Craig Emslie Explains Why Startups Struggle With Sales Hiring—and How to Fix It

Finding the best salespeople is frequently one of the most difficult tasks for startups. While launching an innovative product or service is exciting, ensuring it reaches the right audience through a skilled sales team is critical for growth. Craig Emslie, a seasoned sales leader and startup advisor, offers valuable insights into why so many startups falter in their sales hiring efforts & more importantly, how they can fix it.

The Sales Hiring Problem Most Startups Overlook

For many early-stage companies, product development takes center stage, often at the cost of developing a solid go-to-market strategy. According to Craig Emslie, the root of many hiring issues in startups stems from a fundamental misunderstanding of what type of sales talent is needed at different growth stages.

Common Reasons Startups Struggle With Sales Hiring

Craig Emslie has worked with numerous startups across sectors and consistently sees the same challenges:

• Hiring too early or too late: Startups often rush to hire sales reps before achieving product-market fit or wait until it’s too late and revenue stalls.
• Misalignment between founders and sales: Founders may have unrealistic expectations of what a new sales hire can deliver, especially without a defined sales process.
• Recruiting the wrong profile: Hiring sales professionals with big corporate backgrounds might sound appealing, but they often struggle in the resource-constrained, fast-paced world of startups.
• Lack of onboarding and support: Startups frequently lack the training and infrastructure that enable new sales hires to succeed.

Craig Emslie believes that sales hiring isn’t just about finding experienced people—it’s about finding the right people for the right stage of your startup journey.

Understanding the Stages of Sales Hiring

Every startup goes through key growth stages, and each one requires a different kind of sales expertise. As Craig Emslie points out, a mismatch between sales maturity and sales hiring can cost startups time, money, and market share.

Stage 1: Founder-led Sales

The founder is typically the most effective person to market the product in its early stages. No one knows the vision better. Craig Emslie insists this stage is crucial—not only for securing early customers but also for shaping the sales narrative.

Stage 2: Early Sales Hires

Once the founder has validated the product and gathered customer feedback, it’s time to build a small sales team. At this stage, Craig Emslie recommends hiring builder profiles—people who can sell but are also comfortable creating processes from scratch.

Stage 3: Scaling the Sales Team

When processes and predictable revenue start taking shape, startups can bring in more specialized sales reps, managers, and enablement roles. By now, the company should have a clear go-to-market strategy, defined KPIs, and onboarding in place.

Craig Emslie’s Advice on Hiring Sales Talent That Performs

To help startups navigate this tricky terrain, Craig Emslie offers a structured approach that balances strategy with execution. Here’s how he recommends startups improve their sales hiring outcomes:

1. Define the Sales Role with Clarity

Before posting a job ad, startups must clarify what they need. Is the goal to generate leads, close deals, or build partnerships? Attracting the right fit is more likely when the role is clear.

2. Hire for Startup DNA

Craig Emslie emphasizes hiring individuals who thrive in ambiguity, can wear multiple hats, and are motivated by impact rather than structure. Traditional enterprise sellers may not be equipped to build from zero.

Key traits to look for:

• Resilience and adaptability
• Entrepreneurial mindset
• Comfort with rejection
• Strong communication and listening skills

3. Create a Sales Playbook

A simple sales playbook can make a big difference in results. Documenting buyer personas, objection handling, and key messaging helps new hires hit the ground running. According to Craig Emslie, a repeatable process makes sales hiring scalable.

4. Invest in Onboarding and Support

Startups often underestimate how much onboarding matters. New sales reps should be given time, resources, and clear milestones. Craig Emslie suggests creating a 30-60-90 day plan to measure success and support development.

5. Involve Sales in Feedback Loops

Sales teams are on the front lines—they hear objections, understand buyer needs, and spot trends early. Incorporating their feedback into product and marketing decisions leads to stronger alignment across teams.

The Importance of Culture Fit

Hiring a sales superstar is meaningless if they can’t align with your startup’s culture. Craig Emslie often warns founders not to overlook soft skills and values alignment during interviews.

Tips for Cultural Alignment:

• Involve multiple team members in interviews
• Ask situational questions to test real-world behavior
• Make sure the applicant comprehends the goals and expansion plans of the startup.

When to Bring in a Sales Leader

Too many startups put off hiring a sales leader. Craig Emslie recommends bringing in a Head of Sales once the team grows beyond three or four reps. This person can build infrastructure, coach junior reps, and develop long-term strategy.

The right sales leader can also act as a bridge between the founders and the sales team—ensuring clarity, accountability, and direction.

Metrics to Track Sales Hiring Success

Sales hiring shouldn’t be a guessing game. Craig Emslie advises startups to monitor key performance indicators (KPIs) that reflect hiring effectiveness:

• Time to first deal/cash collected
• Pipeline coverage per rep
• Close Rate
• Average Sales Cycle
• Average deal size
• Ramp time

By tracking these metrics, startups can refine their hiring processes and make better decisions over time.

Craig Emslie’s Final Thoughts

Sales hiring is not a plug-and-play exercise—it’s a strategic growth lever. Startups that invest early in defining their needs, finding the right profiles, and supporting their sales hires set themselves up for sustainable success.

Craig Emslie believes that with the right mindset and a structured approach, any startup can build a world-class sales team, even without big budgets or flashy offices.

It’s not about hiring people who can sell—it’s about hiring people who can help you build something worth selling, and then scale it, says Craig Emslie.

Conclusion

Sales hiring is a critical—but often misunderstood component of startup growth. By learning from experts like Craig Emslie, founders and startup leaders can avoid common pitfalls and build high-performing sales teams from the ground up.

Whether you’re just starting out or preparing to scale, the insights shared by Craig Emslie offer a practical and proven roadmap to help your startup succeed in the long term.