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About Oakes Co.

Anna Oakes is the Founder and CEO of Oakes Co., a trusted speaking and executive consulting firm based in Milwaukee, WI, and serving clients internationally.

Acting as a trusted advisor for numerous startups and sought-after partner for small businesses and Fortune companies alike. Anna works to meet the leader or team where they are and get them where they need to go. She has a proven track record of working within organizations for 19 years as an impactful INTRApreneur, where she played key roles in startups and Fortune 500 companies.

Now, with 5 years as an entrepreneur, Anna is the Founder of Oakes Co., a Co-Founder of Own Your Culture, a tech company source and investor, and the Chief Editor for Quartz at Work.

Quartz has a mission to "make business better," which correlates to Anna's purpose of restoring humanity into our work and workplaces. Anna will continue to work alongside her fellow Quartzians as Oakes Co. shifts to creating change by continuing to offer keynotes, workshops, and leadership training.

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Founders, CEOs, and leaders influence the short- and long-term execution within a company. Anna works with leaders that want to get better to do better.

Example: Coached 1:1, 2:1 between peers, and leadership team; retained key executives, resolved interpersonal conflicts, improved performance and collaboration, supported leadership's execution of key company goals and programs, transitioned executives and CEOs to chairman, retirement, or exit.


Anna pairs her analytical mind with powerful intuition and stellar relationship-building skills to influence the direction of a company.

Example: Designed, piloted, and launched a firm-wide productivity, efficiency, and effectiveness program for 3,000+ employees that resulted in 35,000 hours saved, $2M in hard costs eliminated, and a culture of innovation and empowerment in the first 3 years.


Anna has repeatedly shown that she is able to scale her guidance, bring expertise and best practices, while allowing the client to own the process and work for sustainable success.

Example: Coached a team of executives through a leadership team transition, communication plan, and change management strategy that resulted in: an increase in profitability of 17% and increased client engagement by 42%.



People and performance aren't HR's job and Anna has helped build bridges within companies that reinforce company strategy, goals, and culture to attract and retain the talent needed for the company mission

Example: Has worked with dozens of executives to increase their self-awareness, build understanding and skills in coaching, influencing peers and employees, and guiding performance.

Stop recreating the wheel...


Learn from companies, teams, and leaders that are positively

impacting humanity and performance at work!

What people are saying...

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Talent Acquisition Lead, Kohl's

Anna's content is relevant and extremely beneficial. Our employees loved her passion, energy, and ability to engage even through a virtual platform.

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COO, Charter Manufacturing

Anna has a great skill set for helping individuals, teams, and organizations improve alignment, purpose, and performance. Very authentic and able to flex style and approach to suit the circumstances.

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DE&I, Northwestern Mutual

Anna does a great job of catering the content to people in a variety of different fields and career levels.

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Meet The Team

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Anna Oakes

Founder & CEO

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A hippie heart with an operational mind.

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Avery DeBoer


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A perfectionist high-achiever with a kind heart.

Let's get connected...

PO Box 1301

Brookfield WI 53008

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