Rachel Oldring

Rachel Oldring is the Chief Financial Officer at Two Small Men with Big Hearts, where she oversees the company’s financial operations, strategic planning, and finance team. Since joining the organization in 2022, she has played a key role in strengthening financial processes and helping guide the company’s continued growth across Canada. Rachel is known for translating complex financial information into clear insights that help teams across the organization make informed decisions and focus on initiatives that improve efficiency and long-term performance.

Before joining Two Small Men, Rachel founded Oldring Accounting, an accounting firm specializing in full-stack financial services for entrepreneurial businesses. Originally from Calgary, she brings both an entrepreneurial mindset and strong financial leadership to her role, working closely with leadership and department heads to implement strategy and measure company performance. Outside of work, Rachel enjoys running, traveling—particularly to Croatia—and spending time with family and friends, usually with a strong cup of coffee close at hand.