You always need an exit plan right? While you might not plan on selling your SaaS right away, these SaaS acquisitions can inspire you and show you what is possible.
In this post, we’re covering the biggest acquisitions of all time, plus some that don’t come near the billion dollar mark but can inspire your entrepreneurial journey even more.
We’re also sprinkling in ideas to help you see how these successes could translate into ideas and inspiration for your SaaS business. Don’t just make things up, model what others have done. Right? It’s always fun to play make believe.
In one of his email newsletters SaaS influencer Nathan Latka invites you do to just that. Let’s make believe that you are the founder of a SaaS company doing $20M in revenue. Would you sell for $200M? Nathan would, but the founder wouldn’t.
But that’s just a hypothetical question, of course. In order to actually be in that scenario, where you could decide whether or not you wanted to sell your business for a 9 figure sum, you have to build something the market needs.
You also have to plan beyond building a profitable online businesses. Getting acquired is neither simple nor fast, and it requires foresight across strategy, timing, and execution. Fortunately, there are excellent resources that provide expert guidance for founders navigating this path:
The $100 Million Exit by Andrew Gazdecki – on designing your company to achieve a high-value exit.
Exit Strategy by Rob Walling – on knowing your motivations and preparing your business for acquisition.
Before the Exit by Dan Andrews – on understanding the timing of a sale and the opportunities that follow.
Built to Sell by John Warrillow – on building a scalable, transferable company that can thrive without the founder.
The Art of Selling Your Business by John Warrillow – on packaging, positioning, and negotiating for the best possible deal.
Also, check out this post on how to vet your SaaS ideas before you build, and keep reading for SaaS acquisitions of humongous amounts and unknown sums.
Let’s kick off things off with the biggest. The age of the billion-dollar SaaS acquisition is well under way, and plenty have surpassed that threshold.
CyberArk - acquired by Palo Alto Networks for $25 billion
In one of the largest cybersecurity SaaS software sector deals to date, Palo Alto Networks announced the acquisition of CyberArk for approximately $25 billion. CyberArk, a global leader in identity security and privileged access management, brings a complementary layer of protection to Palo Alto’s portfolio of network, endpoint, and cloud security solutions.
The acquisition reflects the growing convergence of identity and network security, as enterprises seek unified platforms to defend against increasingly sophisticated cyber threats. For Palo Alto Networks, the deal expands its reach into identity-driven security, an area critical for zero-trust architectures. For CyberArk, the combination provides global scale, deeper integration into enterprise security stacks, and access to Palo Alto’s extensive customer base.
Key takeaways from this SaaS M&A transaction
Palo Alto Networks’ $25 billion acquisition of CyberArk highlights the rising strategic importance of identity in the cybersecurity ecosystem.
Identity-first security: CyberArk’s privileged access management expertise complements Palo Alto’s strength in network and cloud security.
Zero trust acceleration: The deal positions Palo Alto to offer unified platforms that align with enterprise adoption of zero-trust architectures.
Market consolidation: This acquisition reflects broader consolidation as enterprises seek fewer vendors with integrated solutions.
Scale and reach: CyberArk gains access to Palo Alto’s global distribution and customer base, accelerating its growth trajectory.
“Sometimes selling is less about what your company is today, and more about what the market is about to become.” — Before the Exit
This transaction shows how large-scale SaaS and security M&A is driven by convergence, integration, and market positioning for future enterprise demand.
Sendgrid - acquired by Twilio for $3B
On February 1 of 2019, Twilio completed their acquisition of SendGrid. It took a while to finalize because SendGrid was already public, and they had to pay shareholders and take the SendGrid stock off the market. The CEO of Twilio says that the company acquired SendGrid to “provide a complete platform for every form of customer engagement.” Essentially, now Twilio offers email in addition to SMS.
Key takeaways from this SaaS M&A transaction
This acquisition marked a turning point in the SaaS M&A market, especially within the communications API ecosystem. The deal highlights several key takeaways:
Expansion into email: Twilio added email to its core of voice, SMS, and video, becoming a complete customer engagement platform.
Enterprise positioning: Analysts highlighted the move as strengthening Twilio’s credibility with enterprise buyers.
Customer workflow consolidation: Clients like Zillow and Okta welcomed one vendor for omnichannel communication.
Cultural alignment: Both companies shared a developer-first approach, easing integration.
This acquisition illustrates how SaaS M&A transactions can create product completeness, enhance enterprise credibility, and drive stronger adoption by simplifying customer engagement.
Qualtrics - acquired by SAP for $8B
This acquisition took place in November of 2018, and it’s quite a high SaaS acquisition price. It led many in the enterprise software world to wonder...why did SAP pay that much to acquire a survey company? What were they hoping to gain?
The long and short of it is that this tool is in an emerging market called experience software, designed to get qualitative and quantitative feedback to help companies make even better products. With this purchase, SAP sees a huge opportunity in an enormous new market. Basically every startup and enterprise needs to do better at customer feedback so they can make outstanding experiences.
Key takeaways from this SaaS M&A transaction
SAP’s acquisition of Qualtrics reflected a growing recognition that customer experience management (CXM) data is as strategically important as operational data in enterprise SaaS. Several key takeaways stand out from this deal:
Union of X-data and O-data: Together, SAP and Qualtrics combined operational and experience data for deeper insights.
Strategic shift: SAP positioned customer experience management as a core growth driver.
Horizontal integration: Unlike SAP’s vertical acquisitions, Qualtrics applied across industries.
Go-to-market boost: Qualtrics gained SAP’s global reach to accelerate enterprise adoption.
Culture considerations: While cultural fit raised questions, leadership emphasized alignment.
“The art of selling a business well comes down to how you package it, the story you tell about it, and the feeling it gives potential buyers when they imagine owning it.” — The Art of Selling Your Business
This transaction shows how software M&A can expand market scope, strengthen positioning, and deliver value through complementary data and global distribution.
GitHub - acquired by Microsoft for $7.5B
Microsoft acquired GitHub so they could extend their cloud-native design-development-run ecosystem. Taking place in June of 2018, this acquisition was poised to help Microsoft continue to be the go-to company for software developers. Microsoft CEO Satya Nadella said, “Developers are the builders of this new era, writing the world’s code. And GitHub is their home.”
Key takeaways from this SaaS M&A transaction
Microsoft’s $7.5 billion acquisition of GitHub underscored how critical developers and open source have become to enterprise strategy and cloud competition. The industry reaction highlights several lessons:
Developer-first alignment: Microsoft positioned GitHub as central to its strategy of empowering developers and expanding its cloud ecosystem.
Strategic enterprise reach: The acquisition aimed to accelerate GitHub adoption in enterprises and link developers more closely to Azure.
DevOps validation: Industry leaders called the move proof that DevOps and open source collaboration are now essential to enterprise innovation.
Ecosystem expansion: Microsoft gained influence across the software delivery chain, from source control to cloud compute.
Competitive ripple effects: Competitors like Atlassian and GitLab reported spikes in migrations, showing how major SaaS M&A can shift market dynamics overnight.
Mulesoft - acquired by Salesforce for $6.5B
The purpose of Salesforce’s acquisition of Mulesoft was to allow organizations to easily synchronize data and increase the value of the applications they build on the Salesforce platform. It’s all about perfect connectivity, which is something Salesforce wasn’t able to offer on their own. The one-billion-dollar acquisition took place in March of 2018.
Key takeaways from this SaaS M&A transaction
The MuleSoft acquisition demonstrated how SaaS leaders will pay a premium for companies that deliver both strong financial performance and strategic technology value.
Premium valuation: MuleSoft commanded nearly 22x trailing revenue due to rapid growth, high margins, and improving cash flow.
Integration advantage: The deal gave Salesforce an “integration cloud,” enabling hybrid deployments and greater enterprise flexibility.
Strategic timing: MuleSoft was acquired while still on a strong growth trajectory, amplifying Salesforce’s ability to enter new markets.
“The most successful M&A transactions don’t just happen passively; they are achieved through hard work.” — The $100 Million Exit
This transaction shows how SaaS acquirers often stretch multiples when strategic fit and growth momentum align.
HotelNinjas - acquired by Booking Holdings for an unknown sum
Booking Holdings (Priceline and Booking.com) acquired HotelNinjas in 2014. The exact amount is unknown but estimates are between $10 and $20 million. HotelNinjas was a cloud-based property management system. The brand was completely absorbed by Booking.com and is used by hoteliers.
This is an inspiring story, because CEO and co-founder Avi Meir knew he was building something that could and likely would get acquired. He’s now building TravelPerk, which has gained over $100M in funding to date. When pressed, Meir maintains that he will likely not sell TravelPerk anytime soon, because the brand can stand all on it’s own and doesn’t need to be acquired to thrive or survive.
Key takeaways from this SaaS M&A transaction
Booking Holdings’ acquisition of HotelNinjas reflected the growing importance of SaaS platforms in the hospitality sector, where property management and booking tools must integrate seamlessly.
Expansion into property management: HotelNinjas offered hotels a SaaS-based property management system that complemented Booking.com’s reservation platform.
End-to-end ecosystem: The deal gave Booking Holdings the ability to cover both guest-facing booking experiences and back-office hotel operations.
Customer stickiness: By embedding itself into hotel workflows, Booking Holdings increased switching costs and deepened long-term customer relationships.
Market consolidation: The acquisition signaled SaaS consolidation in travel tech, where incumbents acquire specialized startups to strengthen their ecosystem.
Scout - acquired by Workday for $540 million
In December of 2019, Workday completed its acquisition of Scout, a cloud-based platform for strategic sourcing and supplier engagement. The goal of the acquisition was for Workday customers to expand and improve how they can plan, execute, and analyze spending in one solution. Essentially, procurement teams now optimize their spend even better, and work towards more transparency and efficiency.
Key takeaways from this SaaS M&A transaction
This acquisition strengthened Workday’s cloud ERP suite by addressing a key gap in procurement and strategic sourcing.
Filling product gaps: The deal added best-in-class sourcing to Workday’s procurement and inventory tools, completing its source-to-pay solution.
Strategic positioning: Analysts noted Workday’s push to be the end-to-end cloud back office provider.
Cultural alignment: Both companies emphasized shared values around customer focus and user experience, easing integration.
Portfolio strategy: Workday Ventures had previously invested in Scout RFP, reflecting a long-term vision.
“Once your business can run without you, you’ll have a valuable—sellable—asset.” — Built to Sell
This acquisition highlights how SaaS leaders use M&A to accelerate roadmaps, fill product gaps, and reinforce cultural fit.
Honey - acquired by PayPal for $4 billion
Acquired in November of 2019, Honey Science became PayPal’s biggest acquisition in its history of over two decades in business. While some analysts are still puzzled as to why PayPal bought Honey for that sum, one thing is clear: it proved that there is “immense value for consumers, merchants, and payment providers in virtual shopping assistants.” So if you’re thinking about building a new SaaS business and B2C doesn’t scare you too much, then maybe start there?
Key takeaways from this SaaS M&A transaction
PayPal’s $4 billion acquisition of Honey Science Corporation reflected the growing importance of consumer engagement tools in shaping e-commerce behavior.
Consumer experience expansion: Honey gave PayPal capabilities beyond checkout, enabling a full shopping journey with price tracking, coupon discovery, and deal alerts.
Merchant value: The integration allowed PayPal to increase sales for merchants by improving consumer engagement and loyalty.
User scale: Honey brought 17 million monthly active users and over $1 billion in annual savings delivered to shoppers.
Strategic growth: This acquisition positioned PayPal as more than a payments provider, strengthening its role in the broader e-commerce ecosystem.
AnsweriQ - acquired by Freshworks for an unknown sum
We don’t know how much Freshworks paid to acquire AnsweriQ, but we do know that Freshworks is currently valued at $3.5 billion and has over 150,000 customers and 2,700 employees. Both of the AnsweriQ co-founders will now join Freshworks. In fact, all 20 of their employees will now join Freshworks. The company’s platform helps automate customer service responses such as cancelled orders.
They’re working towards bringing bots and humans together, so that bots can “gracefully handoff” cases to the human support staff. That sounds like a really smart move.
Key takeaways from this SaaS M&A transaction
Freshworks’ acquisition of AnsweriQ expanded its AI-driven customer engagement capabilities while strengthening its move up-market.
Complementary technology: AnsweriQ’s AI/ML tools fit neatly into Freshworks’ Freddy AI engine.
Talent and leadership: The acquisition added experienced executives, with AnsweriQ’s CEO becoming Freshworks’ chief customer officer.
Market expansion: AnsweriQ’s enterprise customer base opened new opportunities without overlapping existing accounts.
Strategic timing: Facing a funding decision, AnsweriQ chose integration over independence to accelerate adoption and scale.
“The most important thing you can do is understand your reasons for selling—whether you’re being pushed out or pulled toward something new.” — Exit Strategy
This acquisition underscores how timing and strategic alignment often drive SaaS M&A outcomes.
Movere - acquired by Microsoft for an unknown sum
In September of 2019, it acquired Movere, a SaaS company that helps customers plan and execute cloud migrations as well as to optimize and monitor various IT environments. Presumably, this purchase will help Azure cloud to better compete with Amazon AWS. The acquisition complements Azure Migrate and helps make a cloud migration easier for Azure’s customers.
That’s a smart SaaS idea...build a product that it will make it easier for a SaaS company to get customers to migrate from a competitor!
Key takeaways from this SaaS M&A transaction
Microsoft’s acquisition of Movere highlighted the strategic importance of simplifying cloud migration as enterprises accelerate their shift to the cloud.
Enhancing Azure Migrate: Movere’s discovery and assessment tools strengthened Microsoft’s ability to support seamless migrations.
Customer transformation focus: The deal reinforced Microsoft’s positioning of cloud migration as a driver of business transformation.
Proven partner relationship: Movere had been a long-time Microsoft partner, easing integration and trust with shared customers.
Market competition: The acquisition responded to demand for migration tools amid competition from Amazon and Google.
This deal reflects how SaaS acquirers often use M&A to close tactical product gaps in fast-growing markets.
Onshape - acquired by PTC for $470 million
Onshape is the “first Software as a Service (SaaS) product development platform that unites robust computer aided design (CAD) with powerful data management and collaboration tools,” according to this press release. Onshape helps designers and developers work together to greatly reduce the time to market for any new product. This acquisition marks the first step in PTC’s plan to produce a recurring revenue model.
Key takeaways from this SaaS M&A transaction
PTC’s $470 million acquisition of Onshape marked a pivotal moment in the CAD and PLM industries as they began their transition to SaaS delivery models.
Industry shift: Onshape was the first SaaS-native CAD and product development platform, positioning PTC for leadership as the market moved away from on-premises tools.
Recurring revenue growth: The deal advanced PTC’s transition from perpetual licensing toward subscription and SaaS revenue streams.
Customer demand: SaaS delivery lowered upfront costs, simplified IT management, and supported collaboration for distributed teams.
Strategic timing: By acquiring Onshape early, PTC placed itself ahead of the “tipping point” for SaaS adoption.
“Sometimes selling is less about what your company is today, and more about what the market is about to become.” — Before the Exit
This acquisition illustrates how SaaS M&A can be used to secure leadership in industries on the verge of disruption.
ConnectWise - acquired by Thoma Bravo for an unknown sum
ConnectWise is offers their business management suite to technology solution providers. It was acquired by Thoma Bravo, a private equity investment firm. While the amount of the acquisition is unknown, ConnectWise was valued at $1 billion at the time of purchase. There was a really cool success story with this one! Because the company was employee-owned, the acquisition immediately created over 70 millionaires.
Key takeaways from this SaaS M&A transaction
Thoma Bravo’s acquisition of ConnectWise underscored how private equity firms view MSP software as a growth engine for SaaS and IT services.
Succession planning: Founder Arnie Bellini stepped into an advisory role, with longtime COO Jason Magee promoted to CEO.
Private equity strategy: Thoma Bravo positioned ConnectWise for organic growth and selective acquisitions in SaaS and cybersecurity.
Financial strength: ConnectWise posted strong EBITDA and revenue growth leading into the deal, making it attractive to investors.
Cultural transition: Employee shareholders received $270 million, while staff adjustments reflected a shift toward SaaS-first operations.
“The art of selling a business well comes down to how you package it, the story you tell about it, and the feeling it gives potential buyers when they imagine owning it.” — The Art of Selling Your Business
This deal highlights how founder-led SaaS firms can transition leadership while securing private equity backing for future scale.
Keep dreaming those SaaS acquisition dreams, and as Nathan Latka would suggest, sell when the time is right so you can keep that forward momentum going strong.
To learn more about how to build a SaaS business, Get Started with the founder of DevSquad, who successfully exited a SaaS before building our development agency.