“A Back Alley Brawl Every Time”: How Socially Determined Navigates 15-Month Enterprise Sales Cycles

“A Back Alley Brawl Every Time”: How Socially Determined Navigates 15-Month Enterprise Sales Cycles

When your typical sales cycle stretches past 450 days, every deal becomes a test of endurance. In a recent episode of Category Visionaries, Trenor Williams shared how Socially Determined navigates marathon enterprise sales cycles while building a new category in healthcare analytics.

The Reality of Enterprise Sales

“It is a back alley brawl every single time,” Trenor explains. “The average sales cycle was twelve to 15 months. I would say since the pandemic, it’s gotten even longer.” This extended timeline isn’t due to technology resistance but rather what Trenor calls “the tyranny of the urgent” – the constant firefighting that prevents healthcare organizations from implementing new solutions.

Building Beyond Founder-Led Sales

The company’s journey to scale required moving beyond founder-led sales. “This year we turned over and really doubled down on a new sales team,” Trenor shares. They brought in dedicated leaders for their two primary markets – payer and life science – recognizing that different segments required specialized approaches.

The Customer Story Strategy

In healthcare’s risk-averse environment, customer success stories become crucial sales assets. “In healthcare, most people are risk averse, most people don’t want to go first,” Trenor notes. Their breakthrough came when one customer expanded from 160,000 members to 3.2 million members across 14 teams. This story became their most powerful sales tool.

The Multi-Channel Approach

To support their long sales cycles, they developed a multi-channel market presence:

• Conference strategy: “32 conferences that we’ll go out and speak at, half of those this year”
• Customer advocacy: Getting “customers and partners to be able to tell the story”
• Strategic partnerships: “We can be the brains, but we have to have the arms and legs for our insights to be effective”

The Partnership Philosophy

Enterprise sales success came from focusing on relationships over tactics. Drawing from his early mentor, Trenor shares a crucial insight: “100% client reference ability for over a decade… if you do that right, you’ll figure out the money part.”

Evolving the Sales Process

Today, Trenor’s role has shifted: “I am much less involved. I still probably get involved in most deals. I still end up telling the story. What’s nice is I’m not running a lot of the commercial process in that sale, as opposed to, again, it’s more you up building than anything else.”

Lessons for Founders

For founders navigating extended enterprise sales cycles, Socially Determined’s experience offers key insights:

1. Accept the timeline reality but build systems to support it
2. Let customer success stories do the heavy lifting
3. Build presence across multiple channels
4. Focus on relationships over quick wins
5. Create systematic processes that work without founder involvement

The path to shortening these cycles? Trenor suggests focusing on faster customer adoption: “I would invest earlier in getting faster customer adoption, to try more things out at lower cost, just to test the market and worry less about any early revenue and more about established use cases and valued propositions as fast as we could.”

For founders selling to enterprise customers, especially in regulated industries, these extended sales cycles are often unavoidable. The key isn’t trying to dramatically shorten them but rather building a business that can thrive despite them.