At Franchise Sidekick, we help people live life on their terms through business ownership, and we’ve helped place over 10,000 franchises along the way. We’re a franchise advisory company on a mission to make the franchise buying process easier, smarter, and less risky. We do this by combining decades of experience, smart technology, and a people-first approach to guide aspiring entrepreneurs toward franchise opportunities that truly fit their goals, lifestyle, and investment level.

We’re a growth-phase company driven by purpose, grounded in values, and fueled by the idea that work should feel both meaningful and collaborative. Our team is built on trust, transparency, and genuine support where people show up with passion, share ideas openly, and celebrate wins together. Every Sidekick plays a role in helping clients discover the freedom and fulfillment that can come from owning a business. And we have a lot of fun while we do it.

Role Overview

• Job Title: Director of Education
• Job Type: Full-Time W2 Employee
• Reports To: Vice President of Strategic Initiatives
• Department Head: Chief Operating Officer
• Location: Work From Home or Hybrid Work at Omaha Headquarters
• Compensation: $100,000 to $110,000 Base Salary plus bonus and incentive (total compensation estimated at $123,000 to $125,300 based on salary and goal achievement)

Your Impact On Team Sidekick

As the Director of Education, you’ll be the driving force behind how Franchise Sidekick learns, grows, and leads the industry in franchise and business ownership education. You’ll architect the full learning ecosystem—from new hire onboarding and advisor certification to client and partner education programs that set the standard for the industry.

Internally, you’ll equip every Sidekick with the knowledge, tools, and confidence to perform at their best through intentional onboarding, skill development, and leadership training programs like The Forge. Externally, you’ll elevate Sidekick’s reputation as the trusted source for business ownership education, designing experiences that make the process of buying a business smarter, simpler, and more empowering.

Your leadership will transform learning into a competitive advantage, building a culture where growth is intentional, excellence is teachable, and education becomes a defining part of the Sidekick brand. In this role, you will work on:

Strategy & Program Development (30%)

• Own the overall education and learning strategy for Franchise Sidekick—spanning internal training, client education, and industry leadership.
• Define short- and long-term education goals aligned to company objectives and annual priorities.
• Collaborate with leadership to ensure learning programs directly support organizational performance, culture, and brand growth.
• Establish success metrics for all learning initiatives (engagement, proficiency, retention, adoption, and impact).
• Build partnerships with internal subject matter experts and external organizations to enhance Sidekick’s learning ecosystem and industry influence.

Internal Training & Development (30%)

• Oversee new employee onboarding design to ensure every new hire experiences a consistent, high-impact introduction to Sidekick’s mission, values, and operations.
• Develop and manage training plans for every role and department, ensuring clear learning pathways and measurable skill progression.
• Lead Advisor Certification, including curriculum design, testing, and recertification standards to maintain excellence across the advisory team.
• Design and oversee The Forge Leadership Program to develop future leaders within the organization, with a focus on mentorship, accountability, and growth mindset.
• Continuously assess skill gaps across departments and build targeted learning interventions to drive up-skilling and performance improvement.

External Education & Industry Leadership (30%)

• Position Franchise Sidekick as the go-to source for franchise and business ownership education through thought leadership, courses, and strategic partnerships.
• Build and oversee new client and partner education programs that simplify the franchise buying journey and reinforce Sidekick’s expertise.
• Develop educational resources and experiences (e.g., workshops, guides, webinars, and digital learning) for aspiring entrepreneurs, franchise buyers, and brand partners.
• Partner with Marketing to scale educational content that strengthens Sidekick’s brand authority and lead generation.
• Launch and manage The Sidekick Academy (or equivalent initiative) as a branded educational platform for both internal and external audiences.

Learning Systems & Operations (10%)

• Implement and manage learning systems (LMS or equivalent) to house, deliver, and measure education programs.
• Create a centralized repository for learning materials, certifications, and resources—ensuring easy access and version control.
• Use data and analytics to measure program effectiveness, learner engagement, and performance impact.
• Oversee training calendars, instructor assignments, and certification tracking.
• Continuously improve learning delivery models, blending technology, facilitation, and self-paced learning.

A Day in the Life…

No two days will look the same, and that’s what makes this role so impactful. One day, you might be in the room with senior leadership mapping out the future of franchise education. The next, you’re reviewing onboarding feedback to refine the new employee experience or facilitating a session in The Forge Leadership Program.

You’ll collaborate across departments to design role-based training plans, oversee the rollout of certification programs, and use data to show how education directly improves performance. You’ll also partner with Marketing and Brand teams to create public-facing educational content, like webinars, guides, and online courses, that help entrepreneurs make smarter franchise decisions.

Whether you’re coaching internal leaders, shaping curriculum, or amplifying Sidekick’s voice as an industry educator, your days will be centered around one mission: helping people unlock potential through learning—both inside and outside the company.

What's In It For You?

• Paid Time Off- Every Sidekick starts with 16 days of PTO, two floating holidays, and a paid volunteer day annually. We also offer nine paid company holidays each year as well. Team Members earn additional PTO for each year of employment.
• Franchise Ownership Program- After you're established with Sidekick, we offer a Franchise Purchase Discount which allows you to own your own Franchise Business at a $30,000 to $50,000 savings. Some restrictions and minimum qualifications apply to the discount. 
• Client Referral Commission- We encourage every member of Team Sidekick to utilize their network to find qualified candidates for franchise ownership. We pay $3,000 for every qualified lead you submit that ends up purchasing a franchise. 
• Sidekick Benefits- Sidekick offers the following benefits:
• • Full Medical Benefits with up to $875 monthly Employer Contribution (depending on plan type and level)
  • Employer Paid Dental, Vision, and Life Insurance ($0 cost to employees with options for family coverage)
  • Optional Health Savings Account, Supplemental Insurance, and Cybersecurity Coverage
  • 401k with 3% Employer Contribution (no match required)
  • Home Office Stipend For Remote Workers

This Role Might Be a Good Fit For You If You:

• Have 8+ years of experience in learning, education, or organizational development, with at least 3 years leading an L&D or education function.
• Have built or scaled learning programs that drive measurable business outcomes, both internally (onboarding, training, leadership) and externally (client or partner education).
• Have experience in the franchise industry, as a business owner, or are passionate about entrepreneurship
• Are passionate about designing learning experiences that change behavior, not just deliver information.
• Bring expertise in curriculum design, adult learning theory, and blended learning delivery models (in-person, virtual, and self-paced).
• Have experience building and managing programs within an LMS (Learning Management System) and are comfortable working with SCORM authoring tools such as Articulate 360, Rise, Captivate, or similar platforms.
• Know how to evaluate, select, and implement learning technologies that enhance access, engagement, and scalability.
• Are comfortable using data and analytics to measure learning engagement, retention, and ROI, and to continuously improve program design.
• Have strong leadership skills and can mentor a team of instructional designers, facilitators, and training specialists while influencing senior stakeholders.
• Thrive in a fast-paced, collaborative environment where innovation, accountability, and continuous learning are part of the culture.
• Bring energy, curiosity, and a proactive mindset to your work and are not afraid to pitch new ideas, test, learn, and iterate.
• Are excited about helping more people discover the life-changing power of business ownership through franchise opportunities.
• Enjoy being part of a purpose-driven company where your work directly contributes to our brand, mission, and growth.
• Believe in the power of education to transform not only individual performance—but entire industries.

Working Conditions:

• Franchise Sidekick utilizes a hybrid work structure with in-office and blended work 
• Some travel is required (less than 10% annually if Omaha-based)
• Minimal physical requirements

Our Process & Next Steps

At Franchise Sidekick, we’re committed to building a team that reflects our values and supports our mission. We take our hiring process seriously—not just because we want to find the most qualified candidates, but because we care about creating the right fit for both you and our team. After you apply, our team will review your materials and reach out if your background and experience align with the role. From there, our process typically includes a first-round interview to learn more about your goals and how they align with the position, followed by a second-round conversation with additional team members. In some cases, we may ask you to complete a short task or exercise related to the role. Final candidates will be notified of our decision, and if we extend an offer, we’ll walk through the details and next steps together.

Franchise Sidekick is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate on the basis of race, color, religion, national origin, gender identity or expression, sexual orientation, age, disability, veteran status, or any other protected status under applicable laws. If you require accommodations during the hiring process, please don’t hesitate to let us know—we’re happy to support you.