A Founder’s Guide to Building an Enterprise-Ready Sales Machine

Scaling your sales team to tackle enterprise-level deals isn’t about doubling down on effort — it’s about redefining strategy, approach, and mindset.

Here are the five brutally honest lessons every founder needs to understand before building an enterprise-ready sales team, along with actionable steps to overcome these challenges and create a truly transformative sales process.

1. The Comfort Zone of Product-Level Selling: Why Small Thinking Keeps You Small

Enterprises Don’t Buy Products; They Buy Outcomes.

For founders, this is the first big hurdle. Mid-market AEs are often trained to sell on features and product benefits, meeting specific, isolated needs. However, enterprises think differently. They’re looking for solutions that enable strategic transformations, not just quick fixes. Let’s break down the differences between selling features and selling outcomes and why it’s crucial.

The Breakdown

• Feature Selling is when AEs pitch what the product does — e.g., “Our solution will automate your workflows.”
• Outcome Selling is when AEs pitch what the product achieves — e.g., “With our solution, your team can focus on scaling operations instead of manual tasks, helping the company increase its annual growth by 15%.”

Real-World Example

Consider a company selling a SaaS product to automate spreadsheet processes. For a mid-market buyer, this may be a simple way to reduce inefficiencies. But for an enterprise, this product could be a tool to achieve greater data accuracy in strategic decision-making, reducing human error that could otherwise impact millions of dollars.

Founder Insight: Train your team to think in terms of client outcomes. If you’re not helping them see how your product influences their strategic goals, you’ll lose out to competitors who are. Spend time with your AEs to ensure they can connect your product’s value to the buyer’s long-term vision, not just their current pain points.

2. Fake Empathy vs. Real Buyer-Centric Thinking

True empathy in sales goes beyond understanding the buyer’s pain; it’s about understanding their entire internal process.

Empathy can’t be faked in enterprise sales. When you’re selling a six- or seven-figure deal, the stakes are high for everyone involved. Enterprise buyers need confidence that you’re committed to understanding not just the surface problems but also the underlying challenges of internal buy-in and ROI justification.

The Breakdown

• Fake Empathy: “I understand this is frustrating, but let me show you why our solution can help.”
• Real Empathy: “Beyond just solving this issue, how will implementing this help you justify the decision to your CFO? What support do you need from us to make your internal process smoother?”

Real-World Example

Imagine an AE pitching to a procurement officer who will need CFO approval. The AE should anticipate that the CFO may not be interested in technical specs but in financial impact. So, instead of focusing on the bells and whistles, they’d prepare a financial impact assessment the procurement officer can use to build a strong internal case.

Founder Insight: Test for real empathy in your team. Run scenarios where AEs must help a mock buyer justify the purchase within their organization. They should proactively offer resources that ease the buyer’s journey, such as ROI assessments, whitepapers, or even peer references.

3. Closing as a Byproduct, Not a Goal: Stop Worshipping the Finish Line

Enterprise sales are won through process mastery, not last-minute heroics.

In the drive to close deals, many sales teams focus intensely on the final steps. However, in enterprise, the strength of each phase determines success. Rather than focusing on the close, AEs should see closing as the natural outcome of a well-orchestrated process.

The Breakdown

• Mid-Market Mindset: Sprint to the finish line, hoping for a last-minute close.
• Enterprise Mindset: Focus on nurturing each phase so that the final decision becomes straightforward and unresisted.

Real-World Example

Consider an AE who closes mid-market deals by following up relentlessly in the final days. In enterprise sales, persistence alone won’t cut it. Instead, AEs need a business case prepared well in advance, a clear champion who will advocate internally, and buy-in from all relevant departments. In these deals, having consistent progress from day one is essential to success.

Founder Insight: Create a culture of process over results. This may mean you need to adjust metrics for your team. Recognize AEs not just for closing but for achieving milestones, like securing strong internal champions or building consensus within the buying team. When the focus is on executing a rigorous process, closings naturally follow.

4. The Lone Wolf Mentality: Why Heroes Fail in Enterprise Sales

Enterprise sales are a team sport, and no single AE can master it alone.

The “hero AE” who handles everything may work in smaller deals, but in enterprise, you need every possible resource. One person cannot handle all the strategic, technical, and financial aspects. When selling enterprise, every team member brings specialized knowledge to the table, from tech support to the CEO.

The Breakdown

• Lone Wolf Selling: The AE owns every touchpoint and tries to manage it all.
• Team Selling: The AE assembles a team where each member supports a different part of the buyer’s decision-making process.

Real-World Example

Suppose an AE working on a major tech sale tries to handle both technical demos and strategic alignment. But they miss key details in both because they’re stretched too thin. By contrast, an enterprise AE would bring in a product manager for technical deep dives, a finance expert for ROI discussions, and an executive for visionary alignment.

Founder Insight: Foster a collaborative culture. Reinforce to your AEs that enterprise deals are won by showing clients the strength of the entire team. Introduce mandatory “deal team” meetings where everyone involved syncs up on strategy, and make it a point that enterprise wins are team victories.

5. Poor Organization: Enterprise is No Place for Sloppy Sellers

Enterprise sales demand an obsessive level of detail.

Most AEs are used to high-velocity sales, where they can afford a little sloppiness because the volume will make up for it. But in enterprise, that margin for error is nonexistent. Sloppy follow-ups, missed deadlines, or incomplete information can destroy months of effort.

The Breakdown

• Mid-Market Mindset: “As long as I stay on top of my pipeline, I’m good.”
• Enterprise Mindset: “I have a detailed roadmap, and every step is executed to perfection.”

Real-World Example

A top AE handling only 10 deals meticulously tracks each one, customizing their approach to fit each prospect’s decision-making journey. They may build detailed project plans for each account, tracking every interaction, documenting every need, and preparing every stakeholder-facing document meticulously. This attention to detail builds credibility and trust with the client.

Founder Insight: Push your team to adopt a project management mindset. Set up structured playbooks and implement robust CRM hygiene standards. Consider establishing a deal review process where AEs present account plans and get feedback on whether they’re adequately detailed and aligned with buyer needs.

Best Practices Guide: Steps for Founders to Build an Enterprise-Ready Sales Team

Having explored the five most critical issues, let’s dive into actionable best practices for founders looking to transform their mid-market sales team into an enterprise powerhouse.

1. Elevate to Strategic Thinking

• Offer High-Level Sales Training: Train AEs to move beyond features. Hold workshops focusing on client outcomes and strategies, exploring how your solution fits their larger goals.
• Incorporate Customer Success Insights: Use feedback from existing enterprise clients to teach your AEs about the bigger picture and help them learn from real transformations.

2. Cultivate Genuine Empathy

• Empathy Workshops: Run empathy-building exercises where AEs role-play the client’s internal processes.
• Case Studies and Buyer Journeys: Build a repository of buyer journey case studies. Let AEs study these to understand the types of hurdles buyers face and how to address them.

3. Master Each Stage, Don’t Just Close

• Process-Based KPIs: Redefine success metrics beyond quota achievement. Track metrics like the number of internal champions built, engagement in each stage, and meeting each stakeholder’s unique needs.
• Regular Training on Deal Phases: Reinforce skills for each deal stage, from discovery to close. Provide guidance for building champions, securing internal buy-in, and handling objections specific to each phase.

4. Build a Team-Selling Culture

• Cross-Functional Involvement: Create standardized protocols for involving cross-functional leaders in enterprise sales. Encourage AEs to pull in department heads for specific expertise, making it clear that enterprise deals demand more than just one AE.
• Quarterly Team-Building Exercises: Conduct collaborative exercises where AEs present real deals and discuss strategies with support from other departments.

5. Develop a ‘Process Excellence’ Mindset

• CRM Accountability: Institute strict CRM usage policies to maintain consistent deal tracking and documentation.
• Deal Reviews and Audits: Set up regular deal review meetings where AEs showcase their process. Provide feedback on their organizational approach to ensure they’re detail-oriented and process-driven.
• Account Playbooks: Create playbooks that break down enterprise sales into manageable, repeatable steps. This will ensure that AEs don’t miss key details in high-stakes deals.

Common Pitfalls: Mistakes Founders Make When Building Enterprise Teams

In addition to these best practices, let’s consider a few critical pitfalls founders should avoid:

1. Assuming Mid-Market Success Will Translate to Enterprise Moving from mid-market to enterprise isn’t a simple upshift in deal size; it’s an entirely different playbook. Founders who assume their mid-market stars will excel in enterprise sales often face disappointment. Enterprise requires patience, strategic thinking, and teamwork that goes beyond what’s needed in the mid-market.
2. Failing to Build Internal Champions Without internal champions, enterprise deals crumble. Founders need to teach their AEs how to build these champions by establishing trust, aligning on strategic goals, and maintaining constant communication.
3. Overlooking the Buyer’s Journey Complexity Enterprise buyers often navigate complex internal systems before approving a purchase. Failing to understand or support this journey leads to lost deals. Founders must emphasize buyer journey alignment as a critical sales skill.

Conclusion: A Challenge to Founders — Are You Ready for Real Enterprise Sales?

Building an enterprise sales team that succeeds requires an overhaul of the very way you think about sales. If you’re committed to moving from mid-market to enterprise, you must embrace the rigor, attention to detail, and strategic alignment that come with high-stakes deals. Enterprise sales isn’t about quick wins; it’s about building long-term, transformational partnerships.

So, founder-to-founder, I challenge you: are you ready to leave behind the simplicity of mid-market wins and truly prepare your team for enterprise? Are you willing to be relentless in your pursuit of structure, empathy, and a culture of team success?

If the answer is yes, apply these principles with dedication, and watch as your team transforms into the enterprise powerhouse you envision.