The SaaS Podcast: Founder Interviews - Page 16

Matthew Bellows, Yesware

The SaaS Distribution Channel That Drove 100% of Early Users

Matthew Bellows is the co-founder and CEO of Yesware, a sales platform that helps salespeople connect with prospects, track engagement, and close more deals. Yesware serves more than 750,000 salespeople at companies like Adroll, Groupon, Salesforce, Twilio, and Yelp. The company was founded in 2011 and is based in Boston, Massachusetts. To date, the company has raised over $35 million in funding. The Yesware story starts with a frustrating board meeting. Matthew was VP of Sales at a venture-backed startup, putting together his pipeline slide - the one every sales leader has to present showing deals expected to close. He realized he was basically guessing. The CRM industry, a $30 billion market, was built on salespeople manually typing data that nobody trusted. Matthew called his friend Cashman and said "software for salespeople." Cashman said "I can build that." They bootstrapped initially, not taking salaries. When they pitched investors, many said "that's not a category." But Matthew knew that was exactly the point - there was no software built specifically for individual salespeople. One early advisor, Jeremy Allaire, recommended they start with the Google Apps ecosystem instead of the much larger Outlook market. That focus on a smaller but more accessible SaaS distribution channel proved transformative. They built a Chrome browser extension and posted it in the Chrome Store. Within a week they had their first 100 users. Then hundreds per day started flowing in - all free, all organic. Yesware's breakthrough feature wasn't even their first idea. They launched with email templates, which got modest adoption. Then they added email tracking - applying newsletter-level open tracking to individual one-to-one emails for the first time. Engagement went through the roof and became the gateway feature for the product. The challenge came when they needed to convert those free individual users into paying enterprise customers. Matthew shares the difficult period when a 10-person sales team was struggling, what he changed to turn things around, and why he wishes he'd charged more and focused on a narrower target market from the start.

Kreg Peeler, SpinGo

How a Website Metric Sparked a SaaS Go-to-Market Shift

Kreg Peeler's first entrepreneurial venture was at age 12 - selling avocados at a busy California intersection with a cardboard sign. His SaaS go-to-market journey started in a similarly scrappy way, with a DVD containing 6,000 menus that he distributed through university bookstores. That DVD led to a website called Spin Local, which had a local events section. Kreg's wife Amanda manually curated event listings - digging up content from venue websites, correcting typos, and publishing comprehensive calendars. When they checked their analytics, 80% of all website traffic was going to that events section. That one metric changed everything. When newspaper companies tried to acquire Spin Local, Kreg countered with a licensing deal instead. He broke off the events section as a separate product called SpinGo and signed up media companies as clients who paid monthly fees for event content they could embed in their entertainment sections. SpinGo's SaaS go-to-market strategy evolved through three phases. Phase one was licensing event content to media companies and app developers. Phase two was promotions - letting event makers pay for premium placement, featured listings, and self-serve Facebook and Google ad campaigns. Phase three was Event Master, a full SaaS platform that unifies ticketing, marketing, volunteer management, and event apps into one solution. By 2016, SpinGo had grown to 200,000 registered event makers, powered 5,500 entertainment apps reaching 200 million monthly viewers, and raised over $7 million in funding. The Event Master SaaS product, launched in February, signed 254 events in its first few months and was projected to generate 80% of the company's revenue. Kreg's trade show strategy was particularly effective. He brought professional stage lighting, 80-inch TVs, and event production expertise to newspaper industry conferences where competitors showed up with pop-up banners. The visual contrast won attention, and his message - "own local, don't try to be national" - positioned SpinGo as an ally rather than a competitor.