Sam: CEO and co-founder of TestBox. Originally from Australia with a background in computer science. Before starting TestBox, Sam was a Senior Manager at Bain & Co. in San Francisco, where he focused on enterprise software products and GTM strategy. Sam has garnered a strong reputation for vision execution and has been recognized for his extraordinary commitment to customer empathy.

Peter: CTO and co-founder of TestBox. Also originally from Australia with a background in computer science. Peter was previously a Senior Software Engineer at Guidewire in the Bay Area. Peter’s expertise lies in building data pipelines and automation at scale.

This interview presents premium insights into how people, technology and businesses can thrive together. Against the backdrop of the global pandemic, innovators continue to inspire and reshape our world.

Sam Senior and Peter Holland designed the technology behind the first customer-led enterprise software buying platform. In this interview, they’ll share a bit about their strategic vision, their technology, the company culture, their philosophy around company values, and more.

TestBox is transforming the future of software purchasing by making it possible to test and compare software options before buying. Read on to learn more about TestBox, as well as the philosophy and approach that Sam and Peter bring to the company.

The TestBox story

TestBox allows IT to purchase software by testing and comparing software options before buying. The inspiration for TestBox came from when I (Sam) was at Bain & Co., advising enterprise software companies. I repeatedly heard about how incredibly frustrating the software buying experience could be–from the enterprise software buyers I worked with, to sales reps at large tech companies and even my own friends. In every conversation, I heard similar stories where buyers felt that the process was all on the sales team’s terms, often taking many months, and without all the information and access they needed to be truly confident in their decision. This made it clear that there must be a better way. In its design phase, we shared our proposed solution with over 70 buyers, vendors and software experts. With their input, we started writing code and developed the technology behind TestBox.

Brief overview

Our customer-led software buying platform enables enterprise software buyers to test and compare software options side-by-side at no cost. Each product is set up in a live environment, pre-configured to reflect the most common use cases, and pre-populated with AI-generated data to minimize work from the user, including attendance of sales pitches and demos.

Because our platform gives buyers true side-by-side product comparisons, customers can properly test whether or not a solution could work for their team and situation. In addition, the platform makes it easy for buyers to track their feedback on each product and to collaborate with teammates, ensuring that they make the right decision.

Today, we offer integration with customer support software (Zendesk, Freshdesk and Hubspot), with near-term plans to expand to more vendors and across more verticals.

The technology behind customer-lead buying

Our solution is vendor agnostic. Partnership agreements give us roughly the same payment no matter the software selected by a customer. There are no incentives to push a customer towards a specific vendor. In this way, buyers obtain an optimal software purchasing experience.

Company culture vs “move fast and break things”

We make a clear distinction between how we approach building our product and building our company culture. On product, we love to move quickly and are always asking ourselves where ‘good enough’ truly is ‘good enough’ and we’re identifying focus areas where we want to actively differentiate the TestBox experience (both internally and for users).

When it comes to company culture, most importantly, we aren’t building a start-up – we are building a company. This means that we are making decisions now with longevity in mind. We’re really excited about the culture that we’re building – for example: One of our board members has a role as our DEIB advisor, we provide benefits to cover co-pay for mental health therapy, hold monthly celebrations for important events like Veterans Day, Pride, Juneteenth etc., We are actively thinking through what sort of company do we want to be in 10 years and planning for that now.

Leadership insights

Our number one priority when it comes to leading the company is making sure that culture and values are set by the whole team rather than just the leaders. From day one, we’ve build the TestBox values system together as a team, bringing to the table each person’s perspective and discussing and understanding what is most important to us as a group. We have regular quarterly team reviews of the TestBox values that we work by each day. Because each member of the team contributed to these values, each and every person is responsible for embodying, exemplifying, and growing the collective company culture and values. You can read more about our values here:

Connect with TestBox

If you want to try it, just go to and get started. If you’re excited about working with TestBox as a vendor please just reach out to me at [email protected]. Otherwise we’d appreciate any feedback on what we are building and how it could best suit your organization’s needs.