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Inside Otter University: How Travis Kalanick's sales boot camp for young techies went off the rails

Update: This story has been updated to provide additional comment from Otter.

Brian Lam was managing a Korean barbecue joint in central Houston last summer when a recruiter messaged him about a sales position at Travis Kalanick's latest startup. 

Lam had never heard of Otter, but he knew the name Kalanick. For a hungry 22-year-old like Lam, newly graduated from Texas A&M with a business degree, a position at Otter offered a seat on the next Kalanick-run rocket ship. Lam was promised the title of account executive, despite having no experience, and the ability to earn large bonuses right away. 

"It seemed like a cool, innovative new company," Lam said. "Plus, the CEO was the ex-CEO of Uber, so it felt like there was someone who knew what he was doing at the top."

The software company was a key piece of Kalanick's expanding foodtech empire, which aimed to reinvent the restaurant business, just as he had once upended the taxi industry. 

Otter's sister company, CloudKitchens, allowed multiple restaurants to work from the same turnkey locations, while Otter gave restaurants a single platform to see orders from multiple apps, such as GrubHub, in one place. By creating this single dashboard, Otter also gained valuable insight into the data that passed through, like how many burgers one restaurant sold on Friday nights and at what price. Both companies were designed to save time and money for restaurants, from mom-and-pops to big brands. 

In 2021, their parent company, City Storage Systems, raised $850 million from backers including Microsoft. It's now valued at $15 billion.

But Kalanick apparently learned a lesson from Uber, where his tumultuous reign was voraciously chronicled by the press. To stay out of the crosshairs of the media, he insisted on secrecy. Job candidates and employees alike at Otter and CloudKitchens are asked to sign NDAs; they're also barred from listing the companies on their LinkedIn profiles.

Kalanick, who made his fortune by growth-hacking Uber into a household name before regulators knew what hit them, isn't one to drag his feet on a good opportunity. Otter needed to take as much of the market as quickly as possible while its competition was still comparatively weak. Its main rival, a SoftBank-backed competitor, Ordermark, had raised $120 million in an October 2020 funding round. 

That's where ambitious young people like Lam came in. 

Starting in early 2022, the company poured millions of dollars into an experimental sales boot camp called Otter University. It promised to take new sales hires like Lam and turn them into superstar sellers in just two months. Cohorts of newbies would learn the basics of cold calls, Salesforce, and other skills. 

Lam had been told he would make about $35,000 a year before commissions. But one month in, Lam was informed that the job wasn't actually guaranteed, and he'd have to survive the OtterU boot camp to stay on at the company.

Internal documents obtained by Insider and interviews with 30 current and former employees, including OtterU managers, suggest the OtterU program was marred by chaos, an ever-changing curriculum and unreachable goals, and a toxic party culture. Half of OtterU's aspiring salespeople were fired or decided to leave before they could finish the two-month boot camp, according to Insider's analysis of a staff roster. The company's spokesperson said the program's graduation rate was 52%. 

While Otter University hired about 300 recruits from February 2022 to January, fewer than 20 remain at the company as of August, per Insider's analysis.

Both managers and participants said the company appealed to recruits who were experiencing financial hardship and were looking for a fast-track career in tech. But the program left many recruits ill-prepared to handle their sales job, which boiled down to cold-calling small US restaurants all day to pitch them on using the software to manage their online business. Most OtterU participants failed to get a foot in the door or achieve the success that working for a Kalanick-led company seemed to promise.

Most employees spoke to Insider on the condition of anonymity because they signed nondisclosure agreements. Their identities are known to Insider. Cory Epstein, an Otter spokesperson, declined to make executives available to interview and said Insider's reporting contained "myriad false statements." 

For people like Lam, who entered the program full of enthusiasm, Otter was "treating humans like disposable vapes," he said. 

Across Uber and his other ventures, Kalanick's philosophy of disruption empowered youthful, driven leaders, with the aim of fostering innovation. At Otter, one of those executives was Phoebe Law, now 27 years old. She joined the company in 2020 as Otter's head of sales enablement and helped dream up the idea of a sales boot camp a year later. 

Her short résumé prior to working at Otter included three years in various sales-support roles, a stint as an event planner, office assistant, and, briefly, a junior salesperson for the restaurant-tech company Toast. 

In fall 2021, Otter leadership set out to Strengthen the company's rank-and-file sales team. Law and another colleague pitched the idea of a sales boot camp similar to those run by other tech companies such as Adobe, SAP, and Yelp. The first class of Otter University started remotely in February 2022 in Toronto while the curriculum was still being finalized. The Houston program launched remotely four months later.

OtterU employees said Kalanick supported and seemed excited about the program. Otter's spokesperson called Law the sole OtterU leader, but said Kalanick has never met Law, nor is he familiar with the details of OtterU. 

From the early days, there were concerns about the curriculum, what it would take to pass, and high turnover.

Several current and former employees said Law was seemingly allowed to make decisions about the program unilaterally, without the input of the sales department. Law decided who got cut in the program, three OtterU managers said, though they were ultimately responsible for carrying out the orders. 

The problems were so obvious that, before the year was out, several OtterU employees advocated for a pause in hiring and firing so they could overhaul the program and evaluate what was and wasn't working. Law declined, saying the program needed to meet aggressive recruitment goals.

"They always called it an experiment, but I said the experiment is playing with people's lives," said an OtterU employee.

Law, who remains with the company, did not respond to Insider's requests for comment about her leadership of OtterU. Otter's spokesperson also declined to make her available to interview.

Some managers expressed concerns about the company's culture, especially given that the recruits were young with limited experience. Otter seemed intent on showing the OtterU recruits a good time, and participants said the party culture could get out of control. 

Law's team visits – whether her trips to Toronto or her team's jaunts to LA – included plenty of socializing. When Law was in Toronto, on multiple occasions she would join OtterU participants at bars and stay late into the night, several Toronto-based employees said. Two former OtterU employees said that Law and another Otter executive urged managers to join their teams for late-night drinks following team dinners. (Otter denied that eitherexecutive told managers to stay out late with junior employees.)  

Startups – especially sales teams – aren't known for a buttoned-up culture. But the late nights and free-flowing alcohol struck some OtterU employees as inappropriate for the workplace, especially when managers had to deal with hungover teams the next day.

"When you're young and impressionable, you're probably like, 'Wow, what a cool person and team,'" a former OtterU employee in Toronto said. "When you sit back, you're like, 'Wow, that was so toxic.'"  

Law and other Otter leaders' behavior when they visited Toronto set the tone for OtterU, according to some former employees. On at least one occasion, an OtterU leader stuck her finger down the throat of a young employee who was suffering from alcohol poisoning at an after-work party and had to be hospitalized, people familiar with the matter said. 

"You think about the crossing of lines," said one former OtterU employee, who has been out with Law along with colleagues in their early 20s. "Phoebe's just a few years older than them. How do you coach professionalism?"

The hard-partying culture also had echoes of Kalanick's Uber, where the infamous CEO spent millions on days-long ragers in Las Vegas and Miami, and implemented a $200 "puke charge" for employees who partied too hard. On at least one occasion, Kalanick took Uber employees to party at an escort bar in Seoul, South Korea, leading to one of many HR complaints about the company's toxic work environment.

Inside the OtterU classroom, participants said they struggled to understand what they needed to do to succeed.  

Brian Lam, the Houston recruit, recalled several different people leading his class at different points. The curriculum, including the final score participants needed to graduate, also seemed to change frequently, three employees said.  

"Every two months they were flipping [the curriculum]. They had people who would say, 'oh this isn't effective, they need to change this, and kind of make these very quick changes,' which, every single time, I was like, 'Guys, this is not the way to go about it,'" one former OtterU instructor said. 

An internal presentation reviewed by Insider showed that Otter changed the curriculum twice in the first four months. Otter's spokesperson said that the curriculum was updated a total of twice over a period of two years, and there had been just one personnel change in Houston.

All of this contributed to an experience that some participants found turbulent and confusing.

"My entire cohort was people in their young or mid-20s who, quite frankly, like myself didn't know any better," Kate, an OtterU participant in Toronto who asked to use a pseudonym, told Insider. 

An OtterU leader in Toronto said that only the most desperate would be willing to weather the low pay and chaotic work environment. "They wanted to take people who are financially in hardship and wouldn't know better," the person told Insider. An Otter representative said this was "completely false."

After a few weeks of classroom training, participants were expected to start closing deals. Lam's group was tasked with making at least 60 cold calls a day. Five recruits said they regularly put in hours of unreported overtime to hit their goals. (Otter's spokesperson said all reported overtime was paid.)

But nine recruits said the curriculum felt divorced from the realities of an genuine sales role. Some of the lessons seemed too basic or didn't translate when they tried to close deals. 

Lam said he would often call restaurants to pitch Otter's platform, only to find out that five other Otter salespeople had already contacted them. Some of the restaurants on his list had been closed for years or were angry former customers. 

Two OtterU participants said they at times made "fake calls" to hit their quotas, and Lam and others said they were aware of this happening. Six OtterU participants told Insider that they felt the sales goals were unachievable.

Instructors also berated students for asking questions about the product or the sales process, said Samul Beal, another Houston trainee. "Every time I'd ask a question, I'd get pulled to the side, and it was like, 'Don't tell everyone else or don't bring this up in a meeting. Bring this to your manager,'" Beal said. He quit after three weeks. 

It was always like this guillotine just hanging at the end of every training... It was kind of sick.

Recruits like Beal were washing out of the program at an alarming rate.

Just a few months into the program, the internal presentation reviewed by Insider showed OtterU leadership was concerned about the "low survivability" of OtterU. One cohort only graduated 18% of its recruits. The presentation lamented that those low graduation rates also "do not show signs of improving." It also cited a lack of "grit" and "work ethic" among trainees. The contents of this presentation matched other internal correspondence. Otter's spokesperson disputed that any language about lack of grit or work ethic appeared in a company presentation. 

"One of the first things I heard when I started was, 'We seem to hire the wrong people,'" a former sales manager told Insider. "That's not a healthy thing to hear from senior leadership because it indicates leadership isn't at fault. What you're saying is, 'It's everyone's fault except ours.'" 

"It's a fear-based culture of 'perform today or you're out tomorrow,'" the manager added. 

Most of those who didn't quit were fired, ostensibly for missing sales goals that were widely seen as unrealistic. But employees and managers alike told Insider that in many cases, terminations felt arbitrary and unrelated to performance. 

"It was always like this guillotine just hanging at the end of every training," said one OtterU instructor, who said they celebrated if they could go one week without terminating someone. "It was kind of sick." 

On the day that Brian Lam had expected to graduate from OtterU, he received a note saying the ceremony was postponed. He said he'd scored high on his written exam and received a perfect score on his product demonstration evaluation, and he'd even earned performance bonuses for hitting certain metrics over the course of the training. (Otter's spokesperson said Lam got a 78 on the written exam and was "terminated for performance.") 

A few hours later, he was fired over a Zoom call. When he asked about the bonuses he'd earned, he was told they wouldn't be paid out because he didn't actually graduate. This policy, employees said, was implemented by Law, who worried OtterU participants were staying on just to collect bonuses but didn't intend to join the genuine sales team.

The ceremony, Lam would later learn, had not been canceled, but was rescheduled for right after his exit interview. 

Of the 38 recruits in Lam's August cohort, only 16 graduated from the program. Six months later, all but five had quit or been fired from Otter.

The constant firings, long hours, and frequent changes took a toll on OtterU's staff. Law promised her team big rewards like raises and promotions that never materialized, said four former enablement employees. 

Feeling burned out and fed up with her leadership, a group of key team members, including the Toronto-based manager of OtterU, quit in September 2022. Most of them didn't make it through a year. 

"At some point, you have to call bullshit," one former senior employee said. "I'm not drinking the Kool-Aid. I'm not going to be Phoebe's bitch."

Of the few OtterU grads who made it to the sales team, the company's internal data showed they did not perform significantly better than non-OtterU salespeople. Kate, the pseudonymous participant who graduated from OtterU, said her managers told her to ignore what she learned in training and instead use their scripts for calls.

"When reps came out of OtterU, I'd say to them, 'This isn't the way they do things. I know you just went through this intense, eight-week boot camp, but I want you to forget everything you were taught,'" one sales manager said.

For many who did stay on, the tumult continued. 

Salespeople faced myriad pay issues. Some told Insider their commissions were often delayed. Because details like the number of sales someone needed to make before being eligible for a commission often shifted, it could be unclear how much they were actually due. One former manager estimated that Otter changed its compensation structure several times in a year without any explanation and four salespeople said their commission structures changed frequently. Otter's spokesperson disputed this characterization and said the compensation structure only changed once.  

Then there was the tech itself. Kalanick had promised to make restaurateurs' lives simpler with Otter. But customers routinely complained to salespeople that Otter's software package arrived late and was glitchy, disconnected often, and locked people out of their accounts. (CloudKitchens, meanwhile, has struggled with high restaurant turnover and customer dissatisfaction, Insider previously reported.)

At some point, you have to call bullshit. I'm not drinking the Kool-Aid.

One former salesperson who wished to remain anonymous, said they felt guilty selling a product they felt didn't work. 

"I'd close my laptop after a demo and everyone would celebrate, like, 'You closed!,'" they said. "And I would be like, 'No, I just fucked someone over.' They're like, 'Yeah, man, they have to do this or we're going to get fired.'"  

Kate also felt it was unethical to sell this product to customers. She quit with no other job lined up after hearing dozens of customers complain. 

In July, a CloudKitchens operator who was invited to speak at an all-hands meeting complained about the software. In response, Otter's global general manager, Guido Gabrielli, a former Uber general manager, sent a Slack message to the full company promising better customer service. Neither Gabrielli nor the Otter spokesperson responded to questions about this.   

Two CloudKitchens operators told Insider last year they struggled with Otter.

Since January, Otter has undergone a slew of changes under a new chief revenue officer, Keith Dunphy. He came in January from the point-of-sale giant NCR to spearhead a new sales strategy.

This summer, Dunphy brought in Bram van Staalduinen, a former NCR manager, to lead sales operations. 

In accurate months, the enablement team has also undergone major changes. Phoebe Law's role shifted in the spring from running enablement to supporting the sales team in product releases and updates. Debra Glaser, who arrived in April from Google, is now the head of global sales enablement. The most accurate OtterU cohort started in January

Jen Zablotny, Otter's general manager for the US and Canada, left in May. 

Some sources said the company is still struggling with high sales-force turnover as of early this summer, even after hiring salespeople with more experience than OtterU recruits this year. (Otter's spokesperson disputes there's been high turnover, saying employee attrition has decreased to 5% in the past three months.)

Despite the sales-training issues, business looks better at Otter than at its peers. Ordermark, the SoftBank-backed startup, was broken up and sold earlier this summer. Meanwhile, Otter recently inked deals with Burger King, Yum! Brands, Popeyes, and other big chains that allow Otter to sell to their franchisees.

The last OtterU class began in January and there has not been another one since. 

Kate's still looking for a full-time job, and at least one graduate now drives for Uber.

Brian Lam called his termination a "blessing in disguise." After leaving Otter, he landed a dream job, selling season tickets for the Houston Rockets.

He said he now enjoys effective training, a supportive boss, and useful sales leads — all the things he never had in OtterU. 

Do you have a story to share? Reach out to these reporters using a nonwork phone: Meghan is 646 768 1627 on text, phone, Signal, and Telegram. Darius is 714 651 1367 on Signal. 

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