What founders can do to build a supportive and engaging culture

What founders can do to build a supportive and engaging culture
By Andrew Nguyen | On Nov 11, 2021
6 min read

Creating a supportive company culture requires an incredible amount of intentionality — which is why so many companies leave it until it’s almost too late to make a meaningful impact.

Most companies don’t think about the employee experience, DEIB (diversity, equity, inclusion, and belonging), and company culture until they have substantial funding, have scaled up, and been in business for a few years after. Unfortunately, by this point, company culture is already fairly established and employee frustration has festered.

TestBox is the first company where I’ve seen the company founders put culture at the forefront at the onset — from the first draft of their mission statement before their seed round. Because employee experience, culture, and DEIB are at the center of TestBox’s decision-making while the company is still small and scaling, Sam and Peter (CEO and CTO, respectively) are setting culture norms that will help the company stay cohesive and supportive as it grows. At the same time, they’re attracting incredibly talented team members who want to grow with them. 

As a TestBox board member and their DEIB advisor, I’ve been watching from the sidelines and learning from Sam and Peter as they implement surprising, yet incredibly logical, cultural practices. For example, I’ve seen TestBox team members be vulnerable in a meeting and support one another emotionally. Team members thrive in their roles as a result. 

I suppose it’s no surprise that when you take two self-aware, open-minded, and caring humans who constantly ask themselves, “How do I make sure that my team members thrive in their roles?”, you’re going to see some amazing results.

I read a lot about large companies trying to make a difference in DEIB, and there are a ton of consultants out there trying to help companies change their culture with a DEIB lens. However, I haven’t seen coverage and guidance for new companies to ensure that DEIB is a consideration from the beginning, before they get big and need help changing their culture.

TestBox has done this and is getting it right. So, I thought I’d share five things the founders have put in place that might help you develop new DEIB strategies.

In this article:

1. Infuse DEIB as a core pillar & driver of culture

I see TestBox’s leadership living the culture they want to instill in the company. They set an example inside and outside of work, and expect team members to engage similarly. Here are a few of their cornerstone practices:

  • Making DEIB a priority at the Board level. From the start, Sam and Peter dedicated a board seat to culture and DEIB to keep themselves visibly accountable. As their DEIB advisor, I’ve had in-depth conversations with them about diverse and equitable recruiting, compensation and equity, and DEIB and culture.
  • Emphasizing psychological safety. The TestBox leadership encourages vulnerability at work. They do this with a “Weekly Feels” meeting to check on the team’s work/life balance, and to ensure people feel respected and included, can bring their full selves to work, and are having fun as a team.
  • Celebrating wins collectively. As part of the weekly check-in, everyone writes shout-outs for other team members and reads them aloud. TestBox focuses on ways to celebrate people’s successes publicly. This opens up a space in which everyone can jump in with praise and appreciation for each other, and hear about the amazing things others on the team are accomplishing.
  • Giving back to the community. Sam and Peter wanted to build a culture of giving, which can be hard to think about when you’re heads-down building the first product. But this helps set a different tone and remind the team that even though they’re focused on growing the business, TestBox values the wider community. They compensate user study participants and expert interviewees by donating to charities on behalf of the participants. A few charities they’ve supported so far include The Trevor Project, Electronic Frontier Foundation, The Nature Conservancy, and more. Also, users who complete a software purchase through TestBox receive a thank you gift, including an animal adoption in their name and a donation made to Save the Bees in their honor. 

2. Make DEIB a priority in recruiting

Tackling DEIB also means prioritizing DEIB in recruiting. Sam and Peter recognized that having a diverse founding team would ensure diverse thinking in the company and make it easier to stay diverse as they grow. Acknowledging that there’s a problem with diversity in tech, TestBox has deliberately chosen not to follow in the footsteps of the companies causing that discussion. How is TestBox achieving this? The company is:

  • Setting diversity targets. TestBox is seeking to build an engineering team with substantial representation of non-cis-male and individuals from historically minority backgrounds in tech. 
  • Sourcing from outside known networks. For all founding team roles, TestBox posts on job boards beyond their existing networks and those of their investors — including Slack communities and job boards such as Out in Tech, Blacks in Tech, Techqueria, and Tech Ladies, to name a few. Sam and Peter were hyperaware that like-communities clump together. If you post jobs where it’s easy, you’ll find people like yourself and your existing community. To obtain diverse thoughts and experiences, it’s important to have conversations outside the communities you identify with.
  • Pausing interviews when diversity goals aren’t met… especially for critical roles. This one speaks to the team’s intentionality. In many cases, Sam and Peter paused interviews when they noticed that the final candidate pool for a role was not diverse or representative of the company they wanted to build. For example, when there wasn’t a non-cis-male-identifying candidate among the final interviewees for a core engineering role, they paused interviews and went back to source more candidates to make sure that the pool of candidates they were creating was representative and aligned to their goals. 
  • Hiring for career development and trajectory, not past experience. A crucial lens that Sam and Peter have taken to the interview process is looking at a candidate’s approach to learning, experimenting, and developing, instead of just at their qualifications or past experiences. In situations where they have had two candidates for consideration, even if there is a discrepancy in their past experiences on paper, Sam and Peter have always opted to jump on an initial call with both of them — to get to know each person, why they’re excited about TestBox, and to understand how each person might fit into the team. If someone is excited to learn and experiment and has a good foundation, having slightly less experience might not be a concern.

3. Create a pay and equity/options structure that’s employee-friendly

I learned a lot from TestBox here. They took some steps to structure employees’ options that were focused on the employee experience rather than keeping equity in the company. This is completely the opposite of what many small and large startups do. TestBox offers:

  • Transparent and equal pay. The company always lists the compensation in the job description and does not negotiate. This removes the possibility for bias in compensation.
  • A large employee stock options pool. A disproportionate percentage of the company’s equity is reserved for employee stock options to reward the founding team members.
  • Early exercise of stock options before vesting for employees. This one is a game-changer, and it was apparently very easy to implement. It means that employees can purchase the options before they vest, which starts the countdown to avoid capital gains tax. If an employee exercises early and leaves before they vest, they get their money back. 
  • Longer exercise purchase periods on leaving TestBox. At TestBox, the exercise period after leaving is 12 months. This long exercise period removes barriers for anyone ready to leave the company. Typically, the exercise period for vested options is 30-90 days after leaving a company, which means that employees need to find the money (or already have it saved) to buy all of their vested options. After that period, the options are forfeited and returned to the company pool. A short exercise period can make it hard for an employee to leave a company, especially if they do not have the money readily available.

4. Provide full benefits—including mental health, physical health, family and relationship health

Sam and Peter believe that being healthy is well-rounded, and they prioritize that for themselves and for their team. These benefits are expensive, but they enable a supportive culture for employees. TestBox offers the following benefits:

  • Mental health benefits. Sam and Peter are big advocates of weekly therapy and provide a mental health services contribution to cover or, at least, contribute to therapy costs.
  • Full suite of health benefits. Pre-tax FSA, medical, dental, and vision coverage, because Sam and Peter believe that we all deserve to not worry about healthcare.
  • Fitness reimbursement. The founders are incredibly active and they want to make sure that they and their teammates have the opportunity to also be active.
  • Learning budget. TestBox is focused on growth and career development. The company wants to make sure each team member can continue to grow and develop.
  • Unlimited PTO (with a minimum of 15 days per year). The founders typically take 20–25 days off per year. They implemented a minimum of 15 days per year because they know that people tend to take less PTO when on unlimited PTO. They believe that everyone is happier and a better contributor when they have the chance to rest and actually take time away from work to recharge.
  • Paid parental leave. TestBox offers 12 weeks of paid parental leave, with an option to return to work part-time.

5. Build a feedback loop that fosters belonging

Sam and Peter recognize that everyone brings their own unique experiences to the workplace. This means that accepted “norms” are not constant from one person to another. For instance, what work/life balance means to you might not be what it means to someone else.

To build an inclusive and supportive culture, it’s important to recognize and embrace this difference (after level-setting and teaching the team that this difference exists). That’s why Sam and Peter create opportunities for employees to voice feedback and share deeply as the company grows. It also means that TestBox is a constantly iterating culture. The company does this by:

  • Pushing conversations around norms. TestBox wants employees to be able to carve their own career path, so the company encourages team members to work and live in ways that really work for them and their lifestyles.
  • Having deep conversations around expectations and making changes based on those conversations. At the company’s first offsite get-together, I conducted a workshop focused on work personas and what it means for each person to bring their best selves to work. The workshop turned into a discussion about what professionalism means at TestBox and how professionalism means different things to different people, which is rooted in their past work experiences, for better or worse. As a result, TestBox is working on redefining what professionalism means to them, collectively.  
  • Creating opportunities for employees to share feedback, and building it into a roadmap. As part of their “Weekly Feels” meeting, team members collaborate to resolve any issues and frustrations. If someone is having a particularly busy few weeks, whether it’s at work or outside of work, the team rallies around to support that person. When processes are less than efficient, the team reflects on what can be done differently and commits to tactical changes for the upcoming week. Recently, for example, the team decided to incorporate an end-of-day standup meeting via Slack to provide more visibility to team members in other time zones.   
  • Creating a culture of feedback, and supporting that with training on how to give feedback. Sam and Peter recognize that not everyone has been trained in how to give or receive feedback. To make this process more comfortable, the team does regular training sessions as part of their “All Pedals” (All Hands) meetings, and they have incorporated feedback training into some of those training sessions.
  • Hosting vulnerability sessions and practicing vulnerability on an ongoing basis. As part of their inaugural offsite get-together, Sam and Peter led a vulnerability exercise. This is based on the philosophy shared by Adam Grant in his podcast, which is that one moment of vulnerability leads to a full year of psychological safety. Creating a safe environment for a team has to be done through leading by example. Simply having a leadership team that asks for feedback isn’t enough – the leaders have to show that when they receive feedback, they are open to it and won’t turn defensive. Sam and Peter started by sharing professional development areas where they have each struggled in the past. Then, they went on to outline the areas that they want to improve and how the team can support them. This gave the rest of the team a safe space to join in and share their own answers on their professional development goals and how the team could empower them.

In conclusion 

I realize that some leaders will look at this long list and scoff. It’s incredibly expensive and difficult to implement. But, what I think TestBox is really communicating with this approach is that they truly care about their employees. In turn, I think TestBox will achieve intense loyalty, appreciation, and emotional investment from employees, which — I would argue — is a company’s most important asset.

Sam's Face
Andrew Nguyen

Andy is a member of TestBox's board and is their DEIB advisor. He is on the leadership team of Out in Tech, San Francisco and was the Chapter Head for 3 years. He lives in foggy San Francisco, and is a leader in operations at Fellow Products.

TestBox empowers you to have a self-serve, customer-led experience so you can buy new software and feel confident that you made the right choice. Currently focused on Customer Support, TestBox allows you to test out Zendesk, Freshdesk, HubSpot, Dixa, and other products side-by-side. It takes a matter of minutes to sign up and take these products for a test drive. Find out more at TestBox.com or follow on LinkedIn.