Hiring salespeople for a startup is like navigating a maze with no map. Unexpected turns, dead ends. Hiring seems straightforward: find someone with a track record of success, pay them well. Then, let them work their magic. But the process is more nuanced, as startup founders have discovered—often the hard way.
This article dives into the complexities of hiring salespeople for startups. Not based on theory.
I've done the research and am distilling insights from real-life experiences and hard-learned lessons challenging conventional wisdom. I'm offering practical strategies from a cadre of experts so you can avoid costly mistakes they made. I'll cover:
- Why job-hopping isn’t always the red flag it seems.
- How startup dynamics complicate hiring—and what to do about it.
- The “A-player paradox” and why top talent often goes unnoticed.
- The critical questions you need to ask before making the next hire.
If you’re wondering how to balance gut instincts with data, avoid the trap of hiring resumes over people and build a sales team that drives growth, you’re in the right place.
Origins of this research
The below insights and recommendations are a result of Yuriy Zaremba's brave LinkedIn post—sharing his candid frustrations about the challenges of hiring salespeople with commitment issues. Yuriy is a founder navigating the complexities of building a sales team for his startup.
Over 300 comments later, sales professionals, recruiters and founders weighed in—offering raw, often surprising insights, personal stories and challenges to Yuriy’s assumptions. The post became a masterclass in hiring wisdom, revealing the hidden dynamics of the modern job market and the complexities of identifying “the best” hires. This article distills those lessons into actionable insights for anyone building sales teams in uncertain times.
Let’s get into it.

Yuriy Zaremba
Don't rely on past performance
Resumes. They've long been the first filter in the hiring process. But as startup founders like Yuriy Zaremba and sales leaders like Landon Hobbs point out, resumes often hid the real story. A polished LinkedIn profile or a string of short tenures can signal adaptability or a lack of commitment—depending on how you interpret them.
“The most glaring problem with the market is that it’s way too easy to disqualify good candidates without understanding their story," says Landon who points out resumes are just a snapshot—nuance, context, and challenges don’t come through on paper.
A candidate with three short stints in a row may have been laid off due to economic instability, poor leadership, or company pivots, he says. Thus, to assume it’s a commitment issue is unwise.
"Companies need to stop treating hiring like a checklist exercise and start approaching it like a conversation," says Landon.

Landon Hobbs
“Here is what you are missing," Gabriel Moncayo, CEO of AlwaysHired explained to Yuriy.
"If you are unhappy with candidate quality, ask yourself why you are attracting that type of quality. Great tenured candidates are out there, but for some reason, they are not reaching out to you. If your hiring process starts with judging resumes, you’ll always miss out on top talent.”
"I have coaching calls every week on this topic. Salespeople of all experience levels ask how they should explain some short stints on their resume that truly weren’t their fault. This was already an issue, but the pandemic made it 100x worse all at once. Dismissing candidates based on tenure alone is lazy hiring," says Collin Cadmus.
What’s at stake: Resumes often reflect a simplified view of a complex career. Startups hire salespeople expecting immediate results, but someone who thrived in a corporate environment with a long sales cycle may struggle in the fast-paced, scrappy reality of a startup.
Key Takeaway: Look Beyond the Surface
Focus on context rather than optics. Ask:
- Why did they leave previous roles?
- What challenges did they face in their short stints?
- How do they approach ambiguity and uncertainty?
Real-world example: As one sales professional shared, layoffs and unrealistic quotas are all too common in the tech sector. Understanding the “why” behind job moves often reveals more than tenure ever could.
Job-hopping: Red flag or new reality?
“We’ve also had one of the worst economies in history in the past five years, so multiple roles checks out," says Damien DeHart of LoganTech, LLC. "People are adapting to economic realities—they’re not hopping around for fun. This isn’t the 1990s job market anymore."
The last few years have reshaped hiring. Startups have shuttered. Mass layoffs have affected even high performers. And rapid changes in company strategies are leaving salespeople scrambling for stability.
Short tenures have become more common—but not necessarily indicative of a problem.
“The job you signed up for could be so very different 6-9 months into a role," says Rosie Purr of GiddyUp.
"We are people—NOT cogs in a machine. We need to evaluate if it’s still a good deal for us. Sure, if companies provided some more stability and commitment, it’d be easier to stick around for longer. But that’s not the reality today.”
Rosie advises considering how:

Rosie Purr
“There are stories all over the place of people who interviewed for roles, even moved across the country, only to find themselves laid off a few weeks later," says Christopher Goff, a Systems Engineer at Lighthouse. "Instead of failing to bother to interview them, why not take 15 minutes with the best of them to ask WHY they have worked 3-4 different roles in the last few years?”
Why it matters: Startups often over-hire during growth phases, then pivot or downsize, leaving employees to make tough decisions. Dismissing candidates for job-hopping without understanding the broader trends risks missing out on great talent.
Actionable Insight: Reframe the Conversation
Instead of asking, “Why didn’t they stay longer?” ask, “What did they accomplish while they were there?” Evaluate:
- Results delivered in a short time.
- Their ability to adapt to shifting priorities.
- The reasons behind their career moves.
Sometimes high rotation is a healthy sign of someone who refuses to stay in dysfunctional environments.
Startup hiring is different
Dan Dougherty recently found himself in the following situation—despite bringing in the three largest deals the company had seen in its existence. He made the accomplishment in only seven months of active selling.
"Following a reorganization with no notice or communication from our CEO," says Dan who is now a mid and enterprise market Sales Director at TripWorks, "people were let go unexpectedly, my base salary was reduced by $95,000, and the changes effectively ensured I wouldn’t be fairly compensated for my contributions. This left me with no choice but to seek opportunities elsewhere.”
Hiring for a startup is fundamentally different from hiring for an established business. Early-stage startups, in particular, face unique challenges:
- Unproven product-market fit (PMF): Salespeople may be selling a product that’s still evolving.
- Ambiguity: Roles are fluid, and expectations can shift overnight.
- High stakes: Every hire has an outsized impact on company culture and results.
What’s at stake: The traditional markers of success (quota attainment, tenure, accolades) may not translate to the unpredictable nature of startup sales.
“This comes down to being an employer of choice," says John Taylor, a sales director at Abel HR services.
"Is your compensation benchmarked in the market, and are you on the upper part of that? What is the roadmap for success, and is it clearly outlined with training, achievable goals, and tools? If you can’t answer why a top candidate would choose you, that’s where you need to start," says John.
Practical Tip: Hire for Fit, Not Just Skills
When hiring for startups, look for candidates who:
- Thrive in ambiguity.
- Are resilient and resourceful.
- Understand that “figuring it out” is part of the job.
Re-thinking commitment
The debate around job-hopping often focuses on candidates’ perceived lack of commitment. But as many commenters pointed out, commitment works both ways. Salespeople who are undervalued, underpaid, or overpromised are unlikely to stick around.
Key question: What are you offering to earn loyalty?
“Commitment is not hired; it is earned," insists Zafar Ibrohimov, Co-founder & CEO at TeamEx.
"You hire the best fit—whose career goals, values, principles, and vibe match your company—and when you give them purpose, they are committed.”
“Why should an AE commit to a job where not a single person hits quota (for whatever reason)?" asks Avery Holmes, an Enterprise SDR at CB Insights.
"Would you commit to a relationship where your partner doesn’t value you or hold up their promises to the relationship? For the simple argument of ‘having a history of commitment’? Where do you draw the line?”
How to Foster Commitment:
- Transparent compensation: Ensure your commission structure is clear, fair, and competitive.
- Stability: Provide resources and tools to help salespeople succeed.
- Culture: Build an environment where employees feel supported and valued.
Why top talent doesn't apply
One of the most insightful points raised in the debate is this: the best salespeople aren’t scrolling job boards. They’re hitting their numbers and being pursued by recruiters.
Why this matters: If you’re relying on inbound applications, you may never reach top-tier talent. Gabriel Moncayo gives tough love.
“If great candidates aren’t applying, it’s not their fault. Ask yourself why you’re not attracting them, and fix that. Maybe your hiring process signals the wrong things to top performers," he says.
“Top-tier salespeople don’t browse job boards. They’re busy exceeding quotas or being courted by recruiters," says Jonathan Romley, CEO of Lundi. "If you want them, you have to find them where they are.”
Solution: Go Outbound
- Use your network to identify high performers.
- Invest in recruiters who specialize in sourcing sales talent.
- Treat hiring like sales: proactively build a pipeline of qualified candidates.
As one commenter aptly noted, “The best AEs are found outbound, not inbound.”
Innovative ways to screen
With limited time and resources, startups can’t afford to interview everyone. But disqualifying candidates based on surface-level assumptions leads to missed opportunities.
Here's what to do instead:
- Create a structured screening process. Use short questionnaires or quick phone screens to filter candidates.
- Ask high-signal questions. Focus on problem-solving, adaptability, and results.
Also, screening for "why" rather than "what" helps uncover resilience, adaptability, and decision-making abilities that might not be obvious at first glance. Instead of relying solely on resumes, consider asking screening questions that probe into motivations, challenges faced in prior roles, and lessons learned.
Joshua Garrison, a VP at Apollo.io, reminds us of unrealistic promises made during the hiring process. He says to combat candidates overselling themselves, consider roleplaying exercises as part of the screening process. Pose a realistic but challenging sales scenario to assess how candidates think on their feet, uncover needs, and adapt their strategy.
This allows you to gauge skills and ability to align with your sales operations.
Dima Popov, Founder at LeanGTM, says A-players rarely come through inbound applications; instead, they are often found through outbound efforts or referrals.
This insight implies the importance of cultural alignment as a screening criterion. Include value-based questions like,
- “What motivates you to stick with a challenging project?” or
- “How do you decide whether a company is worth your long-term commitment?”
These questions uncover intrinsic drivers and help you identify candidates who align with your company’s mission.
Also, instead of penalizing candidates for short stints, consider screening for grit by asking about how they navigated difficult situations.
For example, Landon Hobbs’s emphasis on how sales roles often require dealing with immense uncertainty could be translated into screening questions like, “Tell me about a time you exceeded expectations in a turbulent environment” or “How do you approach rebuilding your pipeline after a major setback?”
Evan Green has 17 years in enterprise software sales before starting his business. He and others say loyalty is not a one-way expectation. Thus, start asking candidates what they need from you as an employer to stay committed. Whether it’s clarity, fair compensation, or a clear growth path.
This will help filter out those who are merely job-hopping for the next paycheck. This also signals to candidates that you value mutual respect and accountability.
Lessons learned & going forward
The hiring process is rarely perfect, but each misstep provides valuable lessons. Founders like Yuriy Zaremba have shared candid insights into what worked, what didn’t, and how they’ve adjusted their approach over time.
Final thought: Hiring salespeople for startups requires a mindset shift. Instead of looking for the “perfect” candidate, focus on finding someone who aligns with your company’s stage, culture, and vision—and who’s ready to roll up their sleeves and grow with you.
Hiring salespeople for startups is as much an art as it is a science. It requires balancing data with intuition, ambition with realism, and strategy with flexibility. By focusing on adaptability, understanding context, and proactively seeking out talent, you can build a team that drives growth—even in the face of uncertainty.
Remember, every hire is an investment in your startup’s future. Make it count.
This post is based on the wonderful discussion found here.