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5 Tips to Land the Perfect Finance Leadership Role at a SaaS Vendor

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The stakes are high for job-hunting finance executives looking for a new leadership role at a young software-as-a-service (SaaS) company.

In the best case scenario, you land at job at which you can help steer a promising early-stage SaaS vendor to rapid growth and market leadership. You rack up impressive career accomplishments, enjoy lucrative compensation, expand your network, and gain personal satisfaction.

In the worst case, your new job ends up being a dumpster fire inside a train wreck. Misunderstanding, miscommunication, and hidden problems conspire to have you looking for another position in a matter of months.

The interview process is a make-or-break factor for finance execs in the market for a CFO, VP, or director position at a SaaS vendor — but what are the keys to success?

To find out, we brought together a trio of experts in executive search, SaaS financial management, and finance community networking. Tune in to our on-demand webinar, “The 100-Day Ramp Plan for New Finance Hires,” to hear practical guidance from:

Jamie Ceglarz, the founder of Guild Talent, a boutique executive search firm focused on finance and operations leadership placements within venture-backed startups and scale-ups, as well as the founder of the Operators Guild, an online community of early-stage SaaS operating leaders.

Michael Bayer, CFO of cloud storage provider Wasabi Technologies, whose 25-year career in finance leadership includes raising almost $400 million in venture capital over more than 30 funding rounds, and a leader of one of the largest SaaS CFO communities in the Northeast.

Tom Kirby, a leader in Next Series Club, a Midwest-based community of business leaders in finance and accounting focused on best practices for new ventures, and the founder of PrepDD, a workspace for accounting teams.
In this blog post, we focus on top interview process strategies that can help you land the perfect job at a growing SaaS vendor. Be sure to check out our earlier post from the webinar on crafting a 100-day ramp plan once you’re on board at a new SaaS employer.

5 Key Focus Areas for the Interview Process

Ceglarz, based in San Francisco, has more than dozen years of expertise working largely with venture-funded startups and scaleups on executive-level finance and operations placements.

And as a founder of the Operators Guild networking community, Ceglarz has been on the front lines of how tech finance leaders are approaching the job search, and how COVID-19 in prompting a shift to remote work. Being well armed with information is crucial, he said.

“You need to be realistic with what you can do, set expectations with the CEO and the board on what needs to get done and over what period of time,” Ceglarz said. “The only way to do that is to have the right information going into the job.”

Ceglarz laid out five key focus areas for job-hunters to keep top of mind during the hiring process:

#1. ‘There’s Always Going to Be a Mess’

Number one, job seekers need to recognize that “there’s always going to be a mess” in terms of financial consistency, structure, systems, processes at just about any early-stage SaaS vendor, Ceglarz advises.

“CEOs aren’t hiring for an executive finance role because everything is perfectly put together,” Ceglarz said. “The question is not ‘is there a mess?’ Rather, the question is ‘is it a mess I can or want to fix?’”

Bayer echoed that sentiment: “They’re not hiring you because everything is just fine. They’re hiring you to fix problems and create structure.”

Maybe the issues are right in your wheelhouse, maybe you relish a challenge — or maybe you decide that a certain role isn’t for you. Sizing up the situation with due diligence is the critical next step.

#2. Look Under the Hood with Due Diligence

Recognizing that problems are inevitable, Ceglarz said, “it’s your job to put on your detective hat to understand what’s been happening under the hood and what you’d be taking over.”

Pre-interview research into available information on the company and its leadership, both online and through networking, gives you a sense of the situation. And it helps you craft informed questions that you can bring to a first interview. Initial due diligence prepares you for a successful interview and helps you align expectations with the CEO and other executives.

As Kirby noted, “Understanding the current accounting operations and setting expectations with the leadership team are very clear things you need to do during the interview process to make sure everyone’s set up for success. Otherwise, things are going to go off the track very quickly.”

#3. Interviewing Is a Two-Way Street

A good interview doesn’t just entail you answering questions from the CEO and other leaders. You need to be asking your own informed questions as a part of ongoing due diligence and building initial rapport.

“Realizing that interviewing is a two-way street and asking all your questions is really important,” Ceglarz said. “It’s a concern for anyone doing hiring, whether it’s the CEO or a recruiter, if you don’t have enough questions. Be inquisitive — it’s your career.

Ceglarz said he’s observed that some prospective hires tend to think they have less power than they actually do during an interview.

“When companies hire for a first head of finance, they know they need someone — but having never done it before, they don’t know what they need,” Ceglarz said. “What I’ve found is that good candidates have more power than they think.”

Bayer pointed out that disparate views among stakeholders open an opportunity for a new finance leader to become a unifying force.

“Many times the constituents — the CEO and rest of the executive team, the employees, shareholders, lenders — don’t necessarily know what they want, let alone have agreement on it,” Bayer said. “That creates challenges, but also opportunities to understand issues and develop buy-in.”

#4. Working Sessions and the ‘Beers Test’

After a successful first interview, the proverbial “beers test” is a traditional way to size up chemistry among leaders. A mix of business and pleasure conversation over drinks or dinner can help reveal if leaders mesh well to drive a successful business (though such opportunities may be limited by COVID-19).

Ceglarz suggests that a beers test go along with one or more virtual working sessions at which key parties drill into business specifics, go-to-market plans, and financial models, much as they would after a new CFO or finance VP is hired.

“The ‘beers tests’ about whether you get along with someone used to be the final step in an interview process,” Ceglarz said. “What we’ve seen more and more is turning the ‘beers test’ into a working session where you can see how well everyone works together virtually.”

Kirby noted that securing a non-disclosure agreement and reviewing actual financial documentation makes for a more productive working session. It’s a valuable aspect of due diligence and can ultimately pay off with personal and business success.

“As part of the interview process, volunteer to sign an NDA, ask for financial statements and models, and make sure you’re reviewing those ahead of time,” Kirby said. “I know a number of candidates that don’t do that, or overlook it.”

#5. Accounting for COVID-19

COVID-19 has introduced several twists into hiring processes and the outlook for new finance hires. Ceglarz points out that tech company hiring of finance leaders has been rising through late 2020 and into 2021 after a lull during which companies came to grips with the pandemic.

Job seekers can also glean insights into the caliber of a company’s leadership based on its COVID response. Was it coordinated, swift, data-driven, and decisive? If not, that could signal issues.

“Getting a sense of how the company has reacted to COVID and how it’s been affected is really important,” Ceglarz said. “I think is an awesome talking point where again, you’re wearing your detective hat and figuring out with as much clarity as you can what you’re walking into.”

Lastly, a virtual working session is valuable because work-from-home has become the new normal at many companies as a result of COVID. ”Frankly, the number of hours of Zoom calls that you’re going to be doing with the CEO or the rest of the leadership team is really critical,” Ceglarz said.

Learn More

Tune in to our on-demand webinar to hear our experts discuss how finance leaders can land the ideal position, and get on the fast track to success with a sound 100-day ramp plan.

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