Part 2 of the Breaking the Founder-Led Growth Ceiling Series
When a business stalls, the first reaction is often to hire someone to fix it—a salesperson to close more deals or a marketing agency to generate more leads. But most businesses that take this route end up disappointed.
Hiring alone doesn’t fix a broken growth model.
To understand why, I sat down with Miles, founder and CEO of OTM, who has seen firsthand why many sales and marketing hires fail—and what businesses should do instead.
The Growth Trap: Why Hiring Won’t Solve the Problem
“It’s pretty logical,” Miles said. “Businesses want to grow, so they go out and hire a salesperson, a BD person, or a marketing team. But they don’t realize they’re outsourcing the actual issue—without solving it first.”
The problem? There’s no strategy, process, or metrics in place to set those hires up for success.
“What happens is, these new hires don’t have clear directives, oversight, or measurable goals. So they just end up working on busy work,” Miles explained. “Salespeople network inefficiently. Marketing teams run random campaigns. And when the business doesn’t hit its targets, leadership blames those hires—when in reality, they were never set up for success.”
Listen to how strategy and tactics are different hires for you below.
Common Hiring Mistakes That Keep Businesses Stuck
- Hiring before defining the real problem.
“Is it a demand generation issue? A lead conversion issue? A sales process issue? You have to define the problem first before hiring someone to solve it.” - Expecting a new hire to ‘fix’ growth.
“Most companies expect sales and marketing hires to walk in and solve everything. But if the company itself hasn’t figured out a repeatable growth model, those hires are set up to fail.” - Lumping all marketing functions together.
“Marketing has 50 different specialties. If you don’t know whether you need SEO, paid ads, brand awareness, or sales enablement—you’re going to hire the wrong person.” - Skipping the foundational strategy.
“People don’t buy creative, they buy results. You have to map out your ideal customer profile, define your sales process, and establish clear marketing objectives before hiring.”
Think you’re ready to hire a marketing agency? Check out our guide on when to hire a marketing agency to avoid common misconceptions.
The Real Reason Sales & Marketing Often Fail
Hiring alone doesn’t work because most businesses don’t have a structured sales and marketing process.
“We see this all the time,” Miles explained. “Businesses think sales and marketing are two separate functions, but they have to work together. If they’re misaligned, growth stalls.”
Our CEO, Miles Kailburn, taps into why it’s not marketing vs. sales, and how they work together in the video below.
How Sales & Marketing Misalignment Kills Growth
- Marketing generates leads, but sales isn’t equipped to convert them.
“You see this a lot—marketing says, ‘We’re driving leads!’ But sales says, ‘These leads aren’t closing.’ That’s a process problem, not a people problem.” - Sales doesn’t give marketing feedback.
“Marketing should refine its messaging based on what actually converts in sales. If they’re operating in silos, you’re missing a huge opportunity for alignment.” - Marketing efforts aren’t measured correctly.
“Businesses don’t track the right metrics—so they’re making decisions based on gut feeling instead of data.” - Hiring a CRO too soon.
“What absolutely should not be done is simply hiring a Chief Revenue Officer too soon. They walk into a mess of spreadsheets and Post-it notes and are expected to scale it. That has such a low success rate.”
What to Do Before You Hire Sales & Marketing
Step 1: Start Small—Delegate Admin Work First
“Typically, the first step isn’t hiring a sales leader. It’s hiring support,” Miles said. “Start with an assistant or admin who can handle lead intake, appointment setting, and CRM updates. That forces the founder to document their sales process before handing it off.”
Step 2: Systematize Sales Before You Scale It
“The biggest mistake founders make is expecting someone else to figure out their sales process for them,” Miles explained. “Instead, start by breaking it down into repeatable steps.”
Example Process:
- Step 1: Admin handles inbound inquiries and qualification
- Step 2: SDR (Sales Development Rep) runs initial calls and gathers info
- Step 3: Founder steps in only for later-stage sales conversations
- Step 4: Sales process gets optimized before hiring a full-time leader
Step 3: Align Sales & Marketing
Before investing in marketing, businesses need to:
- Define their ICP (Ideal Customer Profile)
- Establish key metrics for success
- Ensure marketing and sales are working toward the same goals
Learn more about setting strategy that connects goals and growth.
The Right Way to Scale Sales & Marketing
Scaling requires hiring at the right time, in the right order—not just hiring out of frustration.
Recommended Sequence:
- Delegate admin & lead qualification first (assistant or SDR)
- Develop a structured, repeatable sales process (document everything!)
- Invest in demand generation marketing (but only once sales can convert leads)
- Hire a full-time sales leader only once the system is working
“If you don’t build the foundation first, hiring more people won’t fix the problem.”
What Comes Next: Scaling Beyond Founder-Led Sales
Now that we know why hiring alone won’t fix a broken growth model, the next step is understanding how to actually transition from founder-led sales to a scalable revenue engine.
In Part 3 of this series, we’ll cover:
- The first hires you should make to step out of day-to-day sales
- How to build a repeatable, scalable sales engine
- How to know when you’re ready to hire a CRO or sales leader
→ Read Part 3: From Founder-Led Sales to Scalable Growth: A Step-by-Step Transition
Ready to Take the Next Step?
Miles Kailburn is the CEO and Co-Founder of OTM, a marketing and sales enablement firm helping founder-led B2B service businesses move from stagnant to scalable. With more than 15 years of experience guiding growth-stage companies through strategic inflection points, Miles leads with a blend of technical acumen and entrepreneurial empathy. His passion lies in helping businesses break out of founder-mode by building systems, aligning teams, and clarifying strategy to drive sustainable revenue growth.
Schedule a 30-Minute Consultation with Miles to get a complimentary strategy call and learn more about the next best steps to take for your business.