A. Kai Armstrong

Professional Profile

Product Manager responsible for product definition, pricing, marketing and launch activities. Able to actively work across functional teams of both internal groups and external partners to build consensus and drive products forward on time and in budget. Successfully launched PaaS and SaaS products for industries including Small Business, Global Telecom and Managed Services resulting in delighted customers and smiling executive management with revenue growth. Experience with software, platform services, hosting, private and public clouds (Azure/AWS); have the experience required to look at the big picture, drive strategic growth and pivot projects in dynamic business environments.


Sr. Product Manager

Hostway / San Antonio, TX / 2016 - Present

Leading Managed Application and Email & Collaboration product offerings in retail small and midsize business (SMB) markets as well as product offerings to the Global Partners (Fortune 500) channel; total product portfolio of $15mm+ annually.

  • Finalized the launch of a Managed Magento product, including defining go-to-market segments and messaging as well as a product roadmap to meet growing customer requirements leading to a nearly $250k annual run rate
  • Conceptualized and launched Hostway’s Managed Microsoft Office 365 product offering which is on track to generate more than $100k of revenue in the first year
  • Successfully introduced a new Anti-Virus/Anti-Spam solution to Hostway’s more than 1.2 million mailbox users resulting in increased customer satisfaction, improved systems reliability and an annual savings of $120k in licensing fees
  • Worked closely with senior leaders and company executives to provide product roadmap updates, weekly product health updates and regular information for board meetings
  • Managed and negotiated important vendor relationships for products and services critical to SMB product offerings

Project Manager

Gray Digital Group / San Antonio, TX / 2015 - 2016

Led SMB and Large Health Organization web projects from customer inception to development completion while keeping projects on schedule and on budget.

  • Spearheaded new product offerings aimed to meet small business budgets and long-term website growth objectives
  • Improved WordPress maintenance procedures to increase timeliness and quality of updates while minimizing developer time

Director of Products and Support

Pressable / San Antonio, TX / 2010 - 2015

Like most startups, wore multiple hats to grow business from the beginning to millions in revenue annually; positioning company for exit to Automattic.

  • Developed Fresh Smiles app to publicly promote customer support feedback ratings; concept adopted by Freshdesk for their Say Cheese marketing campaign
  • Scraped support responses to create more than 50 knowledge base articles for customer self-service support; Reduced support inquirers by more than 10% in the first 30 days
  • Developed self-service billing for customers based on customer feedback reducing billing related support requests by 90%
  • Implemented and managed agile development process increasing monthly recurring revenue by more than 20%
  • Managed relationships with Enterprise customers through continuous communication to ensure exceeding customer expectations

Library Systems Administrator

duPont-Ball Library / DeLand, FL / 2008 - 2011

Provided technical expertise and depth to the Library System Team focusing on the Library’s Integrated System and bringing more than 125 years of history online with the University’s Digital Archives. Was hand selected by the Library Dean to serve on the Stetson University Academic Technology & Computing Committee, which drove university decisions for online learning.


Master of Business Administration, Stetson University - DeLand, FL

BS in Hospitality Management, Minor Computer Science, University of Central Florida - Orlando, FL


AWS Solutions Architect - Associate Level