Webinar Recap: Contracting, Consulting, and Fractional Work in Enablement
In this webinar, Jimmy McFadden and Matt Schalsey shared a practical, honest look at what it really means to work—or hire—in the world of contract, consulting, and fractional enablement. Whether you’re exploring flexible work or considering external support for your team, this conversation definitely offered some valuable clarity and actionable insights.
Key Takeaways from the Webinar:
Defining the Roles
The terms are often used interchangeably, but Jimmy and Matt broke down the distinctions:
Consultants advise on strategy and often guide implementation.
Contractors are project-based and focused on defined deliverables.
Fractional enablement professionals operate more like part-time internal team members, sometimes overseeing ongoing initiatives or filling a gap on a lean team.
When It Makes Sense to Bring Someone In
They covered common triggers for hiring external enablement help:
Burnout or bandwidth issues (especially for teams of one)
High-priority initiatives like onboarding, SKOs, or new product launches
Short-term needs that don’t warrant a full-time hire
Matt also offered a template-style approach to scoping a request—defining the deliverables, hours needed, budget, and how success will be measured.
Best Practices for Success as a Contractor or Consultant
Both speakers emphasized the importance of preparation, communication, and protecting your time and value:
Define your SLA (Service Level Agreement) and know your “done-done” criteria
Build in overage rates and contingency plans
Track your time meticulously
Stay clear on what’s in scope—and push back when things shift
Maintain strong boundaries without sacrificing professionalism; don't be afraid to be blunt!
Real Talk on Challenges
While flexible work can be rewarding, they also shared the harder realities:
You’re often a 1099 worker, responsible for your own taxes and insurance
It can be harder to demonstrate long-term impact when you're brought in for a short engagement
There's no guarantee of a W2 conversion—even if headcount is “coming soon”
Scope creep is a constant risk if boundaries aren’t clear and respected
Tips for Getting Started
If you’re looking to move into contract or consulting work:
Build a strong personal brand
Create a portfolio or sample deliverables
Be proactive—reach out to revenue leaders, not just heads of enablement
Understand what type of engagement you’re signing up for, and set terms that reflect your value
This session was packed with insight and grounded in real experience—both the wins and the lessons learned. Whether you're building a business or building a case for outside support, the recording is worth the watch!
