10 years of running an agency: Chris Montgomery’s top lessons

When you meet Chris Montgomery in person, you can’t help but feel there’s a certain aura about the man.

The Founder of Social Ordeals oozes with success and accomplishment with his flashy checkered jacket and relaxed demeanor. But you can tell that, behind his smile, the journey to become one of California’s leading digital agency owners wasn’t without its fair share of trials and tribulations.

Montgomery has grown Los Angeles-based Social Ordeals from a one-man agency back in 2012 to an operation that now employs over 30 staff and generates approximately $8 million in annual revenue by servicing thousands of small and medium businesses (SMB) across the United States, United Kingdom, and Canada.

So, what’s the secret to his success? 

Simply put, guts and lots of hard work.

“In this business, you get knocked down a lot and you have to learn to get back up and keep going. And you need to learn how to make hard decisions along the way: whether it’s with employees, clients, processes, or partners,” he says.

This year, Montgomery celebrated his 10th year of running an agency, and we’re fortunate he’s agreed to share some of his top lessons for aspiring agency entrepreneurs as well his thoughts on the biggest marketing trends of 2023.

Even when you’re a leader running an agency, you need to be on the phone

When asked about the biggest ongoing challenge he faces as an agency owner, Montgomery immediately points to training his employees and sales reps.

He’s learned that agency owners cannot afford to hire staff and simply become hands off.

“There’s so many different facets of digital marketing, and you’ve got to be able to explain them in a way that your customer can understand,” he says.

“In many of our sales pitches, I either get on the phone myself or I’m there with my reps talking to clients. When we have new employees, they are required to attend many of those before they’re unleashed to deal with clients themselves.”

He strongly recommends that other agencies:

• Develop rigorous sales training and coaching programs including in-person and individual training sessions
• Ensure their reps become intimately familiar with digital marketing concepts including why and how listings, reputation management, and social media play a key role in strengthening an SMB’s online presence
• Ensure their reps are able to genuinely understand a client or prospect’s goals and objectives, and how the products they’re selling will help them achieve those outcomes.

You can’t scale without impeccable service

Every agency owner’s dream is to build a profitable agency—a repeatable, predictable, and scalable business. But that will forever remain a dream if exceptional service isn’t at the heart of your organization’s mantra.

“The one piece of advice I’d give every single owner running an agency: take care of your customer,” he says.

“Once you get your first few clients, you have to service them well. You have to make sure that you’re doing everything that you promised them that you would do, and you’re keeping your word on that.

“When I started running an agency, I had a lot of customers that came on board and I had to work hard to keep them happy. And because I did the work, delivered results, and did the right thing by my customer, I grew my business off referrals.

“And when you earn their trust and business, you need to give them incentives to bring their friends and families with businesses to the table,” explains Montgomery.

 

Get your boots on the ground

Whether you’re a new or experienced agency owner, it’s crucial that you don’t rely solely on calls and emails to win business.

“You’ve got to go and get boots on the ground,” Montgomery says.

Even though Social Ordeals has its own sales team, Montgomery actively gets out and about and capitalizes on opportunities to sell in person when he sees the right opportunity.

For example, he recently dined at a Mediterranean restaurant that served great food but didn’t have a strong online presence. Montgomery felt he could help the restaurant owner get more foot traffic by helping his business rank higher on search.

“I got to know the owner of the business who was making the food and running the place. He asked me ‘how did you find us?’ I said ‘I barely found you, but you had the best reviews’,” Montgomery recalls.

“We got into a conversation three weeks later, he became a customer of mine and I’m still a customer of his. So if you’re just starting out in the agency world, get out there and talk to businesses, understand what their challenges are, and then offer them solutions.”

The secrets to effective prospecting, onboarding, and managing the early phase of a new relationship

Some things in life are a waiting game. Responding to inbound inquiries most definitely isn’t one of them.

Montgomery says time and again, he sees agencies and other service-oriented companies make the mistake of not getting back to prospects and customers quickly.

“People are impatient today. If a prospect calls you and you don’t get back to them for 48 hours or 72 hours, you’re putting a bad taste in their mouth. Most of the time during normal business hours, we call our clients and prospects back within 15 minutes,” he says.

When it comes to onboarding, don’t make the mistake of leaving this crucial step to one person.

“We have an entire onboarding process where clients fill out a form and we get really detailed. We let them fill it out as much as they possibly want to or just fill out the basic things we have. But then we do a video conference call,” he explains.

“We have a few account managers that are onboarding them and a few understudies. So if anybody ever leaves our company, we have somebody that still understands them as well. 

“We have that conversation, build the account out after that onboard process, and then set up another meeting to take them in and actually train them on how to utilize the software we sell them,” Montgomery explains.

But it can’t stop there. It’s a business relationship after all; Montgomery says a common mistake he sees is that agencies fail to continuously prove their value and stop educating their clients on how to use resold software. 

That can lead to a strong chance of churn.

“When we deliver strong results for the client, maybe a new five-star review or we see them ranking high for a particular keyword, we reach out to those customers to inform them of that and let them know about those types of wins,” Montgomery says.

“We then do all our follow ups with clients to make sure that they understand all the products we’ve provided them and actually how it’s helping their business.

“So you’ve got to engage with a customer and have a schedule of when you’re going to call out to your customer, and now we’ve got the experience over the last 10 years of knowing when to reach out at certain points to fill them in on their status and where they’re currently at,” shares Montgomery.

Hiring staff? Don’t fall into this trap

The year 2022 was a tough one for agency recruitment given labor shortages resulting from an extraordinary set of factors. This included the pandemic forcing greater adoption, reduced migration, and the ability to work anywhere for many types of skilled professionals.

But Montgomery suggests agencies need to look at talent like they would the stock market: You don’t want to pay 3–4 times what something (or someone) is actually worth out of sheer desperation.

His solution? Look inside for talent that can be nurtured.

“We don’t want to outbid ourselves in the market and get scared like a lot of businesses we’re seeing out there,” he says.

“I’m promoting from within, which allows me to slowly grow them into a management salary, as opposed to hiring somebody starting out with a management salary.

“We also care about keeping our current employees. We’ve added benefits to our company including increased vacation pay, medical and dental, and pay raises for excellent performance,” says Montgomery.

He believes the labor market situation will eventually correct itself and salary expectations will rebase themselves to more realistic levels over the coming year.

Sometimes, it pays to fire clients

It’s an age-old problem among agencies: undercharging and overservicing. And often, you do it just to keep the client and maintain your cash flow.

But Montgomery says it’s critical agencies take a commercial approach to their business dealings.

“It’s weird to say, but you have to analyze your book of business and make sure that you actually have a profit margin with your clients because with some clients, you don’t,” he explains.

As an example, he had to let go of a client who was demanding a level of service that wasn’t yielding a sufficient margin for Social Ordeals while consuming too many hours for his team.

Two digital marketing trends to watch for 2023

Digital marketing and technology trends are changing at a lightning-fast pace, and agencies must be able to keep up and get the help of partners who can allow them to stay on course.

This year alone, TikTok became the most-downloaded app in the world (an inconceivable thought given the app was invented after Facebook and Instagram).

Montgomery believes agencies who crack the code on Tik Tok to market to SMBs are well-placed to differentiate themselves from the pack.

“You have to pay attention to Tik Tok; I think Tik Tok is becoming not only that video channel, but it’s also becoming a pretty powerful search engine,” Montgomery says.

Another area agencies need to keep their pulse on is voice search as people increasingly demand accurate results when they ask applications such as Google Voice Search questions about SMBs in hands-free settings.

“You have to make sure that all of your descriptions and all of your keywords and everything you’re submitting to your listing providers on your website really defines what you do. Make sure it’s not just bullet points but a deeper description because once we go to voice, we know it’s going to get very descriptive,” he says.

Want to become like Chris Montgomery?

Chris Montgomery is one of Vendasta’s most successful partners. He’s been running an agency for 10 years and has made more than $4.7 million in revenue by reselling products and services using our platform while deepening relationships and increasing retention among his clients. For more details, check out the Social Ordeals case study.

Running an agency FAQs

1. What does it really take to run an agency for 10+ years?

Running an agency long term takes three things more than anything else:

• A high tolerance for getting knocked down and getting back up

• The ability to make hard decisions about people, clients, and partners

• Relentless follow-through on what you promise clients

Chris Montgomery didn’t grow Social Ordeals to $8M+ in revenue by “finding a hack.” He stuck around longer than most, kept learning, and kept fixing what was broken.

2. As an agency owner, should I still be on sales calls?

Yes. Even when you have a full sales team, you shouldn’t disappear from the front lines.

Montgomery still:

• Jumps on sales calls with reps

• Helps explain complex concepts (listings, reviews, social, SEO) in simple language

• Uses those calls as training ground for new hires

If your team can’t confidently explain the value of what you sell, that’s on your training, not their talent.

3. How important is sales training for agency reps?

Critical. You can’t just hire “a sales guy” and hope they figure it out. You need:

• Structured onboarding for reps

• Live call shadowing (not just slide decks)

• Clear scripts and objection handling

• Deep product education tied to real SMB outcomes

The goal is simple: reps must understand the client’s goals and be able to connect your solutions directly to those goals.

4. Can I scale an agency without world-class service?

Short answer: no.

You don’t get referrals, retention, or upsells if you:

• Overpromise and underdeliver

• Go quiet when campaigns struggle

• Only show up when it’s renewal time

Montgomery built his growth on:

• Doing exactly what he said he’d do

• Showing clients the results they’re getting

• Incentivizing happy clients to refer friends and family

Service is not a “nice-to-have.” It is your growth engine.

5. What does “boots on the ground” prospecting look like?

It’s literally getting out of your chair and into local businesses.

Example from Chris:

• Eats at a small restaurant

• Notices amazing food and weak online presence

• Chats with the owner about how he found them

• Three weeks later, that owner is a client

The playbook:

1. Visit local businesses you’d genuinely use

2. Ask how they get customers today

3. Share how you found them (or almost didn’t)

4. Offer a simple, practical way to get them more traffic or calls

Face-to-face conversations build trust faster than any cold email.

6. How fast should I respond to inbound leads?

Think minutes, not days.

Montgomery’s team aims to respond within 15 minutes during business hours. Waiting 48–72 hours:

• Makes you look disorganized

• Opens the door for competitors to win the deal

• Starts the relationship with a bad taste

Speed = trust signal.

7. What does a strong onboarding process look like?

Good onboarding is not one form and a “welcome” email. A solid process usually includes:

• A detailed intake form (with room for extra info)

• A live kickoff call (video if possible)

• Multiple people involved: primary account manager + understudy

• Clear expectations: timelines, deliverables, meeting cadence

• A follow-up training session to walk clients through any software you provide

Onboarding is where you either build confidence or plant the seeds of churn.

8. Why do agencies lose clients even when results are good?

Often because they stop showing the value. Common misses:

• No one calls the client when a big win happens (ranking jump, 5-star review, etc.)

• Reports get sent with no explanation

• Clients aren’t reminded how each product helps their business

Montgomery’s team regularly:

• Alerts clients when something positive happens

• Schedules follow-ups to review progress

• Re-educates clients on tools they already pay for

Results matter, but communication is what makes them visible.

9. When is it okay to fire a client?

When the relationship:

• Consistently drains your team’s time

• Delivers little to no profit

• Creates stress that outweighs the revenue

Chris dropped clients who demanded outsized service on small retainers. It freed capacity for better-fit accounts and healthier margins.

You don’t need to be reckless, but you do need to protect your team and your profit.

10. How should I think about hiring and salaries right now?

Treat hiring like investing: don’t buy at the emotional peak.

Montgomery’s approach:

• Avoid overpaying out of panic

• Promote from within whenever possible

• Grow people into management roles instead of buying them at full “management price” on day one

• Take care of current staff with benefits, raises for performance, and clear paths to grow

You want a team that sticks, not a revolving door of overpaid, under-aligned hires.

11. Which marketing trends should agencies watch (from Chris’s POV)?

Two big ones he calls out:

1. TikTok

   • Not just a “kids’ app” anymore

   • Acts more and more like a search engine

   • Huge opportunity for agencies that can turn short-form video into local demand for SMBs

2. Voice search

   • People expect natural, detailed answers when they ask devices questions

   • Your listings, website copy, and descriptions need to be descriptive, not just bullet points

   • Clear, conversational content will win more “near me” and long-tail voice queries

If you help SMBs, you should be testing both—on your own brand and for clients.

12. How did Chris Montgomery grow with Vendasta?

He used Vendasta as:

• A white-label product stack he could resell under his brand

• A way to fulfill services at scale

• A platform to deepen relationships and increase retention

That combination helped Social Ordeals generate millions in revenue while serving thousands of SMBs across multiple countries.

13. What’s the biggest mindset shift new agency owners need?

Stop thinking like a freelancer and start thinking like an operator:

• Build processes, not one-off miracles

• Train your people instead of “hoping” they figure it out

• Protect your margins, not just your top line

• Stay close to clients, especially early

That’s the thread running through all of Chris Montgomery’s lessons: stay in the game, stay close to the work, and treat your agency like a real business from day one.