The first thing to know about Nic Malianni is that he loves to hustle. Since the age of 12, he’s always had a job: construction, at a golf course, and, most recently, as Head of Accounting at the connected workplace, productivity software company Notion. While in college at California Polytechnic State University in San Luis Obispo, he found himself without a job and felt the itch. So, Nic saw a Craigslist ad from the Donati Family Vineyard and got in touch. “I was 20 years old and you can’t really work at a winery when you’re not 21, but I just said, ‘Hey, I'll do your gardening. I’ll rake your bocce ball court. Whatever you need me to do, I'm happy to get my hands dirty,” he remembers. “So that got me in the door.”

For the next three-and-a-half years, Nic became an indispensable cog at the winery. He took naturally to sales and to systems, getting the young winery’s offerings into local restaurants and grocery stores and managing sales reporting. “Their first vintage was 2003 and I started there when their 2005 was being released,” he says. “So, I consider it my first startup.” He is still a proud wine club member today.

Vineyards to Spreadsheets

Nic graduated with a Business Admin degree with a focus in Accounting, Finance, and Economics and dove into accounting. Many accountants focus on debits and credits and closing the books, but he’s always started with the needs of the business and viewed the problems with an accounting and systems lens. “It’s always been top of mind to help businesses run more efficiently through scalable systems and processes,” he says. He’s held onto the one feeling that’s proved a motor for his work life: “Curiosity.”

“How do we do this? How can we do it better? How can we make it simpler to help us provide the best service for our customers or to alleviate some sort of pain that my team is feeling?” he says. “In general, finance systems have been pretty underserved for a long time. There's always the hottest new engineering tool or the hottest new marketing or sales tool. Finally, we’re seeing more and more new finance tools like Neo.Tax. I'm really excited about what I'm seeing in the market.”

Nic sharpened his accounting skills at Grant Thornton for four years after college, working on the audit side. “I personally chose Grant Thornton, because I wanted to have as many clients as possible to get a broad set of experiences,” he says. He worked with 50 companies, some private and some public, and got a rare look at their practices, their challenges, and what worked and what did not. He tapped the knowledge of colleagues who had extensive experience in audit but also on the technical side. “It’s a very research-driven profession,” he says. “It gives you a window into the why behind the decisions of how a company makes their accounting decisions.”

But after those four years, when Nic felt he understood the why, he began itching to answer another question: “The missing piece at an auditing firm is the how,” he explains. “Or put another way: the actual execution.”

From Why to How

So, Nic joined Intercom, the AI-empowered customer service solution, in 2016 as the Accounting Manager, eventually moving up to the role of Assistant Controller by the time he left in 2021. “When I joined Intercom, I felt ready to exercise my entrepreneurial/building mindset,” he says. “‘How can I help build this thing and translate that why and to the actual execution behind it?’ That really excited me and it was challenging. Very, very challenging.”

The biggest challenge he faced which he hadn’t been expecting was how essential it was to be a champion for your accounting advice. On the audit side, he’d existed in a place where there were clear rules; it was sometimes confusing why best practices weren’t always followed. But on the other side, he realized that a skilled accountant or controller needed to have the ear of a decision-maker to guarantee that the resources were made available. 

“You have to be able to compellingly explain the why in order to get the resources to build the best systems,” he says. “If you don't have resources, then you need to figure out a bandage to account for this in a way that is going to be acceptable until you can build that long-term solution.” Nic realized that was why so many startups struggled with their systems and books early on. “It often falls on the grit of the accounting and finance function to actually go in and just get it done,” he explains.

At Intercom, he used the technical skills he gathered in his years at Grant Thornton and then expanded them by becoming an operator. Eventually, as the company grew, he moved into a management role. “I felt like, ‘Hey, I want to get back to building mode,’” Nic remembers. “That's what attracted me to Notion. And, you know, I've been building ever since.”

The Notion Love Is Real

Nic wanted to get back to “building mode” but he also wanted to join a company that people loved. “If you look at Notion’s YouTube following, Twitter following, and all the socials, it’s insane how much people love the product,” he says. “The affection for a business software product is just absolutely phenomenal. And it's really rare.” 

So, he started talking to people at Notion and realized that their engineers and executives were at the top of their game. “I wanted to be a part of it,” he says. When Nic arrived at Notion in 2021, the company was still just 65-70 employees. He took over as Head of Accounting.

Intercom grew rapidly in Nic’s years there; Notion’s growth has been even more exponential. “I had to grow just as fast as Intercom did and then I joined Notion and the speed has been even faster than that,” he says. “When I first joined, there were a lot of great people and there was a foundation that was put in place. But we’ve had to continue to uplevel the way that we worked, and the way that we serve the business and our customers, and how to do it in a faster manner.”

In his two-plus years so far, his team has added 16 people, Notion’s gone through two acquisitions, and they’ve had to implement numerous systems. ​​With all the steps that I've made in my career, it's kind of been out of curiosity,” Nic says. “If I ever feel like I’ve stagnated from a learning perspective, I know it’s time to change course.” Obviously, the Notion ride has been a learning overload. He’s loved every minute of it.

“It's been a journey,” he says, grinning. “The thing that I've enjoyed the most is that every quarter, there's something new to do and something new to learn.” Obviously, there is ongoing accounting work to be tackled, but “for the most part, it’s not that stereotypical 9-to-5 where you show up and know what you're gonna do every day. That has been very fun from a learning perspective.”

At a startup, the role of accountant becomes a mix of traditional and strategic, which Nic loves. “Especially earlier stage your role is to help the company grow in any way. From a financial side, there are core accounting things like bookkeeping and taxes but there are also strategic tasks like, ‘How can we help design the pricing and packaging to ensure that they’re going to work both from a systems perspective and a customer experience perspective while helping the business grow?’” Nic also mentions that it’s the accountant who looks at every bill and contract, so they should be providing valuable insights to the Go-to-Market teams about how other companies are building their sales engines, pricing their products, and designing their checkout flow.

“The true back-office transactional side is just table stakes,” he says. “But for a startup to succeed, the finance function really has to be strategic. You can live in that land of customer experience and sales strategy, and drive strategic decisions if you want to. I think every accounting and finance person should.”

A reminder from Neo.Tax: The tax deadline for S-Corps is coming soon!

For any S-Corp — defined by the IRS as “corporations that elect to pass corporate income, losses, deductions, and credits through to their shareholders for federal tax purposes” — the extension tax deadline is September 15, 2023. So, now is the time to get your books in order and to file your R&D tax credit.

Set up a call with one of our tax experts who can walk you through our automated, streamlined process — because you’re filing in September, you’ll be able to claim the tens of thousands you’re owed by the start of Q4 rather than waiting until 2024.

An important note for California S-Corps: though the state granted extensions for all California companies impacted by last winter’s storms, S-Corps still need to file in September rather than October along with all other companies.

Don’t hesitate to reach out with any questions — we’re here to help!

What’s the best path to the top finance job at a unicorn? And how does a first-time CFO who guides a company to an $8.2 billion IPO get his start? For Ajay Vashee, General Partner at IVP, who spent 8 years at Dropbox, it started on Wall Street. “I actually had a really good experience in investment banking,” Ajay tells us of his time at Morgan Stanley with a smile. “Most people don’t.”

But for Ajay, who parlayed an internship at Morgan Stanley while a student at Columbia into an analyst role at the bank, the experience was illuminating. The training programs allowed him exposure to Excel, three-statement modeling, and IPOs — all of which would inform the rest of his career. “It was a great way to learn the nuts and bolts of finance,” he says. And another perk? His work on cleantech financing brought him to the West Coast and eventually led him to the world of software.

Ajay went from Morgan Stanley to NEA. He spent time studying Series A startups at a fascinating moment for tech: 2008-2012. There were some misses — “we invested in Fisker over Tesla, which was not a good decision in retrospect” — but also some big wins. “We were one of the earliest investors in Tableau,’” he remembers. “Eventually, Salesforce bought the company for $15.7 billion.”

At the stage of company that Ajay was investing in with NEA, the real strategy is to “bet on the team and the potential,” and one company stood out from the rest: Dropbox. They did their diligence on the firm and tried to invest, but Dropbox didn’t need money at the time. One of his colleagues, Sujay Jaswa, was so taken with Dropbox that when they offered him a job, he decided to leave NEA for the growing startup.

StratFin at Dropbox

For the next year, Sujay and Dropbox cofounders Drew Houston and Arash Ferdowsi recruited Ajay. They finally convinced him. “The pitch which resonated with me was, ‘If you’re convinced that you want to build a career as an investor, a lot of the best investors are folks who were operators themselves,” Ajay says. “‘They understand the businesses and companies they’re looking at better. They’re able to empathize with the founders and entrepreneurs that they fund. They are able to genuinely help the companies they invest in on their journey to an IPO and beyond. And you’re just going to have a better nose for the business.’”   

Ajay arrived and felt like he had “this unfair advantage” because of his time working as a VC. “Dropbox totally was in the early innings, but on that trajectory at the time,” Ajay says. “As a VC, you know how every company is doing and I knew that Dropbox just had something special going on.”

He’d been observing board meetings, so understood what would eventually differentiate Dropbox. “It is bi-directional because you walk in armed as an operator now with all this context on what great looks like across your portfolio: what does a great software company look like? What’s a great growth rate? What are SaaS metrics that matter? When can you tell someone’s going off the rails? How do you have difficult conversations with folks that you have to let go on the team? What do you look for in great talent?” he says.

He had joined a company with “a bare-bones finance organization”: a couple of people on the accounting team and one person working on payroll and accounts payables. He was the first financial planning and analysis (FP&A) hire. Right away, he got started on getting a company model up and running. “Just having a view of the business that was reflective of what was actually happening at Dropbox and working through our first planning process and building a budget and things like that,” he says. “Then there were some one-off projects: ‘Hey, we want help modeling what this new product could look like if we were to launch it’ or ‘We want to understand: if we add this feature, then are we going to improve monetization?’ That's how it worked initially.”

Eventually, Ajay was tasked with building an entire Strategic Finance team. The mandate at the time at Dropbox was “get the very best people in the world to join” to keep the company on a best-in-class growth trajectory. “It was about team building and hiring really smart, high-horsepower folks to join our finance team. We wanted to hire folks who were coming out of Goldman Sachs or top venture funds or awesome consulting programs and a lot of them didn’t want to join in like a traditional FP&A role. They wanted to do something that was a little bit more strategy-oriented; that could have more impact,” he says. “So, we created this team called Strategic Finance to facilitate bringing that talent in. That was the genesis of StratFin.”

Growing Along With the CFO Role

In 2016, Ajay was promoted from Dropbox’s Head of Corporate Development to Dropbox CFO. He’d spent time getting to know “the nuts and bolts of finance” in his first position as Head of Finance and then spent “a lot of time in a more strategic role on M&A” in his next role, which prepared him for the CFO position. But still, Ajay admits that he was an unconventional choice for the position. “Our CEO Drew didn’t feel like he had to go hire the person who’d done it three times if he felt like someone had that potential internally,” Ajay says. “Not all leaders and CEOs operate that way. But he really had a leaning towards that and he had an eye for talent.”

So, Ajay took the reigns of the finance side of a company with 500 million users in 2016. Right away, he looked for mentors and found them on Dropbox’s board. “We had a couple of former CFOs on the board who felt like they could play a really active mentorship role with me when I was there. The former CFO of Priceline and Booking and then the former CFO of Nike were both on our board,” Ajay says. “They were like, ‘Hey, we’re willing to take Ajay on as a mentee and mentor him through stepping into the CFO role through Dropbox’s IPO and beyond.” 

He leaned on those mentors, and his unique experience — starting in investing and then building and growing with the finance team at Dropbox — to master the role. And, critically, Ajay continued to hire the best people for the role and lean on them to get to the best result. “So, I had a CEO who was willing to make that bet. I had a couple of former CFOs on the board who had a lot of credibility. And then I built a team around me that had much more experience than me working at a public company in a finance function and who'd been through the IPO process in the world of accounting FP&A, tax treasury, those kinds of functions,” he says. “So, it was the three different elements there that allowed me to do what I did.” 

The Dropbox IPO

“I became CFO, a year later, we were on file with the SEC to go public, and then three months after that we were public,” Ajay says. “So, like 15 months after I became CFO, we were a public company.”

It’s a staggering feat to imagine going from zero CFO experience to a public offering at $8.2 billion. But Ajay nailed it. He’d spent years watching the finance side of Dropbox from every angle and helped walk everyone else through the intricacies. “We ran mock earnings calls and we had a really buttoned-up accounting-close process. We had world-class auditors we were working with,” he says. “We were operating like a public company almost right away.”

He’d seen the differences on the finance side of a growth-stage private company and of a public company. “The level of rigor with which you’re examining the business, the way you’re running your planning process, the way you’re holding every team accountable to what they deliver for the company, the way you’re narrowing down your forecast accuracy and running your budget versus actual, the way you’re talking about the business and measuring it and writing about it, all that changes,” he says. “It really was night and day.”

But Ajay and his team actually loved the process — I know, it sounds strange! But the guy who’d started as an analyst was invigorated by the process of drilling deep into his own company. “For us, our IPO was actually a very energizing and illuminating process. It forced everyone to come together and think really hard about who we are as a company, what we want to be in the future, and to communicate that in a way that the world could understand,” he says.  “For investors who knew nothing about the business until we walked into a meeting as part of a roadshow, can we communicate in 30 minutes exactly what we do in a way that would be very compelling and get them to invest? They'd have to understand. The press would have to understand. Anyone reading our S-1 would have to understand. So, it forces you to go through that exercise, which is like strategically very beneficial to the company if you get it right.”

Clearly, they got it right. Dropbox’s stock rose more than 40% the day it first traded as a public company in 2018. 

Strategic Financing is Key for Companies

In 2021, Ajay left Dropbox to become a general partner at IVP. But he leans on the lessons he learned at Dropbox when considering investments. He tells us a story about Dropbox which helps illuminate the power of strategic finance for a growing company. 

Dropbox initially scaled on AWS, but there was a moment when they realized they should invest in building their own cloud-based infrastructure. Finance was brought in right away to tackle issues like investment timelines and depreciation schedules for infrastructure. “Our team was really intertwined with everything we did as a business,” he says. “They were intimately involved in: What should we build next? What should we buy next? How is that going to inflect our trajectory?” There was intensive modeling done in unison by the finance and infrastructure teams, and eventually, the decision was made to take on the massive effort. “It was a four-year project. We spent hundreds of millions of dollars to build out our own data center footprint across the country and then migrate exabytes of data from AWS to Dropbox,” Ajay says. “That project allowed us to grow from a 42% gross margin to an 80% gross margin. And speaking of what allows you to go public: moves like that opened up the IPO option for the company. Because the 40% gross margin SaaS business is not super exciting for a public market investor. But an 80% business is very exciting.”

Today, he tells the CFOs and Heads of Finance that he mentors to be pushing for 30-40% of your dollars to be spent on future growth — whether that’s people or other investments that can pay off down the road. “The thing that is a red flag for me is when I hear a finance leader, the go-to-market team, or the sales team, and part of their planning process is asking, ‘What’s the plan for next year?’” he says. “We have a major issue if that’s the way your finance organization is operating versus them saying, ‘Here’s the plan for next year.’ The ones that say, ‘Here’s the plan, and here’s how we’re going to make it happen,’ are the ones who will realize the full potential of a company. If your finance team is not doing that, then you are not realizing your potential.”