I’ve watched companies make the same mistake for years. They need to grow revenue, so they post a job listing for a sales rep, screen for the usual traits — confidence, communication skills, a track record of hitting quota — and then wonder why the new hire flames out within six months.
The problem isn’t the candidate. It’s the assumption that selling software works like selling anything else.
It doesn’t.
Software Sales Operates Under Different Rules
When someone sells office supplies or insurance, the product is tangible or at least well-understood. The buyer knows what they’re getting. The sales cycle might take a few calls, maybe a lunch meeting, and then a handshake.
Enterprise software doesn’t work that way.
A single deal can take nine months. The buyer often doesn’t fully understand what they’re purchasing until they’ve sat through multiple demos, looped in their IT team, gotten sign-off from legal, and navigated internal politics you’ll never see. The salesperson isn’t just selling a product — they’re selling a vision of how the buyer’s business will operate differently after implementation.
That requires a completely different skill set than most sales roles demand.
What Actually Matters When Hiring for Software Sales
After spending years working with software companies trying to build sales teams, I’ve noticed that the candidates who succeed share a few traits that rarely show up on resumes.
They understand the problem before they pitch the solution. The best enterprise software salespeople spend more time asking questions than talking about features. They’re genuinely curious about how the prospect’s business works, where the pain points are, and what’s been tried before. This isn’t a technique they learned in training — it’s how they naturally approach problems.
They can translate technical concepts for non-technical buyers. Most software buying decisions involve people who don’t have technical backgrounds. The CFO approving a seven-figure purchase doesn’t care about API integrations or data architecture. They care about ROI, risk, and whether this decision will make them look smart or stupid in twelve months. Great software salespeople bridge that gap without being condescending.
They have patience that borders on stubbornness. Enterprise deals stall constantly. Budgets get frozen, champions leave for other jobs, priorities shift. The salespeople who thrive in software don’t take these setbacks personally. They keep the relationship warm, stay in touch without being annoying, and recognize that the deal that died in Q2 might come back to life in Q4.
The Hiring Process Most Companies Use Is Broken
Here’s what typically happens: A software company needs salespeople, so they post on job boards and wait for applications. They screen resumes for keywords and relevant experience. They run candidates through a few interviews, maybe a role-play exercise, and then make a decision based on gut feeling and whoever interviewed best.
This process selects for people who are good at interviewing. That’s not the same as being good at selling software.
The candidates who crush interviews — polished, articulate, confident from minute one — sometimes struggle in the field because enterprise software sales rewards a different kind of personality. The best reps I’ve seen are often a little awkward in interviews. They ask too many questions. They pause to think before answering. They don’t have slick responses ready because they’re not performing — they’re actually processing.
Companies that hire well for software sales roles do things differently. They dig into specific deals the candidate has worked. Not just “tell me about a big win” but “walk me through the decision-making process on the buyer’s side and how you navigated it.” They ask about deals that fell apart and listen for whether the candidate learned something or just blames external factors.
Some of the most successful software companies I’ve worked with use software recruiting experts at Neva Recruiting specifically because finding these candidates requires knowing where to look and what to look for. The talent pool for enterprise software sales is smaller than most people realize, and the best candidates are rarely actively job hunting.
The Cost of Getting It Wrong
A bad sales hire in software isn’t just a wasted salary. It’s lost deals, damaged relationships with prospects who got a poor experience, and months of pipeline that went nowhere. In enterprise software, where deal sizes can reach six or seven figures, one wrong hire can cost a company millions in missed revenue.
That’s before you factor in the time spent managing someone out, restarting the search, and ramping a replacement. Most software sales roles take at least six months before a new rep is fully productive. A bad hire doesn’t just set you back by the time they were there — it sets you back by the time it takes to find and ramp their replacement.
Building a Software Sales Team That Actually Works
If there’s one thing I’d tell software companies trying to build sales teams, it’s this: slow down.
The pressure to hit revenue targets makes everyone want to fill seats fast. But a smaller team of the right people will outperform a larger team of the wrong ones every single time. Two great enterprise reps will close more business than five mediocre ones — and they’ll build the kind of customer relationships that lead to expansions and referrals.
Take the time to define what success actually looks like in your specific sales environment. What’s your average deal size? How long is your sales cycle? How technical are your buyers? The answers to these questions should shape who you hire.
And be honest about what your company offers candidates. The best software salespeople have options. They’re evaluating you as much as you’re evaluating them. If your comp plan is confusing, your territory assignments are unclear, or your product has issues you’re not acknowledging, strong candidates will figure that out and walk away.
Frequently Asked Questions
What makes software sales different from other types of sales?
Software sales, particularly at the enterprise level, involves longer sales cycles, more complex buying committees, and products that often require significant explanation. Unlike transactional sales where the product is well-understood, software salespeople must help buyers understand how a solution will change their operations and navigate internal stakeholder dynamics that can take months to resolve.
How long does it take to ramp a new software salesperson?
Most enterprise software sales roles require at least six months before a new rep reaches full productivity. This includes time to learn the product, understand the market, build pipeline, and begin closing deals. Complex products or long sales cycles can extend this timeline to nine months or longer.
What should companies look for when hiring software salespeople?
The most important traits include genuine curiosity about buyer problems, the ability to translate technical concepts for non-technical audiences, and patience for long sales cycles with frequent setbacks. Experience in similar deal sizes and sales cycle lengths matters more than industry-specific background in many cases.
Should software companies use recruiting firms for sales hiring?
For enterprise software sales roles specifically, working with recruiters who specialize in the software industry often produces better results than general job postings. The best candidates are typically not actively searching, and specialized recruiters have networks and screening processes designed for this particular talent pool.
What’s the biggest mistake companies make when hiring software salespeople?
The most common mistake is hiring based on interview performance rather than investigating how candidates actually worked deals. Polished interviewers aren’t always effective in the field. Companies should dig into specific examples of how candidates navigated complex sales processes, not just their presentation skills.
How important is industry experience for software sales roles?
It depends on the complexity of the product. For highly technical products sold to specialized buyers, industry experience matters significantly. For more general business software, transferable skills like deal management, stakeholder navigation, and solution selling often matter more than specific industry background.