Smart Agency Masterclass with Jason Swenk: Podcast for Digital Marketing Agencies Jason Swenk

Do you treat your team like employees or like people? Every agency owner should recognize the immense value of their team and ensure they are treated with the utmost respect. This may entail parting ways with toxic clients, as the well-being of your team is irreplaceable.
Our guest today faced challenging times during the pandemic when they had to terminate their agency's largest client to prevent the team from burning out entirely. It was a difficult decision, but it ultimately demonstrated how much he valued his employees, leading to a shift in the company culture and a newfound appreciation for their skills, which could be harnessed for incubator businesses. Tune in to discover how he faced the loss of a big client to choose the team that was making his dream a reality and how celebrating the small wins helps keep everyone sane and focused.
Miles Marmo is the founder of Agency Squid, a boutique consultancy and creative agency based in Minneapolis. He shares his journey of building a successful agency, navigating challenges, and creating an incubator agency model, as well as the importance of understanding consumer segmentation, industry trends, and merging it with creative outputs.
In this episode, we’ll discuss:
Learning to savor the small wins.
Choosing your team over a bad-fit client.
The benefits of incubator brands for agencies.
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Sponsors and Resources Clutch: This episode is sponsored by Clutch, the #1 marketplace for agencies just like yours. With their innovative process, your agency will be matched with highly motivated buyers looking for the exact services you offer. Leave the lead generation to Clutch and let your team focus on delivery. Get started for FREE at clutch.co/smartagency by creating your agency profile.
Why Agency Owners Need to Savor Every Success Miles, a former athlete with experience working in agencies on the brand side, never anticipated becoming an agency owner. However, his entrepreneurial spirit was ignited by his competitive nature and desire for some degree of control over his work. His love for working with people also made entrepreneurship a natural fit for him.
Overall, he describes owning an agency as a rollercoaster with exhilarating highs and challenging lows, so maintaining a sense of balance is very difficult. In this sense, Miles tries to always remember to celebrate the wins, no matter how small.
Agency owners often dwell on losses and setbacks, leading to demoralization. Success is almost expected and therefore not celebrated as much as it should be. Instead, Miles believes that celebrating even minor wins not only boosts morale but also provides a sense of accomplishment and validation for the hard work put into the agency.
Undoubtedly, agency owners will face common struggles and moments of doubt and burnout when they feel like giving up and taking a job instead. However, he believes that by focusing on celebrating wins and finding joy in the successes, they can stay motivated and inspired to continue growing their businesses.
The Make-or-Break Moment: Choosing Your Team Over a Bad Client One of these hard moments happened to Miles during the pandemic, when he faced the tough decision to part ways with a major client who negatively impacted the agency's culture and caused burnout among employees. It was a moment where he even questioned whether he had chosen the right career path and his effectiveness at managing his team
Although difficult, it became clear the client would never be content with the agency’s work. This decision ultimately led to a sense of relief and a reshaping of the agency's values and its approach to new business. In the end, prioritizing the team's welfare was crucial for the business’s overall health and success.
Letting go of a client that negatively impacts your culture is a way to show your team that you value them much more than any client. At the end of the day, as an owne

Are you prepared to elevate your agency team and pave the path to success? As your agency expands, the need to grow your team becomes inevitable, and having standard operating procedures (SOPs) in place beforehand can save you a lot of headaches.
Today’s guest went through a rapid growth phase with his agency and found he was ill-prepared to delegate responsibilities and clearly define tasks. As a result, he lost employees and clients but has since learned that SOPs should be in place before hiring and that a good SOP takes him out of the process as quickly as possible. Tune in to gain valuable insights on navigating the complexities of scaling an agency effectively.
Robert Brill is the owner of Brill Media, a white-label media buying agency that helps clients supercharge their business. At his agency, Robert works with a fully remote team of passionate experts and has created a culture of promoting from within, keeping the team members engaged, upskilled, and motivated to take leadership roles.
In this episode, we’ll discuss:
When rapid growth meets poor processes.
Consistency and clarity as a result of proper SOPs.
How to correctly implement SOPs.
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Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
From Dreams of Advertisement Glamour to Owning an Agency In a departure from the most typical agency owner narrative, Robert says this is the only thing he’s ever wanted to do professionally. Growing up, the idea of working on high-profile projects, like commercials, sounded like a dream to him. He craved the recognition that would come from showcasing his work. “I didn’t have the ability to become a rock star, so I went into advertising,” he jokes.
After working a couple of marketing jobs as a college student, he continued that path following graduation and spent the next ten years in the advertising business. By 2013, he still had a love for the business but felt himself becoming a bad employee. The desire to operate according to his vision and the prospect of reducing the stress of taking time off motivated him to establish his own business.
Most agency owners know that - contrary to his expectations – running his agency demanded even more and he ended up working twice as hard. However, becoming a CEO and taking on more responsibilities was the only path to what he wanted and it was a big motivator for him.
What Happens When Rapid Growth Meets Poor Processes? Once you start gaining traction with your agency and your brand attracts more clients, you’ll need to be prepared to start hiring as the amount of work increases. For Robert, however, it was particularly challenging since he had to triple his staff throughout one summer.
The big lesson Robert took from that summer is that he should have started hiring sooner. It felt like a big risk earlier in the life of the business. However, he’s learned that of all the big risks, this is one he should have taken sooner.
Initially, he hired people he had worked with previously, assuming they would excel in their roles without much guidance. However, within six months, one of his key hires quit due to dissatisfaction with the lack of structure, organization, and process within the business.
At this point, no one was happy, — not Robert, the new hires, the existing hires, or the clients. It took him six months to figure out the missing piece was standard operating procedures. Simply put, the lack of clear guidelines, workflows, and systems was leading to confusion, frustration, and ultimately, high turnover rates.
Consistency, Clarity, Growth: The Impacts of Finally Implementing SOPs Agency SOPs sounded like t

Is your agency work affecting your family life? Are you challenged by finding the right talent to assemble a team to take over some of the work? Today’s guest thought she’d always be a solopreneur but as her workload mounted, she realized she needed reinforcements to maintain her level of service and keep clients coming back. Getting the right talent to balance it all was not easy but she relied on a largely untapped talent pool: moms looking to keep their careers thriving while raising their families. In this episode, Sara discusses her experiences scaling her agency and balancing motherhood with a creative career.
Sara Jensen owns Brighter Messaging, a digital agency that helps small businesses manage their online presence and generate leads through content-based marketing. Sara shares her journey from being a solopreneur to running a digital marketing agency.
In this episode, we’ll discuss:
Building a compensation model to empower your team.
Taking advantage of the largest untapped talent pool.
Getting wiser about client choices.
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Sponsors and Resources Clutch: This episode is sponsored by Clutch, the #1 marketplace for agencies just like yours. With their innovative process, your agency will be matched with highly motivated buyers looking for the exact services you offer. Leave the lead generation to Clutch and let your team focus on delivery. Get started for FREE at clutch.co/smartagency by creating your agency profile.



Delegating for Success: From Solopreneur to Agency Owner


Starting as a freelance writer, Sara began to build her agency right as she had become a first-time mother. That was twelve years ago and she was building her agency from the ground up while navigating motherhood. At the time, she was ghostwriting, blogging, and juggling clients' demands. As the business grew, clients began requesting more services, and Sara realized she needed to level up by building a team.
The first role she hired was a virtual assistant, although she admits to being hesitant and unsure of how to work with someone else. Despite her initial reservations, Sara took a leap of faith and trusted her VA to help her navigate the process of delegating tasks and creating processes.
One of the key challenges she faced was the fear of losing control and not being able to deliver the same level of quality to her clients. This fear is common among entrepreneurs who are used to doing everything themselves. However, Sara's willingness to trust her team members and let go of some responsibilities ultimately led to the growth and success of her agency.
Incentivizing Success: A Compensation Model to Empower Your Team Sara’s assistant was the first person to introduce a project management system – Asana – to the agency, changing everything about how they worked. To this day, it’s become an essential element of how her team works together and how she manages to get her ideas from her notepad to the team.
Having introduced a more structured system to the team’s everyday work and communications, Sara understood the importance of building processes and started to do so herself, a task she later delegated to the new project manager. For her, having consistent processes is a huge piece that helps set clear expectations for everyone on the team.
Another important factor for finally letting go of many tasks was being intentional about the compensation piece. At her agency, the team works as contractors and they’ve structured their compensation model around client retainer packages. Each role within the agency gets a portion of those retainers, as an incentive to be more invested in the client’s success.
By building trust, setting clear expectations, and providing opportunities for growth and development, agencies can create a culture of success and achievement that benefits both the team and the whole agency.
Taking Advantage of The Largest Untapp

Do you prioritize new clients or building lasting relationships? Would you be willing to lose money on a client in order to build a long-lasting relationship? Today’s guest has built two successful agencies banking on the power of planning for the long term instead of focusing just on the numbers. She’ll explain how she and her partner formed their vision of an agency where people could do their best work, clients felt heard, and it would all translate into business. Tune in to learn all about the visionary approach that led her and her partner to success.
Kim Lawton is a successful agency owner with two agencies under her belt. She’s the founder of Inspira Marketing, a 300-employee agency reaching the nine-figure mark, as well as the president and CEO of Enthuse Marketing, a purpose-driven group committed to building brands through effective experiential marketing strategies. She shares her journey building two agencies and discusses her approach of over-resourcing client relationships, her role as the chief possibilities officer and president/CEO, and her entrepreneurial journey from a young age.
In this episode, we’ll discuss:
The four pillars of relationship building.
Risking losing money for long-term client relationships.
Strategic hiring to fuel growth.
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Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
The Four Pillars of a Relationship-Driven Agency Although she’s an accidental agency owner, according to Kim she’s been an entrepreneur since the age of fourteen, when she managed her father’s pizza shop and fell into the role of marketer. It wasn't until years later, working at an agency during the rise of experiential marketing, that she truly started to believe in her marketing abilities. It was there that she met her current business partner.
As Kim and her partner dreamed of owning their own agency, they kept a journal to define the key elements they wanted to include. Their primary focus was creating a place where people felt seen, heard, and empowered to do their best work. They believed this would translate into a successful business.
Rather than focusing on the numbers, hourly billing, or time spent on each account, like most agencies, they made the strategic decision to invest in relationships over profit. As they planned how this would look as a profitable business, Kim and her partner decided their agency would be built on four main pillars:
People: Their investment in talent.
Organizational development: Tools they invest in that help people do their jobs more effectively.
Client leadership: How they show up for their clients.
Growth and reputation: They measure the previous three elements and look at that to establish how the agency performed that year.
It may seem counterintuitive for business owners who prioritize profit margins and bottom lines, but it was a conscious choice to become their clients' preferred solution, even if it meant potential short-term financial losses. Their long-term relationship investment approach not only allowed them to create long-lasting relationships, but it was also a good way to quickly identify bad clients. If the client didn’t value the time they were investing in their project, it was easy to say goodbye to them and not look back.
Maximizing Client Relationships: A Strategy for Long-Term Success How do you start to set up a structure where the business is set to lose money with each client for the first year? Kim suggests allocating a portion of marketing expenses to client service. This approach allows agencies to prioritize nurturing existing client relationships, leading to inc

What sets high-performing agencies apart from their low-performing counterparts? How are you positioning your agency for success? Our guest today is a seasoned business executive with extensive experience in product marketing and sales leadership. In his current role, he collaborates with agencies and gains insights into what separates successful ones from the rest. Tune in to gain valuable perspectives on agency performance and growth strategies.
Tim Condon is the Chief Revenue Officer of Clutch, a one-stop-shop were businesses can identify leading service providers through an innovative research process that melds the best of traditional B2B research and newer consumer review services. He discusses the difference between high-performing and low-performing agencies and shares insights from working with professional services companies and marketing firms, highlighting key factors that contribute to agency success.
In this episode, we’ll discuss:
Focusing on organic growth.
Making 100,000 leads in one day.
Shortening the sales cycle.
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Sponsors and Resources


Clutch: This episode is sponsored by Clutch, the #1 marketplace for agencies just like yours. With their innovative process, your agency will be matched with highly motivated buyers looking for the exact services you offer. Leave the lead generation to Clutch and let your team focus on delivery. Get started for FREE at clutch.co/smartagency by creating your agency profile.



Organic Growth and Operational Excellence Build a Scalable Agency From his many interactions with agencies at Clutch, Tim has gathered some great intel on what is working for the most successful agencies. First, they start doing something they are really good at and focus on organic growth. Many prominent agency CEOs initially honed their skills in website development, later expanding their expertise to encompass SEO and pay-per-click advertising to drive increased traffic.
As these successful agencies matured, they strategically planned their expansion into new areas, leveraging their organic growth to thrive and deliver exceptional outcomes. Also, Tim has observed a crucial aspect of sustained agency growth lies in establishing a robust infrastructure. Agencies that have mastered this have implemented comprehensive systems for lead tracking, incentivizing sales teams, and organizing their operational structure. These systems are essential for ensuring seamless operations and maximizing growth opportunities.
Without a solid foundational framework, agencies may encounter challenges in effectively attracting, converting, and scaling their business. But by implementing streamlined processes, performance tracking, and identifying areas for improvement, they can enhance their lead generation, and client conversion, and ultimately scale their business to new heights.
Leveraging Brand Power and Partnerships to Land 100,000 Leads! As CRO at Clutch, Tim has seen many different and innovative approaches to generating leads but especially remembers a time when he was working at the Washington Post. At that time, he was tasked with building a platform to showcase the Post’s potential as a local resource with a lot of local merchants.
The Washington Post faced competition from larger companies like Groupon and LivingSocial, so Tim capitalized on the assets at his disposal, particularly the Post's strong brand and local market distribution, to build a robust email list.
Strategically aligning with Papa John's, Tim proposed a mutually beneficial promotion that involved giving away pizzas in exchange for registrations on their site. The campaign's resounding success resulted in 100,000 new leads! And consequently, 100,000 Papa Johns pizzas delivered — which solidified the partnership between the two seemingly unlikely partners.

This was by far the best promotion either brand had done and Tim made it happen by leveraging his

What would you do if you sold your agency tomorrow? Are you clear enough on your purpose that you could keep on creating value? Today’s guest is the founder of a beloved app that changed the way people drive nowadays. He eventually sold that company but hasn’t stopped looking for ways to improve people’s lives through his startups. He’ll share what he’s learned from failure, why he was out of the company as soon as he sold, and why you should always look to understand users to create real value. Tune in to learn valuable insights into building successful startups.
Uri Levine is the co-founder of Waze, a popular app that helps users have a better driving experience, get to their destination faster, and avoid speeding tickets. After his business was acquired by Google a decade ago for over $1 billion dollars, Uri went on to focus on other ventures. He more recently wrote the book Fall In Love With the Problem, Not the Solution.
He shares his entrepreneurial journey, from creating Waze to building Moveit, and discusses the importance of solving real problems to achieve product-market fit and the impact of failing to do so.
In this episode, we’ll discuss:
Fall in love with the problem, not the solution.
Cracking product-market fit.
Making hard choices with conviction.
What comes after selling an agency for $1 billion.
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Sponsors and Resources E2M Solutions: Today's episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out e2msolutions.com/smartagency and get 10% off for the first three months of service.
Find a Problem Worth Solving: Advice for Agencies to Create Lasting Value Years ago, Uri had the chance to meet one of his technological gurus – Steve Wozniak – at an event. He got to take a picture with him and that exchange inspired a chapter of his book called “Understanding Users”. In it, he explains there’s no right or wrong way to use a product, something he always tried to take into account when it came to Waze users and how they overcame problems.
In his view, every entrepreneur should start by solving a problem. “Think about something worth solving,” he advises. If a lot of people have the same problem, speak with them, understand their perception of the problem, and only then set out to build the solution. For Uri, this is the only way to guarantee that you’re creating value. Instead, starting with the solution may lead to creating a solution that no one was asking for.
Uri encourages entrepreneurs to find a problem worth solving and make it the North Star of their journey. This way, you’ll be much less likely to deviate from the path toward your goal and much more likely to succeed. To agencies, he reminds them that the problem is a significant part of their marketing. The story you’ll tell about the problem is much more compelling than one about the solution. An enticing story will help you make customers care, and if they care, they’ll make you successful.
Biggest Successes and Failures Outside of Waze Although Waze has over 700 million users, and even more use Moveit, neither is Uri’s most successful product. His most successful venture was a voicemail company called Converse Technology. At the time, it had many more users than either Waze or Moveit and it was a massive success. Years, later, he switched to software development, always looking for innovation and change.
On the other hand, his first startup focused on mobile email and it became his first big failure. Uri knew focusing on a problem worth solving was the starting point for any successful venture. This should always be followed by speaking with potential consumers. This way, you’ll see whether or not they share your vision of the problem. If not, they may still point you to a different approac