#119: Strategy Roles In Start-Ups Are Bullsh*t, How To Launch Payroll in 53 Days, Stripes Annual Report
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One vSaaS Breakdown:
Strategy Roles In Start-Ups Are Dumb
My friend Chris posted the below on X:
Startup Strategy is Mostly Stupid.
A smart, consulting friend called me looking for a job in startups.
Me: "let's go! what are you looking for?"
Him: "Something in strategy around Series A stage."
Me: "You know strategy is a useless job in startups right? Nothing matters outside of writing code and selling."
Him: "But I can't code so I need to do sales?"
Me: "Yes or you're useless to the company. No one cares about pretty pitch decks in a startup... or if they do, you're in the wrong place."
This sounds harsh. And he easily could think... "look what do you even know anyway?" But to me strategy is the most bullsh*t overused word in startups.
Strategy is what MBAs talk about in fake startup classes. Early stage "strategy" is the 30 minutes you spend on a sunday night talking to your co-founder ahead of a crazy week of execution ahead.
Strategy is anti-execution. And it's a luxury for post product-market fit companies with money printers. But for everyone else, hiring for strategy is an easy way to guarantee failure.
I followed up by saying…
“Agreed. I also think strategy jobs are kind of bullshit even post product market fit. Job of CEO and his close confidants. Hiring someone to do strategy that isn’t the ceo and or the founder makes zero sense to me.”
The conclusion here is that if someone wants to do "strategy" at your start-up OR if your start-up is hiring for someone to do "strategy"
RUN FOR THE HILLS.
One ‘How To’:
How To Launch Payroll In 53 Days
If you’ve been around the newsletter before - we’re a big fan of embedded offerings to juice your revenue, retention, and total addressable market. Today, I wanted to make it more actionable - and study a company that was able to launch embedded payroll in only ~2 months.
Launching a payroll solution is notoriously complex. Traditionally, companies had three options: build their own payroll system, acquire an existing provider, or integrate with a third-party solution—each with significant trade-offs. Creating a fully custom, seamless experience meant building from the ground up, a process that could take years and cost millions.
But Playground—a child care management platform—took a different approach. Instead of spending years developing payroll infrastructure, they launched an embedded payroll product in just 53 days—with a single engineer and only 250 hours of development time. By embedding payroll directly into their platform, Playground eliminated tedious data entry, disconnected tools, and manual processes, giving child care providers a seamless, all-in-one solution.
Here’s how they did it—and how you can too.
Playground’s Path:
Playground built a child care management platform to help businesses like daycare centers and preschools handle scheduling, attendance, parent communication, and staff management. However, payroll remained a major pain point. Providers relied on outdated payroll systems that required multiple logins and data transfers, creating a frustrating and inefficient experience.
“We had been receiving inquiries about payroll for months. Our customers need a streamlined solution that fits within their existing workflows"
—Daniel Andrews, CEO and Co-Founder, Playground
As a lean startup, building and buying payroll were out of the question. Playground didn’t have years to develop or millions to invest, so they needed to take a partnership approach.
At first glance, the classic integration model with third-party payroll providers seems like the quickest and easiest solution. However, this approach has several major drawbacks: customers still need to switch between logins, manually sync their data, and deal with rigid workflows that don't align with industry-specific needs, which would make it harder to differentiate Playground’s offering for their customers.
To offer a seamless experience, Playground chose to embed payroll directly into their platform using an embedded payroll provider, Check. This decision allowed them to deliver a native payroll experience that acted as a natural extension of their platform, connecting directly with their existing scheduling, time tracking, and PTO requests.
With Check Components, Playground dramatically reduced development time while ensuring full compliance. Check’s infrastructure provided:
Money movement & risk management – Prebuilt payment rails for tax deposits and employee payments eliminated the need for custom infrastructure.
Automated tax filings – Check handled all federal, state, and local tax compliance.
Pre-built employer & employee onboarding – Check provided seamless onboarding flows for businesses and workers.
Payroll processing engine – Instead of building a custom payroll calculator, Playground used Check’s proven engine to ensure accurate withholdings across taxes, benefits, and other deductions.
By leveraging these tools, Playground launched native payroll in just 53 days—a timeline that would have been impossible before embedded payroll – and plan to follow the same playbook to expand their offering with embedded insurance, benefits, and retirement planning to further increase their platform’s value.
Takeaways: How to Build New Business Streams, Fast
Playground’s success shows that launching new products doesn’t have to take years. By leveraging embedded solutions like Check, companies can go live in weeks without sacrificing their quality or compliance.
If you’re looking to build new revenue streams for your Vertical SaaS business, follow Playground’s path:
Identify a Pain Point – Listen to your customers.
Go Embedded – Build a native solution instead of relying on third-party integrations.
Leverage Pre-Built Components – Existing infrastructures reduce development time.
Move Fast with a Lean Team – Playground launched with just one engineer.
Focus on your MVP, Expand Over Time – Start with essentials, then build upon success.
With the right approach, launching a new products – like payroll – can be relatively simple.
One Biz Story:
Stripes Annual Report
Stripe's annual report cited 60% of small businesses in the U.S. are using Vertical SaaS to process payments.
That means that roughly half of U.S. businesses still aren't.
So.
Much.
Opportunity.
What are you waiting for?
Check the full report out here.
Have a product or service that would be great for our audience of vertical SaaS founders/operators/investors? Reply to this email or shoot us a note at ls@lukesophinos.com