About
The person behind the work.
A Fractional CSOO (Chief Strategy & Operations Officer) and operations executive who builds systems, teams, and communities that scale without losing stability.

My Story
I lead through relationships and trust.
I'm Jessica D. Maine-Jackson, and I work in a lot of different rooms: a CEO's strategy session, a coworking space strategy review, a nonprofit board meeting, a Monday team stand-up. What connects them is a belief that strong operations start with people who feel trusted and supported. I balance people and performance in everything I build.
I began my career as an educator and spent 14 years in public education, first in the classroom and then as an educational consultant to school districts, where I led a district college and career readiness program. That experience still shapes how I lead. From there I moved into executive leadership, operations, and consulting, with 15+ years across industries. Along the way I became a Certified Chief Strategy and Operating Officer (CSOO) in 2022, a monday.com Master Authorized Consultant, and a certified life coach.
Today my work is varied by design. I oversee strategy and operations for a Dallas coworking space. I lead people operations for teams that include remote and international employees, from employer-of-record support and handbooks to 360 review cycles. I also guide nonprofits through strategic planning, organizational assessments, and executive search support, build the systems and AI workflows that save teams real hours, and coach leaders as they grow.
I've always been a bit of a unicorn. I've resisted being put in a box my whole career, which is why I can move from a classroom to a boardroom to a coworking floor and feel at home in every one. I've also always been allergic to trends and fads. Being classic never goes out of style, so I build foundations that still hold up long after the latest buzzword has faded.
I'm a communications nerd at heart. My BA is in Communication Studies, and I'm now earning an MA in the same field. I believe most operational problems are communication problems in disguise, and listening first solves more of them than any new tool. I care about equity and fairness, and about making sure people have access to the resources they need to thrive.
Jessica
My Range
Where I've led
Executive Leadership
Running the operating rhythm, team cadence, and execution so CEOs and founders can focus on vision.
Coworking and Community Spaces
Overseeing strategy and operations for a Dallas coworking space, and advising owners on bringing their vision to life.
People Operations and HR
Hiring, onboarding, handbooks, and 360 reviews for teams that span remote and international employees.
Nonprofit Strategy
Strategic planning, organizational assessments, executive search support, and proposals that are ready for the board.
Systems and AI
Designing workflows, tech stacks, and practical AI implementations for small teams.
Education and Youth Development
A foundation in public education and educational consulting for school districts, carried forward through youth mentoring and my work founding Foreword Forum.
My Approach
How the work gets done.
Human-First
Strong operations start with people who understand their roles and feel trusted to do them well. I design every system with that in mind.
Data-Driven and Outcome-Based
We agree on what success looks like, measure it, and adjust as we go.
Built to Last
I build sustainable, scalable foundations and leave your team stronger than I found it.
Let's talk about what you're building.
Book a free discovery conversation, or email hello@jessicadmaine.com.