Bullpen needed accountants who understood the business. Especially after they were hit with a surprise $30k tax bill.
Pilot bookkeeping helped them grow profitably. They’ve gone from $30k in sales in their first year to $3 million, and doubled their headcount.
The Pilot team deeply knew the recruiting industry. Bullpen's Pilot CFO had worked in recruiting and was able to transform their operations and advise on the business.
“I can rest a whole lot easier in the evening understanding that everything on our finance and compliance side is just handled.”
Tyler had burned out in the corporate world and was convinced that becoming an entrepreneur would give him more control over his destiny. After a brief stint in investing in real estate, he pivoted to creating a marketplace for real estate talent. His hybrid recruitment process outsourcing model felt approachable and affordable, and he started to see uptake.
But as he grew, questions arose that he couldn’t answer. And the bookkeeping complexity became too much to handle on his own. Eventually, it was the financial operations that were holding him back.
Aided by his experience in recruiting, Tyler understood that knowing which roles to outsource and which roles needed to be in-house would be a key factor in Bullpen’s growth. As annual sales grew, he began by outsourcing the bookkeeping and tax filing. But after one accounting firm miscategorized $150,000 of taxable income, Tyler found himself paying $30,000 more in taxes than he expected to. He’d forgiven their occasional bookkeeping errors. But now he couldn’t overlook it. He ran a search and asked other companies he knew for recommendations.
If our accounting is done in any way that is creative, it throws off a red flag. I need it to be correct.”
Of all the options Tyler evaluated, Pilot seemed like the best fit. While every traditional accounting firm promised essentially the same thing, only Pilot had a team of software engineers dedicated to saving him time. Pilot uses human bookkeepers, but they’re supported by AI-powered income and expense categorization. Tyler had dashboards when he needed to check something, but also a human to talk to if something seemed off.
He was immediately impressed by Pilot’s onboarding. Where previous accounting firms had brushed off potential difficulties, Pilot looked at Tyler’s books with a reassuring level of rigor and organization. After several years of success with Pilot’s accounting, he expanded Bullpen’s engagement to include fractional financial operations and CFO services.
Before working with Pilot, Tyler had effectively been running the entire back office himself. After getting dozens of letters about compliance issues in various markets, he felt overwhelmed trying to figure out which aspects of which notices were meaningful. Pilot’s financial operations person was able to overhaul his onboarding, HR compliance, and insurance offerings. Thanks to these efforts, Bullpen has doubled their headcount. On top of handling operational headaches, their financial operations person has previous experience in Bullpen’s industry, making him an indispensable resource.
Our financial operations person is outstanding. It was a perfect-match situation. They had experience in the recruiting industry.”
Tyler attributes Bullpen’s growth to delegating key business functions—both within the company and to outsourced partners. By entrusting the back office to Pilot, Tyler has freed himself up to see how all the interlocking pieces of Bullpen work together. He’s now able to focus on Bullpen’s marketing, which will be crucial to take the company to the next stages of growth.
I can rest a whole lot easier in the evening understanding that everything on our finance and compliance side is just handled.”
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Bullpen is a freelance marketplace connecting real estate investment firms, developers, and brokerages with highly vetted analysts, underwriters, and marketing professionals.
Tyler had burned out in the corporate world and was convinced that becoming an entrepreneur would give him more control over his destiny. After a brief stint in investing in real estate, he pivoted to creating a marketplace for real estate talent. His hybrid recruitment process outsourcing model felt approachable and affordable, and he started to see uptake.
But as he grew, questions arose that he couldn’t answer. And the bookkeeping complexity became too much to handle on his own. Eventually, it was the financial operations that were holding him back.
Aided by his experience in recruiting, Tyler understood that knowing which roles to outsource and which roles needed to be in-house would be a key factor in Bullpen’s growth. As annual sales grew, he began by outsourcing the bookkeeping and tax filing. But after one accounting firm miscategorized $150,000 of taxable income, Tyler found himself paying $30,000 more in taxes than he expected to. He’d forgiven their occasional bookkeeping errors. But now he couldn’t overlook it. He ran a search and asked other companies he knew for recommendations.
If our accounting is done in any way that is creative, it throws off a red flag. I need it to be correct.”
Of all the options Tyler evaluated, Pilot seemed like the best fit. While every traditional accounting firm promised essentially the same thing, only Pilot had a team of software engineers dedicated to saving him time. Pilot uses human bookkeepers, but they’re supported by AI-powered income and expense categorization. Tyler had dashboards when he needed to check something, but also a human to talk to if something seemed off.
He was immediately impressed by Pilot’s onboarding. Where previous accounting firms had brushed off potential difficulties, Pilot looked at Tyler’s books with a reassuring level of rigor and organization. After several years of success with Pilot’s accounting, he expanded Bullpen’s engagement to include fractional financial operations and CFO services.
Before working with Pilot, Tyler had effectively been running the entire back office himself. After getting dozens of letters about compliance issues in various markets, he felt overwhelmed trying to figure out which aspects of which notices were meaningful. Pilot’s financial operations person was able to overhaul his onboarding, HR compliance, and insurance offerings. Thanks to these efforts, Bullpen has doubled their headcount. On top of handling operational headaches, their financial operations person has previous experience in Bullpen’s industry, making him an indispensable resource.
Our financial operations person is outstanding. It was a perfect-match situation. They had experience in the recruiting industry.”
Tyler attributes Bullpen’s growth to delegating key business functions—both within the company and to outsourced partners. By entrusting the back office to Pilot, Tyler has freed himself up to see how all the interlocking pieces of Bullpen work together. He’s now able to focus on Bullpen’s marketing, which will be crucial to take the company to the next stages of growth.
I can rest a whole lot easier in the evening understanding that everything on our finance and compliance side is just handled.”
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