyone says the quieter thing. We went through that cycle too, including a sales leadership change, and the new leader struggled against the same wall.
The moment the truth landed for me is one I now tell product teams as a parable about your own assumptions. Our reps kept telling me it was hard to win against hybris with PowerPoint, and I could not understand why they were presenting slides instead of demoing. So I insisted on being treated as a prospect, full sales motion, no shortcuts, even though there was some sheepishness in the room about putting the CMO through it. Some history matters here. Years earlier, Elastic Path had built its business-user tooling, the screens where a merchandising team maintains the product catalog and price lists, inside Eclipse, the open-source engineering IDE, as a clever shortcut for shipping a thick client quickly. I had seen it during my advisory years and was told it was on its way to becoming a web application, and I assumed that conversion was long since finished. Then the sales engineer shared his screen to show me catalog management, and there was Eclipse: an engineering workbench doing its best impression of a business application. I knew in that instant why we were losing. On paper we had feature parity or better, including a pricing engine hardened by telco deployments that the big suites needed custom development to match. And the backend simply did not fall over: on a single Tax Day, Intuit’s TurboTax business ran roughly 280,000 concurrent users and more than sixty orders a second at peak through our platform, 3.6 million orders in a day, and T-Mobile trusted it with iPhone launches. None of it mattered in the magical moment of a software demo, when the buyer imagines using the tool every day for the rest of their working life. Our competitors made that moment feel like the future. We made it feel like a build environment. The part I own personally: I had been at the company most of a year and had never asked to see our own product the way a buyer sees it. So much R&D had gone into Cortex, the genuinely hard and differentiated part, that the tooling kept getting punted, year after year. None of that was a failure of talent; it was years of reasonable prioritization adding up to an unreasonable outcome. And some of the irony was mine to own. Back in my Adobe days we had pushed Elastic Path to build administration experiences inside AEM, which they did, precisely because the platform was API-first. It won deals, and I suspect it absorbed the very engineering time that might have replaced Eclipse with a proper web interface years sooner. Coming out of that demo was like coming out of a spell.
The closed-loss data said the same thing at scale. Nearly two thirds of our lost qualified deals named SaaS as the reason; the pipeline increasingly demanded SaaS and microservices; the competitors beating us were cloud-native. The product still delivered for the demanding enterprises that ran on it; what had broken was fit with where new buyers were going. This was not a sales execution problem. It was the market repricing an architecture, and no amount of pipeline could outrun it.
Eat the banana or build the plantation
I could not stay out of product even before it was mine; with my background, it was hard not to pull up a chair to that table. From the CMO seat I pushed for a bridge offering modeled on the playbook I had run at IBM. As it happened, I was not the only one who had arrived at that playbook: Leho Nigul, the engineering leader at the center of IBM’s commerce rebuild, had reached the same conclusion about where to go next entirely on his own. While I was talking to Harry, he was interviewing with Elastic Path’s CTO, and neither of us knew about the other until it was done. With Leho running product development, the teams stood up a single-tenant hosted edition that launched as Elastic Path Commerce Cloud in January 2019. It got us back into deals we had been disqualified from. Around the same time I helped recruit the Forrester analyst who had literally written the B2B commerce evaluation; he joined the product organization and sharpened our focus on B2B, where our depth mattered most. Within a year, an independent B2B scoring report gave us six medals including two golds, with a customer quoted saying that if you want headless, our solution was a no-brainer.
But bridges and focus do not change an architecture, and saying “we have a product-market fit problem” out loud is the conversation everyone avoids, because everyone knows it can be a game-over sentence. I said it anyway, with the closed-loss data to back it, first to Harry and then to the board. In mid-2019 Harry asked me to take over product, and I made one deliberate choice before accepting: the title. Chief Strategy Officer, not Chief Product Officer, because I wanted the board to hear what the title was actually saying: there is complex work to navigate here, and you should start building an appetite for M&A.
We laid out build-versus-buy with full honesty: rewriting our way to multi-tenant SaaS with the team we had meant years we did not have, doing nothing was a slow slide into legacy, and acquiring was the only path that bought architecture and SaaS-native talent at the same time. What finally convinced me was not a spreadsheet. It was when Leho, the builder I trusted most, said we might be better off looking outside than rebuilding. When your best builder says buy, you listen. My line for the decision in the boardroom was less elegant: eat the banana, or keep building the plantation.
Harry and I ran the evaluations ourselves, on a constrained budget, sourcing candidates through every channel we had, including inbound interest once word quietly spread that we were looking. We walked away from one path in diligence, and in January 2020 we acquired Moltin, a startup with offices in Boston and Newcastle. The final call belonged to Harry and the board, as it should in a founder-led company, but the recommendation was mine, and I pushed for Moltin because it gave me every piece I wanted: the architecture, a US presence that mattered to enterprise buyers, and a UK engineering team with real SaaS operations muscle. I knew exactly what Moltin was not: it was nowhere near feature parity with what the enterprise market needed. I also knew that was the wrong test. Moltin was API-first to its bones, genuinely multi-tenant, with a beautiful interface that won the demo moment, and, most importantly, it came with people who had built and operated SaaS, including seasoned go-to-market leadership. Features can be filled in fast; architecture and operating DNA cannot. The market told us we were right almost immediately: prospects told us directly that they would have disqualified us if not for the acquisition, and we started qualifying into deals that had been closed to us. The company that exists today is a recognized leader in what the industry now calls composable commerce.
Why I left
My son Cole was born with microcephaly while I was at IBM, and was later diagnosed with cerebral palsy, epilepsy, and an intellectual disability. In those early years we had far more fear than prognosis, and no map for what his life, or ours, was going to look like. Elastic Path was a global company with customers everywhere and teams in Vancouver, Toronto, Boston, and the UK, and I was a road warrior in the middle of the most demanding transition of the company’s life. Between the product pivot, the integration, and what my family needed, I could not give the company my best, and pretending otherwise would have served no one.
Over a lunch in early 2020, my very first manager from my Andersen Consulting days, by then an executive at Gap, said something like: we cannot give you a big title, but we would love your help on some hard problems. I took it. I deliberately stepped down several levels on the title flagpole for a role with no travel, knowing exactly what I was trading and why. I could do it in good conscience because of the bench we had built: the Moltin leadership was in place and the strategy was set. Cole is in my LinkedIn profile photo, and that is not an accident. How I evaluate work, permanently, now includes whether it lets me be who he and my family need.
What I take from it
Elastic Path is the chapter where my operating philosophy got pressure-tested from every side. It proved I could run the function I had spent a decade selling to, and the evidence held up: a tripled qualified-lead engine, a challenger brand heard at nearly fifteen percent share of voice on under one percent market share, an investor round defended by knowing an industry well enough to orchestrate its voices. But the deeper proof is what happened when the engine worked and the business still stalled. The easy move for a CMO in that position is to keep shipping good marketing numbers and let someone else own the bad news. Instead I went looking for the truth, found it in a demo I should have asked for a year earlier, said the words product-market fit out loud in a boardroom, and, when I was asked to own the fix, took it end to end: a bridge product, a focused B2B bet, and a tuck-in acquisition that bought talent and architecture rather than features.
It also extended a thread that runs through my whole career. At IBM I broke a monolith into containers; at Elastic Path the founding insight was an API layer that decoupled the buying experience from the engine; the work I have done since is built on the same conviction that the valuable thing is rarely the interface, it is the clean separation underneath that lets you replace any piece without losing the whole. And it taught me my most durable lesson about evidence: the data points you trust least are the ones that flatter the work you personally did. The discipline is to chase those hardest. The demand engine was mine, and the most important thing I ever did with it was prove it was not the problem.
The next test of that conviction would come from the other side of the table: inside one of the world’s most recognizable retailers, deciding which of these architectures actually helped a merchant move.
This chapter is part of My Work, my career told one company at a time.
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Elsewhere from this era: Frictionless commerce: the future of customer experience is seamless