Complex deals are everywhere in sales. Whether you’re closing enterprise contracts or navigating a crowded buying committee, every deal feels more involved, more competitive, and loaded with bigger risks and bigger rewards.
“It’s important to understand why a complex deal is different.” —Meridith Elliott Powell
This week on the Sales Logic Podcast, Mark and Meridith break down the essentials for winning these multifaceted sales, from recognizing when you’re in a truly complex deal to building relationships that sustain momentum.
Recognizing Complexity Early
Complex deals involve longer sales cycles, more stakeholders, and often new players emerging deep into negotiations. If you’re seeing timelines stretch, new decision-makers join the conversation, or legal and procurement appear, you’re in complex territory.
“You’ve got to begin developing those relationships long before you need them.” —Mark Hunter
The panelists stress it’s crucial to recognize when complexity enters the picture. It’s not just about dollars or contracts—it’s about mapping every stakeholder, decision-maker, and the unique risks they face.
Building Relationships and Finding Your Coach
In complex sales, relationships are your superpower. Every stakeholder has a different motivation. Sometimes your champion isn’t enough; you need a coach inside the organization who has experience running similar projects and the influence to help you navigate procurement, legal, and other departments.
“Work with your coach or your champion and try to figure out who the players are so that you can do your research on those players.” —Meridith Elliott Powell
These internal allies help you maintain control, reinforce your value proposition, and ensure you’re not blindsided by unknown requirements late in the process.
Visibility and Value Matter
Complex deals often spark competitive RFPs. Simply being “known” can tip the scales. Building visibility through LinkedIn, sharing valuable content, and letting every member of the buying committee recognize your name build credibility.
“Customers only buy when they have confidence. And the last thing anybody wants to do is make a buying decision that makes them look stupid.” —Mark Hunter
If you weren’t involved in helping write the RFP, your chances of winning aren’t great—so focus on relationships and positioning yourself as a trusted, confident solution-provider.
Trust Your Sales Gut—And Know When To Walk Away
Not every slow-moving deal is dead, but you have to trust your intuition. Is your main contact connecting you with others? Are you receiving proprietary information and NDAs? If not, it may be time to move on.
“The moment you say yes to one prospect, you have said no to another.” —Meridith Elliott Powell
Managing micro-commitments, understanding budget cycles, and clarifying ROI and criteria are all signals to watch. If there’s no forward movement—or it doesn’t fit your ideal customer profile—cut bait early and focus attention elsewhere.
Always Research, Always Build Relationships
Homework is non-negotiable in complex sales. Learn everything about the company, the buying cycle, and their challenges so you aren’t caught off guard by shifting stakeholders or surprise requirements. Relationships built ahead of time often make all the difference.
Lightning Round: 10 Sales Metrics You Should Track
- Win ratio: Deals closed versus opportunities.
- Wins versus qualified leads: Track the conversion from lead to prospect to close.
- Pipeline health: Have four to five times your monthly close amount in your pipeline.
- Number of conversations: Qualify what counts as a conversation and track them daily or weekly.
- Average deal size: Stay in your target price range, don’t win deals by giving them away.
- Percentage of repeat customers: Track customers coming back to you.
- Sales cycle length: Measure how long it takes to close a deal.
- Customer-facing time (CFT): Separate time spent between new prospects and existing customers.
- Number of deals lost: Maintain a healthy loss goal. If you aren’t losing deals, you may be underpricing.
- Adjustments after sale that reduce margin: Track changes that lower your margins post-sale.
Complex deals are challenging, but with the right strategies, relationships, and metrics, you can win and win well without sacrificing integrity.
Question: Anna from Ontario asks, “Love the show—not up that early on a Saturday, but my team and I catch it as a podcast. Here’s a question for you: how do you know if a deal is progressing slowly or it is dead and you need to walk away?”
Book: Integrity First Selling by Mark Hunter