User experience design, team building and process coaching during the critical years.





New York City


E-Commerce, Retail, Technology, Home Goods


User experience, agile coaching, strategic planning, team building, corporate planning, leadership, advisor.

Casper Workshop Illustration

About Casper

A company with aspirations of upending the supply chain of mattresses and the $80B sleep industry.

Casper has expanded into the greater “sleep” category with pillows, bedding, bed frames, and accessories. With over 1 million mattresses sold, Casper is one of the most-talked-about consumer startup brands, positioning themselves as the “sleep company.”

Since launch, Casper has reached unicorn status with a $1.1B valuation and raised over $340M in venture capital funding from funds Lerer Hippeau, celebrities like Leonardo DiCaprio, and in 2018 recorded revenue of $250M. Brick and mortar stores were opened in 2018, and in early 2020 the company announced its intentions of filing an IPO.

The Big Picture

Providing user experience leadership and guidance for the company as it rapidly grew.

Throughout 4-years, we delivered user experience expertise for the most critical customer interactions, installed agile for growing teams, added multiple products, and orchestrated international expansion for the digital product.

As sole digital product design consultants, our time with Casper included leadership and team coaching across many disciplines and well as corporate planning. Our work with Casper is an excellent example of the breadth of support Thought Merchants provides to a company that’s taking off in a significant (or more modest) way.

We not only helped them scale, but we also helped them scale efficiently and healthily.  We built lasting relationships with multiple people and teams at Casper and facilitated team building.

$1 Million Sales in The First 28 Days

Thought Merchants delivers UX audit evaluating Casper’s checkout experience before go-to-market launch.

Casper was gearing up to launch their e-commerce store for their new bed in a box mattress concept. Conversion rate from landing on the homepage to adding to cart to payment can make or break a start-up, especially with such a high average order value. We went through our analysis and heuristics evaluation to deliver a Usability Observation report that offers guidance to improve their online experience.

Usability Observation Report delivered to Philip Krim, Casper CEO.

Casper's e-commerce launch was an explosive success. 28 days later, Casper recorded 1mm dollars in sales, and their entire mattress inventory was sold out. In just over a month, they proved selling mattresses online is a fantastic business!

The spectacular mattress growth encouraged Casper to introduce new products: pillows and sheets! We designed a new site architecture to accommodate the latest products, including a new homepage, product index page, product show pages, and checkout improvements.

New information architecture introducing Casper’s new products.
Casper information architecture audit and strategy workflow.

During this time, we introduced lightweight, agile methodologies to help streamline the workflow for the development team that was under immense pressure to match the speed of the business.

The development team enjoyed the new agile practices, and the creation of 2 additional development teams meant we needed to scale up the agile practice to maintain team health. Over 6-months, Thought Merchants lead user experience design while overseeing the agile process across the growing technology organization. That success got us called back for yet another more significant challenge.

The next week’s agile sprint being discussed by the, at the time, small technology team.

Scale Everything Everywhere

More revenue, more products, more teams, more countries, more...

Following their Series B funding round Casper needed to truly scale every aspect of the organization. This meant: grow their tech team, go international, add products, and scale-out their agile development teams that we installed earlier in our time together. Adding more products meant revising the information architecture that would support it. This involved an alignment between designers, developers, and the executive team around what choices we needed to make, how it impacts user flow, and what up-sell considerations to promote during checkout.

We started by reinforcing the agile practices and building trust with all the new recruits. There were now five teams, and we started installing agile software development practices and meeting inside each team while providing product leadership (at the time, there was no VP of Product yet).

Our previous connection and trust with Casper’s founders allowed us to quickly align new teams and push through meaningful initiatives. Now that we had a bunch of teams, we needed a mechanism to coordinate the organization. We created, as this did not exist at this point in time, a monthly planning routine with the entire organization and leadership. Leading this type of operation requires credibility to push leadership and the respect and trust of the tech team.

Announcing the new monthly planning to the organization in their NYC offices.

Over a period of two weeks, we interviewed the leaders of all the different teams at Casper: physical product, marketing, ops, tech, CX, etc. Gathering all their requests for tech (everything needs tech), we capture all their priorities, have them stack rank for their team. When a company hits $10M in revenue, a lot of demand in development resources emerge. This is a typical bottleneck for startups because developers are expensive and hard to hire.

We then take those requests and work with leadership to find out what the global priorities are versus capacity and figure out a way to make the hard decisions. The entire process culminates in a monthly prioritization presentation where the team leads come together to hash out the whole organization’s next month of work.

Monthly planning presentation with the entire leadership present.

Expansion to Transition

Scaling weekly sprints to monthly roadmaps to quarterly corporate planning.

Our monthly process quickly turned into quarterly planning for the company. The planning process involved capturing organization goals, prioritizing them, and turning them into stories for different development teams. This approach enables those teams to actually complete tasks without being blocked by dependencies.  

Winding down our engagement, Casper wanted to lock in the knowledge and continue the agile process evangelism. We implemented agile process coaching with the 10-person Casper data analytics team, a massive driver of the Casper business, and coached the 40-person customer service team to help improve their tooling. We mentored and trained team leaders around agile methodology and helped install it across other departments outside of technology. We coached Valentino Wong, Casper’s Digital Program Manager, on our agile method before wrapping up our time with the brand.

Over four years inside one of the fastest-growing, buzzing startups in the game ended with an ovation from the company during the last quarterly planning we facilitated. Now that was exciting!

Graham sleeping on a Casper dog bed.