Bottleneck #2 – The 3 Hidden Bottlenecks That Doom Sales Hires

Bottleneck #2: I Tried to Hire Sales Reps… and It Blew Up on Me

We have personally seen the damage done by hiring a sales rep who doesn’t work out. It creates literal scar tissue for founders.

We’ve had founders come to us after hiring several salespeople in a row, each one a six-figure investment. Each one a gamble. Each one a disappointment.

One founder we worked with had already hired and let go four different full-time sales reps before he came to us. Each one came with a six-figure salary, relocation package, and health benefits. He ran them through a rigorous hiring process. He got buy-in from the team. He invested time, energy, and hope. Then watched them settle into new homes and new lives, all under the belief that this one would be different.

But by month four of each new hire, the pattern had already started to show. The numbers weren’t there. The conversations felt forced. Deals were stalling or disappearing altogether. 

Deep down, he knew it wasn’t working, but walking away felt impossible. After all, these weren’t just employees. They were people he had moved across the country. People with mortgages, kids in school, and spouses job-hunting in a new city.

So he did what most well-meaning founders do and he kept trying to make it work. Gave more feedback. Extended more grace. Sat through more pipeline reviews. And all the while, sales kept slipping. He told us he had thought he nailed the hiring process, and had other people vet his choice as well, then he asked us, “Where do I keep messing up?” 

By the time he came to Altezza, the walls were up. Thick ones. He was burned out on sales hiring, skeptical of any solution, and doing his best not to give up entirely.

Most Sales Hiring Fails Because the Fit Was Off From the Start

It’s not just about hiring someone with a solid résumé or a few years of industry experience. That’s table stakes. Anyone can look good on paper. But real sales success comes down to fit.

Can this person succeed in your environment?

Every company has its own rhythm. Some are fast-paced and iterative. Others are thoughtful and deliberate. Some thrive in ambiguity; others operate best with clearly defined lanes. A salesperson might have crushed it at a large, structured enterprise with a 90-day onboarding plan and marketing doing half the legwork but that doesn’t mean they’ll succeed at your growing company where they’re expected to jump in, create their own playbook, and make things happen.

We’ve seen fantastic sellers fail simply because the operating environment didn’t match their strengths. They weren’t set up to win.

Founders tend to evaluate candidates based on what they’ve done, not how they work. But cultural misalignment creates friction fast. If your team is collaborative and feedback-driven, and your hire is hyper-competitive and siloed, it’s going to cause tension. If your company moves fast and figures things out as you go, and your new rep is waiting for a perfect process to be handed to them, you’re going to get stalled quickly.

We believe sales isn’t just about results, it’s about how those results are created. If that “how” doesn’t align with your company’s culture, you’ll always be pushing uphill. You also need to consider if they are adaptable enough to sell your product to the market the way you would without hand holding. 

This is where things fall apart for a lot of early-stage companies. Founders often hire someone who’s sold a similar thing in a different context and assume they’ll figure it out. 

But selling a SaaS solution to enterprise healthcare providers is very different from selling a consulting offer to mid-sized tech companies, even if the product category is similar. That level of adaptability and strategic thinking that comes with at least a decade of sales experience, and requires the seller to understand your market as much as they understand your product. 

This is the deeper level of alignment most companies skip. And it’s exactly why even “great” salespeople (you know, the ones with strong track records and polished pitches) can crash and burn when dropped into the wrong role.

At Altezza, when we hire a seller, we ask can they succeed here, with this team, selling this product to this market, at this moment in the company’s growth? That’s the difference between gambling on talent and setting someone up to win.

Our Hiring Philosophy: Skills, Experience, and Culture—Not Necessarily In That Order

At Altezza, we use a tool called Predictive Index to assess whether someone is wired to thrive in the specific kind of company they’re being placed into. We look at behavioral patterns. We evaluate personality alignment. And we never move forward with anyone who scores below an 8 out of 10 on our internal PI scale—unless there’s a very compelling, experience-based reason to make the exception.

This is how we find proven reps who fit the pace, tone, and mission of our clients culture.

That kind of alignment can’t be forced after the fact. You either hire for it intentionally, or you miss it entirely.

What You Lose When You Wait Too Long to Pivot

We’ve worked with founders who knew—deep down—that a sales hire wasn’t working out. But they felt stuck. They had made a commitment. The team was watching. And maybe, just maybe, with a few more months, things would turn around.

We understand that hesitation. It's human. But while you're giving it more time, you're also giving up momentum. New opportunities stall. Marketing gets paused because sales can’t absorb the volume. The team loses clarity and you lose weeks, and sometimes quarters, waiting for something to click.

This is why we approach sales hiring differently. We don’t make big promises about the “perfect fit.” We don’t chase unicorns. And we don’t ask you to take another emotional leap.

Instead, we bring in experienced professionals, apply real-world strategy, and build for alignment from day one so you’re not gambling on potential.