Flow’s Two-Year Cold Email Failure: What Changed in 14 Days to Generate Deals

Flow’s Two-Year Cold Email Failure: What Changed in 14 Days to Generate Deals

In a recent episode of Category Visionaries, Sivan Iram, CEO and Founder of Flow, shared a story that most sales leaders don’t want to admit: they spent two years failing at cold outreach before finally figuring it out.

The results from their early campaigns were brutal. “The first two attempts, which happened two years ago and last year we got zero conversion from, you know, a large number of emails,” Sivan recalls.

Not low conversion. Not disappointing numbers. Zero. Hundreds of emails sent to insurance brokers who fit their ideal customer profile. Zero responses that turned into business.

Then, two weeks before the podcast interview, something changed. A campaign to just a few hundred prospects generated bound deals—actual revenue—within days. Same industry, same target audience, same basic value proposition. But two specific changes made all the difference.

The Failed Campaigns

Flow’s first attempts followed the standard playbook. Build lists of retail insurance brokers. Craft pitches explaining value. Send emails at scale.

“We’ve not been able to do it successfully in the past and that is to do cold calls and cold emails,” Sivan admits. “We tried twice, two separate, different ways. It did not work.”

Complete radio silence from a market that supposedly needed what they offered. Most companies would conclude cold email doesn’t work for their industry. Better to focus on referrals and warm introductions.

Flow could have drawn that conclusion. Instead, they waited. And the waiting turned out to be the key.

What Changed: The Sender

The breakthrough came from a simple change: who the email came from.

“Instead of coming in from a generic company email, we addressed it from our existing brokers and it is still very much a relationship driven business,” Sivan explains. “And, you know, having it to the face of a person really does matter.”

This wasn’t about better subject lines or copy. It was about credibility. An email from info@flowspecialty.com is a cold pitch. An email from an actual broker at Flow is a colleague reaching out.

In relationship-driven industries, the distinction is everything. A name recipients don’t recognize triggers skepticism. A fellow broker’s name signals real insurance professionals work there.

This only works if you have brokers to send from. Which reveals the deeper lesson: Flow’s early campaigns failed partly because they didn’t yet have the credibility to make them work.

What Changed: The Message

The second change was harder to isolate because it came from experience, not experimentation. Flow learned to articulate their value clearly—but only after finding product-market fit.

“I think we learned how to communicate our value in a more concise, articulated way. We found our voice in the past year,” Sivan shares. “We have a much crisper, clearer, better elevator pitch. Whether I meet you in the elevator or whether I send you a cold email, we see better conversion numbers because we can tell the story, we distilled the value better.”

This clarity didn’t come from better copywriting. It came from abandoning their platform, rebuilding around email, serving hundreds of customers, and learning exactly what made brokers switch.

Early campaigns pitched a vision. The successful campaign pitched a proven solution to a felt problem: traditional wholesalers ghosting small accounts for weeks.

You can’t fake this message clarity. It only comes from deeply understanding what customers value because you’ve delivered it repeatedly.

The Prerequisite: Product-Market Fit

Here’s the uncomfortable truth: cold outreach doesn’t work until you’ve earned the right to use it.

You earn that right through product-market fit. Through having customers who genuinely love what you do. Through understanding your value so deeply you can articulate it in a sentence. Through having proof that overcomes skepticism.

Flow’s journey between failed and successful campaigns included pivoting their entire model, finding product-market fit, tripling revenue for nine months, building a team of credible brokers, and refining their message through hundreds of conversations.

“This exercise last week, I think it was only a couple of hundreds of people and we already got already bound deals based on the replies, people started sending a submission,” Sivan reports.

Those deals didn’t come from better tactics. They came from having something worth buying, delivered by people prospects could trust, described in terms that resonated because they were true.

The Low-Friction Trial

The third element that made Flow’s cold outreach work wasn’t about the email at all—it was about what happened after someone responded.

“The barrier to entry, the barrier to try us out is incredibly low. People just need to send us a submission and see the magic happen. We don’t need any appointments, we don’t need any agreement signed,” Sivan explains.

This matters because cold email doesn’t need to close a complex sale. It just needs to get someone to try you once. Flow’s ask isn’t “let’s schedule a demo” or “can I show you our platform.” It’s “send us one submission and see what happens.”

The call-to-action matches the channel. Cold email to strangers shouldn’t ask for high commitment. It should ask for the minimum viable step that lets your product prove itself.

The Broader Lesson

Flow’s evolution reveals something important: channels don’t fail because the channel is bad—they fail because you haven’t earned the right to use them yet.

Many B2B companies give up on outbound after early failures, assuming it doesn’t work. What they’re experiencing is the cost of selling before they have product-market fit, message clarity, or credibility.

The pattern repeats: content fails until you have insights, paid ads fail until conversion is optimized, partnerships fail until you’re valuable enough, cold outreach fails until you can credibly represent value.

Flow spent two years between campaigns. But those years weren’t wasted—they were necessary. They needed time to build the product, find the fit, refine the message, and hire credible people.

The lesson isn’t “cold email works if you do it right.” It’s “cold email works when you’ve earned the right to use it by building something genuinely valuable and learning to articulate why.”

For founders frustrated by failed campaigns, Flow’s journey offers both reassurance and challenge. The reassurance: it’s not the channel’s fault. The challenge: the channel will keep failing until you fix the fundamentals.

Build the product. Find the fit. Refine the message. Hire people who can represent you credibly. Lower the barrier to trial. Then try again.