2024 VSaaS Collective Live Summary

We recently hosted our first annual vertical SaaS conference, VSaaS Collective Live. Nearly 100 Vertical SaaS CEOs from around the world—flying in from Europe, Australia, LATAM, and all across the United States—gathered for a day of knowledge sharing and leveling up among like-minded peers. To our knowledge, this is the largest-ever event of its kind for the VSaaS industry.

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It was an incredible day that further reinforced our belief in the importance of Vertical SaaS. Over the next few weeks, stay tuned for more posts that share highlights from the day, but to give you a quick preview (and to encourage you to indicate your interest in next year’s conference), here are some quick snippets from each of our speakers:

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Leadership and Building Talent Density through Change

Chris Comparato, Former CEO of Toast

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As Chris helped build Toast into a multi-billion dollar company, he evolved as a CEO through many phases of change. He realized that different personas on the team are required at each stage–you can often categorize leaders into four main buckets: 1) Pioneers who have a founder mentality, are innovative, and are placing new bets, 2) Growers who are constantly testing, tweaking, and optimizing, 3) Scalers who build scaffolding and systems to help scale your business lines, and 4) Hardcore Hybrids who can simultaneously understand what will happen in the future, chart navigation for the company, and give directions across product, sales, and ops to all march towards that future.

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How to Create More Value with Embedded Payments and Finance

Neetika Bansal, Business Lead at Stripe, Josh Steinbaum, VP Finance at SimplePractice, and Andrew Walsh, Partner at Tidemark

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Embedding payments is only the start for a VSaaS company. Stripe did a study that found that “companies that embed financial services generate 11x more revenue than ones that only had embedded payments." Tidemark also found in its 2024 Vertical & SMB SaaS Benchmarking Report that companies that add payments as an offering saw greater Gross Revenue Retention and Net Revenue Retention.

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Embedded Ads: Turning Attention into Revenue

Stephen Howard Sarin, Former VP/GM of Retail Media at Instacart

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If you have a sufficient density of merchants and consumers on your platform, ads are an incredible business opportunity. However, the biggest decision to make is whether to build, buy, or partner with your own ad platform. For all but the largest companies, the right choice is to start with a partnership because the technology is harder than you think.

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The Power of Payroll: The Next Chapter for VSaaS?

Andrew Riesen, Co-founder and CEO of Heard

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‍Payroll is one of the most challenging products to launch. However, after extensive customer research, Andrew heard over and over again that his merchants wanted it. They partnered with an embedded payroll company to build payroll quickly and soon found that they had a 50% reduction in churn from merchants who used the embedded payroll functionality. Payroll may be one of the stickiest products a merchant can add to its mix.‍

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Achieving SaaS Success Without Big Funding

Greg Head, Founder, Practical Founders

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Greg is an advisor to 40 founders who are looking to scale their software businesses without taking on large amounts of funding. He covered six different tactics in-depth on how he’s seen folks scale successfully without large amounts of capital. One of these tactics was community building, where you can build a flywheel based on reference selling and word of mouth. The goal is to become known as the best in your market for something important to someone specific.‍

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Scaling GTM from $10M to $900M+ ARR

Dennis Lyandres, Former CRO of Procore

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The surprising answer to scaling GTM to over $900M in revenue? Training. “If you want to attract the best people, maybe you can try paying them top dollar, but that feels like a losing game. I have never had success that way. But, people know you care about them when you invest in training them.” Investing in your people is the best way to grow your business.

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Navigating the Multi-Product Journey to $100M+

Ershad Jamil, Former Chief Growth Officer of ServiceTitan

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The ease of going multi-product is one of the things that makes VSaaS companies so special. However, the sequencing really matters. You want to make sure that each successive product solidifies your advantage over a control point. “I think multi-product requires a phased approach. You don't have to do everything at once. You create a roadmap over the lifecycle of that product."

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We are grateful to our event partners Stripe, Silicon Valley Bank, Gusto, and Duda for helping make this event possible. If you would like to come to future events, please let us know here.

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