28 Acquisition Playbooks CEOs Used to Add $1M ARR Fast

In this article, you will discover how top SaaS CEOs use strategic acquisitions as a powerful growth lever to expand their user base, enter new markets, and drive millions in revenue. This isn’t just theory; these are real-world examples from founders who have successfully bought, integrated, or sold companies to accelerate their growth trajectory. You will get a 4-step playbook to execute your own acquisition strategy, backed by over 40 case studies you can use as inspiration. These examples are from top founders like James Isilay at Cognism, Ryan O’Neil at Curate, and Carson Conant at MediaFly, collected directly from keynotes at Founderpath events.

The 4-Part Playbook for Growth Through Acquisition

1. Define Your Acquisition Thesis: Before you even think about buying a company, you must understand the strategic gap you’re trying to fill. Are you missing a key product feature? Do you need to enter a new market quickly? Are you trying to acquire a specific type of customer or talent? For example, James Isilay at Cognism, a company with a strong direct sales motion, realized they had a significant gap in product-led growth (PLG). Their vision was to acquire a company with PLG expertise to capture the self-serve, individual user market where they had poor retention. This clear thesis guided their entire acquisition search.
2. Identify and Approach Targets: Once you have a thesis, you can start identifying potential targets. This can happen in many ways. Sometimes, like with Cognism, a salesperson will spot a new competitor appearing in deals, signaling a potential target. In other cases, the target may come to you. Curate’s CEO Ryan O’Neil shared that his competitor reached out directly during a market downturn, creating an unexpected opportunity. The key is to be prepared and move fast. Once a target is identified, the founder should personally drive the initial outreach with a clear vision of how the combined companies will become a “superpower.”
3. Structure and Execute the Deal: Making the deal happen is about finding common ground and building relationships. Valuation is always a major hurdle. Cognism’s CEO navigated this by discussing valuation multiples based on current ARR with the founders, while discussing multiples at the close of the transaction with his board, using time as a lever to meet everyone’s expectations. Deals can be structured with cash, equity, or an earn-out structure based on future milestones. Simplicity is often key, especially for smaller deals. As Ryan O’Neil from Curate noted, a clean, simple cash offer of $40,000 was all it took to get their deal done quickly.
4. Integrate to Unlock Growth: The acquisition isn’t done when the papers are signed; that’s when the real work begins. Successful integration is critical to unlocking the value you identified in your thesis. This could mean integrating technology, merging teams, or cross-selling products into a new customer base. Xactly’s CEO Chris Cabrera explained how they executed three acquisitions in 15 months, which allowed them to go back to their 1,600 customers and significantly increase average selling prices by cross-selling the new products. A successful integration turns the acquired company into a growth engine rather than just a liability.

40+ SaaS Acquisition Examples to Inspire Your Growth

• James Isilay, CEO of Cognism, detailed the acquisition of French competitor Casper. This strategic move was to integrate Casper’s product-led growth (PLG) motion, which catered to individual users, into Cognism’s direct-sales model. The acquisition helped Cognism reach $37 million in ARR by creating a seamless customer journey from self-serve to enterprise-level packages.
• Ryan O’Neil of Curate shared how he acquired a competitor, Bloomtrack, for just $40,000 during the 2020 downturn. This single acquisition added an immediate $120,000 in ARR, which has since grown to over $250,000, and increased Curate’s valuation by an estimated $2.5 million.
• Carson Conant, CEO of MediaFly, acquired UK-based iPresent to add a self-serve, freemium model to their enterprise sales-focused platform. This move helped them grow from 150 to 260 customers and put them on a path to hit $20 million in ARR by enabling small teams within large companies to adopt their product without a lengthy procurement process.
• Vikas Bhambri of GTMfund explained how his previous company, Customer, was acquired by Meta for over $1 billion. This exit was driven by building a strong rip-and-replace solution in the competitive CRM space, demonstrating that a well-positioned product can lead to a massive acquisition outcome.
• Manny Medina, CEO of Outreach.io, shared the story of his previous company, GroupTalent. After pivoting, the recruiting services company was effectively “acquired” by its own internal tool when customers became more interested in the sales engagement platform they had built to get meetings. This internal product acquisition led to the creation of Outreach, which now does well over $6 million per month in revenue.
• Chris Federspiel of Blackthorn detailed his acquisition of Texi, funded by a debt facility. This acquisition was strategic to add SMS capabilities to their events platform, a feature highly requested by customers. This move helped Blackthorn grow to nearly $17 million in ARR by enhancing their product suite.
• Diego Gomes, CEO of Rock Content, raised $10 million specifically to acquire ScribbleLive, a company with an existing $8 million revenue run rate. This acquisition brought in the ‘Ion’ interactive content platform and the ‘Visually’ talent marketplace, allowing Rock Content to expand its suite and accelerate its ARR to over $24 million.
• Bynder’s CEO, Chris Hall, acquired their number one US competitor, Webdam, in a deal largely financed through debt. This move significantly grew their team and market share, helping them more than double their revenue from a $19 million run rate to over $48 million in about a year.
• Brandon Bruce of Cirrus Insight acquired Attach, a document management and tracking tool, using cash from operations. They identified a gap in their product suite and found Attach to be a perfect fit, allowing them to add critical features and grow their monthly recurring revenue past $1 million.
• Todd Olson, CEO of Pendo, executed the company’s first acquisition to add mobile capabilities to their product experience platform. This move allowed them to provide a complete solution across both web and mobile, helping them grow to over 400 customers and a $1.2 million monthly run rate.
• Singular CEO Gadi Eliashiv shared that his company acquired a competitor to accelerate growth. This move, along with strong upsells, helped them achieve nearly 100% year-over-year growth, scaling to a run rate of over $25 million.
• Xactly CEO Chris Cabrera described their strategy of using a private equity war chest to make three acquisitions in just 15 months. This expanded their product suite from just sales comp (ICM) to a full sales performance management (SPM) platform, allowing them to cross-sell into their 1,600+ customer base and target a run rate of over $100 million.
• Eric at Solemate built a capital-efficient company and was acquired by Dixa, which had raised $43 million. Eric kept the vast majority of the proceeds from the exit because he had no VCs on his cap table, proving that a lean approach can lead to a highly profitable founder acquisition.
• Raj De Datta, CEO of Bloomreach, revealed that his company has turned down acquisition offers in the $400 million range. By focusing on a massive market opportunity and a clear path to becoming a profitable, high-growth company, they chose to continue scaling independently towards a target of over $100 million in revenue.
• Luke Cooper, founder of Fiix, engineered the acquisition of his company by Assurant. The enterprise software business grew to manage over half a billion dollars in revenue for Assurant, showing how a strategic acquisition can unlock massive scale for the acquirer.
• Armando Biondi’s company, AdEspresso, was acquired by Hootsuite. At the time of the sale, AdEspresso was at a $5 million run rate and growing fast, but the acquisition provided a strategic exit and allowed Hootsuite to integrate a powerful ad tech tool into its social media management platform.
• Jose Caldera’s firm, Identity Mind, was acquired by Acuant. The combination of technologies created a more robust platform for trusted digital identities, showing how acquisitions can be used to build a comprehensive, market-leading solution.
• The team at Cirrus Insight also acquired Assistant.to, a calendaring and scheduling service. This was another product-gap acquisition that allowed them to build out a more all-in-one sales stack for their 150,000 paid users.
• Vijay Tella, now CEO of Workato, sold his previous company Quack, a mobile video app with 20 million users, to Skype for $150 million. This successful exit was a 10x return for his investors on a $15 million raise.
• Percolate’s CEO, Randy Woodton, joined the company post-Series C to scale its go-to-market motion. While not a direct acquisition story, it highlights how founders can bring in experienced leaders to prepare for a future exit or IPO, a key step in the acquisition lifecycle.
• The Blackthorn team, led by Chris Federspiel, acquired PCY to add PCI compliance capabilities to their payments app. Though the acquisition didn’t ultimately work out as planned, it demonstrates the willingness to use M&A to solve critical product needs.
• Adam Broadway’s first SaaS business, Business Catalyst, was acquired by Adobe in 2009. This experience of building and selling a company provided him the strategic knowledge for his current venture, PlatformOS.
• Scott at Contact Monkey bootstrapped his company to over $5 million in revenue using non-dilutive capital before executing a large private equity deal, a significant portion of which was likely a secondary offering for him as the founder.
• MediaFly’s CEO Carson Conant also mentioned the acquisition of Olynyans, which complemented their acquisition of iPresent, to build out their value story and calculator tools, enhancing their sales enablement platform.
• John Oechsle, CEO of Swiftpage, acquired Kuvana as a pure technology play to add marketing automation to their Act! product suite. This allowed them to triple their potential monthly revenue per customer by creating the Act! Grow Suite.
• The CEO of Outreach.io highlighted a critical pivot where they acquired their own company’s destiny by shifting focus from a recruiting service to selling the internal tool they built, which customers were clamoring for.
• Jim Larrison’s previous company, Addify, was acquired by Cox Enterprises for $350 million. This successful exit provided the capital and experience to spin out his current company, Dynamic Signal.
• Mikael Thuneberg of Supermetrics mentioned they are actively looking at acquisitions to add talent and new product directions, aiming to build on their data pipeline capabilities and grow beyond their current $12 million ARR.
• Mike Morgan from Channel Grabber, after selling his previous company in 2016, took over Channel Grabber as CEO and used debt financing to fund product development and get the company back to a 33% year-over-year growth trajectory.
• Cognism’s team also executed an earlier acquisition of Mailtastic in 2020. This was a majority equity deal that illustrates their long-term strategy of using M&A to consolidate their market position.
• The Pendo team acquired a company in Israel to build out their mobile product. CEO Todd Olson emphasized that a key part of the deal structure was ensuring high retention of the acquired employees through financial incentives to integrate their talent successfully.
• Dixa, a venture-backed company, raised $43 million and used a portion of it to acquire Solemate. This is a classic example of using raised capital to acquire smaller, capital-efficient companies to accelerate growth.
• The founder of metadata.io, Gil Allouche, shared a near-death story where his company almost went bankrupt. Surviving this “burn book” phase made the company stronger and ultimately a more attractive target for future partnerships or acquisition.
• The CEO of Showpad mentioned making an acquisition to integrate a new product line. This allowed them to introduce a new add-on, increasing their price per user and driving expansion revenue from their existing customer base.
• Alex Quilici, CEO of YouMail, discussed selling his previous company, Quack, to AOL for $200 million. The offer was a no-brainer compared to a competing venture offer, as it represented the value they hoped to achieve in four to five years, but delivered immediately.
• Thomas Smale of FE International shared insights from over $50 billion in closed M&A deals, explaining that metrics like net dollar retention and revenue growth are key drivers of valuation in an acquisition.
• Workato CEO Vijay Tella sold his consumer video company, Quik, to Skype for $150 million after raising just $15 million. The successful 10x exit demonstrates the power of building a product with massive user adoption.
• Charles Miglietti of Toucan Toco sold his first startup, tldr.io, for a small amount before founding his current company. This “starter” exit provided crucial experience for building his next, larger venture.
• LeadGnome’s CEO, Matt Benati, discussed the potential of being acquired by a competitor like Yesware. While he enjoys the freedom of bootstrapping, he acknowledged that a 2-3x ARR offer would warrant a serious conversation.
• Sam Caucci of 1Huddle, who has grown his company to a $3.5 million run rate, is now considering a $10 million Series A round to accelerate growth, a move that could position the company for a larger acquisition in the future.

Conclusion

You’ve just learned how dozens of top SaaS founders approach acquisitions to add millions in revenue and create massive enterprise value. Whether it’s acquiring a competitor to enter a new market, buying a smaller tool to fill a product gap, or building a capital-efficient company to achieve a life-changing exit, these strategies are proven to work. To get capital for your own growth plays, including acquisitions, check out the options available at Founderpath.

Founderpath invests in ambitious founders looking to grow fast. Click here to submit a capital request