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Erin Steinbruegge of Design Pickle: “Start small, grow big”

Start small, grow big. In the early stages of a business, when resources are limited, focus is critical. Focus on being great with one customer, one vertical, one product — however you want to slice it. Get to product-market-fit and prove those results before expanding, or you can stretch your team too thin. Design Pickle initially only […]

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Start small, grow big. In the early stages of a business, when resources are limited, focus is critical. Focus on being great with one customer, one vertical, one product — however you want to slice it. Get to product-market-fit and prove those results before expanding, or you can stretch your team too thin. Design Pickle initially only focused on delivering a great graphic design experience. Once we achieved that product-market-fit for graphic design, we expanded into custom illustrations, and then launched FreshStock, a premium vector stock and template library to inspire ideas for our clients. We’ll keep expanding into other creative verticals, but only when we’ve hit specific success criteria for each of them.


As part of my series about the “How To Take Your Company From Good To Great”, I had the pleasure of interviewing Erin Steinbruegge, an experienced marketing and operations leader with a proven track record of building and developing teams. With a knack for taking technology startups from pre-revenue to multi-million dollar exits, Steinbruegge has served in roles such as COO for Onespace (formerly CrowdSource), CEO of The Loud Few, and Digital Marketing Leader for MonsterCommerce. In 2015, Steinbruegge was recognized by the St. Louis Business Journal as a 40 Under 40 class member. Steinbruegge currently serves as Chief Operating Officer at Design Pickle, the world’s leading flat-rate graphic design and creative services provider, and as a board member for her alma mater, Washington University.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

My career in the tech space began unintentionally as a result of a national tragedy. After graduating from Washington University in 2001 and taking the summer off, I planned to start a career at an advertising agency. I had a few offers from local agencies when the events of 9/11 occurred and completely shocked the nation. In the wake of the tragedy, ad agencies seemed insignificant — most went on a hiring freeze and rescinded their offers.

I gave up on agencies, and after months of searching, landed a job with Autotrader.com, a company that was booming during this time period. They were selling a smarter way to spend your advertising dollars while the agencies were shrinking. They did a lot of things ahead of the curve — they were even a remote workforce before working remotely was considered “the future of work.” I loved everything about the company, including Chip Perry, who was their CEO at the time and is still an inspiration to me. My experience there allowed me to develop skills in internet advertising, software consulting, and SEO, and, most importantly, made me realize the fast-growth, rapidly changing environment of tech startups was for me.

Since then, my entire career journey has been one of the challenging ups and downs of the startup world: capital raises, acquisitions, pivots, and that work-hard-play-hard mentality that results in a lot of pain (and a lot of joy at the same time). It was definitely the path I was meant to follow.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

In 2011, I had the entrepreneurial bug. Through various experiences, I saw an opportunity to be a digital powerhouse in St. Louis (where I was living at the time). Pulling from my time at Autotrader and MonsterCommerce, I set out to start my own digital marketing agency.

With the agency, my biggest challenge was also the most rewarding part: working with friends. I was fortunate to have built a network of digital marketers who were close friends, and decided to hire several of them in the early stages of the company. There is something to be said about being surrounded by people you can trust wholeheartedly. As a first-time founder, I held a deep fear in the pit of my stomach that I could fail them. It was hard to balance. During the hardest times of the business, though, working with people who were fully ingrained in my life really drove me to be the best version of myself.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

When I was running the agency, I had not yet learned the value of outsourcing or delegating — I was wearing way too many hats. From handling finance to client relations and everything in between, I was absolutely exhausted.

During a particularly chaotic week, I got a strange call from the landlord for our office. He asked, “do you think this is a funny joke?” I remember being so confused — I had just sent the check!

Turns out, in my haste, I had sent the envelope just fine…but without the actual payment. Lesson(s) learned: accounting is probably best left to the professionals, and it’s best to delegate.

What do you think makes your company stand out? Can you share a story?

I believe the introduction to the Design Pickle culture is something team members never forget. Our new hire welcome package includes your very own pickle suit (these are actually a thing — I had never seen so much green fabric until I received this suit), branded swag, colored pencils for participating in coloring contests with our designer-created coloring books, and, most importantly, an invitation to join the Customer Success team as an “intern.”

For two weeks, new hires — no matter what their role or department — act as a Customer Success representative, working directly with clients to address their questions and concerns. Truthfully, this is the best way to learn about the inner workings of the company — if you never know what our clients are going through, how are you supposed to market, build, or sell the product?

By getting our new hires into this customer-first mentality from the very beginning of their careers with us, we’re able to build and maintain the culture that has become so important, both internally and externally.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Burn out is a sensitive topic among leaders and entrepreneurs — a lot of people go through it without being able to pinpoint why they’re feeling the way they do.

I have a few tips for avoiding it, the first being the most important: Know your why. Why did you choose to be part of this company or endeavor? What did you want when you made the decision to join this mission? Is that still aligned? It’s really important to stay grounded with your personal purpose, and to constantly evaluate if your purpose is still aligned with the company’s. When this falls out of line, burnout is often inevitable and it’s usually time for a change.

The second tip is to focus on gratitude. In challenging times, reflect on all the things you have to be grateful for in your current position. Business could be slow or in a downturn, but do you get to experience the journey with friends? Are you creating your best work? Are you able to have creative freedom? Perspective is key — take inventory of what matters the most to you, and focus on that.

Lastly, make sure you aren’t always focused on the destination; enjoy the journey along the way. Sure, it’s easier said than done, and it’s easy to miss key milestones when you’re focused on one goal (for startups, this is often selling). But if you find joy and celebration in the small wins, the end game will be that much more rewarding.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I have so many people to be grateful for along the journey. Athletic coaches, inspirational business leaders, books full of wisdom — it’s a lengthy list. As a female executive, though, I have to give my dad a lot of credit. I grew up with two brothers, and a lot of ambition.

A specific memory that comes to mind is when I was heartbroken about my older brother getting to participate in the Pinewood Derby competition for boy scouts. I was competitive, liked building things, and couldn’t understand why I wasn’t allowed to compete just because I was a girl. My dad told me he understood why I was frustrated, and went out and bought an extra Pinewood Derby kit to build and design a car with me. He even built a racetrack so I could race my brother at home.

He always went out of his way to make sure I was included and didn’t “gender stamp” activities — I was always treated as an equal. Because of this, I saw the world that way and I always believed I could accomplish anything regardless of gender.

Ok thank you for all that. Now let’s shift to the main focus of this interview. The title of this series is “How to take your company from good to great”. Let’s start with defining our terms. How would you define a “good” company, what does that look like? How would you define a “great” company, what does that look like?

A good company has a successful business model and people that will loyally or responsibly show up to work every day.

A great company has a successful business model and a team full of people that love and believe in its vision and mission.

Based on your experience and success, what are the five most important things one should know in order to lead a company from Good to Great? Please share a story or an example for each.

The team is everything. Focus on building “talent density,” which is a phrase I recently picked up from No Rules Rules, Reed Hastings’s book on building the Netflix culture. In this book, they offer advice to consider whether you would fight for someone to stay on your team if they decided to leave. If not, then they probably aren’t crushing it in their role. The rule of thumb I’ve used for years is evaluating whether or not I wake up the next morning after the interview excited about the thought of having that person on the team. The bar has to be kept high when it comes to inviting team members — filling seats because the team is overextended does not pay off in the long run. You overextend yourself more, and again and again, if you don’t focus on bringing in the absolute best talent.

Start small, grow big. In the early stages of a business, when resources are limited, focus is critical. Focus on being great with one customer, one vertical, one product — however you want to slice it. Get to product-market-fit and prove those results before expanding, or you can stretch your team too thin. Design Pickle initially only focused on delivering a great graphic design experience. Once we achieved that product-market-fit for graphic design, we expanded into custom illustrations, and then launched FreshStock, a premium vector stock and template library to inspire ideas for our clients. We’ll keep expanding into other creative verticals, but only when we’ve hit specific success criteria for each of them.

Build a data-driven culture from day one. Make sure all of your teams understand their metrics and have implemented the means to measure them accurately. I think we’ve migrated CRMs at least three times, which has been quite painful — you have to have a “source of truth” in place. I’ve worked with startup founders who make “gut” decisions versus validating the data, which never leads to success. If you make sure everyone is focused on the right data from the very beginning, you can save yourself a lot of pain.

Use a structured methodology for quarterly goal planning and stick to it. I personally love OKRs or the EOS system for goal planning and alignment across the team. Annual planning cycles are common, but they simply don’t work for the fast pace and high growth of startups — or really any modern-day business, especially during a pandemic. By the time you’re halfway through the second quarter, your goals for the rest of the year aren’t as relevant anymore.

Be patient and stay focused on what matters most. Every morning, there are 100 things that need attention. I make it a point to ask myself: “what are the 3 most impactful things I could do today for the business and the team?” If you’ve built a great team that believes in your mission and is doing everything they can to achieve it each day, then success will come.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. Can you help articulate for our readers a few reasons why a business should consider becoming a purpose driven business, or consider having a social impact angle?

Data supports this; I believe our inner intuition does, too. Most of us know what it’s like to be working for a paycheck versus working toward something we feel is meaningful in the world. On one hand, you wake up thinking “I have to go to work.” On the other hand, you wake up thinking “I’m going to spend my day working toward building something I believe is good for the world.” Having that kind of passion and energy for a single mission unifies and inspires a team.

You have to become your mission — not just state it. Your team has to believe it, embrace it, and implement action behind it.

What would you advise to a business leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth and “restart their engines”?

I probably don’t need to drive home the point about being data-driven again, though it is important — you need to analyze the data to understand why the business has reached a standstill. You want to be able to look at the business objectively, and maybe even with an outside advisor or board member who will give you candid feedback. I have seen this occur more than once because a founder or leadership team simply hit their limits without realizing it, and needed to bring in more experienced leaders (or in some cases, just different perspectives) to take the business to the next level.

Leaders should also ask questions like, “Is the business giving the team space to innovate, or is the team completely at capacity maintaining the status quo?” Maybe there is a completely new business model, pricing structure, or feature that would change the game. Or maybe there are new channel strategies to consider that would help you tap new markets. How about an M&A play to acquire new customers and talent?

Moral of the story: assess things as unbiasedly as you can with data and someone that can provide an outside perspective free from internal bias, and give your team time and space to innovate.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

Innovation and focusing on customer relationships are key activities to weathering the storm of a tough economy. This year’s pandemic has proven that to be true for so many businesses. You have to think about what you can do differently that still aligns with your mission, the competencies of your team, and the things your customers value. This can take shape in a multitude of ways.

I’ve been impressed with what I have seen in small business innovation this year — things like winemakers taking the winery tour virtual and creating unique tasting experiences for businesses who want to engage their clients, restaurants reinventing their menu to align better with the takeout experience, and local performing arts groups performing in parking lots.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Communication, communication, communication. Communication will always be the biggest challenge in a business, especially those that are fast-moving and utilize a remote workforce. It’s important to keep in mind that everyone has different communication styles, especially over Zoom or Slack. I should probably say communication two more times because of the rule that you need to say everything seven times for it to stick.

Aside from communication, time is easily the most underestimated aspect in all high-growth companies. We all want to achieve 3 years of results in the first 6 months; however, that’s not realistic. I’ve said this previously, but enjoy the process and be patient! If you focus on setting up the right processes first, everything else will come in due time.

As you know, “conversion” means to convert a visit into a sale. In your experience what are the best strategies a business should use to increase conversion rates?

Identify the right audience and focus on it. If your reach is too broad, you will burn a lot of cash and convert very little. It’s important to narrow your focus to a few buyer personas, then have your marketing and sales teams test each of them to determine if they are a great fit. If you find that one of them is not a fit, that’s a good failure! The sooner you have answers as to who your best customers are, the better.

Second, find ways to lower the barrier to entry as much as possible. Today’s customers are used to free trials, freemium models, no-risk guarantees, monthly subscriptions and DIY onboarding. Make the purchasing process and the onboarding experience as simple as possible.

Third, analyze your best customers. What made them purchase? What makes them a power user? Why do they stay on as a customer? Look for patterns that you can repeat and scale in terms of who you are targeting, what platforms you’re targeting them on, and the messaging you use to engage them.

Of course, the main way to increase conversion rates is to create a trusted and beloved brand. Can you share a few ways that a business can earn a reputation as a trusted and beloved brand?

The best way to create a trusted brand is to create positive memories upon every interaction — whether virtual, in-person, with an ad, or with a salesperson. At Design Pickle, we give out real (giant!) pickles and wear pickle suits at events. Why? Because we want every single person we interact with — even if they don’t have any intention of buying our product — to smile. The hope there is that maybe one day, they will need graphic design and creative services, and we’ll be the first company to come to mind from that one time they got a delicious pickle at an event.

Too often, businesses are so bogged down by the actual work, they forget to have a little fun. General silliness in content is encouraged, as long as it makes sense with your brand. We can be quirky because we have “pickle” in our company name, but finding what resonates with your audience is key. People will associate the feeling of positivity with your brand.

Also, live up to your core values and highlight them in an authentic, organic way. People won’t trust your business if you say your core value is “truth,” then find out they’ve been lied to about the price of your product or service. Make sure everything is consistent with what you’re saying your mission and values are and what’s actually being put into the universe.

Great customer service and great customer experience are essential to build a beloved brand and essential to be successful in general. In your experience what are a few of the most important things a business leader should know in order to create a Wow! Customer Experience?

A smooth and positive onboarding experience is absolutely critical to the customer experience — but don’t let that be your “goodbye” point. Analyze your customer base and segment them into groups based on needs to truly layout what you want the customer experience to be. This analysis is critical to the long-term customer experience — clients in the first 90 days have very different needs than what it takes to create a surprise and delight experience for a customer of 3 years.

What are your thoughts about how a company should be engaged on Social Media? For example, the advisory firm EisnerAmper conducted 6 yearly surveys of United States corporate boards, and directors reported that one of their most pressing concerns was reputational risk as a result of social media. Do you share this concern? We’d love to hear your thoughts about this.

The reality is some people are saying bad things about your business whether you have a presence on social media or not. Why not be proactive and participate in those conversations? Why not see them as an opportunity to learn and innovate?

There are always going to be trolls on the internet, but you shouldn’t let that stop you from engaging happy customers, delivering fun, lighthearted content to fans of your brand, or learning from the experiences of customers who aren’t happy.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

A common mistake I see is going too big, too early. Most founders are filled with passion for their vision, and, understandably, want to start executing everything as soon as possible — usually without a plan. The product will achieve product-market-fit and scale faster if founders adopt a lean approach of starting narrow, testing, learning, and optimizing, rather than diving in headfirst.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Okay, here is a lofty wish: to give everyone in the world the ability to travel and learn about other cultures and experiences in a safe environment. I believe travel develops empathy, understanding, and an appreciation of the differences that make this world a uniquely beautiful experience. Maybe virtual reality will help us achieve this!

How can our readers further follow you online?

You can follow me on LinkedIn or join us in the “pickle jar” — we’re @designpickle across platforms.

This was very inspiring. Thank you so much for the time you spent with this!

Thank you so much for the opportunity to share my story with you.


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