Thrivers Integrated Mentoring Program (TIMP) offers leaders both personal and professional coaching that integrates all aspects of their life including business, community, family and relationships. Group mentoring is open to all growing companies with revenues of approximately $1M with the current cohort including C-level leaders from companies such as Teamworks (  StrongKey ( and First ( who have collectively raised $30M in 2018.


Tim is trained and experienced to go “under the water level,” helping you discover who you really are and how to lead as your truest self. He is a serial entrepreneur who brings over 25 years of experience as an operating CFO with over $1 billion in multiple transactions including Opensite, Appia, iContact and Cherwell. He is the CFO of Prudent Growth Partners. He also has a masters degree in Counseling having provided clinical therapy services, is a Certified Health Coach through Duke Medicine, and currently delivers executive coaching at the Carolina Clinic under the UNC Hospital. 

“Tim has a proven track record of success with several exits in the Triangle, two of which, Opensite and Appia, we partnered on together for big wins. He offers leaders the unique know-how to build growing and accelerating, multimillion dollar companies while using his healthcare skills to also consider the importance of life outside of work. Tim helps leaders combine both their business and personal lives into a thriving, integrated and fulfilling story."
“I've been a member of Tim's Integrative Mentoring program for over three years now, and in that time have come to know him as both a trusted advisor and close friend. His thoughtful guidance and wisdom on matters related to both my personal and professional journey have made him an incredible collaborator on helping me write the story I wish to live. Tim's partnership was particularly invaluable as I lead my team through Atlassian's recent IPO and the related growing pains of scaling a company to over 3,000 employees."
“In the Triangle there are a number of mentoring programs to consider but Thrivers has bottled something unique because they are really addressing the entire package of executive needs in their process. The opportunity to hear a broad range of speakers from Steve Nelson, founder and former CEO of Unicorn Carbon Inc. on scaling for growth to Luke Powery, Dean of Duke Chapel,exploring the diversity of spirituality in the work place, has been invaluable.”
"Tim has been a consistent mentor for me both personally and professionally through some of the most significant transitions in my life. Beyond having tangible business experience, his counseling and integrative health coaching background shine through as he challenges and encourages me to take a holistic approach when balancing the tension between scaling a business and the desire to love and lead well. "
"Tim has provided a unique perspective on the challenges of managing a high growth startup like BombBomb with 130+ people . Whether it is scaling the leadership, mining for conflict, unit economics, or fundraising he partners with us to create company value. As importantly, he has also brought perspective in the integration of my personal story around what matters most in my life."
I have always valued harmony in my work and personal life. It is rare to meet people like Tim who have achieved business results that most people only dream of, while still honoring their own lives, family and friends. Over the last three years, his willingness to share experiences on living in this interdependent way has supported my desire for optimal business results and a life well lived!



Thrivers Integrative Group Mentoring is open to all growing companies with revenues of approximately $1M. The Raleigh/Durham/Chapel Hill Cohort includes a half day monthly group meeting from 4:30-8:30 and three hours of individual dedicated coaching per month. 

  • Where: Raleigh/Durham/Chapel Hill Area
  • Facilitator: Tim Oakley


  • Where: In Person Raleigh/Durham/ Chapel Hill and Virtually Worldwide
  • Facilitator: Tim Oakley

Thrivers Integrative One-on-One Mentoring packages are also available to companies of all sizes with each package consisting of 6-24 sessions typically meeting every two to four weeks. Meetings occur globally by phone or web conferencing  with in-person options available in the Raleigh/Durham/Chapel Hill area.


I have over 25 years as an executive in both public and private companies in the high technology areas of saas, enterprise software, internet, digital media & mobile communications. I have had the good fortune of partnering with amazing people and have conducted $1 billion in financial transactions/exits, including three successes in the Triangle (Appia, iContact, and Opensite each exceeding $100M exits) and Cherwell Software in Colorado who reached $250M in investment from KKR in 2018.

While involved in several activities my primary efforts are currently invested as a principal at Thrivers Integrative Mentoring and as CFO of Prudent Growth Partners.

Thrivers is a framework for business leaders to balance the demands of leading high growth organizations without losing the rest of their lives. Thrivers uniquely combines all the dimensions of a leader’s life including business, family, relationships, health, and spirituality to achieve a high-performance, integrated lifestyle.

Prudent Growth Partners is a private real estate investment company based in Chapel Hill, North Carolina with the goal of building relationships with other like-minded investors who wish to earn above market returns by investing in commercial real estate.

I have provided operational and financial leadership to fast growth start-ups with little revenue and employees to companies with billions in revenue, global operations and over 15,000 employees. Prior to iContact in 2005, I was the CFO of CipherTrust (Now McAfee), and held various financial executive positions with OpenSite Technologies (Oracle), Broadband Technologies, MCI (Now Verizon), and Coopers & Lybrand (Now PWC) where he earned his CPA.

I serve on multiple boards/advisory boards including Cherwell Software, Candle Science/Grow and BombBomb, consults with start-ups, lead a fifteen month integrative mentoring program for growth stage leaders and provide executive coaching at the Carolina Clinic Executive Wellness Center at UNC Hospital. I am a Certified Coach through Duke University’s Center for Integrative Medicine.

I earned an MBA from Emory University, has an undergraduate degree in accounting from East Carolina University (Magna Cum Laude) and is a CPA. In addition to my coaching certification from Duke, I have a Master of Arts in Counseling (Magna Cum Laude) and has provided over 1,000 hours of clinical therapy services to a diverse set of clients. I am native of Durham, NC where I now live with my wife and two sons.