Leaving Big Tech for a startup? These 7 staff members did just that.


  • Leaving a corporate job for a startup is no easy feat and there are a lot of things to consider.
  • Workers are quitting their jobs at record levels in search of more autonomy and flexibility.
  • Seven people who made the switch to a startup shared their experiences with Insider.

Few could have predicted that a pandemic that had long promised one of the worst economic recessions in modern memory would instead lead to waves of workers voluntarily leaving their jobs in droves.

Dubbed by some the “Great Resignation,” staff members have intensely re-evaluated their working lives in record numbers. In the United States, about 242,000 people arrested in August, bringing the total to 4.3 million for the year, according to figures from the Ministry of Labor.

Tech companies are far from immune to the phenomenon as workers seek more flexibility, a dedication to remote work, and more dynamic and stimulating jobs.

For some, startups with cash in venture capital and the prospect of listed stocks have proven to be enticing enough to get them to give up their corporate tech jobs.

Insider spoke to seven people who left Big Tech to join or launch a startup. Each offered an overview of what it’s like to join a startup and what you should consider before taking the plunge.

Startups are fast

The speed and pace of change of startups relative to large corporations has been widely cited.

Colm O’Cuinneain worked at LinkedIn and Oracle before joining software recruiting firm Greenhouse Software as Managing Director of the EMEA region.

“You have to develop your agility,” he told Insider, noting that large companies can be smaller.

Eshchar Ben-Shirit, CEO and co-founder of food technology company Redefine Meat, experienced it firsthand. Defined processes and long-term strategies help order and clarity, he said, but it can slow down large companies and prevent them from changing.

“In the first month of working at a small business, I saw projects start, end, change and be canceled so quickly – I felt I had gained more experience that year, for example. compared to a year at a large company, ”he added.

Madhu Sridharan, vice president of product management at alternative protein company Eat Just – known for its plant-based eggs – initially had reservations about it.

“Decisions are made very quickly and things can move forward,” she said. “Initially I was worried that there wasn’t enough thinking on something, or that someone might not be aligned, but with quick decisions we are able to move projects forward faster and work more efficiently. “

Not only the pace undergoes substantial changes, but also the weight of the daily decisions. Vivek Sharma, who is leading the development of the State Just process, said critical decisions were needed on a “weekly basis”.

“The teams are watching you to make calls in a timely manner,” said the former DuPont Nutrition scientist. “It’s intense but I love every minute.”

Ann-Marie Smith, head of personnel at the payroll start-up Payslip, has 15 years of experience in HR and recruitment, particularly in telecommunications and insurance companies.

While she should focus on current needs and provide recommendations quickly, she said there are additional chances to be creative and have a meaningful contribution in a startup.

Colm O'Cuinneain, Greenhouse

Colm O’Cuinneain previously worked at LinkedIn and Oracle before joining recruiting software startup Greenhouse.


You have access to decision-makers

“Where can an intern ask a CEO a question about their work? Smith from Payslip spoke about startups. “This is a fantastic opportunity for those new to their careers to have immediate access and openness to all levels of management.”

Relationships and culture in the workplace also benefit. “I have to say that the energy, the freedom and the freshness were exhilarating,” she added. “The lack of company policy meant that we could truly form a team and pursue our common goals.”

Eat Just’s Sridharan reiterated the colon. “I was shocked by the team’s willingness to test new ideas, validate them and develop them quickly,” she said. “It was new, exciting and impactful.”

There are more opportunities to grow and learn

Ben-Shirit, the co-founder of Redefine Meat, acknowledged that “comfort, status and the ability to see a future for you” in a large company makes it difficult to get started.

“However, the thrill, the excitement, the stress and the opportunities of a small business is something one has to experience,” he said. “Waiting too long in a large corporation means you are losing the opportunity to learn the true nature of yourself and your abilities.

The boss urges anyone considering taking the step to assume that the big company will still be around and rehire an employee after gaining “the equivalent of a decade of work experience” in three to four years at a startup.

José Martín Quesada, who left Google and McKinsey before founding fitness startup Krew, said insider roles are shaped by the person who composes them.

“Are you working on customer success? You can learn how to create a product by championing your customer’s feedback and seeing it turn into functionality, ”he said. “Do you work in product development? You can move from opinion to reality by learning some data analytics to make sense of the burst of usage data. “

While an “ambitious” person has the freedom and the opportunity to grow, the flip side is that they must be prepared to face uncertainty, Quesada added.

Be prepared to wear different hats

This experience will extend to a whole range of roles, not just why someone was hired.

“In a startup environment, it’s often all on the bridge, and sometimes you have to get involved where you can be most useful, even if it’s not in your expertise,” Madhu said.

Smith agreed and added that people in the industry have to go as fast as he is.

“Be prepared to be involved in absolutely anything,” she said. “You have to maintain your priorities and avoid focusing on a single task. While things change and adapt so quickly, just go with the flow and pace of those around you. “

Regardless of the role, an employee’s level of contribution is likely to be significant compared to a large company, according to O’Cuinneain. “You know, you have the ability to deliver insight, strategy, and critical customer success at all levels,” he said. “For someone new, you know, coming out of college, it’s a huge opportunity just to be able to develop that breadth and set of skills.”

You may need to rethink your approach to problem solving

Many startups will not have a polished process or “plug and play” workflow.

Sridharan, who previously worked at Mattel and IBM, is “constantly challenged” to be creative and solution-oriented in her current role. “I would have liked to have implemented this entrepreneurial reflection and this problem solving from the very day
one at Eat Just, instead of looking for existing processes or systems that are not always the most efficient
procedure, ”she said.

Some people can be held back by confidence.

“You have to be braver in a small organization to have your views heard more,” O’Cuinneain said. “In large organizations, you often do as you’re told rather than finding the answer. In a startup, the opportunity is huge and really comes down to being brave and what bets you’re going to place.”

There is more pressure to deliver

Startups are “more focused on survival than the normal way of doing business,” said Ben-Shirit, who added that teams should do more with less.

“Understanding that success is the only option, and that lack of experience, resources and even people is not a reason,” he said. “However, once you get used to it, it becomes kind of a superpower.”

Sharma described being part of a startup as “a member of a Formula 1 pit crew” – not a small cog in a big machine. “When the team is small, your contribution to the success of the business is obvious and easily measurable,” he said. “Early on, I understood how impactful my work was going to have, and I was ready to contribute.”

Startups fail, so does due diligence

Startups may seem exciting, have good public relations, and good career prospects, but they are inherently risky and many fail.

Holly Stephens went from Google to a number of smaller startups before founding transcription startup Subly. She advises everyone to “take the emotion out of the opportunity” and ask the right questions of recruiters or founders.

Before joining a startup, Stephens said a candidate should ask how they make money, what are their income projections, how many investments or grants they have received, and what are their track and field plans. growth.

“Don’t be afraid to meet the team as part of your interview process and decision,” she added.

“Make sure that the risk you take by joining a startup will help you achieve your goals such as career growth, learning, or gaining knowledge.”

O’Cuinneain recommended asking for data, financial performance, and exploring product-to-market fit to get a feel for the future of the business. When he joined Greenhouse Software, O’Cuinneain looked at who the company worked with and looked for individuals, such as the founders.

“I listened to what they were saying, whether it was podcasts in the media and interviews,” he said. “I watched what people were saying about them on social media, what customers were saying about them, what potential applicants and former employees were saying about them on Glassdoor.”

O’Cuinneain described joining a startup as a “leap of faith” where you end up putting “a lot of trust in the people you work with.”


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