June 30, 2022

StrategisChhr

Skillful Business Crafters

Getting a Startup Job as a Late-Career Candidate

Getting a job at a startup can be very rewarding — emotionally and financially — for executives who are later in their careers. But the day-in, day-out reality of working in a fast-growing business can be challenging. Startups often have an intense pace, a lack of structure and process, constant change, and inexperienced managers. They’re also simply risky — data proves that most startups fail. The author, an executive coach, presents five steps to help you think through your decision and maximize your likelihood of success.

As the great reshuffle continues to unfold, many seasoned professionals have taken stock of their careers. Some, after decades of climbing the corporate ladder, may be looking for the fulfillment of a new professional environment and the excitement of a fast-growing company. As a result, they’re beginning to think more seriously about leaving their safe corporate jobs and taking a role in a startup.

As an executive coach, I’ve worked with many experienced leaders who want to make this leap. I’ve also been a part of the hiring process with many of my startup clients. There are unique challenges for senior executives who want to get a job at a startup, including the need to counteract age bias, which can begin inside of startups at age 36. Here are five steps to help maximize your likelihood of success.

Make sure it’s the right decision for you.

There’s a lot of glamour associated with startups right now, but the day-in, day-out reality of working in a fast-growing business can be challenging. Startups often have an intense pace, a lack of structure and process, constant change, and inexperienced managers. They’re also simply risky — data proves that most startups fail. Running out of money is a real risk, and if things go wrong, you might have to take a pay cut or lose your job. Therefore, it’s important to do some honest reflection to make sure that getting a job at a startup is really the right next move for you.

Here are some questions you can ask yourself or discuss with a trusted colleague to make sure you know what you’re getting yourself into:

  • Are you prepared for the decreased structure and increased ambiguity in the startup world as compared to a corporate job?
  • Are you prepared to have peers and managers who are much younger and less experienced than you?
  • Are you prepared for the risk of what might happen if the startup has tough times, like a pay decrease or even a layoff?

Increase your startup exposure.

One of the benefits of being an older worker is that you can sell yourself as a board member, advisor, or informal mentor to startups, particularly smaller ones. Take advantage of this — you may not get paid, but you’ll build your startup resume, learn about the environment, and add to the repertoire of stories you can tell about your exposure to startups. (This is also a great opportunity to make sure you’re up to speed on tech platforms commonly used in startups, like Asana and Slack.)

You can find these opportunities by networking. Ask your friends and colleagues to see who’s plugged into the startup world. Perhaps your friends’ children used to network with you for career advice; now they can return the favor by sharing their candid experiences and connecting you to potential advisory roles inside of entrepreneurial companies.

The benefit to this kind of networking is that, since you’re looking for advisory and mentoring opportunities instead of a job, you have nothing to hide. You can be very open about asking everyone, including people at your current company.

Use your age strategically.

When you go into interviews, be aware that you might look old to the young people you’re interviewing with.

Rather than try to hide this, make it a feature. One of my private clients, a CFO of a public company, decided to leave after 23 years to join a startup. From the very first interview, I coached him to discuss not only his deep financial expertise, but also the vast network he had amassed over the years. He positioned this as an asset and a source of potential customers and talent to bring to the company for the many roles they were trying to fill.

He also emphasized that because of his maturity and past success, he would not need to jockey for position and could serve as a manager and mentor to the team. Finally, he pointed out that his loyalty to his prior company would translate to loyalty to the new company; in an age of “the Great Resignation” and talent shortages, this would be a benefit. He successfully made the case and got the job.

Showcase your drive.

Another myth you may need to debunk when you’re looking for a job at a startup is that you might not be hungry enough or have the right level of energy. You may know about your passion and drive on the inside, but you have to make sure that comes across to the people interviewing you. Make sure you’re proactive in engaging with the various people in the company and showcase energy in your voice and body language when communicating.

One of my startup clients was interviewing a candidate for a CMO who seemed like a perfect fit: He had spent 18 years at a company, from when it was a startup to its current large enterprise state. He was strategic, could bring structure, and had a lot of experience in my client’s industry.

But during the hiring process, the CEO of the startup was concerned about the candidate’s lack of drive. He took days, not hours, to return messages. He never proactively reached out himself. And when they did meet either by video or in person, the candidate leaned back and didn’t communicate with passion and energy. Even though he had all the skills, the company ultimately passed on him because they weren’t sure if he’d be able to match the intensity when it was needed.

Don’t be surprised by a bumpy hiring process.

In large companies, hiring processes are often very structured. Hiring in a startup can be very fast, surprisingly slow, or first one, then the other. Very often, the internal team hasn’t exactly decided the key characteristics of the role, and sometimes the process gets sidetracked by changes inside the company.

One of my clients was pursuing a job at a startup and the process was running smoothly. The company seemed very enthusiastic about him. Then, suddenly, communication stopped. He checked in twice with the hiring manager and didn’t hear anything. He assumed that meant he was out of the running. However, having spent more than a two decades working with startups, I suspected something else was going on. I urged him to check in directly with his original contact. He did and found out there had been confusion over who was in charge of the process — not atypical in startups. After his contact talked to people internally, my client heard back from the hiring manager, who gave him a profuse apology and a job offer.

Getting a job at a startup can be very rewarding — emotionally and financially — for executives who are later in their careers. Use these guidelines to make sure it’s a good decision for you and to position yourself the right way to land the job.

https://hbr.org/2021/12/getting-a-startup-job-as-a-late-career-candidate