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No CFO is an island. Successful financial executives understand the importance of building strong, cohesive relationships across all departments. This often means adopting a slew of unofficial, ancillary job titles: strategic partner, data translator, career coach — sometimes even part-time therapist.
In other words, being an effective CFO means being relentlessly people-focused. This can be challenging when a large part of your job involves the not-so-fun elements of startup life: realism, practicality, and often, telling people things they don't want to hear. "As CFOs, you probably say no 99.9% of the time," said Gautam Gupta, who served as CFO for Uber and Opendoor before moving on to an independent investor role. "The tough part is you still have to work with those people after saying no, which means you have to invest in those relationships."
In a fireside chat with The F Suite, Gupta shared his insights on building strong cross-departmental connections — and navigating the complexities of the modern CFO role. Read on for a recap of his key takeaways, as well as perspectives from five other seasoned leaders on breaking out of the financial silo.
Key Takeaways
Establishing a strong, trust-based relationship with your CEO is a must— but it's equally critical to collaborate across the entire C-Suite. Adopt a "CXO" ("Chief Experience Officer") mentality to do this effectively.
Build strong partnerships with departments like Product, Engineering, and HR. A combination of effective data management and clear communication can help you clarify and justify decisions that impact these functions.
Embrace a people-centric approach to your role, but don't shy away from tough conversations. Balance empathy with the need for financial discipline — and when possible, break the stereotype of the CFO who always says no.
The CFO-CEO Dream Team
The visionary, optimistic CEO and the practical, data-driven CFO can complement each other perfectly — or become foils that create tension at every turn. For a more harmonious partnership, it's critical to establish:
Strategic alignment: Work closely with your CEO to understand and support the company's vision and goals.
Open communication: Foster a culture of regular, honest dialogue to ensure you're on the same page about company objectives, challenges, and strategies.
Balanced perspectives: Appreciate that CEOs often have different strengths (e.g., product vision, sales leadership) and tailor your support accordingly.
Trust and transparency: Build a relationship where you can have open discussions about the company's financial health and challenges.
Part of building trust involves a dual dynamic — the relationship you have one on one, and the united front you present publicly. This is perhaps most obvious during board meetings, when you often have to balance supporting the CEO's vision with providing transparent, accurate financial information.
"Especially in a founder-driven business, someone's got to dream big — and I'm not the zero-to-100-dream guy," said Muhammad Shahzad, president and CFO at Relativity Space. "So it's a balance between making sure you're not killing the dream — especially at the growth stage — but at the same time, governing all the things that could go wrong, setting strategy, and, in the context of board meetings, keeping the CEO in check."
Part of this, he goes on, involves gently guiding board presentations away from feeling like pitch decks. "Really, the tone needs to be the opposite; it needs to be transparent and direct," he said, emphasizing the importance of tackling tough conversations with the CEO before important board meetings and investor interactions. "There's no problem in facing the hard stuff. But there's a huge problem if you're not even discussing it. My role, tactically, is to use those conversations to plant the topics or the questions I think should be asked in the boardroom."
Cohesion Across the C-Suite
During his time as CFO at Uber, Gupta learned to think of himself not as a CFO, but rather a CXO ("Chief Experience Officer"), considering the company's overall goals rather than just financial metrics. "Your first team is really the executive team around you… The job of this team is to solve the biggest problems and remove the biggest blockers for growth," he said. "If this team isn't growing in the same direction, the entire company isn't going in the same direction."
When working with other executives, you need to:
Understand and respect different roles. Your relationship with other executives, particularly the COO, can vary depending on the organization's structure. Be clear about roles and responsibilities to avoid overlap or gaps.
Focus on financial partnership. Work closely with other executives to help them understand the financial implications of their decisions and develop financially sound strategies for their departments.
Balance priorities. Help mediate between competing priorities of different departments, using financial data and analysis to guide resource allocation decisions.
It's also often the CFO's responsibility to break down existing silos. "As CFOs, we're one of the naturally most cross-functional departments anyway, and so we're sort of broken out by default," said Dave Sheen, CFO at Vestwell, noting that he's worked diligently at the startup to extend this spirit of collaboration to other departments. "I don't want our head of ops thinking he's just on the operations team, or our head of sales thinking she's just on the sales team… It's really important, particularly for rapidly scaling companies, to get those department heads to start thinking about the business as a whole."
One of the ways Vestwell has facilitated this mentality is by implementing a unified incentive compensation structure for the entire executive team, aligning all leaders with the same company-wide goals. (For instance, the head of sales is bonused partially on hitting gross margin targets, rather than just hitting sales numbers.)
Regular meetings are another important component of cross-functional collaboration across the C-Suite. "One-on-ones with individual executive members is a critical piece," said Sheen. "That extra time can help you understand what's going on under the surface and where you can help."
Partner With Product, Innovate With Engineering, and Harmonize With HR
Beyond the executive team, the CFO has organizational-wide influence. "You're often the only other person besides the CEO who has a pulse on every single part of the company," said Gupta. "Really try to understand as much as you can about what other functions do. This way, you're not just making decisions or providing recommendations from behind a spreadsheet — you actually understand the operational implications, the impacts from a recruiting or marketing perspective, and what's going on culturally within a team."
Some of the teams startup CFOs tend to interact with frequently include:
Sales, to balance growth targets with financial prudence.
Product, to understand the product roadmap and its financial implications.
Engineering, to understand development costs and timelines.
Human resources, to align talent acquisition, retention strategies, compensation structures, and overall workforce planning with financial goals.
Business development, to evaluate the financial implications of potential partnerships and acquisitions.
Sarah Bobulsky, CFO at Helix, used to work on the commercial arm of the business, so she's been on both sides of the finance-sales divide. As CFO, she takes on the role of educator, ensuring sales and business development teams understand the financial realities of their decisions. "I have to make sure the commercial teams understand a couple of things — one, from a short-term perspective, the things that really drive costs in the business, and two, the things they can do, i.e. areas where there's more flexibility."
For instance, she said, as a data-driven healthtech company, one of Helix's lines of business is building a robust data set for future monetization. Once, during conversations over contract negotiations, she realized she needed to help team members better understand the company's three-year outlook to avoid them stripping out language that would compromise future revenue streams.
Scott Stockberger, CFO at Cedar, also noted the importance of spending quality time with the people building and selling your company's product. "Creating communication trust layers has been so compounding for our business. When problems come up, we can jointly solve them together," he said. As an example of this collaborative ethos, Stockberger has at least one finance team member sit in on both sales pipeline reviews and product roadmap meetings to ensure visibility.
Another relationship you need to nurture is with HR and the recruiting team. "Our people costs are our biggest costs, but also the most important piece of the business," said Bobulsky. "I think overhiring is probably the easiest way to get over your skis [as a startup], but at the same time, we can't do anything we want to do without hiring the right people." To strike a balance, Bobulsky works closely with HR — which at Helix, reports to her — to ensure they're aligned on compensation bands and general hiring priorities.
While such interactions often involve setting boundaries and managing expectations, you also need to know when to advocate for calculated risk-taking. For his part, Shahzad regularly tries to break the stereotype of the naysaying CFO: "Often, when I feel like it's the right thing to do, I'll actually say, 'We're not spending enough; we're not taking enough risk,'" he said. "The more you dispel whatever preconceived notions people bring to the table, the more they'll trust you to do what's right for the company — whether that's invest more or invest less, or cut costs or add costs, whatever it may be."
Your Role as a Cross-Departmental Data Wrangler
To communicate clearly with other departments, you need to hone your data-wrangling skills. "What a CFO should truly be doing is up-leveling the decision-making at a company," said Gupta. "That means getting the right information in the right people's hands at the right time."
This entails being skilled not only at collecting data, but also at communicating insights to stakeholders in language they understand and avenues they can easily access. "It's not just about coming up with the right data analysis, but also the right procedures, systems, and technology to deliver recommendations in a scalable fashion," said Gupta, adding that a human lens is crucial here. "It can't just be about the data, because every single decision you make has implications for the people, the team, and the culture."
Gupta shared an anecdote about working as CFO at Uber during its hyper-growth stage. The company had a presence in 800 cities — each with its own P&L. To manage the complexity, his team invested in a 30-person financial systems team to provide real-time information to each city's General Manager. The effort ultimately empowered local leaders to make data-driven decisions that aligned with the company's overall strategy.
For Praveer Melwani, head of business operations and finance at Figma, establishing data processes from the ground up has been a blessing. "I wanted our finance team to own a lot of the core infrastructure, and then use that to power all the business applications beyond us," he said. Achieving this goal has involved hiring finance team members with a high level of data and SQL literacy. Today, the company's sales ops and marketing automation systems are all powered with underlying financial data from Stripe.
Figma also uses an internal "KPI tree" that links company-wide metrics to team-specific goals. The tree is continuously evolving to accommodate new products and identify potentially conflicting goals between different business channels. The transparency has proven invaluable. "If you're missing one metric, you as an individual can go and take a look at the key inputs and ask relevant and thoughtful questions as to what is potentially moving and shaking that number," explained Melwani.
Breaking out of the financial silo and embracing your role as a cross-departmental leader has benefits that extend far beyond the balance sheet. With a holistic understanding of the business and strong relationships across departments, you can play a key role in managing your company's most valuable asset — its people.
For more advice on developing strong cross-functional relationships from leading CFOs, The F Suite community can offer valuable insights and resources — apply to join today.
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