How to Find a Good B2B Salesperson Before It Costs You $150K

Originally published 12/15/2024

I talk to two kinds of CEOs. Both are planning for growth. Both know their sales motion needs work. Both are weighing a real investment to fix it. One is willing to work on the structure underneath first, so whatever comes next actually has a shot at working. The other wants to skip that part and place an expensive bet on a person to figure it out for them.

Which one are you?

It changes everything else in this post, including whether self-sourcing this hire makes sense for you, or whether you should already be on the phone with someone like John Mason-Smith (JMS), CEO of HireWith (below). A bad sales hire (or a couple) costs $150K to $500K once you count salary (including taxes and benefits), training and mentoring, ramp time, and the deals that quietly stalled while you found out it wasn't working.

That number doesn't move based on who sources the hire. What changes the outcome is whether the structure got built first.

Let me back up a bit. I'm a sales leader by trade, not a recruiter, but I do help founders

transition out of sales or scale small teams. It's an exciting and scary time for most involved, the business is growing and can't depend on only you anymore, but you've heard plenty of horror stories about failed sales hires.

Whether you find your next salesperson through your own network, hand the search to a recruiter, or run it yourself, three things still land on you and nobody else: figuring out who your ideal candidate actually is, writing the job description that attracts them, and interviewing well enough that you don't get duped.

Note: this skews toward the founder or CEO sourcing their own sales talent. But if you've brought in a recruiter, you're still going to tell them the type of candidate you need and run at least one interview before you make the final decision. Read these as your decision filter instead of the full sourcing-to-hire process.

Before You Post the Role

Most CEOs I talk to close deals at a solid rate, even if they never worked in sales before they had to sell their own service or product. (Spoiler: people actually want to talk to the head honcho.) They can't tell you why or how they closed it. And the honest ones will tell you they can close when someone's ready to buy, and that if the deal requires follow-up, it generally dies on the vine.

That's the gap that kills first sales hires. Not effort, not talent, a founder who's been carrying sales in their head for two years and has never had to explain it to anyone else. No documented process to show a salesperson how to move a deal from interest to live. A new rep asks what deals they should focus on, what compels prospects to move forward, or why deals are lost. Without that intel, they're likely to sit and wait for sales-ready leads, which doesn't give you the value you need to justify the hire in the first place.

Before you post the role, write down the answers to three things, specific to your business, not the general version:

• What does a sales-ready lead actually look like for you? Not "interested." A real signal: they've named a budget range, a timeline, a person who has to say yes.

• What questions get you the real answer instead of the polite one? The ones you ask without thinking, because you've done it a hundred times.

• What objection means "not yet" versus what objection means "never"? You already know the difference. Your new hire won't, unless you tell them.

Skip this, and you're not hiring a salesperson. You're hiring someone to guess at your job and take the blame when they guess wrong.

Self-Source or Call a Recruiter?

Both paths work. Neither one is automatically right for you, or for this hire specifically.

From my experience, and I have done both repeatedly, it depends. On what exactly you need, and how soon. Which is why I wanted you to start with what an ideal candidate looks like for you. And you'll also need to weigh just how soon you really need that hire.

• Need a highly-specialized skill? Recruiter. I am currently working with a partner on hardware startups, and we will have to get outside help for this one.

• Territory already vacant? Recruiter. If you need someone urgently so you don't lose momentum, a recruiter might be able to fill it faster than an organic search.

• Need a founding employee or VP or C-level talent? Recruiter. They can perform incognito searches and find the special talent you need in their warm network.

• Don't have experience hiring salespeople or don't have time to do the search well? Recruiter. The stakes are too high to half-a** this.

• Entry-level or early career? Making plans for future growth? Have a good track record successfully hiring talent, especially in sales? You might be able to self-source your new salesperson.

Here's what I do know from watching both play out. A recruiter or talent scout can run the search for you and surface talent you might not otherwise find yourself, saving time, delivering pre-vetted candidates, and generally making for a smoother candidate experience. What they can't do is sit in your interview or make the call for you. Whether you're sourcing candidates yourself or leveraging a recruiter, you're still the one running the final interview and living with the outcome.

My colleague JMS places salespeople for a living. That's not what I do, and it's worth keeping straight if you end up working with him for payroll sales talent, or with any recruiter.

"I won't drop a salesperson into a company if no one can actually say what they're supposed to do. Even the best rep can’t fix a process that only exists in the founder's head. When things go sideways, everyone points fingers at the new hire instead of the real problem: the system." John Mason-Smith

Hiring a Good B2B Salesperson: 6 Tips

Hiring a good B2B salesperson is paramount for your company's growth. At some point, you have to stop setting sales aside when things get busy or waiting another quarter for your numbers to improve. You're entrusting these individuals with the task of expanding your revenue, profitably, and a misstep in this process can be costly. With years of experience and quite a few lessons learned the hard way, here are six essentials and a bonus.

1. Experience in Your Industry? Not Required.

Contrary to popular belief, a candidate doesn't necessarily need extensive experience in your specific industry. You and your existing team, implementation, customer service, or operations, are the real subject matter experts. The salesperson can be trained and mentored on your industry basics. As long as they know the right questions to ask, what to listen for, and have answers to the FAQs, they'll be fine.

Your intel can be trained, good sales instincts cannot.

Note: B2B experience does matter, and hardware versus software matters too. They should have sold something intangible, a service or software, to a business customer.

2. Ethics Above All

Work ethic and personal ethic are non-negotiables. The interview process gives you limited time to judge these qualities, so use "what if" scenarios and long-form conversation to see how someone actually thinks. Ask their references how they structure their day and generate leads. It reveals whether a candidate runs on self-motivation or leans on external support to get moving.

3. Understand the Game of Sales

Sales isn't a hole-in-one kind of game. It takes persistence and multiple channels of engagement. RAIN Groups research indicates that it takes an average of 8 touches just to get the first meeting. And according to McKinsey, B2B buyers report using an average of 10 channels across their buying journey. It means the person you hire needs to vary their approach, calls, emails, social, video, and know when a channel isn't landing instead of grinding through the same script four more times. And they need to know the stats well enough to stay in it long enough to statistically win.

4. Relationship Building is Key

In B2B sales, especially in 2026 when both outbound and inbound are in flux, partnerships are gold. Referred leads close faster and carry a close ratio 2x to 5x higher than rep- or marketing-generated leads. Hire someone who understands the value of building relationships with clients, partners, and internal departments, not just their one favorite contact in the account, and who understands that partnerships are solidly "give first," playing the long game, because no one sends leads immediately after meeting them.

5. Genuine Care for Customer Success

A good B2B salesperson sticks around to ensure the ongoing success of their customer, and understands that your clients can be your referral partners too. Are they follow-through champions, or do they vanish after the contract is signed, or after their commission hits? Ask them what they typically do after the contract is signed. A surprising number of candidates will struggle to answer. Someone who genuinely wants to understand and solve customer problems will stand out.

6. Consultative Approach

The ideal salesperson asks more questions than they answer. During the interview, present common objections and scenarios and watch how they work through them. Do they engage by understanding what's important to the prospect, or do they jump straight into product features? The former is a consultative mindset, and it's the one more likely to succeed with buyers who already avoid the reps who don't listen first.

Note: the consultative salesperson will also ask you questions, and not the kind about comp and benefits.

Bonus Tip: Where to Find Them

You might find your next star salesperson closer than you think. Pay attention to excellent salespeople you interact with and build relationships over time. You're the head coach here, and you should always be scouting for talent.

Bring in a recruiter when you need someone excellent. Or now. Or both.

Aside from someone already in your network, or a recruiter, LinkedIn is still the best platform for finding a non-entry-level hire. It's not the cheapest option, but the quality outweighs the cost. (A client of mine burned a couple of months and some extra money trying a couple of "cheaper" options before flipping to LinkedIn and finding someone great in the first pass.) Some of the other platforms might be fine for entry-level or service roles in B2B. For self-sourcing an experienced hire, LinkedIn is the one.

What's Happened Since This Was First Written

This post first went up in 2024. One thing has played out in real time since. A client used these exact criteria to hire their first salesperson that year, and the rep is still on the team today, more than two years later. Read about the founder's journey here.

Recap

• Confirm you've documented what sales-ready looks like before you post the role

• Prior experience in your industry is not critical

• Focus on ethics, personal and work, use long, casual conversations to learn more

• Look for an understanding of persistence and multi-channel engagement, not just volume of outreach

• Prioritize relationship-building skills

• Ensure they care about continued customer success

• Find someone who takes a consultative approach

Frequently Asked Questions

Do I need a recruiter to find a good B2B salesperson? It depends on the ideal candidate you need and how soon you need them, and whether you have time to run the search. What matters more than where you post the role is whether you've documented what sales-ready actually looks like before you hire anyone.

How much does a bad sales hire actually cost?

$150K to $500K once you count salary, ramp time, training, and the deals that stalled while you found out it wasn't working.

What's the most common reason a new sales hire doesn't work out? The process only lives in the founder's head or there's no structured onboarding and training. A great rep can't execute a system that was never written down, and when it fails, the hire usually takes the blame instead of the gap.

Once this role goes live, the pressure to fill it starts working against you. Resumes come in, a timeline forms in your head, and the diagnostic work you were supposed to do first quietly gets skipped because now there's an actual person in front of you who seems close enough. Do the work in this post before you post the role, not after someone's already in your pipeline and the clock starts making the decision for you. Schedule a 15-minute chat before you post the role.

---

Rise of Us, led by revenue architect Summer Poletti, works with B2B SaaS and fintech companies between $2M and $30M ARR that need to avoid wasted money, momentum, or reputation on sales investments that fall flat. Through the Revenue RISE™ Framework, we diagnose what's actually blocking the revenue, stop the waste, and build the architecture that fits your company.