The Management Style of a $13.5B SaaS CEO

Presented by GOTO Market Institute

Hey SaaS Sentinel reader. Welcome back. This week, we’re looking at viable alternatives for founders who are struggling to stay funded, how a 13.5 billion dollar CEO runs his company, and why some founders should consider against building a best-in-breed point solution for their next venture.

• Selling a startup in an ‘acqui-hire’ is more lucrative than it seems, founders and VCs say

• The hands-on management style of a $13.5 billion dollar tech CEO

• Why this founder believes that “point solutions” are the wrong way to build a SaaS company

Struggling to stay funded? Here’s why you may want to get “acqui-hired”

When times get tough and fundraising dries up, most startup founders facing the end of their runway have two options—shut down or sell. And while selling may seem like admitting defeat compared to dreams of building a unicorn, getting acqui-hired can actually be a lucrative path according to many in the startup world.

Take it from Nivas Ravichandran. He was one of the first employees of the marketing startup Frilp when it was acquired by Freshworks in 2015. At the time, it felt disappointing—they had their sights set higher. But Nivas shares, "Acquisitions are a great opportunity from a financial standpoint. If you come in via an acquisition, the pay and equity are better than if you join as a lateral hire."

How so? Buyers will often give startup teams leapfrog promotions. Founders can go directly into senior principal engineer roles despite having way less experience than industry norms. And multiple directors or VPs from recent acqui-hires share they reached leadership levels it could have taken 5-10 years to attain otherwise.

Comp deals reinforce the appeal too. Unlike standard M&A where investors see returns, the latest acqui-hire terms focus on talent retention. Freshworks and others structure deals with founder salaries and back-loaded equity vests to keep entrepreneurs engaged for 2+ years post-sale.

So while giving up independence isn't easy, acqui-hires can unlock career growth and leadership opportunities that just aren't accessible for early-stage operators. As Nivas discovered, they also sometimes lead to rewarding long-term homes. Despite early skepticism, he and his co-founders stuck around Freshworks for 5+ years after the sale, playing key roles in its 2021 IPO.

You can read more about Nivas’s experience being “acqui-hired” in the full article below.

Read more.

The old marketing playbook is dying

Customer acquisition costs are rising. Marketing teams are cutting headcount. And the old tried-and-true marketing tactics just won’t cut it anymore.

If you want to win in today’s market, you need a proven playbook.

GOTO Market Institute’s founders built tech companies worth over $8 billion, and they’re finally spilling their secrets. With over 10 masterclasses, 50 implementation tools, and a real-world approach, you can elevate your team, outperform competitors, and maximize your revenue growth.

Want to improve the performance of your marketing efforts? Get the training below.

Our newsletter subscribers get an exclusive 10% discount! Use code SENTINEL

The hands-on management style of a $13.5 billion dollar tech CEO

Take it from Rippling's Parker Conrad—if something's not working at your company, CEOs need to obsess over the root issues themselves.

Despite leading a high-growth 13.5 billion dollar company with thousands of employees, Conrad still approves every expense report and runs payroll using Rippling's own HR software. He says it keeps him close to the customer experience and funnels product feedback straight from the top.

But Conrad takes a hands-on approach well beyond dogfooding in practice. If sales or support face problems, he'll personally review recent calls and even "work as a rep" for days to pinpoint solutions. Conrad dubs it collecting "anecdotal data" versus detached dashboards.

The Rippling founder also eschews the common wisdom of delegating your weak points to specialized hires. He argues that founders should instead "bear hug" headaches outside their comfort zone. Says Conrad, "The things you hate...that's where you should spend all your time."

In other words, don't pawn off pain points because they're unfamiliar or simply uncomfortable. 

Battle through frustrations firsthand to understand how they hinder the company. As Nobel laureate Bob Dylan famously penned, "When you ain't got nothing, you got nothing to lose." What weaknesses or blindspots could be holding your startup back from its purpose?

You can learn more about Parker’s hands-on management style in the full article below.

Read more.

This founder believes that “point solutions” are the wrong way to build a SaaS company. Here’s why.

Serial entrepreneur Parker Conrad is calling bull on the classic advice given to software startup founders. You know, niche down and just solve one specific customer problem? According to Conrad, that approach has actually led the software industry astray for the past 20 years.

As founder and CEO of red-hot HR platform Rippling, Conrad believes over-specialization has created mass customer frustration. As businesses have to juggle "100 different pieces" of narrowly focused software, efficiency and experience take a major hit.

Instead, Conrad advocates for building integrated platforms that combine capabilities and data structures right from the start. At Rippling, that means tying together everything from payroll and finance to IT management and apps. While it may sacrifice a startup’s initial focus, Conrad says this unified foundation allows for better pricing, user experience, and sticking power when competitors abound.

Conrad's big swing approach looks increasingly shrewd as solo-utility startups consolidate under budget pressure. VCs now prefer "moat"-building platforms over niche tools facing copycats. And similarly, many enterprises favor simplicity over purchasing best-of-breed point solutions.

Whether you fully buy into Conrad's thesis or not, it just goes to show that there are many alternate paths to running a successful software business. Rather than constrict capabilities, carefully expanding horizons may unlock the most customer value long-term. Because there's more than one way to pave the road to scalability and saturation.

Read more.

Parting Thoughts

Well, that’s the tech news for this week. Hit reply and let us know—did you learn something from today’s newsletter?

Until next time!