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Extra Crunch roundup: Crucial API metrics, US startup funding, advanced SEO tactics

On a recent episode of Extra Crunch Live, Retail Zipline founder Melissa Wong and Emergence Capital investor Lotti Siniscalco joined Managing Editor Jordan Crook to walk attendees through Zipline’s Series A deck.

Interestingly, the conversation revealed that Wong declined an invitation to do a virtual pitch and insisted on an in-person meeting.

“She was one of the few or maybe the only CEO who ever stood up to pitch the entire team,” said Siniscalco.

“She pointed to the screen projected behind her to help us stay on the most relevant piece of information. The way she did it really made us stay with her. Like, we couldn’t break eye contact.”


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Beyond Wong’s pitch technique, this post also examines some of the key “customer love” metrics that helped Zipline win the day, such as CAC, churn rates and net promoter score.

“In retrospect, I really underestimated the competitive advantage of coming from the industry,” said Wong. “But it resulted in the numbers in our deck, because I know what customers want, what they want to buy next, how to keep them happy and I was able to be way more capital-efficient.”

Read our recap with highlights from their conversation, or click though to watch a video with their entire chat.

Thanks very much for reading Extra Crunch this week!

Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist

Investors don’t expect the US startup funding market to slow down

Global venture capital reached $156 billion in Q2 2021, a YOY increase of 157%. A record number of unicorns found their feet during the same period and valuations rose across the board, report Anna Heim and Alex Wilhelm in today’s edition of The Exchange.

Even if round counts didn’t set all-time highs, “the general vibe of Q2 venture capital data was clear: It’s a great time for startups looking to raise capital.”

Anna and Alex are interviewing VCs in different regions to find out why they’re feeling so generous and optimistic. Today, they started with the following U.S.-based investors:

  • Amy Cheetham, principal, Costanoa Ventures
  • Marlon Nichols, founding managing partner, MaC Venture Capital
  • Vanessa Larco, partner, New Enterprise Associates
  • Jeff Grabow, venture capital leader, EY US

Despite the hype, construction tech will be hard to disrupt

Image of two construction workers examining blueprints next to a laptop to represent tech on construction sites.

Image Credits: AzmanJaka (opens in a new window) / Getty Images

The construction industry might seem like a sector wanting innovation, Safe Site Check In CEO and founder David Ward writes in a guest column, but there are unique challenges that make construction firms slow to adapt to new technology.

From the way construction projects are funded to complicated local regulations, there’s no one-size-fits-all solution for the construction industry’s tech problems.

Construction tech might be appealing to investors, Ward writes, but it must be “easy to use, easy to deploy or access while on a job site, and improve productivity almost immediately.”

 

3 analysts weigh in: What are Andy Jassy’s top priorities as Amazon’s new CEO?

Jeff Bezos, executive chairman and Andy Jassy, CEO at Amazon

Image Credits: AP Photo/Isaac Brekken/John Locher

Now that he’s stepping away from AWS and taking over for Jeff Bezos, what are the biggest challenges facing incoming Amazon CEO Andy Jassy?

Enterprise reporter Ron Miller reached out to three analysts to get their take:

  • Robin Ody, Canalys
  • Sucharita Kodali, Forrester
  • Ed Anderson, Gartner

Amazon is listed second in the Fortune 500, but it’s not all sunshine and roses — maintaining growth, unionization, and the potential for antitrust regulation at home and abroad are just a few of his responsibilities.

“I think the biggest to-do is to just continue that momentum that the company has had for the last several years,” Kodali says. “He has to make sure that they don’t lose that. If he does that, I mean, he will win.”

The most important API metric is time to first call

Close up of a stopwatch resting on a laptop's trackpad.

Image Credits: Peter Dazeley (opens in a new window) / Getty Images

Publishing an API isn’t enough for any startup: Once it’s released, the hard work of cultivating a developer base begins.

Postman’s head of developer relations, Joyce Lin, wrote a guest post for Extra Crunch based on the findings of a study aimed at increasing adoption of APIs that utilize a public workspace.

Lin found that the most important metric for a public API is time to first call (TTFC). It makes sense — faster TTFC allows developers to begin using new tools quickly. As a result, “legitimately streamlining TTFC results in a larger market potential of better-educated users for the later stages of your developer journey,” writes Lin.

This post isn’t just for the developers in our audience: TTFC is a metric that product and growth teams should also keep top of mind, they suggest.

“Even if your market is defined as a limited subset of the developer community, any enhancements you make to TTFC equate to a larger available market.”

 

Q3 IPO cycle starts strong with Couchbase pricing and Kaltura relisting

Image Credits: olli0815/iStock

Couchbase and Kaltura offered new filings Monday, with NoSQL provider Couchbase setting an initial price range for its IPO and Kaltura resurrecting its public offering with a fresh price range and new financial information.

“Both bits of news should help us get a handle on how the Q3 2021 IPO cycle is shaping up at the start,” Alex Wilhelm writes.

 

5 advanced-ish SEO tactics to win in 2021

SEO tactics for the underdog

Image Credits: PM Images (opens in a new window)/ Getty Images

Mark Spera, the head of growth marketing at Minted, offers SEO tips to help smaller sites stand out.

He writes in a guest column that Google’s algorithm “errs on the side of caution,” which leads the search engine to favor larger, more established websites.

“The cards aren’t in your favor, so you need to be even more strategic than the big guys,” he writes. “This means executing on some cutting-edge hacks to increase your SEO throughput and capitalize on some of the arbitrage still left in organic search. I call these five tactics ‘advanced-ish,’ because none of them are complicated, but all of them are supremely important for search marketers in 2021.”

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3 analysts weigh in: What are Andy Jassy’s top priorities as Amazon’s new CEO?

It’s not easy following a larger-than-life founder and CEO of an iconic company, but that’s what former AWS CEO Andy Jassy faces this week as he takes over for Jeff Bezos, who moves into the executive chairman role. Jassy must deal with myriad challenges as he becomes the head honcho at the No. 2 company on the Fortune 500.

How he handles these challenges will define his tenure at the helm of the online retail giant. We asked several analysts to identify the top problems he will have to address in his new role.

Ensure a smooth transition

Handling that transition smoothly and showing investors and the rest of the world that it’s business as usual at Amazon is going to be a big priority for Jassy, said Robin Ody, an analyst at Canalys. He said it’s not unlike what Satya Nadella faced when he took over as CEO at Microsoft in 2014.

Handling the transition smoothly and showing investors and the rest of the world that it’s business as usual at Amazon is going to be a big priority for Jassy.

“The biggest task is that you’re following Jeff Bezos, so his overarching issue is going to be stability and continuity. … The eyes of the world are on that succession. So managing that I think is the overall issue and would be for anyone in the same position,” Ody said.

Forrester analyst Sucharita Kodali said Jassy’s biggest job is just to keep the revenue train rolling. “I think the biggest to-do is to just continue that momentum that the company has had for the last several years. He has to make sure that they don’t lose that. If he does that, I mean, he will win,” she said.

Maintain company growth

As an online retailer, the company has thrived during COVID, generating $386 billion in revenue in 2020, up more than $100 billion over the prior year. As Jassy takes over and things return to something closer to normal, will he be able to keep the revenue pedal to the metal?

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Nobody wins as DoD finally pulls the plug on controversial $10B JEDI contract

After several years of fighting and jockeying for position by the biggest cloud infrastructure companies in the world, the Pentagon finally pulled the plug on the controversial winner-take-all, $10 billion JEDI contract today. In the end, nobody won.

“With the shifting technology environment, it has become clear that the JEDI cloud contract, which has long been delayed, no longer meets the requirements to fill the DoD’s capability gaps,” a Pentagon spokesperson stated.

The contract procurement process began in 2018 with a call for RFPs for a $10 billion, decade-long contract to handle the cloud infrastructure strategy for The Pentagon. Pentagon spokesperson Heather Babb told TechCrunch why they were going with the. single-winner approach: “Single award is advantageous because, among other things, it improves security, improves data accessibility and simplifies the Department’s ability to adopt and use cloud services,” she said at the time.

From the start though, companies objected to the single-winner approach, believing that the Pentagon would be better served with a multi-vendor approach. Some companies, particularly Oracle believed the procurement process was designed to favor Amazon.

In the end it came down to a pair of finalists — Amazon and Microsoft — and in the end Microsoft won. But Amazon believed that it had superior technology and only lost the deal because of direct interference by the previous president who had open disdain for then-CEO Jeff Bezos (who is also the owner of the Washington Post newspaper).

Amazon decided to fight the decision in court, and after months of delay, the Pentagon made the decision that it was time to move on. In a blog post, Microsoft took a swipe at Amazon for precipitating the delay.

“The 20 months since DoD selected Microsoft as its JEDI partner highlights issues that warrant the attention of policymakers: When one company can delay, for years, critical technology upgrades for those who defend our nation, the protest process needs reform. Amazon filed its protest in November 2019 and its case was expected to take at least another year to litigate and yield a decision, with potential appeals afterward,” Microsoft wrote in its blog post about the end of the deal.

But in a statement of its own, Amazon reiterated its belief that the process was not fairly executed. “We understand and agree with the DoD’s decision. Unfortunately, the contract award was not based on the merits of the proposals and instead was the result of outside influence that has no place in government procurement. Our commitment to supporting our nation’s military and ensuring that our warfighters and defense partners have access to the best technology at the best price is stronger than ever. We look forward to continuing to support the DoD’s modernization efforts and building solutions that help accomplish their critical missions,” a company spokesperson said.

It seems like a fitting end to a project that I felt was doomed from the beginning. From the moment the Pentagon announced this contract with the cutesy twist on the Star Wars name, the procurement process has taken more twists and turns than a TV soap.

In the beginning, there was a lot of sound and fury and it led to a lot of nothing. We move onto whatever cloud procurement process happens next.

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Equity Monday: Jeff’s going to space, and everyone wants a piece of Flipkart

Hello and welcome back to Equity, TechCrunch’s venture capital-focused podcast where we unpack the numbers behind the headlines.

This is Equity Monday, our weekly kickoff that tracks the latest private market news, talks about the coming week, digs into some recent funding rounds and mulls over a larger theme or narrative from the private markets. You can follow the show on Twitter here and myself here.

It’s WWDC week, so expect a deluge of Apple news to overtake your Twitter feed here and there over the next few days. But there’s a lot more going on, so let’s dig in:

And that’s your start to the week. More to come from your friends here on Wednesday, and Friday. Chat soon!

Equity drops every Monday at 7:00 a.m. PST, Wednesday, and Friday at 6:00 AM PST, so subscribe to us on Apple PodcastsOvercastSpotify and all the casts!

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As concerns rise over forest carbon offsets, Pachama’s verified offset marketplace gets $15 million

Restoring and preserving the world’s forests has long been considered one of the easiest, lowest-cost and simplest ways to reduce the amount of greenhouse gases in the atmosphere.

It’s by far the most popular method for corporations looking to take an easy first step on the long road to decarbonizing or offsetting their industrial operations. But in recent months the efficacy, validity and reliability of a number of forest offsets have been called into question thanks to some blockbuster reporting from Bloomberg.

It’s against this uncertain backdrop that investors are coming in to shore up financing for Pachama, a company building a marketplace for forest carbon credits that it says is more transparent and verifiable thanks to its use of satellite imagery and machine learning technologies.

That pitch has brought in $15 million in new financing for the company, which co-founder and chief executive Diego Saez Gil said would be used for product development and the continued expansion of the company’s marketplace.

Launched only one year ago, Pachama has managed to land some impressive customers and backers. No less an authority on things environmental than Jeff Bezos (given how much of a negative impact Amazon operations have on the planet), gave the company a shoutout in his last letter to shareholders as Amazon’s outgoing chief executive. And the largest e-commerce company in Latin America, Mercado Libre, tapped the company to manage an $8 million offset project that’s part of a broader commitment to sustainability by the retailing giant.

Amazon’s Climate Pledge Fund is an investor in the latest round, which was led by Bill Gates’ investment firm Breakthrough Energy Ventures. Other investors included Lowercarbon Capital (the climate-focused fund from über-successful angel investor, Chris Sacca), former Uber executive Ryan Graves’ Saltwater, the MCJ Collective, and new backers like Tim O’Reilly’s OATV, Ram Fhiram, Joe Gebbia, Marcos Galperin, NBA All-star Manu Ginobili, James Beshara, Fabrice Grinda, Sahil Lavignia and Tomi Pierucci.

That’s not even the full list of the company’s backers. What’s made Pachama so successful, and given the company the ability to attract top talent from companies like Google, Facebook, SpaceX, Tesla, OpenAI, Microsoft, Impossible Foods and Orbital Insights, is the combination of its climate mission applied to the well-understood forest offset market, said Saez Gil.

“Restoring nature is one of the most important solutions to climate change. Forests, oceans and other ecosystems not only sequester enormous amounts of CO2 from the atmosphere, but they also provide critical habitat for biodiversity and are sources of livelihood for communities worldwide. We are building the technology stack required to be able to drive funding to the restoration and conservation of these ecosystems with integrity, transparency and efficiency” said Saez Gil. “We feel honored and excited to have the support of such an incredible group of investors who believe in our mission and are demonstrating their willingness to support our growth for the long term.” 

Customers outside of Latin America are also clamoring for access to Pachama’s offset marketplace. Microsoft, Shopify and SoftBank are also among the company’s paying buyers.

It’s another reason that investors like Y Combinator, Social Capital, Tobi Lutke, Serena Williams, Aglaé Ventures (LVMH’s tech investment arm), Paul Graham, AirAngels, Global Founders, ThirdKind Ventures, Sweet Capital, Xplorer Capital, Scott Belsky, Tim Schumacher, Gustaf Alstromer, Facundo Garreton and Terrence Rohan were able to commit to backing the company’s nearly $24 million haul since its 2020 launch. 

“Pachama is working on unlocking the full potential of nature to remove CO2 from the atmosphere,” said Carmichael Roberts from BEV, in a statement. “Their technology-based approach will have an enormous multiplier effect by using machine learning models for forest analysis to validate, monitor and measure impactful carbon neutrality initiatives. We are impressed by the progress that the team has made in a short period of time and look forward to working with them to scale their unique solution globally.” 

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How Pilot charted a course of not raising too much money

A few weeks ago, we wrote about fintech Pilot raising a $100 million Series C that doubled the company’s valuation to $1.2 billion.

Bezos Expeditions — Amazon founder Jeff Bezos’ personal investment fund — and Whale Rock Capital joined the round, adding $40 million to a $60 million raise led by Sequoia about one month prior.

That raise came after a $40 million Series B in April 2019 co-led by Stripe and Index Ventures that valued the company at $355 million.

Both raises were notable and warranted coverage. But sometimes it’s fun to take a peek at the stories behind the raises and dig deeper into the numbers.

So here we go.

First off, San Francisco-based Pilot — which has a mission of affordably providing back-office services such as bookkeeping to startups and SMBs — apparently had term sheets that offered “2x the $40M” raised in its Series B. But it chose not to raise so much capital. 

I also heard that the same investor that ended up leading a now defunct competitor’s $60 million raise first asked to invest $60 million in Pilot as a follow-on to that Series B prior to making the other investment. While I don’t know for sure, I can only presume that what is being referred to is ScaleFactor’s $60 million Series C raise in August 2019 that was led by Coatue Management. (ScaleFactor crashed and burned last year.)

According to CFO Paul Jun: “There were many periods when Pilot turned away new customers and growth capital instead of absolutely maximizing short-term growth…Pilot prioritized building the foundational investments needed for scalability, reliability and high velocity. When it was presented with the opportunity for additional funding towards further growth in 2019, it declined to do so.”

Co-founder and CEO Waseem Daher elaborates, pointing out that the first company that Pilot’s founding team ran, Ksplice, was bootstrapped before getting acquired by Oracle in 2011. (It’s also worth noting that the founding team are all MIT computer scientists.)

“Ultimately, the reason to raise money is you believe that you can deploy the capital, to grow the company or to basically cause the company to grow at the rate you’d like to grow. And it doesn’t make sense to raise money if you don’t need it, or don’t have a good plan for what to do with it,” Daher told TechCrunch. “Too much capital can be bad because it sort of leads you to bad habits…When you have the money, you spend the money.”

So despite what he describes as “a great deal of institutional interest” in 2019, Pilot opted to raise just $40 million, instead of $80 million to $100 million, because it was the amount of capital the company had confidence that it could deploy successfully.

Also, Jun shared some numbers beyond the recent raise amount and valuation.

  • The company has tripled revenue every year since inception, except for 2020 when it doubled revenue.
  • Pilot claims to have had a cash burn of $800,000 per month in 2020 against a starting balance of $40 million.
  • The startup touts a 60% GAAP gross margin. Daher notes: “We feel really good about having long-term unit economics that will work for this business without resorting to offshoring or outsourcing in a way that could compromise quality and compromise relationships.”

Bottom line is companies don’t have to accept all the capital that’s offered to them. And maybe in some cases, they shouldn’t.

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Jeff Bezos’ investment fund is backing a startup hoping to be the AWS for SMB accounting

One of the biggest pain points for startups and small businesses is keeping up with back office tasks such as bookkeeping and managing taxes.

QuickBooks, it seems, just doesn’t always cut it.

Three-time co-founders Waseem Daher, Jeff Arnold, and Jessica McKellar formed Pilot with the mission of affordably providing back office services to startups and SMBs. With over 1,000 customers, it has gained serious traction over the years. And Pilot has now also received validation from some big-name investors. On Friday, the company announced a $100 million Series C that doubles the company’s valuation to $1.2 billion.

Bezos Expeditions — Amazon founder Jeff Bezos’ personal investment fund — and Whale Rock Capital (a $10 billion hedge fund) co-led the round, which also included participation from Sequoia Capital, Index Ventures, Authentic Ventures and others. 

Stripe and Index Ventures co-led Pilot’s $40 million Series B in April 2019. The latest financing brings the company’s total funding raised to over $158 million since its 2017 inception.

The founding team certainly has an impressive track record, having founded and sold two previous companies: Ksplice  (to Oracle) and Zupli (to Dropbox).

Pilot’s pitch is about more than just software. The company combines its software with accountants to do things such as provide “CFO Services” to SMBs without a full-stack finance team. It also provides monthly variance analysis for all its bookkeeping customers, essentially serving as a controller for those companies, so they can make better budgeting and spending decisions.

It also helps companies access small business tax credits they may not have otherwise known about. 

Last year, Pilot completed more than $3 billion in bookkeeping transactions for its customers, which range from pre-revenue startups to larger companies with more than $30M of revenue a year. Customers include Bolt, r2c and Pathrise, among others.

Pilot has also inked a number of co-marketing partnerships with companies such as American Express, Bill.com, Brex, Carta, Gusto, Rippling, Stripe, SVB, and Techstars.

Ironically, Pilot says it aspires to the “AWS of SMB backoffice.” (In fact, co-founder Waseem Daher started his career as an intern at Amazon). Put simply, Pilot wants to take care of all those back office tasks so companies can focus more on growth and winning business.

Pilot strives to offer an “exceptional customer experience,” which is reflected in the fact that over 80% of the company’s business is driven by customer referrals and organic interest, according to Daher.

Whale Rock Partner Kristov Paulus said that white-glove customer service experience and Pilot’s “carefully-engineered” software make a powerful combination.

“We look forward to supporting Pilot in their vision to make back office services as easy-to-use, scalable, and ubiquitous as AWS has with the cloud,” he said.

Pilot’s model reminds me a lot of that of ScaleFactor’s, an Austin-based startup that raised $100 million in a year before it crashed and burned. But the difference in this case is that Pilot seems to have satisfied customers.

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Tableau CEO Adam Selipsky is returning to AWS to replace Andy Jassy as CEO

When Amazon announced last month that Jeff Bezos was moving into the executive chairman role, and AWS CEO Andy Jassy would be taking over the entire Amazon operation, speculation began about who would replace Jassy.

People considered a number of internal candidates viable, such as Peter DeSantis, vice president of global infrastructure at AWS and Matt Garman, who is vice president of sales and marketing. Not many would have chosen Tableau CEO Adam Selipsky, but sure enough he is returning home to run the division he left in 2016.

In an email to employees, Jassy wasted no time getting to the point that Selipsky was his choice, saying that the former employee helped launch the division when they hired him in 2005, then spent 11 years helping Jassy build the unit before taking the job at Tableau. Through that lens, the choice makes perfect sense.

“Adam brings strong judgment, customer obsession, team building, demand generation, and CEO experience to an already very strong AWS leadership team. And, having been in such a senior role at AWS for 11 years, he knows our culture and business well,” Jassy wrote in the email.

Jassy has run AWS since its earliest days, taking it from humble beginnings as a kind of internal experiment on running a storage web service to building a mega division currently on a $51 billion run rate. It is that juggernaut that will be Selipsky’s to run, but he seems well-suited for the job.

He is a seasoned executive, and while he’s been away from AWS since before it really began to grow into a huge operation, he should still understand the culture well enough to step smoothly into the role.  At the same time, he’s leaving Tableau, a company he helped transform from a desktop software company into one firmly based in the cloud.

Salesforce bought Tableau in June 2019 for a cool $15.7 billion and Selipsky has remained at the helm since then, but perhaps the lure of running AWS was too great and he decided to take the leap to the new job.

When we wrote a story at the end of last year about Salesforce’s deep bench of executive talent, Selipsky was one of the CEOs we pointed at as a possible replacement should CEO and chairman Marc Benioff step down. But with it looking more like president and COO Bret Taylor would be the heir apparent, perhaps Selipsky was ready for a new challenge.

Selipsky will make his return to AWS on May 17th and spend a few weeks with Jassy in a transitional time before taking over the division to run on his own. As Jassy slides into the Amazon CEO role, it’s clear the two will continue to work closely together, just as they did for over a decade.

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Could Marc Benioff be the next CEO to move to executive chairman?

Last month Jeff Bezos announced he would step down as CEO of Amazon later this year, moving into the executive chairman role, while passing the baton to AWS CEO Andy Jassy. Could Marc Benioff, co-founder, chairman and CEO at Salesforce be the next big-name executive to make a similar move?

A Reuter’s story published on Monday suggested that could be the case. Citing unnamed sources, the story indicated that Benioff’s CEO exit could happen this year. Further those same sources suggested that current Salesforce president and COO Bret Taylor is the likely heir apparent.

We wrote a story at the end of last year speculating on possible successors to Benioff, were he to step away from the CEO role. There were a number of worthy candidates, several of whom, like Taylor, came to the company via an acquisition. All the same, we thought that Taylor seemed to be the most likely candidate to replace Benioff.

We asked Salesforce for a comment on the Reuter’s story. A company spokesperson told us that the company doesn’t comment on rumors or speculation.

While the entire scenario fits firmly in the rumor and speculation column, it is not entirely unlikely either. What would it mean if Benioff stepped away and what if Taylor was truly the next in line? And how would that swap compare with the Bezos decision were it to happen?

Similar yet different

Salesforce and Amazon are both companies founded in the 1990s, each looking to shake up its industry.

For Amazon, it was changing the way goods (starting with books) were bought and sold. And for Benioff the goal was changing the way software was sold. Bezos famously founded his company in his garage. Benioff built his in a rented apartment. From these humble beginnings both have built iconic companies and accumulated enormous wealth. You could understand why either could be ready to step away from the daily grind of running a company after all these years.

Bezos announced that veteran executive Andy Jassy, who runs the company’s cloud arm, would be his replacement when the handoff comes. Jassy knows the organization’s priority mix as he’s been working at the company for more than two decades. He’s locked into the culture and helped take AWS from idea to $50 billion juggernaut.

While Benioff hasn’t made any actual firm pronouncement, we have seen Bret Taylor — who joined the company in 2016 when Salesforce purchased his startup Quip for $750 million — move quickly up the ladder.

Laurie McCabe, co-founder and analyst at SMB Group, who has been following Salesforce since its earliest days, says that if Benioff were to leave, he would obviously leave big shoes to fill. But she agreed that everything seems to point to Taylor as his successor should that happen.

“Salesforce has been grooming Taylor for awhile. He has some stellar credentials both at Salesforce, his own start-up, Quip, that Salesforce acquired, and at Facebook. There’s no doubt in my mind he can lead Salesforce forward, but he’ll bring a different more low-key style to the role. And I’m sure Benioff will stay very involved […],” McCabe said.

Two different situations

Brent Leary, founder and principal analyst at CRM Essentials says that while he believes Taylor could be chosen as Benioff’s successor, and would be qualified to lead the company, he’s taken a very different path from Jassy.

“I think Benioff moving on could be different from Bezos in the sense that Jassy has been at Amazon for over 20 years and was there to basically see and be part of most of the story. […] But if Taylor were to succeed Benioff there’s not as much [history] at Salesforce with him not being on board until the Quip acquisition in 2016,” Leary said.

Leary wonders if this relatively short history with the company could create some political friction in the organization if he were chosen to succeed Benioff. “I’m not saying that this would happen, but choosing one of the many possible heirs that have come via a number of high profile acquisitions could possibly lead to high level turnover from those not picked to succeed Benioff,” he said.

But Holger Mueller, an analyst at Constellation Research says that if you look at the range of candidates available, he believes that Taylor would be the best choice. “I don’t expect any issue because there is no one with a similar or even better background, which is when there are problems — that or when people are in an open competition as it used to be at GE,” he said.

We don’t know for sure what the final outcome will be, but if Benioff does decide to join Bezos and takes the executive chairman mantle at the company, it makes sense that the person to replace him will be Taylor. But for now, it remains in the realm of speculation, and we’ll just to wait and see if that’s what comes to pass.

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Is overseeing cloud operations the new career path to CEO?

When Amazon announced last week that founder and CEO Jeff Bezos planned to step back from overseeing operations and shift into an executive chairman role, it also revealed that AWS CEO Andy Jassy, head of the company’s profitable cloud division, would replace him.

As Bessemer partner Byron Deeter pointed out on Twitter, Jassy’s promotion was similar to Satya Nadella’s ascent at Microsoft: in 2014, he moved from executive VP in charge of Azure to the chief exec’s office. Similarly, Arvind Krishna, who was promoted to replace Ginni Rometti as IBM CEO last year, also was formerly head of the company’s cloud business.

Could Nadella’s successful rise serve as a blueprint for Amazon as it makes a similar transition? While there are major differences in the missions of these companies, it’s inevitable that we will compare these two executives based on their former jobs. It’s true that they have an awful lot in common, but there are some stark differences, too.

Replacing a legend

For starters, Jassy is taking over for someone who founded one of the world’s biggest corporations. Nadella replaced Steve Ballmer, who had taken over for the company’s face, Bill Gates. Holger Mueller, an analyst at Constellation Research, says this notable difference could have a huge impact for Jassy with his founder boss still looking over his shoulder.

“There’s a lot of similarity in the two situations, but Satya was a little removed from the founder Gates. Bezos will always hover and be there, whereas Gates (and Ballmer) had retired for good. [ … ] It was clear [they] would not be coming back. [ … ] For Jassy, the owner could [conceivably] come back anytime,” Mueller said.

But Andrew Bartels, an analyst at Forrester Research, says it’s not a coincidence that both leaders were plucked from the cloud divisions of their respective companies, even if it was seven years apart.

“In both cases, these hyperscale business units of Microsoft and Amazon were the fastest-growing and best-performing units of the companies. [ … ] In both cases, cloud infrastructure was seen as a platform on top of which and around which other cloud offerings could be developed,” Bartels said. The companies both believe that the leaders of these two growth engines were best suited to lead the company into the future.

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