Focus on strategic alignment

Jamal Reimer highlights how sellers can align with CFOs and CIOs to close bigger enterprise deals by addressing both financial and technical priorities.

1. Focus on strategic alignment

• Start with the priorities of the CFO and CIO, not your product features.

• Re-state their goals, highlight challenges, and explain how your solution addresses them.

2. Speak to both financial and technical needs

• For the CFO: Build a value story with input from their team. Show ROI, cost timelines, and financial benefits based on their assumptions.

• For the CIO: Focus on scalability, integration, and how your solution aligns with their technical strategy. Show its impact on infrastructure.

3. Develop shared tools

• Create cost-benefit analyses that link financial ROI to technical outcomes.

• Show mutual wins like reduced total cost of ownership (TCO) and improved system efficiency.

4. Facilitate joint sessions

• Host sessions with both CFOs and CIOs.

• Start with financial metrics (ROI, payback period), then address technical feasibility (scalability, integration).

• End with how shared benefits meet their strategic goals.

5. Visualize impacts in real time

• Use dashboards or ROI calculators during discussions.

• Real-time visuals keep both leaders engaged and accelerate decisions.

Breaking into a multi-billion-dollar company

Troy Munson shares how he broke into a large enterprise account, detailing the steps that worked and how he used creative outreach to secure a high-level meeting.

What worked for him:

1. Connected with key employees

   • Troy started by connecting with every relevant person on LinkedIn.

   • He engaged regularly by commenting on their posts to stay visible.

2. Built trust with entry-level employees

   • He reached out to entry-level staff by offering value, like sharing threat insights.

   • Through these conversations, he uncovered the company’s key goals and challenges.

3. Personalized his prospecting efforts

   • Using the insights he gained, Troy crafted targeted LinkedIn messages, emails, and calls.

   • When these didn’t work, he tried different creative approaches.

4. Got creative with outreach to executives

   • He sent a personalized video to the C-level executive, which was opened but not answered.

   • Troy noticed another executive’s LinkedIn post about sports and invited him to an NFL game.

   • Though declined, the conversation led to a polite exchange.

5. Asked for introductions

   • Instead of giving up, Troy asked the sports-loving executive to introduce him to the right person.

   • He explained why it made sense and outlined the value he could bring.

   • The introduction led to a booked meeting within a week.

6. Used employee insights to strengthen his pitch

   • Troy leveraged what he learned from entry-level employees to craft a message tailored to company priorities.

   • This internal knowledge made his approach more relevant and credible.

Confidence comes from competence

The Brutal Truth about Sales Podcast, hosted by Brian Burns, features Greg Piser, Global VP of Sales at ARA Cyber Security Solutions, discussing his journey from engineering to sales and strategies for closing large enterprise deals.

⇢ Understanding the shift

• Transitioning from technical roles to sales is challenging but rewarding.

• Use problem-solving skills and technical expertise to stand out.

⇢ Focus on solving problems

• Sales success starts with understanding the customer’s pain points.

• Present clear, tailored solutions that directly meet their needs.

⇢ Master the business side

• Learn how enterprise organizations handle funding and decision-making.

• Understand the internal politics that influence large deals.

⇢ Partner with the right players

• Small companies often need partnerships to compete in large deals.

• Align with established players to boost your credibility and reach.

⇢ Embrace trial and error

• Success in enterprise sales often comes through experimentation.

• Refine your approach based on what works over time.

⇢ Build genuine relationships

• Customers value authenticity—show you genuinely care about their goals.

• Long-term partnerships are built on trust and shared success.

⇢ Tackle leadership challenges

• Leading sales teams means understanding different personalities and roles.

• Tools like assessments can help align people with the right responsibilities.

⇢ Treat people individually

• Avoid cookie-cutter approaches.

• Adapt your communication and strategies for each unique customer or team member.

⇢ Confidence comes from competence

• Confidence is rooted in deep knowledge of your product and market.

• Deliver value with assurance, not arrogance.

⇢ Never stop improving

• The best sales leaders focus on learning and mentoring others.

• Stay adaptable to outpace competition in complex sales environments.

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