By Josh Chernikoff
One of the most common questions I hear from education founders is: When should I hire a sales team?
It’s a great question—but also the wrong one. The real question should be: Am I actually ready to hire a sales team?
Bringing in sales reps too early can be a costly mistake. I’ve seen it happen firsthand—hiring before a repeatable system is in place leads to frustration, wasted money, and missed revenue opportunities. If you want your sales hires to succeed, there are a few critical steps you need to take first. Let’s break them down.
The Costly Mistake of Hiring Too Soon
I made this mistake myself back when I was running Flex Academies. I thought, If I just bring in a salesperson, sales will take off. But I hadn’t built a system yet. There was no structured lead generation, no clear messaging, and no process for follow-up.
What happened? That salesperson struggled, and ultimately, the hire didn’t work out. Not because they weren’t good, but because I wasn’t ready.
The truth is, salespeople don’t create systems—they amplify what’s already working. If you don’t have a process for generating leads and closing deals, they won’t magically create one for you. You’ll end up churning through sales reps who “just weren’t the right fit,” when in reality, the problem was that there wasn’t a foundation in place.
The Founder’s Role in Early Sales
Before you even think about hiring, you need to be the one selling. That’s not just my opinion—it’s what I’ve seen work time and time again.
Take Catherine from Go Pursue. She knew she needed a system before bringing on sales help. So she built out a LinkedIn strategy, refined her messaging, and increased engagement by 450%. Only then did she hire a salesperson, who was able to step into a well-oiled machine and start closing deals immediately.
Here’s the key: As a founder, you need to be in the trenches. That means:
Talking to potential customers daily
Testing messaging to see what resonates
Tracking what works (and what doesn’t)
Building relationships and gathering insights directly from the market
I tell founders to commit to at least 12 weeks of founder-led sales—ideally six months—before hiring. You don’t need to become a lifelong salesperson, but you do need to prove that your product sells. Otherwise, how can you expect a new hire to do it for you?
Are You Ready to Hire? Ask Yourself These Questions
Before hiring, run through this quick checklist:
Are you closing deals consistently? If you’re still struggling to land sales, bringing on a salesperson won’t fix that. First, nail down a repeatable process.
Do you have a predictable lead generation system? Where are your leads coming from? Cold email? LinkedIn? Webinars? If you don’t have a steady pipeline, a salesperson will be spinning their wheels.
Do you have a clear sales process? What happens when a lead comes in? What’s your follow-up process? What objections come up most often? A salesperson needs structure to succeed.
Is your brand strong enough to attract top sales talent? The best salespeople don’t want to build from scratch. They want to step into a system that works and grow it further.
If you can’t confidently answer “yes” to these questions, you’re not ready yet—and that’s okay. It just means there’s work to do first.
How to Set Up Your Sales Team for Success
Once you’ve validated your sales process and have a steady pipeline, it’s time to hire. But even then, it’s important to do it the right way.
Here’s how:
Start with one salesperson
Hiring one person first allows you to refine your process before scaling. You can identify bottlenecks, improve training, and tweak messaging before bringing in a full team.
Have a clear onboarding plan
Give them the tools they need to succeed. That means sales scripts, outreach guidelines, and a CRM system that tracks their progress.
Train them properly
Many founders make the mistake of assuming salespeople will “figure it out.” Instead, focus on training them in:
Product knowledge (so they can confidently answer questions)
Objection handling (so they don’t get stuck in conversations)
Outreach strategy (so they’re not just guessing who to contact)
Set clear expectations
Define what success looks like. How many outbound messages per day? What’s the expected conversion rate? Having clear benchmarks keeps everyone aligned.
The LinkedIn Strategy: Founders vs. Sales Teams
One of the biggest mistakes I see founders make is assuming that their sales team will take over their LinkedIn presence. Bad idea.
Founders on LinkedIn: Thought leadership, brand-building, industry insights, personal stories.
As a founder, your LinkedIn presence should position you as a thought leader. That means sharing your journey, insights on the industry, and valuable lessons learned. Your posts should focus on big-picture ideas, market trends, and personal experiences that humanize your brand and make people want to engage with you.
Sales team on LinkedIn: Direct outreach, relationship-building, personalized messaging.
Your sales team, on the other hand, should be using LinkedIn for direct outreach and relationship-building. Their role isn’t to post broad thought leadership but to start one-on-one conversations with potential customers. That means engaging in comments, sending connection requests, and crafting personalized messages that move prospects toward sales conversations.
Your LinkedIn is your brand. Your sales team should be using their own profiles, not trying to duplicate yours. This avoids confusion and builds credibility with prospects.
Key Takeaways for Hiring a Sales Team in the Education Space
Hiring a sales team at the right time can accelerate your growth, but doing it too soon can be costly. Before bringing on sales reps, founders need to establish a solid foundation. Here’s how to ensure your sales team is set up for success:
Build a Sales System Before Hiring Sales reps don’t create systems—they amplify what’s already working. Before hiring, make sure you have a repeatable process for generating leads, converting prospects, and closing deals.
Lead Sales as the Founder First In the early stages, you should be the one selling. Talking directly to potential customers helps refine your messaging, understand objections, and prove that your product can sell. This firsthand experience will guide your future sales hires.
Ensure a Steady Flow of Leads Bringing on a salesperson without a predictable pipeline will lead to frustration and wasted resources. Before hiring, confirm that you have a reliable system for generating and nurturing leads.
Define a Clear Sales Process Your sales team needs structure. Map out the steps from initial contact to closing a deal, document common objections, and establish a follow-up strategy so your team knows exactly what to do.
Hire Strategically—Start Small Begin with one salesperson instead of building a full team right away. This allows you to refine your process, provide targeted training, and make adjustments before scaling further.
Invest in Training and Onboarding Don’t assume a new sales hire will “figure it out.” Provide clear training on your product, messaging, objection handling, and outreach strategy to set them up for success.
Use LinkedIn Effectively: Founders vs. Sales Teams Your LinkedIn strategy should be divided:
Founders: Focus on thought leadership, brand-building, industry insights, and sharing personal experiences.
Sales Teams: Prioritize direct outreach, relationship-building, and personalized messaging to convert leads into sales.
Final Thoughts: Build First, Then Hire
If there’s one takeaway from this post, it’s this: a sales team won’t fix a broken process—they’ll amplify what’s already working. Before you hire, you need to prove that your product sells, establish a repeatable system for generating and converting leads, and refine your messaging so your team knows exactly how to position your solution. Sales reps thrive when they have a clear process to follow, not when they’re left to figure it out themselves.
When you’ve built a strong foundation, hiring won’t feel like a risk—it’ll be the logical next step. And when you bring in the right people at the right time, they won’t just contribute to growth—they’ll accelerate it, turning a steady trickle of deals into a scalable, predictable revenue engine.
If you want a steady flow of leads—without paying for expensive ads or wasting time on content no one sees—join the waitlist for the EdSales Elevation Experience. It’s the only group coaching program designed to take education companies from no leads to a reliable pipeline in just 90 days.
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