About Jennifer

I am most commonly found using the handle “@dearjenna” across the internet. I am 26 years old, married, from the South and living in the Pacific Northwest.

I hold a position with the Twitter handle @XboxSupport where I provide technical support and give Xbox-related advice to community members across Xbox Live. Along with this position, I am a freelance writer and designer.

I am published under both names Jennifer Gleason (maiden) and Jennifer Sheffield. Due to my English degree, I am a fan of art, layout design, AP style, stylebooks of any kind really, finding newsprint all over my hands for no reason and leaving out the Oxford comma.


Bachelor of Arts, in English (emphasis in print journalism)
Valdosta State University, class of 2013


Elite Community Support Analyst for Xbox Community Support
Microsoft, via VMC Consulting, June 2014 – August 2015
Microsoft, via Affirma Consulting, August 2015 – Present

  • Tweet under the chops “^JP” for @XboxSupport on Twitter, providing technical and gaming support to the Xbox Live community.
  • Assist in leading the evening shift of the Twitter team – coaching, training and leading agents.
  • Communicate with partners and escalating internal issues.
  • Organize and curate training documentation for the team.
  • Accountability for personal and team-wide KPI.
  • Work to maintain communication between internal partners and monitor vital service information.

Co-Creator and Editor
The Community Blog, Xbox Community Support
Microsoft, April 2016 (launch) – May 2017

  • Created the blog alongside coworker Savannah Harrison.
  • Created content under the community byline “Misses Apple,” some content originally attributed as “Xbox Ambassadors”.
  • Facilitated graphics, interviews and outreach through the Xbox Ambassadors Program for the purpose of the blog – with internal partners and community members internationally
  • Educated the Xbox Ambassadors Program community members about developer updates, announcements, spotlights of notable members and interviews with Team Xbox members.

Co-Personality and Creator
Within Walking Distance, podcast
April 2017 (launch) – Present

Freelance writer, editor, designer

Editor-in-Chief, The Spectator
Valdosta State University, May 2013 – December 2013