How To Startup Part 8: Exits

Spencer Rascoff

Spencer Rascoff serves as executive chairman of dot.LA. He is an entrepreneur and company leader who co-founded Zillow, Hotwire, dot.LA, Pacaso and Supernova, and who served as Zillow's CEO for a decade. During Spencer's time as CEO, Zillow won dozens of "best places to work" awards as it grew to over 4,500 employees, $3 billion in revenue, and $10 billion in market capitalization. Prior to Zillow, Spencer co-founded and was VP Corporate Development of Hotwire, which was sold to Expedia for $685 million in 2003. Through his startup studio and venture capital firm, 75 & Sunny, Spencer is an active angel investor in over 100 companies and is incubating several more.

How To Startup Part 8: Exits
Image by Master1305/ Shutterstock

Welcome to the last installment in the “How To Startup” series and an often overlooked step when creating a business: exiting. In short, an exit strategy is exactly what it sounds like - a way out, sort of. I say sort of because frequently a sale of a company is just a new beginning, but more on that below. Startups usually seek an exit to generate investment returns for their investors and shareholders (usually including their employees), or sometimes to limit losses. It is important for founders to keep the possibility of an exit in the back of their minds at different stages of the business’ growth. Some startups are “big swings” where founders and their investors believe the idea and the team have the potential to turn the company into a multi-billion dollar public company. But many startups are smaller ideas where a smaller sale is a good outcome and is something always to be explored. It is important for founders to know which of these best describes their company.


As we’ve already learned in previous installments, the most successful entrepreneurs are the ones who plan ahead. So now that your company has traction and growth—or you’re a proactive entrepreneur who wants to get ahead—it’s time to think about an exit for the business.

Types of Exits

There are many different common exit strategies, but ultimately the one you choose will depend on your own business, personal and financial goals. I cover some of the pros and cons of each strategy below.

Liquidation

Failing, but “failing fast” and liquidating can sometimes be the best route to minimize losses for a business. You’ll likely find yourself in one of two scenarios when considering a liquidation: you’re already at the end of your rope - be it financially or otherwise - or you can see the end coming. If you’re fresh out of cash, evaluate how you can responsibly wind down the business for all parties involved - yourself, employees and investors. If you can tell early on that you don’t have product-market fit or traction and you still have cash left, plan to exit early and return money to investors. A great example of this is when Jeffrey Katzenberg returned $350M to investors instead of simply running Quibi until it was out of cash.

Sale or Acquisition

If you plan to sell your company (a.k.a. if it is getting acquired), you can receive payment from the acquirer in cash, stock or a combination of both. The acquirer can pay you cash for the company or you can exchange your stock in your company for shares of stock in the newly combined company. This will let you maintain being an active participant and shareholder as the company continues to grow. It’s not common in tech for acquisitions to involve both cash and stock. If you believe the company is poised to continue scaling, then definitely consider receiving stock as a part of the transaction. A famous example of this is when Facebook purchased Whatsapp for $4B in cash and $12B in Facebook shares in 2014, helping them grow into developing markets. The Facebook stock that Whatsapp shareholders received ended up being worth many multiples of the $12B which it was valued at during the time of the deal.

The amount a startup can sell for is determined by a few factors. Here are a couple of examples of how valuations are determined:

- If it’s a small company worth <$10M, it’s probably an acquihire (the process of acquiring a company primarily to recruit its employees). In this case, acquirers usually value the target based on how many engineers or product people are at the company.

- If it’s a deal worth <$100M, it’s usually priced more on strategic fit than real analysis such as what the target brings to the acquirer. This could be technology, a great team, a new business line they can build on, great potential of the merger, etc. For example, when I was CEO of Zillow we acquired 16 companies, most of which were in the $10M-$100M price range, and we always determined fair value by focusing on the overall level of strategic fit of the target more than evaluating the actual financial results of the target.

- If it’s a bigger deal with >$100M, the target’s financial results are usually benchmarked against other public comps and require real math to analyze. At deals of this size, advisors such as investment bankers usually participate in the deal and bring the analytical rigor and external perspective needed to evaluate the fairness of the deal for both sides.

Sometimes a sale is the end of the road for a company. But more often than not, it is just the beginning of the next chapter. For example, when Zillow acquired StreetEasy, the leading real estate portal in New York, we invested significant resources to grow the company after the acquisition. We added headcount, rebranded the company, invested in advertising and grew it substantially post-acquisition. Far from the sale being the end of the company, it was really just the beginning. Another example is Google’s acquisition of YouTube in 2006 for $1.65B of stock. At the time, YouTube was struggling with a myriad of legal and copyright infringement issues from content owners and was struggling to keep up with user demand. Under Google’s ownership, YouTube cleaned up its content copyright issues, invested tens of millions of dollars in technology to improve the service, and today YouTube is probably worth at least $100 billion under Google’s ownership and stewardship.

Initial Public Offerings (IPOs)

Traditional: Taking a company public is one of the ultimate goals for many founders, but it’s not exactly the finish line. In fact, it’s quite the opposite. For example, I named our IPO preparation at Zillow “Project Step” to emphasize to the team that it was just a “step” along the way towards building a great business.

In an Initial Public Offering, a company sells shares for the first time to public shareholders, and the stock is then traded on a stock exchange. This can be beneficial for a few reasons, such as being able to raise capital, get research reports written about the company and create liquidity for your investors so they can sell their stock. On the flip side, IPOs can be expensive (the fees are usually 5-7% of the amount raised) and come with a lot of uncertainty. One of the biggest challenges with this method is that the IPO window can be open or closed, and is dependent on things out of your control.

If you do pick this method, a piece of advice I often tell founders is to act and operate like a public company well before you actually are one. More on this and IPOs at a later date as I’ll probably do a separate piece on it.

SPAC Merger: A Special Purpose Acquisition Company (SPAC) is another way for a company to go public. With a SPAC, a publicly traded company is created for the purpose of acquiring or merging with an existing private company. One benefit of going the SPAC route is that, for now, company projections are permitted to be shared with investors during a SPAC merger which allows investors insight into a company’s growth prospects. I say “for now” because the SEC is evaluating this and there is speculation that it will no longer be permissible in the future. Another advantage is that you can select your shareholders through the Private Investment in Public Equity (PIPE) process plus receive advice and “sponsorship” from the SPAC itself which can be helpful to the company. The cons of a SPAC process are that it can be difficult to get enough investor focus on the company once you’ve gone public in this way, and SPACs are currently out of favor with investors.

Direct Listing: In a direct listing, a private company converts into being publicly traded but doesn’t actually sell any shares. Companies that choose to go public using this method usually have different goals than those that use an IPO - specifically, they do not need to raise capital through the offering. Direct listings create liquidity for existing shareholders and are usually less expensive than an IPO, but companies miss out on the chance to raise money.

Lessons On Exits

No matter what route you end up taking, when preparing for an exit: Always aim to be on the radar and top of mind for acquirers, understand your cap table and the goals of your shareholders, utilize investment banks and investors as resources and hire great M&A lawyers.

Missed a part or looking to reread? Part 1: Ideation, Part 2: Naming Your Business, Part 3: How To Pitch, Part 4: Surviving A Downturn, Part 5: Minimum Viable Product, Part 6: Product-Market Fit, Part 7: Scaling or read them all.

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The Legal System Just Got Its AI Upgrade

🔦 Spotlight

Hello Los Angeles!

We talk a lot about AI in L.A., usually in the context of streaming platforms that “recommend” a movie you regret watching or apps that let you swap your face onto a Marvel poster. But the most interesting AI stories here aren’t gimmicks; they’re rewiring the hidden machinery of massive, slow moving industries. And this week, that spotlight falls on…lawyers.

LawPro.ai, a Los Angeles based legal tech startup, just closed a priced seed round led by Scopus Ventures to bring AI deeper into the world of injury claims. Their new “Case Assistant” isn’t about flashy automation, it’s about instantly surfacing case insights, cutting down endless hours of drafting, and helping law firms run with the precision of a Formula 1 pit crew.

Here’s why this matters: the legal industry has been one of the last holdouts when it comes to adopting tech that actually speeds things up. Now, with AI making its way from the red carpet to the courtroom, we’re watching the early stages of a shift that could change how justice is delivered in real time. In L.A., we’ve already seen AI startups shaking up entertainment, aerospace, and healthcare. Legal might be next.

And if LawPro.ai pulls it off, you might not just get a faster verdict, you might see the ripple effect across an industry that has spent decades charging by the hour. In other words, the billable clock might finally start running in our favor.


🤝 Venture Deals

LA Companies

    • Equatic, a company using a patented seawater electrolysis process to remove atmospheric carbon dioxide while producing green hydrogen, has raised $11.6M in a Series A funding round. The round was co-led by Temasek Trust’s Catalytic Capital for Climate and Health (C3H) and Singapore-based Kibo Invest, and the capital will support the engineering, commercialization, and construction of its first 100‑kilotonne carbon removal facility, as well as broader manufacturing and technological development. - learn more
    • SetPoint Medical has secured $140M in private financing, comprising a $25M second tranche of its Series C round and a $115M Series D round co-led by Elevage Medical Technologies and Ally Bridge Group. The funds will be used to launch and scale commercialization of the FDA approved SetPoint System, a pioneering neuroimmune modulation implant that targets the vagus nerve to treat moderate to severe rheumatoid arthritis, as well as to advance development of therapies for other autoimmune conditions. - learn more

    LA Venture Funds

      • Bonfire Ventures participated in Topline Pro’s $27M Series B funding round to help the company scale its AI driven platform for local home service businesses. Topline Pro provides tools for plumbers, landscapers, painters, and other service providers to manage websites, marketing, CRM, payments, and more, enabling them to operate as scalable, autonomous enterprises. The new funding will be used to enhance its AI agent suite and expand onboarding, customer success, and product development capabilities to deliver greater ROI for small businesses. - learn more
      • B Capital participated in Isaac Health’s $10.5M Series A funding round, backing the company’s mission to expand access to brain health and dementia care. Isaac Health provides virtual and in-home services nationwide and will use the funds to enhance its AI-driven screening tools, strengthen its technology platform, and grow partnerships with health systems and payers. - learn more
      • Bold Capital Partners joined a $44M Series C financing round for Gameto, a clinical stage biotech company developing stem cell derived reproductive therapies. The new funding, which brings Gameto’s total capital raised to approximately $127M, will support completion of its pivotal Phase 3 trial of Fertilo, an iPSC derived egg maturation therapy, and the company’s global regulatory filings and commercialization efforts. - learn more
      • M13 led a seed round that raised $8.5M for Mako, a New York based AI startup focused on automating GPU code optimization. Mako’s platform lets developers write in familiar high level languages while its AI intelligently generates and continuously tunes low level GPU kernels, yielding faster performance, cost savings, and compatibility across hardware like NVIDIA, AMD, and Tenstorrent. The fresh funding will be used to expand the engineering team, deepen hardware support, and bring Mako’s performance tools to a broader audience in AI, graphics, simulation, and scientific computing. - learn more
      • Rebel Fund participated in a $9M Series A round for Chowdeck, a profitable Nigerian food delivery startup aiming to build Africa’s next super app for food, groceries, and essentials. With this capital, Chowdeck plans to roll out its quick commerce strategy, powered by a network of dark stores and hyper local logistics, to speed up delivery across Nigeria and Ghana. - learn more
        LA Exits
        • Mayweather Boxing + Fitness has been acquired by Giant Ideas, LLC, alongside KickHouse, and will be combined with the company’s flagship brand Legends Boxing to form the largest skill based boutique fitness network with more than 70 studios worldwide. Rather than focusing solely on rapid expansion, the unified brands will prioritize operational excellence, franchisee success, and community driven skill development. - learn more

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                  Locket, Disney, Instagram and the Battle for Your Attention

                  🔦 Spotlight

                  Happy Friday, Los Angeles!

                  This week, LA’s biggest tech and media players made one thing clear: they want to own the relationship. Whether it’s a celebrity sending selfies straight to your home screen or a content giant rewriting the rules of sports broadcasting, the power shift toward more curated, direct experiences is unmistakable, and it’s being engineered right here.

                  Image Source : Locket

                  📸 Locket Doubles Down on Star Power

                  Venice-based Locket, the viral photo sharing app that made homescreen widgets cool, is now leaning into what LA does best: celebrity. Its new feature, Celebrity Lockets, allows artists to send exclusive photos directly to fans’ home screens. Early adopters include Suki Waterhouse and JVKE, with creators curating limited fan access to maintain intimacy and exclusivity. As Locket evolves from a casual social tool into a direct fan engagement platform, it’s becoming an increasingly relevant player in LA’s creator tech ecosystem.

                  🏈 Disney’s ESPN Plays Offense

                  Disney made a trio of bold moves this week that solidify ESPN’s future and its dominance in sports media. It’s buying out the NFL’s stake in ESPN, securing exclusive NFL Draft and behind the scenes content through 2033, and finally giving its standalone ESPN streaming service a launch date: August 21, 2025. That’s a power play straight out of Burbank. At the same time, Disney announced it will no longer report individual subscriber numbers for Disney Plus and Hulu, signaling a shift in how it wants investors and maybe consumers to measure success.

                  🗞️ The New York Post Bets on LA

                  In a sign of LA’s growing national influence not just in entertainment, but in news, the New York Post is launching a West Coast vertical called The California Post. With an editorial mission to cover the state’s cultural and political pulse, this move reflects a broader trend of major media brands planting roots in LA to chase both readers and relevance. For local media startups, content creators, and civic tech players, it’s yet another sign that the competition and the opportunity is growing.

                  Image Source: Meta

                  📱 Instagram Wants Your Inner Circle

                  Instagram rolled out a new set of features this week that prioritize connection with close friends. Users can now share what they’re doing, watching, or feeling with a smaller group, clearly borrowing from the intimacy playbooks of apps like BeReal, Snapchat, and yes, Locket. As social platforms shift from mass broadcast to curated circles, LA-based creators and consumer startups should take note: the next frontier might not be going viral, it might be going personal.

                  From star-powered lockets to streaming shakeups and platform reinventions, this week’s stories highlight how LA’s tech and media companies are rewriting the rules on connection and control.

                  Now onto this week’s venture deals 👇

                  🤝 Venture Deals

                  LA Venture Funds

                    • Starburst co-invested in Madrid-based SpaceTech startup Orbital Paradigm’s €470,000 raise, part of an ongoing €2M funding round led by Akka. The company is developing reusable orbital re-entry capsules aimed at reducing costs and increasing sustainability for space missions. Starburst’s participation underscores its focus on backing innovative aerospace technologies with commercial and defense applications. - learn more
                    • Rebel Fund participated in Orbital Operations’ $8.8M seed round, which came shortly after the company graduated from Y Combinator. The funding will support development of the company’s high-thrust orbital transfer vehicle, designed to maneuver satellites and other payloads in space more efficiently. - learn more
                    • Fourth Revolution Capital participated in SuperGaming’s $15M Series B round, which valued the company at $100M, five times its previous valuation. The funds will help expand titles like Indus Battle Royale internationally and scale SuperGaming’s tools for developers in emerging markets. - learn more
                    • Cedars-Sinai Health Ventures participated in Elion’s $9.3M seed round, joining NEA and others in backing the AI-powered healthcare research and intelligence platform. Elion helps over 60% of U.S. health systems evaluate emerging technologies through its structured vendor marketplace. The funds will support platform development, new product launches, market expansion, and team growth. - learn more
                    • M13 led the $10M seed round for Kontext, an AI-powered contextual advertising startup emerging from stealth mode. Kontext’s platform enables real-time ads inside chatbot responses using large language models, and the funding will help expand its engineering team and develop image-based ad formats. - learn more
                    • STORY3 Capital Partners made a significant minority investment in U.K.-based activewear brand Adanola, valuing the company at approximately $530 million. This strategic partnership brings STORY3’s deep experience in consumer brand scaling to support Adanola’s global expansion, particularly across the U.K. and U.S. markets. - learn more
                    • Walkabout Ventures participated in OLarry’s $10M Series A round, which was led by TTV Capital and included Marin Sonoma Impact Ventures. The funding brings OLarry’s total capital raised to $14.5M and will be used to scale its AI-powered tax advisory platform for high-net-worth individuals and to acquire regional CPA firms as part of its growth strategy. - learn more
                    • Glendon Capital Management participated in Grasshopper’s $46.6M funding round, which was led by Patriot Financial Partners, to support the bank’s merger with Auto Club Trust in April 2025. Their investment reflects confidence in Grasshopper’s ability to scale its digital banking platform and expand its suite of business and consumer financial products. Growth metrics as of June 30, 2025 showed a 53% increase in assets, an 81% surge in deposits, and a 49% rise in loans, all backed by this strategic capital infusion. - learn more
                    • Mucker Capital participated in beatBread’s $124M capital raise, alongside Citi’s SPRINT team, Deciens Capital, and Advantage Capital. Their involvement supports beatBread’s strategy to expand sales, marketing, and technology operations, while enabling greater funding flexibility for independent artists, songwriters, and labels through its AI-powered platform. - learn more
                    • B Capital co-led Positive Development’s $51.5M Series C funding round alongside aMoon and Flare Capital Partners, helping to fuel expansion of its developmental therapy model for autistic children. Their involvement underscores confidence in the company’s family-centered, play-based approach—which lowers costs by about 50% compared to traditional ABA therapy—and supports growth through new Medicaid partnerships and technology enhancements. - learn more
                    • Clocktower Ventures participated in Creditop’s latest $3.7M funding round, which was led by Collide Capital and also included Alaya Capital, Amador Holdings, Newtopia, and Driven VC. Their involvement supports Creditop’s mission to enable credit access at the point of sale, without a credit card, and will help fintech deepen its footprint in Colombia while exploring expansion across Central America and Peru. - learn more
                    • Thiel Capital participated in Pilgrim’s $4.3 million seed funding round, backing the biotech startup founded by 21-year-old Jake Adler after he demonstrated its hemostatic dressing, Kingsfoil, on himself. Their support underscores confidence in Pilgrim’s aggressive R&D and dual-use medical platform targeting both military and civilian emergency care. - learn more
                    LA Exits
                    • ElectroMagnetic Systems, Inc., a California-based specialist in AI and machine learning-powered target recognition software for space-based radar, has been acquired by Voyager. The deal strengthens Voyager’s AI-native surveillance and intelligence capabilities, enabling real-time monitoring across ground, air, and space domains to meet evolving defense and commercial demands. - learn more
                    • Daring Foods is being acquired by Australia’s leading plant-based meat company, v2food, in a move that strengthens v2food’s push into the U.S. market. Daring will continue operating under its own brand and will serve as a platform to introduce v2food’s own products across the States. The deal, paired with a strategic partnership with Japanese food giant Ajinomoto, aims to accelerate innovation in clean-label protein and expand global reach. - learn more
                    • Irwin Naturals is being acquired by FitLife Brands in an all-cash transaction valued at $42.5M, which includes approximately $16M in net working capital. The deal, expected to close around August 8, 2025, will nearly double FitLife’s scale, with projected combined annual revenue of over $120M and adjusted EBITDA between $20–25M. It will be funded with cash on hand, a new term loan, and a revolving credit facility, and is expected to generate synergies through complementary product lines, broader mass-market distribution, and improved operational efficiencies. - learn more
                    • Solsniper, a Solana-focused trading and analytics platform known for high-speed memecoin execution, has been acquired by Phantom as part of its strategy to expand beyond wallets into full-service on-chain finance. The Solsniper team will join Phantom to enhance its advanced trading features, while the platform will continue operating independently. The move underscores Phantom’s ambition to offer seamless, integrated trading tools within the Solana ecosystem. - learn more
                    • Cinelease is being acquired by Zello, a private investment platform dedicated to scaling businesses across the entertainment industry, in a strategic move to bolster production infrastructure and amplify its presence across North America. Under Zello’s ownership, Cinelease will continue operating as a standalone company led by its veteran team, enhancing its lighting, grip, and studio offerings for film, TV, and commercial productions. This acquisition sets the stage for disciplined growth and stronger relationships within the film and television production ecosystem. - learn more

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                            Smart Shoes for Kids? Skechers Thinks So 👟

                            🔦 Spotlight

                            Happy Friday, LA!

                            This week, Skechers may have just kicked off a new trend that’s bound to have parents and tech lovers talking. They've unveiled the "Find My Skechers" line, kids’ sneakers that come with a hidden compartment to securely hold an Apple AirTag. For $52 to $58, parents can now track their child’s shoes in real-time using the Find My app, giving a whole new meaning to "keeping an eye on things." While these tech-savvy kicks are already gaining attention, will they become the new norm in kids' footwear? And who’s next? Will Nike or Adidas be jumping on the AirTag bandwagon, or is Skechers setting the stage for a whole new wave of tech-integrated fashion?

                            But it’s not all smooth sailing. This innovation raises some interesting questions about privacy and surveillance. Are we crossing a line when we start tracking our kids’ every move through their shoes? While Apple’s anti-stalking features are in place to prevent misuse, it will be intriguing to see how other brands and parents respond to this new blend of fashion and tech.

                            What do you think? Could this become a must-have feature in the next generation of kids' gear, or is it a step too far? Let us know your thoughts!

                            🤝 Venture Deals

                            LA Companies

                            • LakeFS, a provider of Git-like version control for data lakes, has secured $20M in a growth funding round led by Maor Investments. The funds will support the company's expansion efforts and product development aimed at enhancing data engineering and AI initiatives within enterprise and public sector environments. - learn more

                            LA Venture Funds

                              • Sound Ventures co-led the $16.1M Series A funding round for Knit, an AI-powered consumer research platform. The funds will be used to accelerate product development, enhance AI capabilities, and expand global research operations. This investment underscores the growing trend of combining AI with human expertise to deliver faster, cost-effective, and high-quality insights for enterprise research. - learn more
                              • Anthos Capital co-led a $60M Series A funding round for Good Job Games, a mobile game developer known for creating casual and hyper-casual games. The investment, co-led by Menlo Ventures, will support the company's growth, enabling the expansion of its game portfolio and enhancing user engagement through innovative gameplay features. This funding marks a significant step in scaling Good Job Games’ operations and solidifying its position in the competitive mobile gaming market. - learn more
                              • Pinegrove Capital Partners participated in Ramp's $500M Series E-2 funding round, which values the company at $22.5 billion. The funds will be used to accelerate Ramp's AI-driven financial tools, aiming to enhance automation and efficiency in corporate finance operations. - learn more
                              • Riot Ventures participated in Oxide Computer Company's $100M Series B funding round, led by the U.S. Innovative Technology Fund (USIT). This investment will enable Oxide to scale its manufacturing capabilities, enhance customer support, and accelerate product delivery to meet the growing demand for on-premises cloud computing solutions. - learn more
                              • Rebel Fund participated in a $3.2M seed funding round for Caseflood.ai, a San Francisco-based legal tech startup offering AI-powered client intake solutions for law firms. The funds will support the development of Caseflood's advanced voice agent, Luna, which autonomously handles client interactions, including consultations and retainer signings, aiming to enhance conversion rates and operational efficiency for law firms. - learn more
                              • Smash Capital participated in Ambience Healthcare's $243M Series C funding round, co-led by Oak HC/FT and Andreessen Horowitz (a16z). The investment will support Ambience's expansion of its ambient AI platform, which automates clinical documentation, coding, and workflow tasks across over 200 specialties. The platform integrates directly with electronic health records, enhancing efficiency and compliance in healthcare settings. - learn more
                              • ARTBIO, a clinical-stage radiopharmaceutical company developing alpha radioligand therapies for cancer treatment, has secured $132M in a Series B funding round. The round was co-led by Sofinnova Investments and B Capital, with participation from Alexandria Venture Investments and other investors. The funds will support the advancement of ARTBIO's lead program, AB001, through Phase II clinical trials, and facilitate the expansion of its manufacturing and supply chain infrastructure. - learn more
                              • Rebel Fund participated in OffDeal's $12M Series A funding round, led by Radical Ventures, to support the company's mission of building the world's first AI-native investment bank. OffDeal aims to democratize access to high-quality M&A advisory services for small and mid-sized businesses by automating analyst tasks with AI, enabling efficient sell-side transactions. The funds will help scale OffDeal's technology-driven, advisor-led approach to facilitate successful exits for entrepreneurs. - learn more
                              • Sandbox Studios participated in a $3M seed funding round for Sarelly Sarelly, a Mexican cosmetics brand, with backing from U.S. investors like Wollef, Morgan Creek Capital Management, and Hyve Ventures. The funds will support Sarelly Sarelly's expansion into the U.S. market, including retail launches at Ulta Beauty and growth on digital platforms like TikTok Shop. - learn more

                              LA Exits
                              • NEOGOV, an El Segundo-based provider of HR and compliance software for U.S. public sector agencies, has been acquired by EQT and CPP Investments in a deal valued at over $3 billion. The acquisition will help NEOGOV expand its product offerings and grow its presence across North America. - learn more

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