Meet DTC’s Head of Portfolio Development, Chris Falloon

Few have the expertise needed to navigate the early stages of the enterprise startup lifecycle alone. Translating vision to a repeatable and scalable revenue engine is challenging, especially when a founding team’s focus is the tech and not the levers and nuances of sales. That’s why DTC built out a portfolio development team with a mission to support its founders across every aspect of the go to market process.

DTC portfolio development is a concept that was built out by DTC investor Chris Hillock to provide coaching and connections to help companies launch and hone their go to market and sales functions. To achieve escape velocity. The team facilitates hundreds of customer connections, hosts dozens of customer-facing events, and provides more than 400 hours of GTM coaching on average every year.

This week, DTC’s Chris Falloon is taking over as the head of portfolio development. With a career spanning telecom, consulting, media, and technology transformation, Falloon brings over two decades of expertise in operations, solutioning, messaging, and market-making to help startups refine their positioning and build scale. A former founder and CEO, Falloon also knows the journey firsthand — from making critical early hires to securing pivotal first contracts. He comes to the role with a deep understanding of Dell and DTC, and has plans for continuing to improve DTC’s business development support for founders.

Falloon shared more about how his decades-long career in technology led to this moment, and what makes a winning sales strategy in the AI era.

Portfolio development – What excites you about the role?

[Falloon] Following an early tech startup role, I spent 15 years in global corporate leadership.  As my scope expanded, I found myself operating further away from the hands-on build. That distance made one thing clear: I missed the raw energy, sharp accountability, and fast pace of front-line innovation.

I see this role as an opportunity to go back to the things I love: unpacking strategy, delivering results, and seeing ideas put into action in hours and days instead of weeks and months. Working directly with dozens of founders, each with reckless enthusiasm and boundless energy, it’s infectious. It’s a privilege to spend my time surrounded by people in the relentless pursuit of something they believe in.

You’re a former founder and CEO yourself. Why is that valuable for DTC’s portfolio companies?

[Falloon] If there’s a common blind spot in tech, it’s enterprise sales. Solution selling and enterprise decision-making can often feel like a black box, especially for deeply technical founders.

Demystifying that process takes both hands-on experience and continuous refinement. Over 20 years of architecting and selling technology solutions globally, I’ve helped build complex GTM, channel, and product strategies from the ground up. Equally important is the trusted network of enterprise relationships I’ve built along the way—a practical sounding board I lean on to gather real-world feedback, test ideas, and continually refine strategy.

That’s why I’m so excited about this opportunity at DTC. It brings that experience and network together, giving me the chance to help our founders and their teams navigate the complexities of an enterprise GTM.

What’s the top challenge for enterprise founders today?

[Falloon] Right now, the signal to noise ratio is extreme. Startups are facing an onslaught of competition. Anyone can spin up a technology company, a nice website and a compelling demo overnight that on the surface, looks to be a real competitor.

So, if you can’t compete on the front end, you better have evidence of traction, some sort of detailed design partner win, a thoughtful integrations and operational model, a comprehensive TCO analysis; there’s a bunch of things that build credentials. But building credentials while you’re building a product, especially at today’s pace of innovation, is not easy.

We’ve talked with a lot of startups in the last couple months about ways they can bring their credentials to the surface. At a certain stage of growth they all have evidence of success. But adapting marketing, and sales messaging and approach to make sure it’s clear they have real traction is far more important than it was just six months ago.

It's the only real way to rise above the noise. Decision makers don’t want to look at 40 different solutions for the same problem. They want to see one or two credible options.  

How can founders navigate this new believability challenge?

[Falloon] A classic technology pitch is a crisply articulated industry problem statement, a few flashy slides about what the startup is doing differently, followed by a demo.

Today, we need to reconsider how we handle the demo. We need to show how the product is actively solving real-world problems, in production. The case-study method. If it’s compelling, people will engage. For many, it’s not obvious to tell stories in this way. Logo slides and casual anecdotes don’t cut it anymore. There are all sorts of logo slides littered with pilot projects. Customers want to see something they know is real. An honest recounting of how projects are going. What has been learned so far in production. Any attempt to oversell creates disbelief.  

Buyer frustration is making headlines right now. Where is that coming from?

[Falloon] Billions of dollars have been spent on AI over the last three years, and CIOs are facing growing scrutiny for investments that have yet to deliver on early promises. This pressure has made them deeply anxious about spending another penny without a guaranteed return.

This creates a clear moment for companies embracing outcome-based commercial models. While many startups already charge for technical outcomes, we think the next wave of enterprise AI investment will favor companies focused on business outcomes—often very specific ones. Startups with GTM models adapted for this shift will hold a significant edge over those that don't.

How are you using AI in your own work and what have you learned?

[Falloon] I’ve spent quite a bit of time using the various vibe coding platforms to see how we can improve our own tech stack that supports the port dev team. We’ve built a few different tools within our operations, including a lightweight CRM and event management application, as well as a targeted list-builder for our portcos. It really is easier than it looks to stand something up.

But as we’ve built these tools, it’s also taught us a few things. First - You have to raise the bar on yourself, immediately. There really is no excuse not to build simple automations to do the things you’re already doing - but with more accuracy, more fidelity. I think we are already measurably better at creating quality connections across our network based on our early efforts to build some extremely basic tools.

It also takes time to make things actually usable, not just look good. Any fool can build a web app over the weekend. We did that. But it turns out, weeks of effort go by before you can use it in a secure, reliable way. The front end is easy, the back end is hard. Some lessons there for everyone.

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