Jenn Drummond


Jenn Drummond

Virtual Assistant

Based in Kentucky
With Trusty Oak since 2021

With a bit of humor, a dash of savvy, and a healthy amount of hard work I’ll have your business running smoother than a fresh jar of Skippy.

Currently Taking New Clients


About Jenn

Born in the wilds of Alaska, Jenn now resides in the humid hills of Kentucky where she works as a professional right-hand woman to a variety of business professionals. As someone with a penchant for having her fingers in every pie, her experience is manifold and she brings a diverse assortment of skills to the table. Jenn nimbly wields a can-do attitude to tackle all those tedious or time-consuming tasks that are bogging you down.

How much could you accomplish for your brand if you weren’t having to spend time on all the dull stuff? Whether you’re looking for a content creator, marketing maverick, project manager, personal assistant, or just a second set of hands, Jenn is on the scene. She can use her diversified writing experience to create content for your brand, apply her honed marketing experience to build and establish your brand identity, or employ her 10 years of customer service experience to boost your customer growth and retention – and she won’t stop there. If you don’t have the time, savvy, or willpower for a task, let Jenn handle it.

As for the woman behind the words, Jenn is a serial learner with an unquenchable curiosity and a predilection for humor. She is a PC and Nintendo gamer, sci-fi and fantasy book devourer, horror movie aficionado, snack connoisseur, and craft queen. She also cries at both happy and sad dog videos. Jenn always has at least four different crafts in the works because she wants to do ALL the things. When not home, you can find Jenn adventuring with her partner and her pup, Moose, at live music events, dive bars, ice cream parlors, and nature trails.

Working Hours

Mon-Fri, 10am-6pm



Support Skills

Creative Content Creation: Blog Writing & Editing, Copywriting & Copyediting, Newsletters, Infographics, Charts, Presentations, GIFs, Graphics, Journalistic Articles, Brand Design

Project Management: Organization & Management, Webinar Meeting & Organization, Customer Service Analysis & Strategy, Campaigning

Marketing: Email & Social Media Automation & Management, Email Campaigns, Marketing Calendar Creation, Brand Strategy, Advertisements, Community Outreach & Engagement, Social Listening & Monitoring, SEO Diagnostics

Personal Assistance: Professional Correspondence, Event Planning, Travel Planning & Booking, Meeting Planning & Booking, Calendar & Appointment Management, Gift Shopping & Delivery, Bill Management, Hiring Manager, Reminder of Things

Admin & Beyond:  Inbox Organization, Asset & File Organization, Research & Analysis, Data Entry, Invoicing & Payments, Business Development, General Admin, Communication

Industry Experience

Tech Startups

Video Game Industry 


AI Development

Convention Industry


Restaurant & Retail

Direct & B2B Sales

Entertainment Journalism

Construction Industry

Marketing Industry

Nonprofit Programs

Travel & Hospitality

Software Experience

Admin software: Google Suite, Microsoft Office, OneDrive

Communication software: Slack, Zoom, Google Meet, Microsoft Teams, Skype, Doodle, Globafy

Content Creation software: Adobe Spark, Canva Pro, Boomerang, Biteable, Google Charts & Slides, Giphy, Audacity, DropBox, Shootproof

CRM software: Salesforce, Zendesk, HubSpot, HoneyBook

Marketing software: ActiveCampaign, Constant Contact, Google Analytics, MailChimp, SurveyMonkey

Project Management software: Trello, Evernote, Todoist, Teamwork,, Wrike, Asana

Social Media Management software: Tweetdeck, Canva, Hootsuite, All basic social media platforms


Why people love Trusty Oak


The Trusty Oak team has been instrumental in helping me build my career. From administrative support and social media management to business planning, Amber and the Trusty Oak team have all the resources and people strength that I need to be successful. When a business need arises, I can trust that Trusty Oak will have a number of options and solutions that will work within my budget and time frame.

Todd Merry

Home of Hope Ministries


The Trusty Oak team has been instrumental in helping me build my career. From administrative support and social media management to business planning, Amber and the Trusty Oak team have all the resources and people strength that I need to be successful. When a business need arises, I can trust that Trusty Oak will have a number of options and solutions that will work within my budget and time frame.

Brandi R. Muñoz

Principal Workforce Development Consultant, People Culture Consulting


My experience with TRUSTY OAK was wonderful…getting my website more organized and cohesive. Having someone else take a deeper look at my website was really helpful and inspiring — we literally gave it a whole new look and feel. This freed up my time to focus on other things that I don’t usually have time for. Hannah was always available when I needed her and had a lot of great ideas and brought a fresh new perspective to my marketing. I felt like I was in really good hands and can highly recommend TRUSTY OAK.

Pascal Simon

Owner and Founder of Bake Austin


TRUSTY OAK rocks! I couldn’t be more pleased about the quality of work and their personal touch. With Amber as CEO, I can count on her to understand our needs, to be a great communicator, and a wonderful resource for us. I am continually impressed with how professional and capable TRUSTY OAK’s virtual assistants are. I highly recommend TRUSTY OAK to provide outstanding administrative assistance to organizations like ours.

Dona Raskin

Founder of Austin Kids Can!


Working with TRUSTY OAK has been an absolute pleasure. After several failed attempts with other VA firms, I have finally found a responsive, trustworthy, dependable assistant…adding much more value than the bare bones inbox and calendar management I was looking for. If you’re looking for a fractional assistant you can trust from day one, I highly recommend you work with TRUSTY OAK.

Tim Hamilton

Founder & CEO of Praxent, Austin, TX


My VA has done more for me in 20 hours of work than I’ve done in probably a year of just making things up on my own. That’s not a sales pitch, infomercial, or me being paid to say what I’m saying. It’s true. I’ve gotten a business card designed, a logo designed, website updated, streamlined for SEO, content written, colors and fonts changed, things I would have never thought about if I was doing this on my own.

Dave Bahr

Founder and CEO, In-Sightful Living


Adulting is hard. Entrepreneuring is harder. I don’t know where I would be on either if Trusty Oak hadn’t come into my life when they did. Partnering with them has allowed me to scale my business, organize my life, and accomplish goals that would have been out of my reach without their support. Their team is diverse in skillset and background—over the years I have been able to lean on them for everything from scheduling and travel booking to bookkeeping and invoicing to process engineering and implementation. They are proactive, trustworthy, and receive an enthusiastic recommendation from me!

Ilana Zivkovich

CEO, Werq


As an entrepreneur with several projects going in different directions, it’s hard to prevent some things from falling through the cracks. I’ve asked for a diverse list of tasks and they have done them all in stride, quickly, and way too politely. You can count on TRUSTY OAK to get things done fast and correctly, freeing you up to focus on building your business.

Clint Greenleaf

Board Director, CEO, Entrepreneur, Content Expert, CPA


It took a while to open to the idea of a VA – as a new business owner, I thought I could do everything. Well, I was wrong! Letting go of the things I don’t know how to do, or don’t do well at all and handing them to TRUSTY OAK helped me immensely. They take care of my website and social media and much more, and leave me time as the business owner to do the stuff I’m good at.

Eyal Gallico

Founder & IT Professional at TopMac, Austin, TX


I have worked with Amber on several website projects and her work is top notch. I am amazed by her attention to detail and her ability to drive a schedule. If you want something done well, and fast, TRUSTY OAK is what you are looking for!

Erika Heilman


Trusty Oak’s virtual assistant services have plugged a gap in our administrative needs and made my life easier during a year of hectic travel. Genny got up to speed quickly in understanding the nature of my work, and she’s efficient and professional in helping to manage complex calendaring and travel arrangements. This virtual arrangement has worked seamlessly for us!

Juila Freeland Fisher

Director of Education Research, Clayton Christensen Institute


Working with the VAs at Trusty Oak, I am better equipped to scale and grow my business. Their varied skill sets help open up the Cabéza Advertising portfolio of services, allowing us to better serve our clients and improve our value proposition.

Hose Garcia

CEO and Founder, Cabeza Advertising

Thought Leadership