Startup life with Gentry Craig


Gentry Craig started his career at PwC and is now the Director of Finance at Payit, a govtech startup in Kansas City. Gentry is also working on an interesting side project! Hope you enjoy the read.

Appreciate you being here! Tell us about your background.

I went to MidAmerica Nazarene University in Olathe, Kansas (part of the Kansas City metro) and studied accounting, then I got my master’s in accounting at the University of Kansas. I went to MidAmerica to play football. It was also close enough to home so I could keep running a lawncare business and earn extra cash to help pay for school. I knew I wanted to do a business track. My parents had their own business for 25 years. Growing up I got to see them growing the business, and I saw that it was a lot of work. So I knew I wanted to go into business, but I wasn’t sure about an entrepreneurship track. Entrepreneurs seem to work around the clock and there's a lot of potential instability. I found that I was good at accounting and it was helpful for the lawn care business. I also had a professor that was really pushing me towards it. So I ended up choosing accounting, which has worked out pretty well. After my junior year I started to think about what’s after college. I met someone through a mutual friend that was doing an internship at a Big Four firm. They recommended checking that out, so I did and got an internship with PwC. The internship led to a full-time offer starting in August of 2013.

How was your experience with PwC?

The PwC office in Kansas City PwC has a pretty unique culture, maybe even compared to the other PwC offices around the US. I think it’s partly because KC is a smaller city, but still big enough for some large clients. You get a lot of talented people, and you also get family oriented people as well. So it's really easy to connect with others and have the opportunity to work on jobs where you can learn quickly and that have prominence.
I was on the audit team and the Kansas City office has a pretty high concentration of insurance and asset management clients. But I was able to do retail and consumer engagements and some technology companies. I enjoyed the relationships that I built while I was there. I still keep in touch with a few people that I worked with. Also, you meet a lot of PwC and other Big Four alum out in the world. You’re kind of kindred spirits with those people with similar experiences to share. PwC gave me the opportunity to learn really quickly in a structured environment. They know how to do a lot of things really well, including how to grow their people. I’m really grateful that PwC gave me the opportunity to start my career there.

How were your busy seasons?

My first busy season was pretty intense - 80 hour weeks starting in January, 100 hour weeks for the last three weeks, and 150 hours in the last 10 days of the audit. It was kind of a perfect storm of turnover on the team and some new complexities added to the business. But we had a really good team that worked well together. We didn’t take frustration out on each other, we just worked through everything together. But it was definitely a trial by fire. It was funny, during my performance review with the partner, he was like “whoa you worked 20% more hours than your peer group!”.
That was probably my hardest busy season. The firm later implemented some programs to try and balance the workload and push more work out of busy season. It actually helped quite a bit. My last busy season was just 60 hours a week with a few late nights. I went to the senior retreat that year. I remember sitting with some of my peers who were all talking about how rough that year was for them. I was thinking “I'm actually doing pretty good, enjoying the team, the hours are good”. 😂

Why did you leave?

I was interested in startups and small businesses and wanted to move into FP&A work. I felt like there was definitely an opportunity to stay at PwC and have a great career. But I wanted to take a bit of a risk and prove myself outside of the typical accounting track. I also wanted to see if I could take the knowledge I had gained at PwC and apply it elsewhere. I wanted to see how valuable that knowledge was. I had a friend that was at a small startup called ProfessionalChats. They had 25 employees when I joined and were completely bootstrapped. The company was putting live chat windows on websites. This was in 2017 when chat was getting a lot of traction. I was their VP of Finance and Controller, an appropriate title for someone who was the entire finance and accounting function. I was doing payroll, AR/AP, month-end, FP&A. We implemented Salesforce while I was there so I did some sales operations. I wore a ton of different hats. Took out the trash. I even chatted a few times to learn the business. It was a really good learning experience. I always joke that I got my MBA at ProfessionalChats. I spent fifteen months trying to keep up while we grew like crazy. At that point, we were acquired. I spent another year on the other side of the transaction helping fit the two businesses together.

Where are you currently working?

I work for PayIt. We are transforming how citizens interact with their governments and helping aid the drive towards digital government. It's a really cool company. I had known about them for four or five years and been keeping an eye on them. A few months ago a friend of mine recommended that I talk with their CFO. So I ended up connecting with him and having a discussion. One thing that drew me to the company is the challenge that they're trying to solve. In addition to that is the opportunity to work directly for Mike, whose title is co-founder/COO/CFO. I think that represents the learning opportunity in front of me. Yes, I'm going to learn the finance and accounting function. But I'm also going to get to see how somebody operates a business and rolls up their sleeves. That was one of the most exciting things about the opportunity. Working shoulder-to-shoulder with Mike, who's not your typical CFO.
My title is Director of Finance. What I’ve spent a lot of time on in these first five months is understanding the market that we play in. We are doing a top down approach to understand the market. This will enable us to fully formulate forecasts and go-to-market strategies. I would encourage anyone stepping into a new business or industry to really understand the market. This will help you understand the opportunities, what strengths to focus on, what prospects to go after.

What are some of the big differences between PwC and your industry roles?

Coming from public accounting, you think that the accounting has to be perfect. And the execution on every piece of the business has to be perfect. But I’ve realized, it doesn't need to be. It needs to be correct and you need to be able to support the decisions you've made. But sometimes there are more important things than getting the books GAAP closed at a small business or startup. Maybe there are FP&A items or a sales analysis that needs to be done first so you can enable the sales team or customer success team. Things are going to be messy, but you've got to stay focused on the tasks that will keep the company alive and thriving. Getting an opportunity to work in a small business really helps you see what it is to run a business.
Also, if you’re working at a small business and not in a sales or growth function, then you’re a cost center. You don’t have a lot of room for error. Compare this to PwC or any big firm where there are a lot of people in similar roles. You still have to perform but maybe there’s more of a safety net. So going to a small business taught me to prioritize things in a different way.

What are the most important things that accounting and finance departments need to do for a business?

Thinking of the finance and accounting function as one, it's really important to efficiently and timely report historicals. The department also needs to disseminate that data to the leadership team so they can easily digest it. The executives need to be able to understand what’s going on in the business and make decisions quickly based on the information. A big part of my current job is taking financial information and some operational information and disseminating it in a format that can be used by different teams. We make sure our different departments have the information they need and in the right format so they can make appropriate decisions.
It’s important to have a solid understanding of your businesses on a financial level. But also understanding the business on an operational level is imperative. The financial numbers and metrics translate into levers that you should be pulling or not pulling. This was a huge piece of ProfessionalChats’ success. We were monitoring data points every week to make sure we were pulling the right levers.

What advice would you give to anyone still working in public accounting?

My advice is probably geared towards those earlier in their public accounting journey. I would say work hard but try to find some balance while you're there. Early in your career, you're going to be very focused on working as hard as possible, learning as much as possible and trying to prove yourself. But you can't leave your health or mental well being behind. It's a critical time to figure out how to live a balanced lifestyle. You always hear people talk about work life balance, but I’ve heard it described as work life symbiosis and I think that is more fitting. If you work in public accounting or at a startup, your schedule isn’t going to be 8:00-6:00 every day. There are going to be some late nights, times you need to make sure the business is running after hours. So you need to learn when to give yourself breaks, when to pull away.
Also, don't be afraid to make mistakes or look stupid. You won't start out knowing everything, you need to be willing to learn and be a life-long student. You will have clients who are experts in their industry. Then there’s you with six months’ experience, and you don’t want to look stupid in front of them. You want to look like you know what you’re talking about, but there will be a lot of times that you’re not going to. You just need to be okay with that. Be comfortable with the fact that you’re learning, you’re not an expert but you still have value to provide.

How can you get the most out of public accounting?

I did a bit of a rotation in the advisory practice shortly before I left. It was interesting work, but traveling Monday through Thursday just wouldn't fit with what I want to accomplish in life. I’m glad I did it and would definitely encourage others to do rotations. Also the bigger firms offer secondments where you can go overseas for several years. So I’d encourage everyone to explore those options. The firms have large networks of interesting people that are doing similar things to you. Connect with them and see if you can learn from them.

Any advice for students or recent graduates?

Do internships if you can. Even if they're not formal internships, just go talk to people and network. See if they'll let you come in and observe them for a day or two. Universities will bring in alumni and have them talk about the industries that they're in. Go to those and see if you can get a coffee with those people afterwards. You don't have to be asking for a job that night, but try to understand why they chose to do what they do. There can be a lot of benefit to just meeting other people, even if there's nothing you're getting out of it right away. It could lead to jobs or introductions to other interesting people. Obviously you're going to go to job boards and career fairs, do that. But also try to identify companies that are interesting to you. And companies that look like places you'd want to work. See if you can go talk to them and create a job there.

Anything you wish you’d done differently early in your career?

I kind of wish I'd double majored in finance and accounting. But I am doing my best to be a continual student and to keep learning new things. Accounting was a great foundation to build on. But I also wanted to understand the strategic side, like FP&A and operations. So I’ve tried to find roles that allow me to learn those things. I also ask my peers for best practices and recommendations. I’m learning R programming right now because I think it can help me be more efficient with forecasting and analyzing data. The ability to work with unruly data comes in handy, especially when working at a startup with limited resources.

What are your long term goals?

Never stop learning and challenging myself. I'd like to continue to be in roles that allow me to learn as well as teach. I’ve also started a side project called SheetShare.

Can you tell us more about SheetShare?

It's cliché, and I know a lot of people are using the catchword democratize, but I think it’s an appropriate term for the current movement in many fields. Experts & their knowledge are more accessible. I want to continue that trend and democratize access to financial literacy. Not every small business has a CPA or finance function. And not every finance professional, wearing multiple hats, has the time to build robust financial templates. What ends up happening is many people start from scratch when they don’t need to, or they don’t analyze something that they should. SheetShare is a community curated marketplace for sharing and discovering high quality, easy to use spreadsheet templates. For example, currently, you can go online and search for a coffee shop financial model, a SaaS company KPI dashboard, or a cash flow model, but you won’t find a resource where there’s an appropriate level of curation or vetting by a user base that cares about identifying the best and most user-friendly template. I’ve wanted a resource like this in my career. I will use it, and I think others will too.

I like the concept! How can readers connect with you?

Ping me on LinkedIn!

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