I asked more than a dozen successful agency CEOs to share how they’ve navigated critical moments—getting started, landing (and keeping) clients, scaling teams, and marketing their agency.
Spoiler alert: It all comes down to people.
- Professional networks are the starting point (and growth engine).
- The familiar name of an agency CEO is a proxy for trust.
- Scaling a people-intensive business requires hiring and retaining exceptional talent.
- Client retention hinges on relationships—and the people who maintain them.
Here’s how they’ve done it—and what they’re still working on.
From individual contributor to agency owner
“I’m your stereotypical great independent contributor who was fantastic at the work and then ended up running a business,” recounts Michael King, founder of iPullRank. He isn’t the only CEO whose individual consultancy grew into an agency.
For many, that transition was possible not just because of quality work but because of a network built over a career. Bill Sebald of Greenlane Marketing explains:
WiderFunnel’s Chris Goward had a similar experience:
Those nascent networks—nurtured through speaking events, writing, and social media engagement—can grow into a personal brand capable of bringing in not just a client but that first whale of an account.
“I got my first big client simply by announcing I was starting an agency,” recalls Siege Media’s Ross Hudgens. “I was only able to pull this off by putting in work to build a personal brand, though—that made the risk lower for them.”
The formula has worked for others.
Landing that first big client
In 2011, “I was speaking at Mozcon in Seattle,” remembers Conversion.com’s Stephen Pavlovich.
I noticed that Facebook’s director of growth was speaking at the same event. So I quickly changed my deck the night before to use some examples from Facebook. Long story short…
If that experience seems serendipitous, only a slightly more structured approach worked for others, like Distilled’s Will Critchlow:
It doesn’t take a prominent speaking gig or compelling research study to land big accounts. The common thread? A genuine interest in helping marketers.
Samantha Noble of Biddable Moments used a training course:
André Morys of konversionsKRAFT offered companies a free experiment:
Sebald developed tools:
Others, like Goward, won the attention of big brands not from industry inspiration but, rather, ignorance:
John Ekman of Conversionista took a similarly contrarian approach:
A similar investment paid off for Animalz and its founder, Walter Chen:
There are traditional approaches, too, like the one King employed to win his first big client:
Or the simplest option, from Seer Interactive’s Wil Reynolds: “I knocked on their door.”
Winning big accounts isn’t just to add a logo-trophy on the homepage. There are other benefits, as CXL’s Peep Laja explains:
Big success means a new challenge: scale.
Scaling people, processes, and financial acumen
There’s an old joke: How do porcupines mate? The answer: carefully. The same, it seems, applies to scaling.
“If you try and scale too quickly,” cautions Noble, “all your processes and way of working gets left behind.” Scaling is a people challenge: hiring the right ones, getting them up to speed, building career paths for them, and keeping them around.
It’s a challenge that’s difficult to anticipate, admits Goward:
“One of the hardest parts of building an agency is hiring,” agrees Talia Wolf of GetUplift:
Nor, in most cases, is keeping those people around a financial issue. “It’s rarely about the money for people,” adds Wolf. “It’s mostly about continuous growth and a sense of achievement.”
Defining “growth” can take several forms. Wolf has given every team member a niche to own:
The sense of purpose, Reynolds learned, may require explicit acknowledgement:
A team of expert analysts may also need development paths outside of management, something Brian Forrester of Workshop Digital discovered:
For Forrester, the solution was a process:
- Defining paths forward to identify necessary skills for each role.
- Using the list of skills to create Individual Development Plans for analysts to move from junior to senior roles.
- Adapting those plans to inform hiring and train new employees so they can take on client work as quickly as possible.
A final component, adds Forrester, has helped spot analysts who might excel as managers:
Building management pathways into career advancement for certain team members who are interested—and giving those team members exposure to some of the management concepts early—has been hugely successful.
As Chen details, exceptional managers, in turn, are critical to agency profitability:
Johnathan Dane of KlientBoost built his team’s processes by codifying then refining his workflow:
I’ve made the infrastructure to have a system work before I hand it off.
Then I audit the system over time to make sure it still produces the same or better results.
And yet, notes Sebald, the temptation to scale quickly—often to meet demand—introduces potential problems:
Where’s the balance? King has experienced both sides—overbearing processes that restricted analysts and the flawed assumption that work would get done the right way without them:
Another challenge? You can’t scale people and processes unless you scale financial management, too.
3. Financial acumen
“Before I started working for myself,” says Noble, “I understood bits about the financial and tax side of running a business, but flashing forward two years, I know so much more than I did previously.”
Financial expertise is something agency founders, Sebald included, wished they had picked up earlier in their careers:
Good financial management may even slow company growth, as it did for Reynolds:
Pavlovich echoed Reynold’s caution:
The structure that helped Hudgens was a revenue-per-analyst calculation:
Those calculations can be complex. There are confounders: “The bigger the client, the lower the likelihood that they pay on time,” says King.
The temptation to offer a full array of services can similarly undermine stability, King continues:
Ultimately, scaling requires greater financial stability—something referrals alone won’t bring you.
Marketing an agency that’s lived off referrals
“Doing great work for clients has been our single best strategy,” says Reynolds. “That builds trust and word of mouth.”
The value of referrals isn’t news to agency owners—nor are the risks of a live-and-die-by-referrals strategy. As Laja explains:
Referrals are great, but you don’t control the inputs or outputs. If there’s a slow month due to seasonality or whatever, you can do very little. You can’t wait harder for referrals.
Among the other options, what doesn’t work? Paid ads, apparently.
- “We tried some boosting of our content on Facebook. I’m still not convinced that did too much for us.” (Hudgens)
- “Ads for clients (haven’t really tried to be honest). We’ve done lots of paid on Facebook for our lead magnets, courses, etc., but not for ‘landing clients.’” (Wolf)
To be fair, Dane argues that a half-hearted commitment to campaigns often explains their failure:
As you go beyond word-of-mouth, says Hudgens, inbound marketing is a natural fit:
In general, you are competing on knowledge in most areas, so by standing out with that you are, by default, showing you are worth hiring.
Too often, Chen says, agencies get stuck:
The long-term value of inbound marketing was a common refrain:
- “The most effective thing for us has been content creation at the edge of thought leadership for our space and public speaking. We haven’t seen much measurable impact from anything else.” (King)
- “We have two in-house, full-time writers and an outsourced team of writers. We also have an in-house, full-time person running our podcast (another form of content) and an in-house, full-time videographer (another form of content).” (Dane)
- “Our business grows mostly from all the content we create, and I’m producing content nonstop.” (Wolf)
The strength of inbound campaigns is a perfect fit for CEOs like Ekman, who love that work far more than the traditional wine-and-dine strategy of client acquisition:
Even if speaking isn’t a natural fit, contends Pavlovich, that doesn’t make it less important:
If you’re the founder, you have to be out speaking and networking. That wasn’t a natural fit for me, and still makes me uncomfortable, but it’s been crucial to our growth.
That’s not to say that a single speech will change your agency. “Speaking at events has rarely delivered clients for me,” says Wolf.
The benefits, Noble explains, are often downstream:
Of course, once you’ve put in the effort to win clients, you want to keep them around.
Keeping clients around (so you can step off the treadmill)
“Agencies are hard to run,” concedes Pavlovich. “Without wanting to state the obvious, to grow you have to win/retain more clients and lose fewer clients than you did before. At times that can create a relentless treadmill.”
The key to keeping clients around? It’s not results, says Wolf:
I used to believe that our work and results would retain business. It does—to a degree—but it’s probably less important than your client relationship.
While “building relationships” is a soft skill, there are tactical steps to support it, says Noble:
Picking up the phone rather than emailing is one thing I try and do. You can build a relationship with your clients much easier over the phone or in person than you can on an email.
As Goward notes, hiring good people—not just talented analysts—can go a long way:
It’s difficult to incentivize team members to build that rapport, Dane learned:
We gave higher commission percentages to our account managers, hoping that rising and falling with the company revenue would make them more aggressive to want to keep clients—still didn’t have the impact we hoped for.
Not every client relationship will work. Indeed, it’s easy to fail at the outset. One of Wolf’s keys to retaining clients is to “only bring in clients that are a good fit for our service.”
Part of “fit” includes a client’s ability to execute on recommendations. To help solve for that, King says, analysts at iPullRank now write “Jira tickets and include them in our SEO site audits. That way, we cut down on the time it takes to get into the dev queue.”
It helps solve a problem that Hudgens has seen derail his agreements: “The thing that has hurt us has been saying yes to work we couldn’t properly fulfill.”
In rare instances, Hudgens adds, they’ve given refunds or extra time and attention—a salve to retain clients while an agency improves client fit or strengthens existing relationships.
There’s a final thread that’s gone unmentioned, though it was implicit in so many responses: humility.
When I asked, “Compared to when you started your agency, which of your skill(s) have improved the most?”, the answers had a constant—there was so much room to improve:
- “Financial acumen went way up, but I still suck at it :)” (Reynolds)
- “Definitely management. I still feel like a beginner, but I also look back on some of the mistakes I made, or things I didn’t know to do in the early days and cringe. I hope to look back on today some day and cringe, too, because I have improved so much from where I am now.” (Critchlow)
- “Leadership. Hands-down. But I’ll still be learning that for the rest of my life.” (Sebald)
- “Self-awareness. I now know more than ever that I still have a lot to learn in all areas.” (Goward)
- “I understand that the things that motivate me aren’t necessarily what motivates my team, and the whole thing is to identify what motivates them and leverage that to help them improve their performance. However, I still feel like there’s a lot for me to continue to learn in that area.” (King)
For successful agency owners, humility sparks motivation, even though there are few quick fixes to look forward to:
If that sounds exhausting, it is. “You don’t ever switch off,” says Noble, “You are constantly working!”
“Running your own business means you’re working 24/7,” confirms Wolf. “You sleep, eat, walk, and talk work—especially when you have employees and you’re paying monthly salaries. The stress is 10X stronger, and every dollar matters.”
But then again, Wolf offers, “I can’t even imagine going back to working for someone.”