Struggling with unstable revenue and the constant chase for new clients? Discover how Bear North Digital escaped the feast-famine cycle by adopting a retainer model. Learn actionable steps to stabilize cash flow, build lasting client relationships, and scale your agency sustainably—essential insights for any agency leader seeking predictable growth.
For many agency owners, the allure of big-ticket projects often leads to a harsh reality: unpredictable revenue, stretched resources, and a constant scramble to land the next client. We get it: The temptation of a high-dollar contract that promises prestige and immediate financial rewards is hard to resist.
However, as Bear North Digital founder Josh Kimmes discovered, chasing these “shiny object” projects often comes with hidden costs that leave agencies stretched thin and questioning their direction.
In the early days of Bear North Digital, Josh landed what felt like a dream project: a $25,000 website build. For a small but ambitious agency, it was the kind of win that could elevate credibility, attract new clients, and signal success. But reality quickly set in.
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My ego was just huge. I was like, “My God, that was just awesome, right?” And I ended up losing money on the project—I had to go into the red to make it happen. It was a real wake-up call.
What started as a moment of triumph quickly unraveled. Sleepless nights, stretched budgets, and mounting frustration consumed Josh as the project spiraled beyond scope. Margins vanished, and Josh faced the sobering reality that big wins weren’t always victories.
That experience forced Josh to confront the flaws in the feast-famine model of relying on one-off projects. The constant chase was unsustainable—it prevented Bear North Digital from building the kind of long-term relationships that could fuel predictable growth.
Determined to find a better way, Josh pivoted his agency toward a retainer-based model, prioritizing stability and recurring revenue over flashy short-term wins. The result? A more balanced, scalable agency built on trust and collaboration.
Today, Bear North Digital’s story offers a blueprint for any agency owner looking to escape the rollercoaster of project-based work and build a sustainable future.
Name
Agency
Agency Stats
Location
Josh Kimmes
Bear North Digital
6 full-time employees
20+ clients
75-100 websites
Est. 2018
Wisconsin, USA
From Freelance Hustle To Full-Fledged Agency
Josh Kimmes’ journey into marketing didn’t start with a grand vision of owning an agency. It began humbly in northern Wisconsin, where he grew up, and later attended the University of Minnesota-Twin Cities.
After graduating, Josh stepped into the corporate marketing world, gaining experience that sharpened his technical skills. However, something was missing.
“I’ve always been someone who really believes in learning,” Josh says. “Especially on the digital side, there’s not necessarily a blueprint where you can read this book and learn everything you need to know. It’s more so that you’ve got to ‘trial-by-fire’ and kind of figure things out.”
Josh started small, taking on SEO and marketing projects on Upwork under the name Kimmes Consulting. He intentionally avoided reaching out to family or friends for business, opting instead to prove his skills in the freelance marketplace.
I didn’t want to go to family and friends or people in my community and try to get them as my first clients. I wanted to essentially prove to myself, like, “Hey, I can do quality work.”
Josh Kimmes, CEO, Bear North Digital
Scaling To Keep Up With Client Demand
As demand for his services grew, freelancing alone couldn’t keep up.
In 2018, Josh transitioned Kimmes Consulting into Bear North Digital—a full-fledged digital marketing agency. From the start, the agency carved out a niche in websites, SEO, Google Ads, and marketing automation. Bear North also took on white-label projects for other agencies, filling technical gaps they couldn’t manage themselves.
But scaling quickly wasn’t without its challenges. Enthusiasm and grit fueled early growth, but the lack of systems made the process chaotic.
When I started out, it scaled super quick because I had white label clients that had 10 to 15 SEO campaigns that they needed work on. That ultimately quickly led to thinking, “OK, I need a team to help me solve all these things.”
Josh Kimmes, CEO, Bear North Digital
Josh initially relied on freelancers to meet client demand, mirroring his start as a solo marketer. This approach gave him the flexibility to tackle growing workloads without committing to permanent hires too soon.
Growing an Agency Team and Mastering the Art of Delegation
By 2019, Josh made his first full-time hires, bringing on a digital marketing strategist and an account coordinator. These new full-time positions were crucial for spreading the workload and ensuring that Bear North Digital’s growing client base received the attention they needed.
While he was initially concerned about the financial commitment, Josh found inspiration in Dan Sullivan’s best-selling book, Who Not How, which emphasized the power of delegating responsibilities to skilled team members.
I was apprehensive, for sure. But I realized that by focusing on building a team, I could elevate the agency and let others excel in areas where they could ultimately surpass me.
Josh Kimmes, CEO, Bear North Digital
To address technical needs, Josh also hired a part-time web developer who transitioned to a full-time role. These hires helped him delegate tasks and allowed the agency to handle more complex projects without bottlenecks while refining internal systems for scalability.
As Bear North Digital’s team expanded, so did Josh’s perspective on leadership. With four children at home, ages six and under, Josh knew he couldn’t juggle everything alone.
Once I had kids, I realized, “OK, I can’t just be the ‘hustler.’” I looked at myself in the mirror and said, “You just can’t do all this stuff.”
Josh Kimmes, CEO, Bear North Digital
This realization became the catalyst for building a team he could trust, empowering them to handle day-to-day execution while he focused on steering the agency’s long-term strategy and acquiring new clients.
However, Josh soon learned that not all client projects were created equal. While some offered growth opportunities, others—like that $25,000 project—stretched the budding agency’s resources to the breaking point.
Josh realized one-off projects were eating away at profitability and stability. Bear North Digital needed to prioritize long-term relationships and predictable revenue over big, unpredictable wins to build a sustainable agency.
Scale Your Agency Faster With Automated Client Reporting
For Bear North Digital, the shift to a retainer model was more than a strategic move—it was a means of survival.
One-off projects are a feast-famine world. We now try to avoid them as much as possible.
Josh Kimmes, CEO, Bear North Digital
The constant chase for the next big win was unsustainable. Josh realized Bear North Digital needed a system that offered consistent revenue, scalable operations, and the ability to prioritize what mattered.
Josh and the Bear North Digital team used a four-step approach to transitioning to a retainer model. Let’s examine each step in more detail.
Step 1: Identify Recurring Client Needs
Every agency has those repeat requests that seem to pop up like clockwork.
For Bear North Digital, SEO, Google Ads, and website design and maintenance stood out as the natural building blocks for retainer services. These weren’t one-and-done tasks—they required regular attention, optimization, and updates.
SEO, for the most part, should be done on a retainer model.
Josh Kimmes, CEO, Bear North Digital
Even site audits, a common entry point for clients, were reimagined. Instead of running a standalone audit, Josh rolled it into the first month of a retainer plan, creating a seamless transition to long-term support.
Step 2: Bundle Marketing Services Into Tiers
No one likes confusing pricing models, so Bear North Digital simplified its offerings. Website builds came with a clear setup fee and a monthly care plan for hosting and ongoing maintenance.
The care plan helps us get away from the project side of things and definitely reduces friction in general.
Josh Kimmes, CEO, Bear North Digital
By bundling services into predictable packages, Josh gave clients the peace of mind of knowing exactly what they were getting—and Bear North gained the benefit of stable, recurring income.
Step 3: Communicate Long-Term Benefits to Clients
For Josh, retainers weren’t just about building predictability—they were about building partnerships. He made sure clients understood the value of ongoing collaboration, from consistent support to proactive problem-solving.
The mindset shifted Bear North Digital’s relationships from transactional to strategic. Instead of one-and-done projects, clients saw the agency as a partner invested in their success.
Step 4: Adopt the Right Tools to Scale
As the retainer model took off, efficiency became the name of the game. Josh turned to tools like AgencyAnalytics to handle time-consuming tasks like reporting.
There’s so much that can be done with AgencyAnalytics. It’s such a game-changer for us.
Josh Kimmes, CEO, Bear North Digital
Automated dashboards and streamlined workflows meant more time for big-picture thinking—and fewer late nights buried in admin work. (Well, maybe just a few.)
And speaking of late nights, efficiency was more than a business win—it was a personal lifesaver. As a busy father, Josh’s days are packed with client calls, toddler tantrums, and everything in between.
Josh Kimmes has a packed schedule running Bear North Digital and taking care of his young family.
Josh also sought to implement processes and tools to empower his fully remote team. With tools like ClickUp keeping team and collaboration on track and AgencyAnalytics automating client reporting, Bear North created a culture of trust and adaptability inside and out.
Life comes first. It’s about making it all work—whether it’s with your clients or your kids.
Josh Kimmes, CEO, Bear North Digital
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Building Client Trust Through Transparency
As Bear North Digital embraced the retainer model, one thing became clear: Trust was the key to success. For Josh Kimmes, delivering results wasn’t enough—clients needed to see and understand the value the agency was providing.
A lot of agency owners are wrong about communication and the need for it when working with clients. It’s rarely just about what you do; it’s also about how you communicate it. The best account managers I’ve seen are the ones where clients don’t have to reach out for updates. It’s about having a routine cadence of communication.
Josh Kimmes, CEO, Bear North Digital
Emphasizing proactive communication and transparency helped Bear North deepen client relationships. Tools like ClickUp and AgencyAnalytics became essential for keeping clients informed, with detailed dashboards and scheduled reports offering a clear window into ongoing work.
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Optimizing Processes for Scalability
Scaling an agency is no small feat, and for Bear North, it required more than just adding clients. Streamlined processes became a cornerstone of their success, enabling the team to deliver consistent quality across all projects.
Josh credits early investments in documenting workflows as a critical factor in Bear North’s ability to scale.
Documentation was really important to me. I’ve always been into using tools to make things scalable and document processes so everything doesn’t fall on my shoulders.
Josh Kimmes, CEO, Bear North Digital
From task checklists to video tutorials, Bear North ensures team members have the resources to succeed. For new hires, onboarding includes a month-long training period, emphasizing skill-building through online courses and internal documentation.
Josh actively encourages his team members to look for new learning opportunities and trends Bear North Digital should stay on top of.
I always say, ‘Keep your eyes open’. I’m rarely going to say ‘no’ to investing in training because that’s what got me here.
Josh Kimmes, CEO, Bear North Digital
Leveraging Technology for Agency Efficiency
Bear North’s tech stack was critical in optimizing internal operations and client-facing deliverables. The agency relied heavily on ClickUp for project management, using its chat and task-tracking features to centralize communication and reduce tool fatigue.
“It keeps everything in one space, so the team isn’t juggling too many apps,” Josh notes.
For reporting, AgencyAnalytics became a cornerstone tool, especially for retainer clients. The integrations and customization capabilities streamlined the reporting process, reducing manual effort and providing tailored dashboards for each client.
The process of building a report is so much easier with AgencyAnalytics. It’s frictionless and allows us to customize and tailor reports for clients, which is a game-changer.
With Bear North Digital thriving under its retainer-based model, Josh Kimmes is focused on refining the agency’s approach and doubling down on what works. A key part of that future lies in exploring niche specialization—a strategy he’s resisted in the past but now sees as essential for scalability.
Being in a niche is really pushed for agencies in general, and I’ve had a lot of resistance to it. I’ve always been interested in being able to do multiple different things, but ultimately, a lot of that’s not scalable.
So, looking at the niches where we perform well and essentially doing more outreach to those specific verticals is something that we’re going to be taking on going into 2025.
Josh Kimmes, CEO, Bear North Digital
At the heart of this strategy is a commitment to finding the right clients. Josh emphasizes that growth isn’t just about numbers—it’s about maintaining quality and alignment with the agency’s strengths.
“There’s not necessarily a target acquisition number,” he says. “It’s more about feeling really comfortable and happy with the delivery that we’re providing and just continuing to find the right clients that are the right fit.”
Bear North Digital’s journey is a powerful reminder for agency leaders: Success isn’t about chasing every opportunity but building a sustainable business and prioritizing long-term value over short-term wins.
From documenting processes to adopting scalable tools, Josh’s experiences highlight the importance of preparation and intentional growth. His advice for agencies considering big-ticket projects is clear:
Know how long things are going to take you and have a really good idea of the scope. You’ve got to establish boundaries. Say yes too many times, and there are no boundaries. It’s a slippery slope.
Josh Kimmes, CEO, Bear North Digital
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It’s Your Turn To Build Sustainable Growth for Your Agency
Retainer models, proactive communication, and streamlined workflows have helped Bear North Digital escape the feast-famine cycle, creating a blueprint for agencies looking to do the same.
For agency owners ready to transform their business model, the lessons from Bear North Digital are both inspiring and practical:
Start by identifying recurring client needs that lend themselves to retainers.
Invest in the right tools and documentation to streamline operations.
Above all, focus on building relationships that last.
The retainer model isn’t just about stability—it’s about creating partnerships with clients who trust you to deliver results month after month.
Josh Kimmes, CEO, Bear North Digital
The retainer model is a proven path to stability and growth. Use Bear North Digital’s journey as your guide and take the first step toward building sustainable, long-term client relationships today.
Written by
Francois Marchand
Francois Marchand brings more than 20 years of experience in marketing, journalism, content production, and artificial intelligence (AI). His goal is to equip agency leaders with innovative strategies and actionable advice to succeed in digital marketing, SaaS, and ecommerce.
