As the Chief Revenue Officer (CRO), I led a transformative journey, achieving a 2x sales increase in under three years at a fintech/services company. This experience taught me invaluable lessons that can guide others through similar challenges.

 

1. Embrace Diversity in Hiring Early:

Identify the ideal sales representative profile by hiring individuals from varied backgrounds. Avoid the comfort of familiar networks. For instance, my background was in sales and servicing, while our top Sales Development Representative (SDR) brought insights from a lending background. Such diversity allows you to explore different approaches and discover what truly resonates with your market.

 

2. Establish Achievable Quotas:

Morale is the cornerstone of success. Set realistic quotas to cultivate a culture where top performers excel and friendly competition thrives. Aim for 80% of your team to achieve at least 80% of their targets, ensuring a balanced environment that motivates all.

 

3. Value Understanding Over Product Knowledge:

While product knowledge is essential, understanding the needs and challenges of your target persona and grasping the competitive landscape is far more impactful. The best representatives will naturally acquire the necessary product insights as they engage with clients and prospects.

 

4. Invest in RevOps and Enablement Without Delay:

Move beyond lip service and proactively invest in RevOps and enablement. Initially, I managed Salesforce through YouTube tutorials, but hiring professionals proved far more effective. This frees your team to focus on what truly matters: building relationships with prospects and customers.

 

5. Leverage External Win/Loss Analysis:

Conducting win/loss analysis internally may yield limited results. An external perspective can unveil deeper insights. Our first outsourced project led to a refined pitch deck and a 20% increase in conversion rates. Trust external experts to reveal the full picture.

 

6. Assess Your Enterprise-Readiness Honestly:

Resist premature pressure to hire high-cost, high-profile representatives if your company lacks the necessary resources to support their success. Evaluate your industry expertise, support structures, and solutions before committing to significant hires.

 

7. Explore Motivations Beyond Monetary Rewards:

Understanding what drives your team beyond financial incentives is crucial. A question from our CEO—"What motivates each of your reps aside from money?"—prompted me to delve deeper. Engage with your top performers to discover what fuels their passion, be it learning opportunities, mentorship, or side projects, and support them in achieving these goals.

 

8. Foster Open Collaboration with Senior Leadership:

Your role is to empower C-suite success. During leadership transitions, I maintained open communication with our new CEO, sharing team sentiments, key influencers, and potential risks. Building a transparent relationship with leadership not only supports your boss but also strengthens your company.

 

TAKEAWAY:

Even with the right strategies, navigating startup and transformative sales is challenging and mistakes are inevitable. The key is to learn from each misstep and continuously adapt. Embrace these lessons and approach your journey with resilience and openness to growth.