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

Have you ever wondered what it takes to scale an agency from millions to tens of millions in revenue? Or how to successfully pivot from services to products? Today's guest has walked that path - not once but twice.
He’s built two successful agencies with the mission to lift brands up, tell compelling stories and recognize new products. As he reflects on his journey, he recounts the differences between scaling an agency to $25 million and to $50 million, as well as the pivotal decision of starting to sell a SaaS product. Tune in for valuable insights and inspiring stories from his entrepreneurial experience.
Phil Case is the President and Chief Client Officer of Max Connect Digital, a digital marketing agency that combines the most extensive real-time consumer data sets with personalized and dynamic ads. Phil shares his journey of growing his first agency from $300,000 to around $5 million and then scaling his current agency from $18 million to over $50 million. He discusses profit margins, business growth strategies, and the competitive mindset needed to succeed in the industry.
In this episode, we’ll discuss:
A smarter approach to sustainable growth.
Attracting talent through an SVP structure.
The path to becoming a $50 million agency.
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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.
Foundational Clients: The Smart Approach to Fueling Sustainable Growth Looking back, Phil knows he would scale his first agency differently. Back then, he worked grueling 60 to 80-hour workweeks, constantly putting out fires while striving to appease everyone. He also fell into the trap of trying to cater to every need, becoming a jack-of-all-trades for his clients.
If he could go back he would tell himself to focus and maintain high standards. He now understands that striving to excel in a specific area and establish a strong reputation for himself and his agency and have a minimum threshold of what they will do for clients. The growth process would’ve been slower, but it would have prevented them from taking on clients who placed excessive demands on the agency.
Admittedly, committing to a single niche at the outset can be challenging, especially when faced with numerous options and critical decisions. Furthermore, you can’t control your inbound and the type of opportunities that come to you when you’re just starting out. If given a do-over, Phil would be deliberate in building a stable foundation with a select group of clients, who would serve as the cornerstone for the agency's continued growth.
Aligning Talent and Vision for Exponential Growth When it came to enhancing the agency’s growth and focus, Phil found it crucial to expand his team with individuals he trusted to excel beyond his own capabilities. Understanding the agency’s ideal client and vision is essential for attracting a team aligned with the common goal. This alignment empowers the team to make autonomous decisions for the agency, freeing Phil from constant oversight.
Empowering a team, trusting them to make decisions, delegating responsibilities, and allowing them to grow within the organization are key components of scaling an agency effectively. Once he had a big enough team, Phil appreciated the ability to spread the responsibility and burden of running the agency across a group of people. With a diversity of voices now up to speed on the agency’s goals and vision, they make way better decisions than Phil would haveon his own. This is where exponential growth started for his agency.
Attracting Top Talent Through an SVP Structure Even as Phil successfully built a top-notch sales team at his second a

Are you debating the value of building your brand? Perhaps you're wary of the effort needed to establish your identity, only to feel confined to your business once you become the face of the agency. Our guest today specializes in helping clients effectively brand themselves and elevate their agencies.
He understands the common fears and reservations surrounding personal branding and offers valuable insights into its benefits. Above all, he wants entrepreneurs to understand that personal brands should evolve continually, ensuring that they don't limit your growth. Tune in for expert advice on cultivating trust and credibility in the industry through consistent branding efforts.
Jason Barnard is an entrepreneur, writer, and CEO of Kalicube, a digital marketing agency that makes your online brand representation irresistible to potential customers. Jason loves to solve the puzzle of how algorithms work and figure out how clients can use them in their favor. In this conversation, both Jasons emphasize the significance of branding yourself to elevate your agency to the next level in the digital marketing space.
In this episode, we’ll discuss:
Why a personal brand won’t tie you to the business.
How to build and pivot your brand.
Communicating your evolving value.
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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.
The Relatable Factor: Using Personal Branding to Connect with Clients Building a strong brand requires consistency above all else. Without it, your company risks fading into obscurity. As long as you provide value, consistency will help you gain your audience’s trust over time. For Jason, it’s also very much about believing in the value you bring and being proactive. It’s a journey that never ends, Jason says, and a game you lose unless you devote enough time to building that brand over time.
Most agency owners believe they need to choose between building the agency’s brand or their personal brand. Commonly, a personal brand is seen as something that will tie you to the business forever, turning you into the face of the company. However, you need to be the face of your agency, especially in the beginning, and this doesn’t necessarily mean you’ll never be able to walk away.
Being the face of the agency simply means that you are the relatable figure that people associate with the business. People prefer to interact with individuals rather than faceless entities, and having a recognizable figure can significantly enhance their connection to your agency.
According to Jason, we all have a personal brand, whether we like it or not. As soon as you step into the digital landscape you’re leaving a footprint and, even if you try to stay in the background, people will seek you out to figure out who’s behind the agency.
Furthermore, agency owners should consider their career trajectory beyond the agency. Whether that means transitioning to roles like investor or author, having an established brand can make this pivot much smoother than starting from scratch.
Building and Pivoting Your Brand on Your Own Terms For many people, one of the scariest parts of building a brand is thinking they’ll have to be very active on social media. To this, Jason says: not necessarily. To build your brand, you need to do things that make sense to you. This might be appearances on podcasts, writing articles, or social media. It all depends on your talent set, how you want to be presented, and how your audience is going to consume the information you provide.
If, instead, you’re looking to pivot an existing brand, Jason

Are you striving to refine your selling strategy and cultivate enduring client relationships that stand the test of time? How can you elevate your approach to not just closing deals but fostering long-term partnerships that drive mutual growth and success? Today's guest started her business with the idea of embodying a strategic dance of trust, value creation, and genuine connection. Tune in to learn how leading with strategy can lead to success in the agency world.
Molly Baker is the founder and CEO of Indie Consulting, a marketing agency that specializes in strategic planning and activation. Molly shares her journey from working with big brands to starting her agency. She explains her reasons for prioritizing strategy and highlights the need to deeply understand client goals and strengths before making recommendations. 
In this episode, we’ll discuss:
Why Molly chose to sell strategy to gain clients’ trust.
The challenge of developing a repeatable process. 
Offering a foot-in-the-door and client workshops to become a trusted advisor.
A unique approach to account management. 
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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.
Ditching the Agency Model and Forging Her Own Strategic Path After graduating from college, Molly kicked off her career working at a prominent agency, where she mostly worked in digital media buying for a few years. She learned a lot and enjoyed all the great things that come with working at bigger agencies. After that, she went to work on the brand side at Ben & Jerry’s, a great experience that allowed her to work with all types of agency partners. However, the brand side ultimately wasn’t for her.
Wanting to find her own way in the industry led her to work freelance for some time as she gained more and more interest for the strategy-based offer. Eventually, it was time to give her vision a shot and see what happened.
She always saw herself starting a company, although she refrained from categorizing it as an agency, aligning with her distinct vision. This leap of faith has proven successful, as her business continues to thrive five years later.
Selling Strategy and Building Long-Term Client Relationships Most agency owners typically start by leveraging their expertise and working as freelancers, tailoring their services to meet their clients’ specific needs, all while trying to establish a successful business model. For her part, Molly took a distinct approach from the beginning.
Initially, her value proposition centered around offering businesses the opportunity to hire her for a period of 3 to 6 months, instead of bringing in an in-house marketing director or digital strategist. This allowed business owners to thoroughly assess their needs and devise a plan before committing to a permanent in-house hire. It proved to be an appealing offer, especially at a time when business owners were overwhelmed by the options presented by digital but knew they had to embrace it to be relevant.
As her business evolved, Molly expanded her services to include addressing traditional strategy inquiries, such as the most effective investment models or creative strategies tailored to each business. This evolution ultimately led to the development of a fractional resourcing offering, providing clients with a dedicated partner who could seamlessly integrate with their team on a full-time basis.
It’s a very effective way to gain clients’ trust and get over the initial hesitancy that can come when they suspect the agency is just trying to sell something. Molly built a true consultancy where they sit down and help clients figure out the gaps in the

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.
Subscribe Apple | Spotify | iHeart Radio
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