Building a Winning Culture Through Trust and Empowerment with Jason Nyhus

Jason Nyhus is the general manager for Shopware US, an enterprise commerce platform built for B2C and B2B organizations. He is passionate about inspiring sales team excellence and building winning cultures. He and Amy were introduced through a mutual connection, Matt Christensen from Distributor Data Solutions, a previous guest on the show, after a conversation about personality first hiring. Matt has been impressed with the team and his experience working with Jason at Shopware.

Jason opens by saying he is not an expert on the topic, that he leads with his heart and tries to make good decisions to build a great team.

He frames the company first, because it helps explain the cultural pieces. He has been in e-commerce his whole career, about 26 years, and for 22 of those years he had no idea who Shopware was. Shopware has been around since the year 2000. About four years ago a recruiter called about a general manager position for a business called Shopware, and his first reaction was to ask who that was and why the world needed another commerce platform.

The data changed his mind. Shopware had raised $100 million from the Carlyle Group, one of the top five private equity firms in the world, and from PayPal. Digging in further, he realized Shopware is dominant in Germany, Austria, and Switzerland, the region they refer to as DACH. For scale, Shopify is something like 10 or 12 percent of all commerce in North America. In the DACH region, Shopware is 25 percent of all commerce. Smart money investing, plus 40,000 to 50,000 clients and that kind of dominance, got his attention.

The business itself is a 450-person company doing roughly $100 million in revenue and growing at about 40 percent, with about 20 employees in North America. Last year it was rated a great place to work.

E-commerce is known for high turnover and high stress. It is a tough industry because of the sheer amount of competition. There were 19 vendors on the last Gartner Magic Quadrant, which means there is a tremendous amount of competition on every opportunity, and for every customer you have there are people who would love to over-service them and undercut you on price. He calls it a highly competitive space, and one he loves, because it is the only thing he knows.

He got into it by accident. He worked for Pillsbury as a retail sales rep for about three months. They flew everyone into Minneapolis, where he lives and where the headquarters of what is now General Mills sits, and let 600 people go on the same day. That got him out of consumer packaged goods retail sales. He went across the street to the Mall of America, where CNBC was broadcasting about the information superhighway with executives from Digital River and 3M on stage talking about how e-commerce was going to change everything. The CEO of Digital River, Joel Ronning, was speaking. Jason knew someone who worked there, got an interview, and had an offer by Friday. He went from CPG to e-commerce in about a week and has not looked back.

That was the year 2000, during the hyper growth of everyone needing to be online and the overvaluation of everything e-commerce. Companies would call Digital River, sign up, and Digital River would crank out cookie cutter e-commerce sites for them. His job on day one was 600 accounts and a spreadsheet. Call them, figure out where to spend your time, figure out how to grow them, figure out what tech they need, and get paid based on how well those businesses do. His training was essentially a spreadsheet that said figure it out.

He stayed 20 years. What is interesting about that is he lived through every phase of e-commerce: the race to get online, the best of suite model where one company did all the services for you, then best of breed, then mobile commerce, social commerce, and globalization. He survived several regimes within Digital River and got to see the world through what was at the time one of the largest e-commerce platform providers in the world.

He has lived through some crazy times, and says he has never seen anything like this moment with AI. He thinks those years prepared them well for what is coming, but the world is changing as we know it.

What drew him toward people and culture came from reflecting on being the youngest person in the room in a lot of scenarios, which is now the opposite. He paid attention to how great leaders let people make a lot of choices and gave them a lot of authority. He uses a term internally called wielding power. How do you get people to follow you even if you are not their boss, and how do you get them to do things you would want them to do without actually being in the room?

That runs through hiring, recruiting, and retention. They look for people who are able to wield power, because it is a big skill set. In e-commerce, buying Shopware also requires someone to deliver the services, technologies to integrate, payments to work. To be successful you have to be able to wield power, and you need the right people doing it day in and day out, because it can be exhausting.

He started thinking intentionally about the people side about a decade ago. He had a mentor, Vic Pacor, who was on the board and was assigned to him, and who started talking about getting the right talent and giving them the right rope to be successful. What triggered it was noticing that when he was in the room, doing the work, delivering the pitch, convincing someone of something, their odds of success were very high, and when he was not in the room there was a fall-off in productivity. He read that as meaning he had to be in the room. Vic told him no. Train them and empower them to be successful without you, because that is where the real unlock of scalability and potential comes from. It takes a real leader to recognize that training people to be in the room and succeed without you is actually a better measure of success, and that it scales.

Part of what he loves is being part of an ecosystem, where they play their role but are highly reliant on others playing theirs. Instead of making $100 on a transaction, he would rather make 8 and make sure other people get the opportunity to eat the other 92 pennies on the dollar. When you embrace that ecosystem ethos, recruiting changes. You do not just post the role. You first tell your partners what you are looking for, and they become an incredible source of referrals. Generally speaking they do not have to hire recruiters. They post online, share it with partners, ask their own internal networks, and that is the pool of candidates they fish from.

That only works because of the reputation behind it. It is all built on trust and relationships, and they protect that at all costs, because it drives business both directions and it is also how they get and retain talent. The practical implication is that if things go poorly for a merchant trying to launch with Shopware, they have to step up and make it right, deploy resources to make sure it goes well, and eat costs they did not plan on. They are paying for really good talent, just through other mechanisms of earning trust through the ecosystem.

That is the opposite of a short-term view where you have an opening and you need to fill it. The relationship with a partner like Matt at DDS is an example: they provide value Jason says he could not touch, so Shopware relies heavily on that partnership. The way they treat each other, show up, and support each other's events is evidence of a real relationship, and when the time is right for Matt to refer people, Jason is sure he would have no problem doing it, and the same in reverse.

On making sure new hires align to the ethos, he says they do not always get it right. It is always best effort. But one unique piece is their view of failure. He hates firing people and does not think that is a weakness, but more of an empathy point. They hire people with great backgrounds and great relationships, largely referrals, and not all of them are successful. His view is that it has to do with the company: how much time and energy they invested in those people, what position they put them in on the field, and which partners they aligned them to. There is a lot more accountability at his level and his management layer for making employees successful than you will see in other places.

Companies at different points in their life cycle behave differently. A pure growth company that is the market leader can bring in sales people, overpay them, expect immediate results, and fire them if they do not see it. That is not them. They are building a brand and long-term relationships, and there will be patches where things are great and patches where things are not, so they design their employee management to weather those storms and for management to take accountability in getting people through those periods.

He even produced a slide about it. Failure at certain companies is on the individual. Failure where they are in this market is on management and the employee. If you are failing, there are multiple people who should step up and be accountable for it, and then there are conversations about what has to change to set you up for success.

On tracking it, the classic sales measures apply: quota attainment, pipeline size, conversion rate, deal size. They look a level deeper because so much of winning new business is attributable to tech partners, agencies, and influencers. So they take a data-driven approach alongside a softer one, asking what the vibe of the ecosystem is and whether people are doing the things they believe will compound in the future. Both the art and the science.

When there is a misalignment, he thinks it is more often skill than attitude or effort. They have not had the attitude problem, because on a 20-person team they hire for attitude and effort and look for those fits. Sometimes it is skill set, like asking a former customer success person to be a seller. But the goal is not to fire people. The goal is to find a way to put them in a position inside Shopware where they can succeed, or to help them find a job in the ecosystem where they can thrive, and they have seen some of that as well.

He turns the question around and asks Amy to describe the best place she ever worked, because that is all he did to figure out what kind of company to build at Shopware North America. Her answer is that her favorite job aligned with what she valued and the way she works best: highly autonomous, a lot of room for creativity, very relationship driven, and surrounded by people who supported and encouraged that.

He says it sounds a lot like his own list. What the management team tries to do, not just him, is create the environment of their favorite moment of their career and recreate it there. He says it is not more complicated than that.

The caveat is that not everyone's favorite thing is the same. Some people love autonomy, gray area, and creating things from nothing, and others find that stressful and would rather have step by step instructions. You have to hire a mix of people who do not all think exactly the same. His chief of staff for Shopware North America, Stephanie Ryan, is purely process driven and an unbelievable cultural fit and champion. Process is where he suffers, so he leans on her, and where she suffers she leans on him. At the end of the day they both want to work somewhere that allows autonomy, creativity, and flexibility. Those attributes are common, and the other things are more specific.

In the hiring process they ask what type of company you like to work for, to tell them about your favorite time in your career and describe what that felt like, and to describe who you worked with and how you worked well with them. They are really looking for cultural fit, and for the most part they have a very high cultural match rate because almost everything is a referral.

By the time people get to him they have already been assessed on technical fit, history in e-commerce, and connections to agencies or tech partners. So the majority of what he cares about is entrepreneurial spirit. Will they be a good teammate? Will they work well in times when they do not have clear direction and have to invent the direction? They want people who are not scared about making a call, because there is no relentless pursuit of the guilty. They are going to figure it out together. People who come from businesses where everything is cookie cutter and you do exactly what is on the sheet do not thrive in that environment, because the world they live in is far more agile.

He says the universal truth is that the world is going to need great people for a long time. There are great people who apply that they do not hire, and great people who work there who could all leave and make more money. They have all been well trained in e-commerce. They stay for a different reason. They stay because they feel like they are part of something, because they have autonomy and authority, and because when they go to bed on Sunday night they are not dreading Monday and a pipeline review. They stay because it connects to where they want to work.

On rhythms, he says he does not think they have this nailed and would take advice. They have a lot of rhythm of the business meetings, pipeline meetings everyone is invited to, event calls everyone is invited to. The tax they are paying is that they are making everything everybody's business, and while that may sound good, there is a big tax in having to learn everything about everything.

There are three things they do as a company to ground and connect everybody. The first is Partner Day in North America, last year in Austin, Texas, where they fly their tier one and tier two partners together to talk about the product, the culture, and the ideal customer profile. The second is Shopware Community Day in Germany, a similar vibe but global. The third is Shoptoberfest, this year in Nashville, Tennessee, with about 250 people, and its entire purpose is to build community.

Shoptoberfest is a seven-hour event from two o'clock to nine at night. Jason is the MC, so Shopware is present in theory, but the only agenda is eight TED talks by eight merchants. The rest is German games in a beer hall and a good time, all in the context of building community and best practices. Zero commercials for Shopware. Zero.

The seed for it came from his own experience. Previously at Digital River they were a layer inside Salesforce, Adobe, and BigCommerce, and he found himself spending money to attend events run by great software companies only to show up and feel like he was at a commercial for their products. That was not why he went. He went to meet other merchants and other partners and be part of a community. Since he got little value from learning about new features and all the value from the human side, they created an event that eliminated the fat and went all in on what people valued most.

There was no resistance at the start, but a lot of people saying it sounded interesting and maybe they would go next year, a wait-and-see vibe about whether it would last. Year one had about 80 people in Brooklyn, New York. Last year was 150. This year will be close to 250. The resistance is gone, and now the agencies and tech partners, including DDS, are asking how they can sponsor it and help fuel the community.

He finds e-commerce and technology generally to be very relationship driven, and says a surprising amount of it is decided by a small number of firms. Whoever the Accentures and Deloittes of the world recommend to a merchant largely gets installed and becomes the operating system going forward. Shopware targets mid-market and lower enterprise merchants, so their goal is to build tools for the agencies, because the agencies need to be the recommender of the platform that best serves the merchant. His blunt version is that all software companies will tell you what you want to hear to get you to buy their product and you should not trust a single one of them. Find a trusted advisor and let them pick what is right for your business. That is why Shopware relies so heavily on relationships.

There are two very different ways to go to market. One is product led with direct sales motions, generally an SMB-like motion, where you hope the world comes to you. Shopify is probably the greatest e-commerce box in the world, about 70 percent of the market fits in that box, and he says you should buy from them if you do. Their strategy has largely been direct with some partner influence. Shopware goes the other way, looking for the complex merchant, and a complex merchant needs a trail guide, a system integrator or agency who understands their business and recommends something. Shopware fits by leaning on the industry and the agencies to tell that story, which is why they trade on trust.

When you buy any software platform you are in a way betting your career that it will go well, that it will lower costs or increase revenue or make you more efficient. People need to trade on trust. And once you are in it, there are always complications, because that is how it goes. Knowing those people have your back and will walk you through it is the difference.

That connects directly to employee empowerment. They sell the dream of what is possible, the agencies recommend which platform solves it, and if it comes to them they have to be accountable for delivering what they sold. For some companies that is a reality check and a moment where they have to prove they will support what they sold. Part of why Matt from DDS likes them is that when times get tough, they view it as an opportunity to deliver against what they said, go through the tough times together, and come out with a referenceable customer willing to say these guys did what they said. Internally they send that message constantly: we said this, we are going to honor this, even if it means writing a check to solve the problem. They have done that a few times.

The team is all remote. When he started there was an office in the financial district in New York City. It was beautiful, it was expensive, and they did not go there enough to justify it. What concerned him most was that keeping a single location would prevent them from finding great people in different places. Of the 20 employees, about seven are in Minnesota, five or six in Detroit, and a few in Austin, Texas. The goal is to find the best fit wherever they live. They also make sure to spend at least one or two full days together per quarter, and they do.

They hold those quarterly meetings where their people already are, having done them in Michigan, Minnesota, Austin, and Chicago, so somebody gets to host.

The structure of that time is about understanding the moment, what the team is facing, and how to knock those things down together. The last time they were together in Minneapolis at the end of the quarter, they recognized three or four things they were not executing at a high level. Instead of deciding top down how to solve it, they created tiger teams. They took the four or five biggest problems, asked people which team they were passionate about and which problem they wanted to solve, and told each team this is your problem, tell us how you are going to solve it, come back and tell us what you want to do, create your own timeline. One of their big challenges was going to so many events that they all lost track of where everyone was, so the team said they should buy a tool called Notion to project manage it, create tasks and reporting, and it has been unbelievably useful. That is an example of empowerment, ownership, and authority to make change.

On whether it took work to get people comfortable bringing ideas, he is not sure. He would far rather spend time talking about where they can do better than where they did great, which he calls probably a character flaw. He is always thinking about how to turn the dials, and that mindset permeates the team. There is no bad idea, only priority. Some things go on the back burner and some get solved today, and the list never gets shorter.

Continuous improvement is part of what they hire for, under the term entrepreneurial spirit. His favorite example is walking into an unbelievably cool main street store in a small town that is really well kept, where the people helping you take pride in it. That experience is the entrepreneurial spirit they are looking for, applied to e-commerce. People with pride of ownership, who want the place well kept, well organized, and well merchandised.

Attracting talent in North America is a different problem than in Europe. They have a mature business at scale in Europe and a sub-scale startup here that nobody had heard of four years ago. Merchants show up at their door in Europe. Nobody was knocking on the door in North America when he started, though they are now. So it comes down to figuring out why they are different and what makes them special, and hiring people who want to text with you, have conversations, and brainstorm. Back to entrepreneurial spirit, he can live with someone who does not have the perfect experience if they have an unbelievable attitude and willingness to work. Finding that mix has been the secret.

He cannot think of a hire in the last two years that was not a referral. It did not start that way. When he landed, the first thing he did was look at his own network and ask who he had to bring on the journey with him. He personally recruited a decent chunk of who is still at Shopware, and a lot of them came from Digital River.

What prompted the jump after 20 years at Digital River was a fork in the road. He was thinking about doing a startup, and recognized the potential growth at Digital River was going to be tough sledding. He was right, and the company eventually went out of business and sold off parts of itself. Looking at what he liked and had learned there, he loved being part of an ecosystem, because it creates competitive advantages. He loved being part of modern technology with advantages they could tell stories around. He loved that Shopware would give him authority to price, package, and partner however he needed to win in the market. And he saw a market opportunity if they positioned it correctly. It was a startup in the sense of no customers, no partners, and no revenue, but well funded with $100 million from Carlyle and PayPal and 50,000 existing clients to work from. The best of both worlds.

The first 18 months were real difficult. He was trying to take the European playbook and apply it to this market, and they got runner up a lot, losing second place to Shopify in the standard B2C market. The market flipped when they recognized that the deals they won all had a complexity level above a certain threshold. Now when they recruit employees, merchants, or partners, they look at it through the lens of their ideal customer profile and the kinds of places they are having success, and that has made the entire difference.

It is hard for a lot of companies to admit they are purpose-built for a certain segment of the market and that anything outside of it is a waste of time. In e-commerce specifically, Shopify is the answer 70 percent of the time and Shopware is the answer 30 percent of the time. Spending virtually all of your sales, marketing, and partnering motions on that 30 percent takes discipline, and it is hard.

The people who thrive in that segment are different too. He calls the Shopify use case simple commerce, though nothing about it is simple: the classic trading pattern between a merchant and a customer, shopping cart, product detail page, checkout, payments, done. In B2B it is a very complex sale involving sales reps, territories, rights to distribute, and all sorts of rules driving a complex use case. For a seller to be successful in that motion they have to appreciate the difference, so they recruit people who understand it.

The overarching theme of how they work is entrepreneurial spirit and finding ways to wield power, but the thing that makes the engine go is trust. All trust. Sometimes that means they eat last, and that is okay, because over time trust is a boomerang. It will come back, and you just do not know when.

On how you actually wield power, he says it is never done. If you are a manager and someone works for you and you can simply tell them what to do and control their raises and promotion cycle, that is not wielding power. That is being their boss. True wielding of power is giving someone enough information and enough reason to do something without you having to ask. His favorite illustration is that if you sit down across a table from someone and put two Lego pieces on the table without saying a word, something like 98 percent of the time the person on the other side will pick them up and put them together. All you have done is put them in the right environment with the Legos in front of them, and on their own free will they did what you wanted. He applies that to how an agency comes to trust Shopware enough to recommend them, and how a tech partner gets excited enough about Shoptoberfest to post on LinkedIn in lederhosen. How do you create environments where you put the Lego pieces on the table and people put them together?

They spend real time with employees brainstorming how to be different. His competitors are Adobe, one of the largest software companies on the planet, BigCommerce, a public company, and Shopify, the market leader in simple commerce, along with the legacy of IBM, now HCL, and Oracle. To compete against them, Shopware has to price, package, partner, and deliver differently. They have to create a counterculture and be different in a way that people want to be part of. Doing the same things everybody else does, just their version of it, is a losing strategy.

He describes the company as build a bigger table, not a higher wall kind of people. Shoptoberfest is at shoptoberfest.com, free for merchants to register, in Nashville, Tennessee.

On what they are working on now, the world is changing quickly with AI, and he says it is less about the technology and more about change management for organizations. When a company installs a new commerce system, the hard part is usually less about what the technology can do and more about what has to change inside the business to take advantage of it. So they are trying to help merchants through the change management cycle while also helping them think about agentic commerce, how to apply it, where to apply it, what changes and what does not, because that is the big unknown for a lot of merchants and distributors. He would like to believe they are out front of it, and says there is certainly more they do not know than they do.

On balancing AI and people, he struggles with it. He has never met anybody in e-commerce who has been able to get all the way through their to-do list, and that is still true with AI. There is a lot of blue-collar work being done by white-collar people. The question is how to use AI on the things that are highly repeatable, what AI is built to do, rather than using AI to scale existing problems, because done wrong it amplifies them. How do you use AI smartly and put your humans on the strategic, important things? AI can do a lot of the analysis, but what you decide to do at this moment is human driven, and the job is empowering that to go faster.

The innate creativity of people is worth trusting rather than handing over to an artificial system. They are in the trust game, and it will get harder. People have to continue to be the person in the loop around that trust layer, at least for the foreseeable future. That is what they are banking on and how they are behaving: hire people you can like and trust, and try to deliver that across the ecosystem.

Jason closes by saying he usually gets brought onto podcasts to talk about e-commerce tech and rarely gets asked about philosophies on hiring, retaining, and partnering, so saying it out loud was fun for him.