Escaping the IT Room

In the world of enterprise tech sales, it’s hard to succeed by just selling into IT. While IT decision-makers are important partners in any software buying decision, long-term success depends on building relationships with and delivering value to the business.

Business stakeholders are focused on different issues and challenges than their IT counterparts.  They think more about strategic outcomes, operational performance, and measurable ROI based on metrics meaningful to the business.  Put simply: 

‍ "IT cares about features, the business cares about futures."

To be successful with leaders across different lines of business (LoBs), you must enable and motivate your sellers to speak their language and understand the industry-specific challenges. 

The enablement teams and sales leaders have a critical role to play here. So how do you enable sellers to break out of the IT department and into the business? You’ll need more than just new internal messaging. You will need a fundamental transformation in how you motivate, train, support, and measure your sales teams.  Here’s a four-step plan to enable enterprise software sellers to engage business audiences effectively and close deals that drive real impact.

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1. Make the Case to Sellers

“The biggest deals aren't closed with IT. They're co-created with the business.”

Before skills can be built, sellers need to believe in and commit to the approach. Motivation is the critical foundation for enablement.

Start with a clear go-to-market (GTM) strategy that centers business engagement. The GTM strategy must explicitly prioritize business engagement, not just as an aspiration, but as a core tenet of how the company sells. For example, Salesforce restructured its sales approach in recent years to emphasize customer business outcomes, embedding industry-aligned value engineering teams into account planning cycles.

Align incentives with desired behaviors. Compensation structures should reward engagement with business stakeholders and deals tied to measurable outcomes, not just revenue. According to a 2023 Forrester study,

"65% of B2B sales leaders reported improved win rates when incentive plans emphasized business outcomes and cross-functional stakeholder engagement."

Ensure leadership sets the tone. Executives must champion the shift, providing clear calls to action and reinforcing expectations. Sales managers play a pivotal role by holding teams accountable: Are reps including business personas in discovery? Are proposals tied to customer-specific success metrics?

Share success stories and best practices. Sellers respond to the success of their colleagues in sales. Regularly capture and distribute examples of successful business-led deals, including the roles engaged, outcomes achieved, and the tactics that worked. Celebrate wins tied to business value at all-hands or regional meetings.

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2. Train Seller to Know the Customer and How Solutions Drive Outcomes

“The fastest way to grow your deal size, reduce your sales cycle, and build champions is to connect your solution to the customer’s strategy.”

Knowledge is power, but only when it’s relevant and contextualized. Sellers must build conversational fluency in their customers’ industries, challenges, and strategic goals.

Teach the business. Sellers must speak the language of the customer’s industry. You must provide the right set of resources to help sellers learn the basics.   This means understanding industry trends, strategic imperatives, regulatory challenges, and key metrics. In manufacturing, it could be overall equipment effectiveness (OEE); in financial services, return on equity or cost-to-income ratios. Leaving sellers to figure the basics out on their own will lead to wasted time, frustrated teams, and a missed opportunity to get sellers engaging leaders outside the IT organization.

Provide tailored value frameworks. Equip sellers with value guides and conversation tools that show how your solutions map to these industry-specific pain points. SAP does this effectively with its industry cloud strategy, offering curated content and case studies aligned to 25+ verticals, from automotive to life sciences.

Tie solutions to outcomes. Each sales motion should clearly link product capabilities to measurable business impact. This goes beyond ROI calculators; it requires relevant use cases, customer success stories, and outcome-oriented messaging. For example, showing how a supply chain optimization tool improved on-time delivery by 15% is far more powerful than a list of technical features.

Teach account-level research. Reps should be trained on how to analyze 10-Ks, earnings calls, and analyst reports to uncover a target account’s strategic priorities. Tools like LinkedIn Sales Navigator, ZoomInfo, and AlphaSense can accelerate this research. Mapping your solution portfolio to those priorities gives sellers clear paths to value-based conversations.

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3. Guide Sellers to the Right Skills and Behaviors to Engage Business Audiences

“Customers don’t care how much you know until they know how much you care.”

Once a seller has the industry knowledge and can identify what value they can bring, they must have the skills to communicate it effectively. This requires strong sales behaviors, methodologies, and collaboration across roles.

Standardize a value-selling approach. Whether adopting Challenger, MEDDICC, or a homegrown methodology, the sales organization must have a common language for value engagement. The key is focusing conversations on problems, business impact, and outcomes, not just features.

Teach customer discovery. Business stakeholders expect sellers to understand their world. Teach reps to ask insightful, open-ended questions that reveal underlying drivers of pain. Techniques from value engineering—like benchmarking and success metric modeling—can guide conversations toward impact.

Emphasize storytelling. Business audiences respond to stories. Train sellers to frame value narratives using the Problem → Impact → Solution → Outcome model. This structure helps reps convey how your solution addresses a real business issue, what’s at stake, and what results can be expected.

Define each role’s contribution. Define how different customer-facing roles—account executives, solutions engineers, industry experts, executives—can support business engagement. For example, account executives may open the conversation, while executive sponsors join key meetings to elevate the relationship.

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4. Create Opportunities for Practice

“If you haven’t practiced the conversation, you’re practicing on the customer.”

Sellers build mastery not through reading alone but through doing. Enablement must create safe, supportive environments to build confidence and muscle memory.

Simulate the real thing. Regular role-plays and simulations should reflect actual business conversations, not just product pitches. Involve executives or line-of-business managers in rehearsals. Use common scenarios like "engaging a CFO resistant to new spending" or "aligning with a COO on transformation metrics."

Embrace new technologies. AI tools like Second Nature or Yoodli can simulate buyer conversations and provide coaching feedback. These tools offer scalable, low-risk environments to practice discovery, objection handling, and storytelling.

Encourage external exposure. Sellers who engage with industry forums, customer events, or professional groups gain credibility and insight. Consider incentivizing participation in conferences or panel discussions, especially for strategic accounts.

Create communities of practice. Internal peer groups, deal reviews, and value-focused Slack channels can foster knowledge sharing. Salesforce’s “Tribal Knowledge” forums or Microsoft’s “Industry Connect” calls are examples of how organizations create spaces for sellers to learn from each other.

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Final Thoughts: The Time to Start is Now

The truth is, no enterprise software company can be successful in the long term by selling only to IT.  Eventually, your sales success will depend on having sellers who can engage and deliver value to any line of business. 

But this is not a quick fix. Motivating and enabling sellers to engage the business is not a one-time training event; it’s an ongoing cultural transformation. The time to start this journey is now!

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