Fighting for the Top Spot: Analyzing the workforce in Payment Processing Companies — Stripe, Checkout.com and Gravity payments!

Julian Herzog
9 min readDec 9, 2022

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Is the old saying “cash is king” still true today? Being the one and only payment method, other than goods exchange of course 🙂, cash has been experiencing a steady decline ever since plastic came onto the scene. From the dominance of the old days, cash has fallen hard from grace, with recent shifts towards e-commerce and contactless payment methods only reasserting what is inevitably coming.

The 2021 Diary of Consumer Payment Choice found that the recent pandemic and advancements in other payment methods caused the cash usage to drop to mere 20% in 2021. Comparing that to 30% just five years ago, it seems that the trend is only accelerating.. This study also found that consumers under 25 years of age used cash for even less than 20% of transactions.

This transition creates a new opportunity space in transaction processing, which many companies have taken advantage of. We could single out three successful companies that focus on payment processing are Gravity Payments, Checkout.com and Stripe, as leaders in this domain.

Gravity was started in 2004 by brothers Dan and Lucas Price in Seattle, Washington, reaching a recent valuation of $284.07 million. Dwarfing Gravity Payments is Checkout.com, which received a $40 billion valuation after raising $1 billion in funding in January. Checkout.com was started by Guillaume Pousaz in 2012. Similarly, Stripe also saw its inception in 2010 by Patrick and John Collison, showing an ever rising trend with a whooping $78–95billion valuation.

One of the top factors that set the foundation for a successful company is its founders. The founders of each of these three companies take a unique approach to management of their own, setting the tone at the top for their most important resource: the employees.

Comparing the employment specifics of these companies will give insights into the management styles the founders promote, highlighting both shortcomings and innovative strategies. The data we will use for comparison is provided by Osterus, a data analytics software which combines thousands of individual data points to generate comparable statistics. In this article, we are going to do just that — compare these three giants and reveal their strengths and weaknesses.

Let’s start by looking at the demographics, specifically the gender ratio. All three companies are male dominant with 60%, 61%, and 70% in Checkout.com, Stripe, and Gravity Payments, respectively. Gravity has some catching up to do compared to Checkout.com and Stripe.

Bug here, but the color coding should have been blue on the 70.02% and pink on the 29.8%

Moving on to the age group distribution, it also gives us insight into company strategies. Both Checkout.com and Stripe have a majority of employees in the 25–35 age group with 60% and 50%, respectively. The next highest category for these two companies is the 35–55 category with 30% and 40% of employees found there for Checkout.com and Stripe, respectively.

Gravity Payments has different results, clearly gravitating (pun intended) towards older workforce, with the largest number of employees falling in the 35–55 age grouping with roughly half the workforce. The next highest category for Gravity is the 25–35 age grouping with less than 40% of employees found there. Although the distribution is similar, one of the reasons that Gravity may not have reached the valuation levels of Checkout.com and Stripe is because of poor innovation. We will offer our opinion why.

Consumers under 35 are the most likely group to be using payment processing software, making them most knowledgeable about what consumers are really looking for. With Gravity employing older individuals, they may be lacking the creative talent and firsthand insight to create an effective competitive edge. After all, younger generations are usually the innovators, older generations the conservatives. Today’s technological advancements are rapidly changing the #fintech landscape and companies need a strong innovative drive at their helm.

Diving into education, we can also see some differences in the languages spoken. Transaction processing companies aren’t limited to a specific geographic area. Instead, the software can be used in every country and in a variety of industries, making the elimination of language barriers a priority.

The data shows us that Checkout.com and Stripe have diversified their Sales function with an average 6 and 4 languages spoken, respectively. Gravity only has an average of 3 languages spoken in the Sales function. This may be another contributing factor to the lagging success of Gravity. The engineering and software development categories show similar results with Checkout.com and Stripe outperforming Gravity.

The specifics of jobs and experience at each of these three companies are useful to consider. Starting with the breakdown of employees by job title we see some discrepancies on which areas of the business these companies are prioritizing. Stripe and Checkout.com place the most emphasis on software development with 16% and 18% of employees found in that role, while Gravity reports 8%.

With the abundance of new payment processing businesses entering the industry, having differentiating software is not just suggested; it’s required. Gravity has shifted its focus to sales with 26% of employees there. Checkout.com and Stripe prioritize sales 5th with engineering data science and analysis, and customer service all having more employees.

Sales is an important function in any business, but solely focusing on finding new customers risks losing existing ones because of a lack of innovation. Innovation often comes down to the founder or the individual in charge of running operations. Take Checkout.com’s founder for example. Guillaume Pousaz is constantly searching for ways to innovate and leverage the popularity of the e-commerce realm, recently starting a new investment firm, Zinial Growth, that focuses on investments into e-commerce startups. This observation strongly ties in with the age groups observation we made previously, and how it all plays into the innovation department.

Building strategic relationships with e-commerce businesses adds to the value of Checkout.com and allows them to consistently innovate and grow without having to place a quarter of their staff in sales.

Now, let’s look at the work experience in the current company. All three companies have a majority of employees in the 0–3 category with 91%, 83%, and 50% for Checkout.com, Stripe, and Gravity, respectively. Employee turnover ratios have reached new highs post-pandemic with employees leaving for new opportunities.

The significant allocation of employees in the 0–3 category tells us that these three companies went through extensive hiring efforts to obtain the needed staff. In the coming years, we would like to see the distribution begin to shift left, indicating the companies are able to keep employees for longer than 3 years.

Gravity does have a higher number of employees with more experience compared to Checkout.com and Stripe with 14% with 10+ years with the company. Keep in mind that Gravity was formed in 2004 while Checkout.com and Stripe were formed in 2012 and 2010, this does make sense.

Looking at the work experience, total distribution shows comparable results between the three companies despite Gravity being formed nearly a decade before Checkout.com and Stripe. In the 10+ category, Checkout.com, Stripe, and Gravity report 57%, 65%, and 70%, respectively. The 5–10 year category is also high with 28%, 20%, and 12% for Checkout.com, Stripe, and Gravity, respectively.

This tells us that each of these companies isn’t looking for fresh college graduates. Instead, they may be leaning more toward professionals with over 5 years of experience. Bringing on employees with experience can reduce inefficiencies associated with the “learning curve” and help these companies utilize their talent from day one.

These companies need to keep in mind that innovation can stem from diversifying the age of the workforce, allowing different demographics to collaborate and tackle consumer demand. Nevertheless, the work experience distribution also goes along the lines of age distribution and it seems that Stripe and Checkout.com both have struck a better balance between experience and age in relation to innovation

Osterus also provides an overview section, allowing us to get a glimpse of the overall loyalty score, diversity score, and competitiveness score. Surprisingly, we find that all companies have a relatively low loyalty score. This score is an indicator, which can help you interpret tenure / churn ratios and overall stickiness of an organization to their employees. There are a few schools of thought on the retention rate within a company, most commonly a high rate is associated with a healthy work environment. GE’s famous CEO Jack Welch once stated that by removing the bottom 10% of employees it helps drive innovation and helps his business strive. He also said that it worked for them, as they had a performance culture in place, which could operate on such a turnover.

The employment type ratio gives us some key insight into the employee structure of these companies, with full-time employees creating a higher score compared to consultants. Checkout.com and Stripe retain the employment type ratio as their highest category with 0.47 and 0.41, respectively. Gravity falls short with 0.22.

Gravity does have a higher current employee tenure ratio compared to Checkout.com and Stripe. However, this is expected considering that Gravity has been around longer compared to the other two.

Research shows that diversity in your team can boost productivity by 35%. Diversity is a top success driver, often differentiating successful businesses from those struggling. This helps explain the success of Checkout.com and Stripe as both companies boast a high and very high diversity score compared to Gravity’s medium score.

All three companies excel in gender diversity with 0.87, 0.87, and 0.82 for Checkout.com, Stripe, and Gravity, respectively. Education and language diversity are also two areas that Checkout.com and Stripe have made significant strides, retaining above 0.8 while Gravity has a 0.56. By diversifying the language and education throughout the business, Checkout.com and Stripe have been able to properly position themselves.

The final factor we will analyze is the competitiveness score. Each company has room for improvement as the scores remain low. However, each company does retain a high demand and retention growth ratio. The boomerang ratio and Ph.D. ratio are bringing down the scores.

Hopefully, you were able to see the impact of employment on company success through the analysis of Checkout.com, Stripe, and Gravity. The tone at the top does matter, setting the foundation for the direction the business is headed.

Although Checkout.com and Stripe seem to be excelling, they too have room for improvement in certain areas. Only time will tell how these companies navigate the new shifts in both employee and consumer demand.

The data provided by Osterus is only the beginning of the insights we can derive from looking at employment information. Soon we will be able to visualize what working for these companies looks like and more.

For more information or to schedule a demo, reach out to contact us directly or on LinkedIn.

https://www.linkedin.com/company/osterus

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