Salesforce wants to battle Microsoft. But will it get Slack right?

Late last year, Salesforce threw down a weighty gauntlet to Microsoft’s work-from-home Teams software business: It snapped up Slack for $27.7 billion, its biggest acquisition ever.

There were digital gasps, oohs, and ahhs, with one burning question: Will Salesforce be able to jumpstart Slack and go head-to-head with the Bill Gates-founded titan? At tens of billions of dollars, the customer relationship management software giant was making one risky bet on a company that, while very sticky, had not caught the same boom in revenue felt by the likes of Zoom during the pandemic.

As Salesforce and Slack get ready to close the deal, my colleague Michal Lev-Ram dove into the Salesforce story—taking a closer look at a company that many people know better for its founder’s personality than for the software it produces. 

An excerpt from Michal’s conversation with Slack CEO Stewart Butterfield shows how much the balance of personalities means to Salesforce’s future:

“While Benioff has a flair for bombast, Butterfield has a reputation for nuance—and when we talk about the sale to Salesforce, he acknowledges that the gamble remains a big one: ‘Most M&A doesn’t work, so you kind of have to go into this believing that this is exceptional,’ he says. Butterfield is quick to add that he believes this arrangement is exceptional. One of the reasons he’s optimistic, despite the odds being against the long-term success of the deal, is that he knows Benioff is throwing his full weight behind the plans for a deep integration of the two companies’ products. And if Benioff is on board, well, then it just might come to fruition. ‘He has demonstrated over and over again that when he really wants something to happen, it happens,’ says Butterfield.” 

The bottom line? The duo aren’t starting from the most favorable position, and it’s too early to tell how exactly this tie-up will shake out. But much of how this story plays out will depend on the characters at the top of Salesforce. While Benioff says he is now devoting 50% to 75% of his time to “causes outside Salesforce,” his larger-than-life personality still drives the company’s vision and narrative on Wall Street. But no doubt, other characters will also play an outsized role not only on the deal itself, but in terms of Salesforce’s larger strategy. Slack’s Butterfield could prove to be another major player within Salesforce after the deal closes this summer. 

Amid all the talk about Benioff and Butterfield, there’s another person to watch at Salesforce: Bret Taylor, the chief operating officer. Taylor joined the company via another acquisition: That of Quip, which makes collaboration software, in 2016. Currently considered by many to be Benioff’s heir apparent, it was actually Taylor alongside Butterfield who brought the idea of a tie-up with Slack to the Salesforce CEO. (As it so happens, Taylor is also a board member at Twitter and was Facebook’s chief technology officer between 2009 and 2012.)

Of course, as Michal points out, Salesforce has a checkered past when it comes to keeping founders from companies it acquires—so the big question now is how well Benioff, Butterfield, and Taylor get along once the companies are fully integrated. Read the full story here.

Lucinda Shen
Twitter: @shenlucinda
Email: lucinda.shen@fortune.com

Today’s Term Sheet was compiled by Rey Mashayekhi with help from Lucinda Shen. 

VENTURE DEALS

- Celonis, a Munich- and New York City-based enterprise software company focused on data analysis, raised $1 billion in Series D funding, valuing it at $11 billion. Durable Capital Partners and T. Rowe Price Associates led the round, and were joined by investors Franklin Templeton, Splunk Ventures, and Arena Holdings.

- FlixMobility, a Munich-based transportation startup, raised $650 million in Series G funding, valuing it at $3 billion. Investors included Canyon Partners, General Atlantic, Permira, TCV, HV Capital, BlackRock, Baillie Gifford, and Silver Lake. 

- Gong, a Palo Alto-based sales software platform, raised $250 million in Series E funding, valuing it at $7.25 billion. Franklin Templeton led the round and was joined by investors Coatue, Salesforce Ventures, Sequoia Capital, Thrive Capital, and Tiger Global.

- Urban Company, an India-based home services marketplace, raised $255 million in Series F funding, valuing it at $2.1 billion. Prosus Ventures, Dragoneer and Wellington Management led the round and were joined by investors Vy Capital, Tiger Global, and Steadview.

- Outreach, a Seattle-based sales intelligence startup, raised $200 million, valuing it at $4.2 billion. Premji Invest and Steadfast Capital Ventures led the round and were joined by investors including Sequoia Capital, Tiger Global Management, and Vista Equity Partners. 

- Guild Education, a Denver-based firm enabling employer-sponsored education opportunities, raised $150 million in Series E funding, valuing it at $3.75 billion. Investors included Bessemer Venture Partners, Cowboy Ventures, D1 Capital Partners, Emerson Collective, General Catalyst, GSV, Harrison Metal, ICONIQ Capital, Next Play Capital, Redpoint Ventures, and Salesforce Ventures.

- Thirty Madison, a New York City-based health care startup, raised $140 million in Series C funding, valuing it at more than $1 billion. HealthQuest Capital led the round and was joined by investors Mousse Partners, Bracket Capital, Polaris Partners, Johnson & Johnson, Northzone, and Greycroft.

- Intrinsic, a New York City-based company acquiring health and wellness e-commerce companies, raised $113 million in Series A funding. Define Ventures led the round and was joined by investors including Link Ventures.

- Locus, an India-based supply chain logistics platform, raised $50 million in Series C funding. GIC led the round and was joined by investors Qualcomm Ventures, Tiger Global, and Falcon Edge.

- Shippo, a San Francisco-based shipping logistics startup, raised $50 million, valuing it $1 billion. Bessemer Venture Partners led the round.

- Phil, a San Francisco-based software therapy deployment platform, raised $56 million in Series D funding. Warburg Pincus led the round.

- Synchron, a New York City-based neurotechnology company developing brain-machine interfaces, raised $40 million in Series B funding. Khosla Ventures led the round and was joined by investors Forepont Capital Partners, ID8 Investments, Shanda Group, General Advance, Subversive Capital, re.Mind Capital, NeuroTechnology Investors, METIS Innovative, and the University of Melbourne.

- Realtime Robotics, a Boston-based maker of software for industrial robots, raised $31.4 million in Series A funding. Investors include HAHN Automation and SAIC Capital Management.

- Jeeves, a New York City-based expense management platform for startups, raised $31 million in seed and Series A funding. Andreessen Horowitz led the $26 million Series A round and was joined by investors YC Continuity Fund, Jaguar Ventures, Urban Innovation Fund, Uncorrelated Ventures, Clocktower Technology Ventures, 9 Yards Capital, BlockFi Ventures, and Stanford University. Plaid co-founder William Hockey led the $5 million seed round.

- Comunix, an Israel-based social gaming startup, raised $30 million in Series A funding. March Gaming led the round.

- Zenflow, a South San Francisco-based medical device company, raised $24 million in Series B funding. Invus Opportunities led the round and was joined by investors F-Prime Capital, Medical Technology Venture Partners, Golden Seeds, Astia Angels, CloudStone Capital, and SV Tech Ventures.

- Shef, a Redwood City, Calif.-based platform enabling cooks to sell homemade meals, raised $20 million in Series A funding. Andreessen Horowitz led the round and was joined by investors Craft Ventures, M13, Y Combinator, Padma Lakshmi, Tiffany Haddish, Katy Perry, Orlando Bloom, chef Aaron Sanchez, and NBA player Andre Iguodala. 

- Iterative, a San Francisco-based enterprise machine learning platform, raised $20 million in Series A funding. 468 Capital and Mesosphere co-founder Florian Leibert led the round and were joined by investors True Ventures and Afore Capital. 

- Hypori, an Austin-based mobile cybersecurity startup, raised $20 million in Series A funding. GreatPoint Ventures led the round.

- Bobbie, a San Francisco-based infant formula company, raised $15 million in Series A funding. VMG led the round. 

OroraTech, a Munich-based provider of wildfire detection and monitoring services, raised €5.8 million ($7.1 million) in Series A funding. Findus Venture and Ananda Impact Ventures led the round and were joined by investors including APEX Ventures and BayernKapital.

- Moonshot, a London-based data analytics company focused on online harms, raised $7 million in Series A funding. Beringea and Mercia invested.

- Oak9, a Chicago-based security startup, raised $5.9 million in seed funding. Menlo Ventures led the round and was joined by investors including Hyde Park Angels and Uncorrelated Ventures.

- Kin, a Chicago-based insurance technology startup, raised an additional $5.3 million in Series C funding. Symphony Ventures and Flourish Ventures invested.

- Stemma, a Redmond, Wash.-based database company, raised $4.8 million in seed funding. Sequoia Capital led the round.

- Faction Technology, a South San Francisco, Calif-based maker of electric, driverless fleets, raised $4.3 million in seed funding. Trucks Venture Capital and Fifty Years led the round.

- Paloma, a New York City-based sales communication company, raised $4 million in seed funding. Laconia Capital Group led the round and was joined by investors including Philip Krim from Casper and David Heath from Bombas.

PRIVATE EQUITY

- Symphony Technology Group led a consortium acquiring the products business of Milpitas, Calif.-based cybersecurity firm FireEye (NASDAQ: FEYE) for $1.2 billion.

- PSG invested 42 million euro ($51 million) in Artur’In, a Paris-based automated digital marketing provider.

- Aquiline Capital Partners invested in SurePoint Technologies, a Cincinnati-based maker of software for law firms. Financial terms weren't disclosed.

- Arcline Investment Management acquired a controlling stake in Resolution Medical, a Minneapolis-based medical devices company. Financial terms weren't disclosed. 

- Banneker Partners invested in iGrafx, a Tualatin, Ore.-based automation software provider. Financial terms weren't disclosed.

The Carlyle Group and Warburg Pincus invested in NEOGOV, a Los Angeles-based provider of human resources software for the public sector. Financial terms were not disclosed. 

- Corsair invested in Xceptor, a no-code automation software provider owned by Astorg. Financial terms weren't disclosed.

- CVC invested in A Bathing Ape, a Japanese fashion brand, after it became an independent company from I.T. Limited. Financial terms weren't disclosed.

- Enlightened Hospitality Investments, which counts Shake Shack founder Danny Meyer as a partner, invested in NotCo, a Chile-based plant-based food company backed by Jeff Bezos. Financial terms were not disclosed.

- Lincolnshire Management completed a dividend recapitalization of Schumacher Electric, a supplier of power conversion products. Financial terms weren't disclosed.

- Quatrro Business Support Services, backed by VSS Capital Partners, acquired EAB Solutions, a Chicago-based provider of outsourced finance and accounting, and human resource services to not-for-profit organizations. Financial terms weren't disclosed.

- Swander Pace Capital acquired Mommy’s Bliss, a Richmond, Calif.-based wellness brand for infants and mothers. Financial terms were not disclosed.

- York Capital Management invested in Cennox, an Atlanta-based provider of integrated services to the financial services, retail, and transportation industries. Financial terms were not disclosed.

EXITS

- Etsy (NASDAQ: ETSY) agreed to acquire Depop, a London-based platform for used fashion, for $1.6 billion. Depop investors have included Balderton Capital and Octopus Ventures.

- Warburg Pincus acquired a stake in Global Healthcare Exchange, a Louisville, Colo.-based operator of a trading network for patient care. Thoma Bravo has exited its investment. Financial terms weren't disclosed.

- Wind Point Partners acquired American Trailer Rental Group, an Evansville, Ind.-based provider of trailer rental solutions, from Milton Street. Financial terms weren't disclosed.

OTHER

- Prosus agreed to acquire Stack Overflow, a New York City-based platform for developers, for $1.8 billion. Investors including a16z and Spark Capital back Stack Overflow.

- Morphosys agreed to Constellation Pharmaceuticals (NASDAQ: CNST), a Cambridge, Mass.-based cancer specialist, for $1.7 billion.

IPOS

- WeTransfer, a Germany-based file transfer platform, plans to seek an IPO in Amsterdam that would value it at €1 billion ($1.2 billion), per Bloomberg. 

- TaskUs, a New Braunfels, Tx.-based provider of outsourcing services, now plans to raise $304 million in an offering of 13.2 million shares (58% sold by insiders) priced between $22 to $24. Blackstone backs the firm. 

- Mister Car Wash, a Tuscon, Ariz.-based car wash brand, filed to raise $100 million. Leonard Green & Partners backs the firm.

- 1stdibs.com, a New York City-based e-commerce platform for artwork and antiques, plans to raise $112 million in an offering of 5.8 million shares priced between $18 to $21. Benchmark, Insight Partners, and Spark Capital back the firm.

F+FS

- TA Associates, a Boston-based private equity firm, closed its 14th flagship growth equity fund with $12.5 billion and its second select opportunities fund with $1.5 billion.

- Lux Capital, a New York City-based venture capital firm, closed an opportunities fund with $800 million and its seventh early-stage venture fund with $675 million.

- venBio, a San Francisco-based firm, closed its fourth life sciences venture capital fund with $550 million.

- Primavera Capital Group, a Beijing-based investment firm, has raised nearly $547 million for its fourth U.S. dollar fund, which is targeting up to $5 billion, per DealStreetAsia.

- Paceline Equity Partners, aDallas-based private equity firm, closed Paceline Equity Partners Opportunity Fund I woth $350 million.

- Mercato Partners, a Salt Lake City-based private equity investor, closed its second fund devoted exclusively to backing emerging and profitable restaurant concepts, with $100 million.

- Refactor Capital, a Silicon Valley-based venture capital firm, has closed its third fund at $50 million.

PEOPLE

- Oak Hill Capital named Mark Piunho  as a partner. He was most recently at 4x4 Capital.

- Varagon Capital Partners named Suraj Panjwani as a managing director. He was most recently at Invesco.

- Felicis Ventures promoted Grace Chou from vice president to principal.

CORRECTION

Yesterday’s newsletter reported that investment firm Eldridge had invested $100 million in Illuminarium Experiences, an Atlanta-based experiential entertainment company. While Eldridge has invested in Illuminarium, it did not invest that dollar amount; rather, Illuminarium has now raised $100 million in initial funding with Eldridge’s investment.