Twilio Ventures Founder Spotlight: Aaron Matos, Paradox

December 01, 2023
Written by
Reviewed by
Paul Kamp

Company Name: Paradox
Founder Name(s): Aaron Matos
LinkedIn: Paradox Company Page
Industry: Talent Acquisition Technology
Stage/Funding: Series C, $200 Million USD 
Location: Scottsdale, Arizona

This is a post in a series of interviews with startup founders who have worked with Twilio Ventures. Twilio Ventures invests in companies building tomorrow’s solutions for developers and customer engagement applications. We had the pleasure of working with Aaron Matos on their startup, Paradox.

Describe Paradox’s startup journey in 160 characters or less (the original length of a text message)

Paradox is a leading conversational AI innovator, helping 700+ global clients get recruiting and HR work done faster through frictionless experiences people love.

What does Paradox mean and/or how did it originate?

We’ve always believed that recruiting is a people game – and if you get the people thing right, you can build teams that change the world. The problem, however, is that recruiting at most organizations is plagued by software, systems, and processes that slow things down and create bad experiences for candidates, recruiters, and managers. The net result: Inefficiencies that hurt hiring productivity and make companies less competitive for the best candidates on the market.

We’re obsessed with the idea that conversational AI – or what we sometimes call “assistive intelligence” – can transform that paradigm by fundamentally transforming how we think about the core systems that drive enterprise hiring (ATS, CRM, the career site, etc.). We see a future where enterprise software feels invisible and conversational experiences become the new UI – automating repetitive tasks to help people spend more time with people, not software. That’s ultimately the mission that influenced our name — the paradoxical idea that we can create software that helps us spend less time… with software.

What have you enjoyed most about building Paradox?

For us, it’s all about building an amazing team that’s driven by helping our clients drive real results. One of our values is that we measure client success in hugs. For some, that’s a weird thing to say, but we take it to heart. We don’t celebrate until we see a client achieve the business impact they set out to achieve when they partnered with Paradox. When a client goes live and they first start to see the impact of their transformation, that’s what we live for. When they see candidates chat with their assistant, thank them for being helpful, schedule an interview in seconds (and in some cases get hired that same day) – their eyes light up, and you can really see them grasp how this could change the way they hire forever.

What is one decision you made building Paradox that you would make differently today?

I don’t worry too much about what we could have done differently. I worry about what we can do today that will make us better tomorrow. Some of that comes from learning from previous mistakes, but we try to think more practically with a growth mindset. We take responsibility for our successes and failures, and our curiosity and perseverance drive us every day. I could second guess a lot of things we’ve done, but I’m not sure it’s worth wondering what I would’ve done differently in that exact moment. It’s easy to play revisionist history, but I’m more focused on what we can learn from the decisions we did make and how we can use that to become better professionals and people.

What should potential customers know that is unique about Paradox?

We’re a product and a client-focused company first – one that’s driven by how we can build things that help our clients solve real business challenges. We’re not about flash or buzzwords, or promoting our own success. We’re obsessed with truly transforming the industry and organizations we serve. We do believe we bring a new lens and frame to enterprise recruiting and HR technology that’s helping our clients completely re-think what’s possible, and that frame centers around some key pillars:

  • Transform the experience: We believe it’s possible to deliver true consumer-like software experiences in hiring, onboarding, and employee engagement – experiences that differentiate against legacy systems by fully embracing a mobile-first, conversational-led philosophy every step of the way.
  • Hire faster with less work: Paradox helps eliminate bottlenecks and friction in the process, automating work people might’ve otherwise needed to do – giving time back to recruiters and getting candidates through the process faster. By returning time to hiring teams and managers, we’re helping clients reallocate headcount to focus on higher-value work.
  • Convert more to spend less: Most organizations spend a ton of money to attract candidates — only to send them through traditional enterprise ATS systems that weren’t built around experience or conversion. By removing friction and building the experience around conversational experiences, we can help increase candidate conversion to reduce ad spend and create immediate value.

How are you building on Twilio? E.g., how do you use Email, SMS, WhatsApp, Verify, etc. to communicate with your customers?

We built on Twilio from the earliest prototype because of its scalable model and ease of use. We’ve always been a messaging-first platform, using SMS as the primary channel for communicating about a job. As our platform has expanded globally, Twilio was an obvious partner to use for SMS, and as our platform demanded more services such as Verify and video, audio and other services, Twilio has always been the first choice for us. Our business is built on the reliability and scalability of Twilio, so we were honored to have Twilio join us as an investor in our Series C fundraise as well.

Why did you select Twilio Ventures as an investor?

As we did our Series C, we wanted to continue our strategy of getting “smart money” around the table. Along with a fantastic coalition of financial investors, we were honored to have Workday Ventures and Twilio Ventures join as investors. Given our success building with Twilio and how core it is to our business, being closer with Twilio made all the sense in the world.

How has Paradox benefited from partnering with Twilio?

As a Twilio Ventures company, we have been able to get access to executives, understand future initiatives, and participate in the strategic direction of Twilio that’s important to us. We fully believe that great partnerships start with the shared goal of doing right by the client and serving their needs first. Twilio has shared in that philosophy and our partnership allows us to do more to further that mission together.

Thank you for reading. If you would like to read more Twilio Startup Labs Founder Spotlight interviews and learn how others build, prototype, and demo on Twilio, please check out the series of articles here.

For questions about Twilio Startup Labs or to learn how to get involved, please contact Frank Y. Owusu at

To find out more about how Twilio supports Startups, check out Grow with Twilio.