Enterprise deals are intricate, lengthy, and require navigating numerous challenges, but they don't have to be insurmountable.

During our recent webinar, Adam Baker, CEO of Dealpad, and seasoned deal coach Mark Phinick shared strategies and stories to empower sellers and champions alike. Whether you joined the live session or missed it, here’s a rundown of the actionable insights and compelling examples discussed.

Key Takeaway #1: The Power of Understanding the "Why"

Mark underscored the importance of understanding not just why a company needs your solution but why now. Without a clear grasp of the business problem your technology addresses and the urgency driving the decision, deals are more likely to stall.

One of Mark's clients had been courting a company for months. The deal was slated for next quarter, but the rep discovered that their solution could save the organization $10 million annually. The catch? A gatekeeper was blocking access to key decision-makers. Taking a calculated risk, the rep reached out directly to the stakeholder most affected by the potential savings. Within hours, that person took action, fast-tracking a deal originally forecasted for months later.

Know your stakeholders’ pain points and speak to the people who have the most to gain from solving the problem.

Key Takeaway #2: The Importance of Coaches and Champions

Enterprise sales often hinge on relationships. A strong champion can open doors, but without a coach—someone who trusts you, wants you to win, and understands their organization’s inner workings—your deal might lack the necessary momentum.

Mark shared a memorable experience where a competing vendor tried to undercut his pricing by contacting senior executives directly. Despite this move, Mark's coach—a mid-level manager—advocated for him internally. Their loyalty and trust were pivotal in securing the deal, proving that fostering genuine relationships with coaches can withstand external pressures.

Coaches and champions play distinct but complementary roles. While champions rally for your solution, coaches guide you through the organizational maze.

Key Takeaway #3: Value Over Product Features

It’s easy to focus on the bells and whistles of your product, but enterprise buyers care about outcomes. Mark and Adam emphasized tailoring your pitch to the specific outcomes that matter to different stakeholders.

Adam recalled working with a $5 billion conglomerate. While his team initially engaged a small subsidiary, they later uncovered a massive $30 million compliance issue at the parent level. By elevating their conversations and demonstrating the value of their solution to top executives, they expanded a modest $15k ACV deal into a $9 million enterprise contract.

Different stakeholders have different definitions of value. Take the time to understand and address each one’s unique goals.

Key Takeaway #4: Mutual Action Plans (MAPs) Are Essential

Mark described MAPs as a "treasure map" for buyers and sellers. These collaborative plans outline clear actions, owners, and deadlines to ensure deals stay on track—even when internal changes occur, like champions leaving or organizational priorities shifting.

Mark highlighted how a MAP helped a rep maintain deal momentum when their champion was promoted out of the organization. The plan provided continuity, allowing the buying team to pick up where the champion left off.

A well-maintained MAP not only keeps deals moving but also creates transparency and alignment between you and your buyer.

Key Takeaway #5: Empathy Drives Enterprise Sales Success

Adam and Mark emphasized the importance of empathy—understanding the customer’s journey, their challenges, and their aspirations. This extends to building relationships that are based on trust and respect.

In one example, Mark helped a university system streamline its operations. His approach wasn’t about pushing a product but about genuinely understanding the administrators’ daily struggles and aligning his solution to alleviate their pain points. His effort led to strong relationships that translated into long-term partnerships.

Empathy isn’t a “soft skill”; it’s a competitive advantage in enterprise sales.

Wrapping Up

Mark left us with one profound observation:

"Enterprise sales happen when we stop selling and start collaborating."

Helping champions buy isn’t just about selling software—it’s about partnering with your buyers to solve their biggest problems and achieve their most ambitious outcomes.

For those of you racing to close deals this quarter, we hope these insights provide the clarity and inspiration you need. If you’d like more tips or hands-on deal coaching, reach out to Adam or Mark—we’re here to help.

Here’s to smashing your sales goals!

Resources

This webinar is sponsored by dealpad, an AI tool that gives sales reps insights into how buyers are interacting in the process and recommendations to action to fill gaps and know where to focus time. 🕰️

With Dealpad, you'll be able to let your buyers work with you in a way they like to buy, whilst having full control and visibility of how the buying team are engaging. 📈

Watch the full webinar recording here:

For more information about Adam and dealpad:

Adam Baker: https://www.linkedin.com/in/adamlbaker/

Dealpad: https://www.dealpad.io/

For more information about Mark and Let's Make It Rain:

Mark Phinick: https://www.linkedin.com/in/markphinick/

Let's Make It Rain: https://www.letsmakeitrain.net/