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Letter from the CEO: Announcing Siro’s Series B

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Sales Enablement
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Jake Cronin
Co-Founder & Co-CEO of Siro
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May 21, 2025
Letter from the CEO: Announcing Siro’s Series B

Today, I’m proud to share that we’ve raised a $50 million Series B, led by SignalFire, with participation from our existing investors.

This round is more than a financial milestone – it’s a vote of confidence in a part of the workforce that’s been underserved for too long. While tech has raced ahead for remote work and digital sales, the people selling in person have largely been overlooked. This raise is a step toward changing that.

Why we started Siro

We built Siro for the reps and managers who sell face-to-face – at the kitchen table, on the front porch, in the showroom, or on the job site. While inside sales teams have tools that track every call and email, in-person teams have historically been left in the dark. No Zoom recordings. No call summaries. No safety net.

Siro gives them visibility for the first time. Our mobile app captures real customer conversations, turns them into structured data, and delivers insights that help reps close more, managers coach better, and companies grow faster.

Already, sales teams using Siro have seen:
- 36% higher close rates
- 10x faster coaching cycles
- 30% lower rep turnover

But the most meaningful results aren’t metrics. They’re lives changed.

The impact on the ground

Our customers, whether they’re reps, managers, or owners, consistently show us what’s possible when the right tools are in their hands. Their stories are what keep us moving. Jennifer in Austin closed $140,000 in her first week – after years of struggling with training formats that didn’t work for her learning style. Nick went from nearly being fired to the top of the leaderboard, and is now saving for his first home. Eric, a 20-year veteran of door-to-door sales, told us that Siro gave him something even more valuable than insight: time back with his family.

One rep told us he received a 75-cent paycheck during the slowest stretch of his career. He was on a performance plan and expected to be let go. But he doubled down – not just on effort, but on learning. He became the #1 rep in his office just months later, paid off his tax bill, and is now putting in a down payment on a home.

Another manager, based in Utah, used to spend two months each year away from home riding along with reps on the East Coast. Now, with Siro giving him full visibility into team performance, he’s coaching effectively from home and was able to be there when his newborn daughter came into the world.

There are hundreds more stories like these. Stories of pride, second chances, upward mobility, and financial security where there wasn’t any before. They’re happening across industries and across the country. We don’t take credit for these outcomes. We just built a tool that helps hardworking people get better and we’re doing everything we can to make that tool more powerful every day.

What this funding makes possible

This raise will let us move faster and dream bigger. We’re investing deeply in R&D to bring leapfrog improvements to the product. What’s coming next will feel like science fiction – adaptive coaching, predictive insights, and real-time visibility into what’s working across your team.

For the first time ever, in-person sales pros will have access to the kind of cutting-edge technology that usually gets reserved for desk workers – and they’ll get it first.

We’re also expanding the team across engineering, product, customer success, and sales. If you want to build cool technology for real people, please reach out.

Our mission is personal – and just getting started

I founded Siro because I know what this kind of job can mean. When I was 18, I sold Cutco kitchen knives. I was a college student trying to make extra money, but I ended up learning far more than I expected. That job taught me how to communicate, how to handle rejection, and how to bet on myself. It also showed me that sales–especially in-person sales–can change the trajectory of someone’s life.

Our vision is to make that path more accessible, and more effective, for millions of people in the field.

And one day, we hope to hear from even more reps who say:
- Siro helped me pay off my credit card debt.
- Siro helped me afford a home.
- Siro made me proud of what I do.

A final thank you

To our earliest customers – thank you for believing in us when we were just an idea.

To our team – thank you for building a product that’s worthy of the people we serve.

To our investors – thank you for believing in our vision.
And to the reps out there, working hard and betting on themselves every day – we’re building for you.

This is what drives us. This is why we’re here. And this is just the beginning.

– Jake

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Best,
Jake Cronin & Joseph Jordan
Co-CEOs, Siro.ai
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