Erin Steinbruegge is a business leader with vast knowledge and experience in transformative and results-oriented marketing and operations. She has built a proven track record of “developing, implementing, and supporting strategic initiatives that lead technology startups from ground zero to multi-million dollar exits.”
As a business leader, Erin Steinbruegge is able to “leverage strong analytical, collaborative, and decisive leadership to capitalize on market opportunities and develop operations that scale.” Her work as an entrepreneur and leader have earned her several recognitions for her “creative problem-solving, direct and transparent communication, team engagement” and for her ability to build a “data-driven culture.”
In 2015, Erin Steinbruegge was selected by the St. Louis Business Journal as one of its “40 Under 40” class. She has also served as the Vice President of Ad Club STL, as a founding committee member of the STL Digital Symposium, a judge in the software and technology category for Arch Grants Global Startup Program. Finally, she has also been a board member of the Webster University School of Communications.
Currently, Erin Steinbruegge is a Fractional Chief Marketing Officer/Chief Operating Officer, where she uses her leadership experience at “several high-growth startups to help early-stage technology companies implement the foundations for success in Marketing, Sales Enablement and Operations.” Previously, she was VP of Marketing and Chief Operating Officer of Design Pickle.
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Jerome Knyszewski: 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?
Erin Steinbruegge: 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 In the wake of the tragedy, ad agencies seemed insignificant — most went on a hiring freeze and rescinded their offers.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.
Jerome Knyszewski: 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?
Erin Steinbruegge: 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.
Jerome Knyszewski: 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?
Erin Steinbruegge: 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.
Jerome Knyszewski: 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.
Erin Steinbruegge: 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.
Jerome Knyszewski: 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?
Erin Steinbruegge: 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.
Jerome Knyszewski: 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?
Erin Steinbruegge: 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.
Jerome Knyszewski: 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?
Erin Steinbruegge: 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.
Jerome Knyszewski: How can our readers further follow you online?
Erin Steinbruegge: You can follow me on LinkedIn or join us in the “pickle jar” — we’re @designpickle across platforms.
Jerome Knyszewski: This was very inspiring. Thank you so much for the time you spent with this!
Erin Steinbruegge: Thank you so much for the opportunity to share my story with you.
