Though Twitter and its investors continue to feed into the media frenzy surrounding Twitter's vacant CEO slot, the rumors and public opinions leave us with more questions than answers.

Today, Bloomberg published an article saying that Square advisors are making preparations in case CEO Jack Dorsey, who is currently serving as interim chief exec at Twitter, leaves to head up the social network full-time. The report comes amid rumors that Square has confidentially filed for a public offering.

If that's the case, Square needs to get a few things just right.

Timing

The Twitter drama couldn't come at a worse time for Square. In June, Twitter CEO Dick Costolo stepped down and Dorsey took over as interim chief while the board considered its options for a full replacement. Since being appointed, Dorsey has not once rebuffed the notion that he may stay on permanently at Twitter, raising questions about what would happen to Square if he did. Investors are likely to be hesitant about putting their money on a company whose leader is missing in action. But if Square needs money, it doesn't have a lot of choices, and Dorsey's (possibly brief) return to Twitter is unfortunately timed to interfere with Square's plans.

Leadership

Over the course of the last three years Square has pulled together team of leaders, most of whom have star-studded backgrounds. CFO Sarah Friar, for instance, spent 10 years at Goldman Sachs as a senior software analyst during the early days of Web 2.0. There's also Francoise Brougher, former head of Google's small business sales and operations department. At Square, Brougher is focused on building out Square's customer base and it may have been her work that helped the company acquire its millions of merchants.

Three other Square execs also come from Google: communications lead Aaron Zamost, general counsel Dana Wagner, and human services lead Aditya Roy. Gokul Rajaram, who now leads engineering efforts for Square's food delivery business also spent time at Google before becoming a product director for Facebook's ad business.

The company's hardware executive, Jesse Dorogusker, hails from Apple and famously redesigned Square's signature reader, while Alyssa Henry, who led engineering teams at Amazon, has helped build out Square's line of merchant services like Appointments and Payroll.

Finally there's Brian Grassadonia, who handles Square's Cash business. Unlike most of Square's executive team, Grassadonia has been at Square since the beginning, though he also has worked for a number of big names like UBS and Google.

A cast like this could be enough to convince investors that Dorsey's split attention shouldn't be a concern.

Let's not forget the business

The payments company has come a long way from its position a year ago, when the Wall Street Journal reported Square was bleeding money. It has pivoted, moving away from consumer payments products like Square Wallet and Square Order and toward merchant services. Square has built out a slew of back-office products, as well as two restaurant delivery apps. Though it competes against a growing list of rivals likes First Data, PayPal, Amazon, Poynt, and Etsy, the company seems to have carved out a space for itself as a tool for small businesses and pop-up shops. In 2014, Square processed $30 billion in payments.

But Square has racked up an immense amount of investor funding, valuing it at around $6 billion, if not more, which forces the company to prove its worth.

That can be hard for payments processors, which often rely on processing an enormous number of payments to illustrate their value. Look at First Data, which is again seeking a public offering this year. In 2014, the company processed $1.7 trillion in payments. Vantiv's merchant services business was processing sales volume of $426 billion annually before it went public in 2012. Vantiv was estimated to worth roughly $3.6 billion at the time. Square has a ways to go to prove the value of its merchant tools in addition to its processing business.

A Square IPO while Jack is away can happen, but the stars need to align for Square to succeed on the public markets.