Investors Back Siro To Support The Overlooked World Of Field Sales

Field sales has long been a blind spot for software innovation. While remote and digital sales teams have benefitted from an explosion of tools, automated transcriptions, real-time analytics, integrated CRM systems, sales reps on the ground have often been left behind, their customer conversations invisible and their coaching intermittent at best.

Siro, a startup built specifically for these in-person sales reps, is aiming to change that. On Wednesday, the company announced a $50 million Series B funding round led by SignalFire, with participation from 01 Advisors (founded by Dick Costolo and Adam Bain), Square Chief Product Officer Saumil Mehta, Squire founders Songe LaRon and Dave Salvant, former Yelp SVP of Engineering Michael Stoppelman, and former Snap VP of Engineering Ding Zhou. This brings Siro’s total funding to $75 million to date.

Siro was founded to serve a segment of the workforce often left out of the software boom: people who sell products in person, from home visits to job sites. The company’s mobile app captures sales conversations, transcribes them, and converts them into structured data that can be used to coach salespeople, share successful call examples, and provide insights into performance.

Jake Cronin, Siro’s founder, came up with the idea during college after selling Cutco kitchen knives door to door. He made decent money doing it and later opened an office to hire and train other sales reps. But he quickly realized the limitations of managing field teams without being physically present. Years later, after working at McKinsey, he began building Siro and coded the first version himself.

“A lot of sales work is manual, and good software could have a lot of value,” Cronin told TechCrunch. “The more I researched sales, I thought that the biggest opportunity here is not in data enrichment or customer relationship management, but it is in improving the lives of sales reps who are on the ground.”

Siro’s platform includes a company-wide dashboard that lets reps share successful calls, which others can sort based on peer engagement. Managers can use these examples to train their teams. Siro also builds custom models for different industries, such as HVAC, and uses broader models to assess how salespeople build rapport and respond to rejection.

Wayne Hu, a partner at SignalFire, said the investment was driven by Siro’s unique data advantage. “Siro’s solution is helping digitize the dark matter of offline conversations comprising field sales engagements. This has broad extensibility across verticals and depth in downstream actions that can be instrumented from this data, such as customer and product insights.”

Siro sees its approach as a departure from traditional B2B software sales. “Conventional wisdom says to serve the person with the money, like the VP of Sales, and everyone else is secondary,” the company wrote. “But we are building for the sales rep, because we’ve been there.”

According to the company, customers using Siro have seen measurable results. Close rates have improved by 36 percent, coaching cycles have become 10 times faster, and rep turnover has dropped by 30 percent.

But the company emphasizes the human impact behind those numbers. Jennifer in Austin closed $140,000 in her first week after struggling for years with traditional training. Nick, once on the verge of being fired, now tops the leaderboard and is saving for a home. A Utah-based manager who used to spend two months a year away from his family now coaches his team remotely using Siro and was able to be home for his daughter’s birth.

One rep recalled receiving a 75-cent paycheck during the slowest stretch of his career. He was on a performance plan and expected to be let go. But with renewed focus on learning, he became the top performer in his office within months, paid off his debt, and is now putting a down payment on a home.

“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,” the company said.

These stories reflect a larger mission. Siro is not built for the sales executive alone but for the rep on the ground who often lacks the tools needed to succeed. The company believes that technology should make coaching more abundant and accessible, helping people succeed in careers that often change lives.

“For the first time, in-person sales pros will have access to the kind of technology that usually gets reserved for desk workers and they’ll get it first,” the company stated.

Revenue has grown more than tenfold over the past year, largely driven by referrals. With the new funding, Siro plans to expand its engineering, product, customer success, and sales teams. The company is investing in research and development to add new features like adaptive coaching and predictive performance insights.

The broader goal is to bring real support to a part of the workforce that’s long been underserved by technology. “I founded Siro because I know what this kind of job can mean,” Cronin wrote. “That job taught me how to communicate, how to handle rejection, and how to bet on myself. Our vision is to make that path more accessible and more effective for millions of people in the field.”