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Josh StephensCTO

Why Becoming an Operating Advisor Was My Best Career Decision Yet

Since becoming an operating advisor with Elsewhere Partners, I have acted as a mentor and a career coach to countless founders, product leaders, CTOs, and their teams.

After working with us, they often ask how they can get more involved with software investing. But I’ve found that the “why” of becoming an operating advisor is actually more important than the “how.”

If you’ve had success as a SaaS founder yourself—or were part of the leadership team of the startup—joining a software investment firm’s bench of advisors can be very advantageous. You’ll gain valuable connections, experience, and potentially financial backing that is much harder to come by otherwise.

Below, you’ll find four important benefits of joining a software investment firm’s advisory team that you may not be thinking about.

You’ll get an inside look at the investment process

For startup founders, choosing an investment partner usually entails an arduous and complicated process smack-dab in the midst of an intense period of growth for your company. Steering your business through the transition from start-up to scale-up is complicated enough without adding in the work of vetting investors and raising capital.

Becoming an operating advisor for a growth capital firm such as Elsewhere Partners gives you an opportunity to get to know the firm, its partners, and other operators in its network before it’s time to raise capital. If you can find the time to invest now, you’ll gain a deep understanding of what it’s like to be on the other side of the table during funding —inside knowledge that will pay off in spades when raising money yourself.

You can test-drive your next job

Entrepreneurship, with its long path to success, isn’t for everyone. If you’re a superstar in pursuit of your next leadership role within an existing company, finding your next awesome job opportunity requires being highly selective about the team, company culture, and growth potential of your next gig.

No matter the macroeconomic climate, the job market is always white-hot for top performers. But it’s nearly impossible to deeply evaluate the opportunity of joining a new company when you’re on the outside.

Think about it: How many times have you joined companies only to learn within the first six months that those really aren’t the people you want to work with? Or accepted an offer only to learn a few months later that the company’s strategy is flawed and that they won’t gain market traction until after you’ve made shifts within the leadership team? These issues can be hard to see from the outside.

Working with the software investment firm that helped to fund the company and likely continues to be involved can provide valuable insight not available to the general public (if you can help with the diligence work leading up to the investment, even better). You may also be able to engage with the portfolio company as an advisor or board member before deciding to join the company full-time—so you can thoroughly kick the tires before committing.

You’ll expand your network

My number one takeaway from my years working with Elsewhere is the fact that, first and foremost, we invest in people. The right team can take a mediocre company and turn it into a winner. Conversely, the wrong team can take even the sexiest product in the hottest market and flub it epically.

This is why successful investors often invest in the same people repeatedly. And why stellar operating teams tend to travel together from company to company.

The downside to being part of these cohorts? Your network may be limited to a relatively small, albeit high-performing, team.

Working with a software investment firm allows you to expand your professional network to include every high-performing team within its portfolio—as well as other operating advisors within your industry. This affords you greater flexibility on when you enter and exit professional roles and expands your options for joining high-performing teams you already know and trust.

You can build your own portfolio

Perhaps you’ve had some successful exits and are ready to make small investments yourself—but you don’t want the overhead of structuring your own investment vehicles and don’t have the expertise of a more experienced investor.

This was my background when I came to Elsewhere Partners, and being able to make my own investments while learning from the firm’s partners has been one of the most important benefits of the experience.

When I’m helping with market research and doing diligence on technology companies, if I feel particularly excited about a given company, I am excited to invest some of my own money. It’s a win-win for everyone, since having skin in the game further focuses my efforts on making a quality recommendation and gives me a personal stake in helping that company succeed post-investment.

Remember: Time is your most valuable investment

Choosing wisely at key junctures is one of the most important aspects of advancing your personal and professional goals. This holds true whether you’re debating where to invest your own capital or the next few years of your life. The stronger your network and the deeper your experience, the easier it becomes to make faster, better decisions that will lead to long-term success.

While there’s no such thing as a quick fix to building that depth and breadth of experience, working with a software investment firm can help shorten your path—no matter your career stage.

As for that “how” of getting connected to a software investment firm like Elsewhere Partners? It’s all about networking. Reach out to me, one of our investors, or a fellow Operating Advisor. I’m also always on the hunt for SaaS leaders for my podcast, CapitalGeek, so shoot me a note if you’d like to share your story.

Josh Stephens Headshot

About the Author

Josh Stephens

Josh is CTO at Elsewhere, supporting the investment pipeline and providing portfolio companies operational and domain expertise beyond capital investment. He has been an Elsewhere Operating Advisor since 2015 and advised numerous companies including Vyopta, ActivTrak, BurstIQ, and others.