Who We Are
At Tailored HR, we believe strong businesses are built by people who feel supported, guided, and valued. We help growing companies create clear, reliable HR systems that protect leaders, empower employees, and support long-term growth.
With more than 25 years of real-world HR and recruiting experience, our team partners with small and mid-sized businesses to handle people challenges with confidence, clarity, and care.
IAN Olson
Ceo at
Tailored HR
Ian Olson brings more than 25 years of HR and people operations experience, along with deep leadership in client services, sales, and business development. He currently serves as the Principal Owner at TailoredHR.
He has built his career helping organizations scale through strong partnerships, working with companies of all sizes across technology, consulting, and staffing before focusing on health benefits and retirement solutions for small and medium-sized businesses.
Known for his hands-on, relationship-driven approach, Ian combines a deep understanding of employer needs with a commitment to responsive, solutions-oriented customer service. Today, he leverages his decades of HR experience, leading high-performing teams and advising executives to help business owners design benefit strategies that attract talent, protect their people, and support long-term growth.
Anna Olson
CO-Owner at Tailored HR
Anna Olson is a nimble and creative people and culture leader with more than 25 years of experience building high-performing teams and healthy workplaces. She has led HR and people functions across respected organizations, including Urban Renaissance Group, Big Fish Games, Nintendo, Moss Adams, and BSQUARE, where she designed and implemented programs spanning talent development, compensation, employee engagement, diversity and inclusion, and organizational change.
Known for her collaborative, hands-on leadership style, Anna partners closely with executives and managers to align people strategy with business goals while maintaining a strong focus on employee experience and organizational health. Her combination of advanced education, senior-level certifications, and deep practical experience enables her to deliver thoughtful, data-informed HR solutions that support both long-term growth and day-to-day operational excellence.
Building Practical HR That Grows With Your Business
Growing a business often means juggling people problems alongside everything else. Founders and leaders are often left managing sensitive HR issues after hours or in between client work. Tailored HR steps in to take that weight off your shoulders so you can stay focused on leading your company forward.
We deliver customized HR outsourcing and consulting designed around how your business truly operates. From recruiting and employee relations to manager coaching, performance management, and workplace investigations, our approach is flexible, practical, and aligned with your goals.
Unlike rigid one-size solutions, we adapt as your team grows. Our support scales with your business, giving you expert guidance without locking you into long-term commitments or complex PEO structures.
Tailored Hr has 100+ satisfied clients
100+ employees multiple industries
Our clients AND PARTNERS
We partner with small and mid-sized businesses across professional services, technology, healthcare, manufacturing, retail and nonprofit sectors.
Our clients rely on us as an extension of their internal team, providing consistent HR support as they grow, evolve, and face new challenges. Every partnership is built on trust, transparency, and long-term success.
What Our Clients Say
“Tailored HR helped us clean up our HR processes and gave our managers the support they needed. Everything feels clearer more organized and far less stressful. They truly understand the realities of a growing business.”
