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Michael MassadVice President

3 Tips for Software Executives Aspiring to Investment Firm Roles

For executives at software companies who have gone through an exit or are ready for the next career transition, bringing hard-won operational expertise to an investment firm and/or its portfolio is often a natural progression.

While advisory roles often harness your operating background and functional leadership from your software executive days, making the move into an investor-adjacent role often requires an intentional approach and different skill set than the one you have cultivated while climbing the ranks in the software sector.

We recently talked to Shelley Perry, an Elsewhere operating advisor (OA) who served as the executive chair of Airbrake, for her perspective on this common career evolution and transition. Read below for her tips on how seasoned operators can plan and shape their move into board roles or working directly with an investment firm, which often involves taking on board roles with their portfolio companies.

1. Learn to speak the language of investors

What’s that language? Financials. While a board seat or advisory role is often seen as a natural next step, the business model of investment firms is quite different from that of scaling software companies.

“Investors are being entrusted with someone else's money; they have the fiduciary responsibility to manage that money. If you are interested in working with them, you need to understand the finances and converse in their terms — not yours,” says Shelley. “It doesn't mean that you have to be an investor; it means you have to have enough understanding to ask the right questions.”

Shelley likens it to the experience of having conversational abilities in a foreign language while traveling abroad.

“You need to speak that language well enough to have smart conversations and pull the two parties (ScaleUp and investor) together. Once you can do that fluently, it’s really impactful, because what you're doing as an investment firm advisor is working between the operators and the investors.”

Functional leaders may have experience managing budgets and hiring for their departments, but this skill set differs from the financial acumen needed to provide strategic guidance as a board member or to evaluate deals alongside an investment team.

Investment firm advisors who take on board roles don’t need to produce company financial reports, but they need to be able to interpret them and sign off on them. An understanding of terms such as growth ratios, profitability ratios, and income statements is critical. Operators interested in making this move don’t necessarily need to go out and get their MBA or CPA, but they do need to have the curiosity to learn and a network to go to with financial questions.

2. Network generously

Speaking of networking… Networking is ultimately about generosity — being willing to help another professional without seeking anything immediately in return, says Shelley. This framing of networking helped transform her career path.

Software executives looking to expand into the investment world should look to build long-term relationships with future potential partners through this spirit of generosity. Sharing knowledge, experience, connections, and speciality industry expertise with investors is a great way to show the value you’ll bring if you work with them more formally in the future.

“Investors are always looking for friends, advisors, and the right help with understanding the latest technologies or sourcing deals,” Shelley says. “Be a friend to them before you want to work with them. Investors appreciate the tips because they live in a different world.” Investors are always eager to hear the latest ideas on industry or sector trends and would gladly “talk shop” with an accomplished operator.

Another approach is opening up your network proactively. Building relationships with investment firms through connections to potential hires, partners, and customers is yet another way to show the value you could bring one day. Ultimately a big part of the role you’ll bring as an investment firm advisor or board member will be helping to refer talent and influence prospects. This responsibility is particularly important in firms whose strategy embraces buyouts, as they will often reshape the executive team after providing the initial founders their liquidity. The investors that work on these types of deals will hire new executives to steer the company through the next stage of growth or exit, as Shelley did while working as the executive chair of Airbrake (which was acquired by LogicMonitor earlier this year).

3. Evaluate firm culture thoughtfully

A career evolution from operator to board member (either representing the investment firm’s board seat or as an independent) requires a mindset shift. Plus, the culture and investment theses among different investment firms is certainly not one-size-fits-all. It’s one thing to know you want to make the move working with an investment firm, and another to define the type of investing team you’d work best with. Investment theses can be shaped around sectors, geographies, market opportunities, business models, founder backgrounds, and more.

Some investment firms take riskier bets that won’t all pay off, in the hopes that one or two portfolio companies are a runaway success to make up for the others’ losses. Other firms work more broadly across the portfolio, resourcing each company with operational expertise and building toward a more measured and predictable outcome that the financial ecosystem can more predictably absorb.

Some firms help portfolio companies build on tighter timelines for the private equity buyer, while others intend to steer companies through multiple institutional rounds on the path toward an IPO or large strategic acquisition.

There’s not necessarily a right or wrong approach, but operators should have a clear sense of what investment style they value, how they’d like to interact with portfolio company leaders, and where their strengths are.

Working for an investment firm’s portfolio company is a great way to get a sense of the firm’s culture from the proverbial other side of the table. You’ll see how they govern and guide a portfolio company and what operational expertise they activate to help that company succeed. All of that will inform whether this firm is truly a cultural fit with the investment or investor-adjacent role you aspire to.

Additionally, there is a wide range of roles a former operator can take on once they’ve engaged with a firm. These opportunities include working closely alongside full-time investors to evaluate deals, engaging as a strategic advisor to help a company navigate a shift in their business model or into a new industry, or even taking on a full-time leadership role to guide the company towards a sale. Be honest and transparent with how you’d like to help an investment firm bring value to their portfolio companies, to ensure your interests align with the opportunities actually available.

Software executives, plot your career transition to an investment firm role carefully

Software operators have a lot of value to bring to investment firms, but like any meaningful career transition, it won’t happen overnight or by happenstance. Leaders looking to make this move should engage proactively with firms, long before they expect to join one.

At Elsewhere, we love connecting with operators interested in evaluating deals or guiding portfolio companies, and we welcome expertise and ideas early and often. Feel free to reach out at outlier@elsewhere.partners to connect. Shelley is just one of many Elsewhere Operating Advisors, all with different career paths—check out more here.


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About the Author

Michael Massad

Michael is a software investor at Elsewhere Partners where he co-leads all sourcing and diligence efforts in the IT infrastructure and cybersecurity sectors. Michael strives to connect capital and operational expertise with growing software companies across industries that are located outside of traditional VC hubs.