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Ep.170 - Josh McAfee & Sheila Bailey - Refining Internal Operations & Structure

Josh McAfee / Headway

Josh McAfee is co-founder and VP of Recruiting at Headway. Josh was the founder of Velossent and has over 20 years of recruiting and human capital experience in the Information Technology, Sales, Marketing, Executive, Finance and Accounting, and Legal fields. He has worked with Enterprise Clients such as Turner, VMWare, Veritiv, NCR, Sharecare, Suntrust, IBM, Weather Channel, IHG, Mitsubishi Electric, Cox, Aaron’s, Emerson, HD supply and Startup Clients such as AchieveIT, Ally commerce, Experience App, ControlScan,  eVestment, Marketo, Membersuite, Nanolumens, Nexidia, Optima Healthcare Solutions, Oversight Systems, ParkMobile, Pindrop, QA Symphony, Salesloft, and SecureWorks.



Sheila Bailey / Headway

Sheila Bailey is co-founder and VP of Operations & Finance at Headway.  She has over 20 years of expertise in scaling financial and operational metrics in both small and highly matrixed organizations.  Sheila was Vice President of Finance for Luma Home that was acquired by a Fortune 500 in 2018. Preceding Luma, Sheila served as Vice President of Finance and Operations and subsequently Chief Compliance Officer for Rubicon Global, an Atlanta unicorn (1.2B valuation).  Currently, she is a Founding Partner of Headway, LLC and leads finance and operations. Sheila holds a B.S. from Emory University and MBA from Georgia State University.

Paul Judge is a technology entrepreneur and investor. He is Co-Founder & Partner of TechSquare Labs and Co-Founder & Executive Chairman of Pindrop. Paul was a co-founder of Luma Home, a consumer WiFi company, that was acquired by a Fortune 500 in 2018. Paul was also the co-founder of Purewire, a web security company, that was acquired by Barracuda in 2008. Paul served as Chief Research Officer at Barracuda through its IPO in 2013. Prior to this, Paul was CTO of CipherTrust, a leader in email security, that was acquired by Secure Computing in 2006. Paul holds a B.S. from Morehouse College and Ph.D. from Georgia Tech.

Things Startups don’t think about

  • Opportunity Cost of doing things yourself
  • Time – Handling things like F&A and Recruiting take leaders and teams away from the most important things. Their Customers and Product/Services.
  • Cost – The cost of outsourcing something is often less than the cost of the time invested in non-core activities.
  • Hassles – the hassle factor of doing F&A and Recruiting internally while building a company can be chaotic for the team and candidates and can affect company culture in a negative way.

Why Choose Headway – Many growing companies become overwhelmed by the cost involved in using an outside services company and the variable costs are simply not affordable or in the budget.  We decided to change the model and work on a subscription model. While growing companies struggle to afford the big fees associated with these services, they can afford a reasonable fixed monthly subscription.  We’re able to leverage economies of scale, best practices around recruiting and team building, and F&A to our client’s benefits AND at a rate that is way more affordable than the typical models.



Lee R. Heisman /Savant, LLC

Mike Casey Formula IQ

Josh McAfee / Headway

Sheila Bailey / Headway