169: Elena Hassan: Visa acquires your startup but nobody warns you about the tech stack aftermath and enterprise culture shock

Summary: Elena has done what most startup marketers only guess at; made it through multiple acquisitions and now leads global integrated marketing at Visa. In this episode, she breaks down what actually changes when you go from scrappy lead gen to enterprise brand building, why most martech tools don’t survive security reviews, and how leadership without authority is the skill that really matters. We get into messy tech migrations, broken attribution dreams, and why picking up the phone still beats Slack. If you’ve ever wondered why your startup playbook stops working at scale, this conversation spells it out.

What Startup Marketers Learn the Hard Way When They Land at a Big Corporation

Elena does not call herself an “acquisition master,” even though her resume might suggest otherwise. Three startups she worked at were acquired, Sivan by Refinitiv, WorkMarket by ADP, and Currencycloud by Visa, where she works today. Some might spin that track record as a strategic playbook for career navigation. Elena sees it differently. She credits great teams and good companies, not some personal Midas touch.

The truth is, you cannot force an acquisition. What you can do is get really good at reading the room. Elena’s career started deep in the weeds of lead generation and demand marketing, chasing performance metrics and measuring everything that moved. Early on, she dipped into other areas, event planning, employee engagement, but demand gen was where she built muscle. That was her lane at WorkMarket, where the first big learning curve hit.

It turns out the skills that build the lead gen engine are not the same ones you need when a company shifts from hypergrowth to prepping for acquisition. Elena experienced firsthand the moment when leadership stops asking about lead volume and starts asking about brand perception. Suddenly the focus pivots from how many MQLs you can squeeze out of a campaign to how the company is positioned in the market, what the media is saying, and whether the brand looks credible at scale. She admitted she did not fully appreciate that switch at first.

> "I came there with a mindset of if I can't track it, I'm not gonna do it," Elena said. "Every performance marketer would probably relate."

That perspective doesn’t fly for long in environments where brand and reputation start to outweigh click-through rates. Elena’s time at Visa has only reinforced that lesson. Today, much of her work revolves around brand building and awareness, the same areas she once side-eyed for being soft and unmeasurable. It is one thing to believe in brand. It is another thing entirely to understand how hard it is to build one well.

The scale jump from startup life to a company with over 30,000 employees does not just change the headcount. It rewires the entire pace and process of how work gets done. Elena described the gut-check moment that made it clear she was not at a scrappy startup anymore. It was not a high-level strategy meeting or a sweeping corporate memo. It was the moment she tried to get a simple social graphic approved.

In a startup, that kind of thing takes a few minutes on Canva and the green light from whoever’s closest to the Slack channel. At Visa, especially as a regulated financial institution, it involves legal reviews, vendor contracts, approval workflows, and enough compliance checks to make your head spin. Campaigns that once rolled out in days now take months. Not because anyone is slow, but because the stakes are high and the rules are different.

That culture shock is where many startup marketers either adapt or tap out. What Elena figured out is that the skills that work at one stage of company life are not the ones that get you through the next. If you want to survive the jump from lean team to enterprise machine, you have to stop resenting the process and start respecting what it protects.

Key takeaway: If you're coming from startup life, expect a painful adjustment when you move into a large, regulated company. The speed, autonomy, and scrappiness you are used to will collide hard with approval chains and compliance processes. The faster you stop fighting it and start learning why those systems exist, the faster you'll find your footing. Metrics-driven marketing only gets you so far. To thrive at scale, you need to understand the power and patience required to build brand trust.

What Nobody Tells You About Merging Tech Stacks After an Acquisition

The fantasy version of an acquisition is clean and celebratory. Two companies come together, the deal closes, the press release goes out, and life moves on. The reality, especially for marketing teams, is a long, often frustrating grind of systems audits, security reviews, and endless conversations about whether your beloved tools will survive the merger.

Elena has lived through that grind more than once. When Visa acquired Currencycloud, she was not navigating that shift alone. Many of her teammates made the journey with her, which helped. But solidarity does not make the process move faster. It just means you have people to vent to while you wait for approvals.

One of the first and hardest parts of that transition was not a debate between marketers. It was the clash between marketing teams and security teams. Every single piece of tech Currencycloud used, whether it was their website hosting, HubSpot marketing automation, or even individual add-ons, had to go under the microscope. Security teams needed to assess, vet, and approve each tool, often asking questions that made sense from a cybersecurity perspective but sounded completely out of touch to anyone in marketing.

The back-and-forth was not casual. It escalated all the way up to the chief technology officer and the cybersecurity team at HubSpot sitting down with Elena's group to explain, in detail, what the platform could and could not do. None of this was about malice or incompetence. It was about two fundamentally different mindsets trying to find common ground.

> "These are security people. They’re not marketers. They don’t always know why we need a particular tool or what it does," Elena explained.

That learning curve is brutal if you're not prepared for it. The deeper into operations you sit, the more of these conversations you end up having. Elena found herself in rooms with people from multiple marketing ops teams across Visa, comparing tech stacks, workflows, and priorities. There was no easy answer to which system would win out. Sometimes the decision was clear. Other times it came down to questions like, is it really worth fighting for this tool, or is now the time to adapt to what already exists?

She describes it as less like transferring from one job to another and more like moving from a Montessori school to a traditional classroom. Both systems can deliver a good education. They just teach in wildly different ways. One thrives on flexibility and autonomy. The other runs on structure and process. Neither is wrong. They are simply different environments, and surviving the switch requires a willingness to adjust.

The biggest mistake marketers make in these situations is believing the process is about what *they* want. Elena was quick to point out that the companies she has worked for, especially Visa, keep customer experience at the center of these decisions. It is not about which tool is most familiar to the internal team. It is about which systems create the least friction for the end user. That mindset helps keep the process grounded, even when the day-to-day feels like a slow march through bureaucracy.

Patience is not optional in these transitions. You will hit walls. You will repeat yourself. You will explain the same use case to five different people across three different teams. And eventually, you will e...