Will Conway is the CEO of Pathwire, a company that provides clients with services to build apps and develop email programs. He led the company through several transitions while maintaining more than 50% year-over-year growth, including a successful spinout from Rackspace Technology in 2017 and its 2019 acquisition by private equity firm Thoma Bravo. Pathwire combines two companies -- Mailgun Technologies Inc. and Mailjet, which merged in early 2021. The two companies are now brands under the Pathwire name. Pathwire recently added another brand, Email on Acid. Prior to Pathwire, Conway spent nearly a decade deploying go-to-market strategies as part of Rackspace Technology's public cloud and OpenStack teams.
What are the top three qualities of a great leader?
I think everything starts with your motivation. This can be a lot of things, but it needs to start deep inside you, something that keeps you up at night. Next, you need a vision; something that both inspires you and can be communicated to inspire others, which works best when motivations are similar. Finally, you need to be able to flex and evolve. The only thing I know for certain is that my vision, tactics, and at times, motivations will be wrong. A leader needs people around them who are willing to push back and the humility to listen.
What makes you a great leader?
If I am a great leader, it would only be because of the people that choose to trust and follow me. Typically, my strategy is, be honest with my motivation, vision, and then ask them to tell me where they think I’m wrong. Through that feedback loop, we can outperform other companies, even when they are better funded. We also build strong relationships at the same time, which makes the hard work go down a bit easier.
What are some diversity, equity and inclusion programs you have implemented at your company?
We brought in a third-party consultant to evaluate our practices and potential biases, then make recommendations. We’ve also formed a DEI committee of passionate people from a variety of backgrounds to implement and advise future recommendations with a focus on hiring practices, career development, and reviewing all company-wide material for bias. We are leveraging these tools to suss out bias in our job postings and external-facing materials and have engaged with several diversity focussed hiring platforms. We also survey our employees on DEI questions and present the findings in company-wide town halls -- good or bad -- and our plan of improvement. We have access and measure our diversity index amongst our peers to measure our progress objectively.
The Essentials
Career: CEO, Pathwire, 2017- present; various positions in sales and partnership development, Rackspace, 2008-2017
Education: Bachelor's degrees in political science and legal studies, The University of Texas at San Antonio
