PEAK6 Insurtech Services LLC

Director, Franchise Development

United States full-time Executive Salary not listed
full-time Executive level Technology & IT Curated
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About the role

Who We Are.
At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client’s unique needs, ensuring they feel confident and supported in every decision.
As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results.
What sets us apart? We’re data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We're building something meaningful and looking for purpose-driven individuals to help lead the way.
Your Impact.
We Insure is seeking the Director, Franchise Development role to expand our franchise agency network and grow our national presence. This person will lead franchise recruitment for We Insure, driving brand and enterprise growth by identifying, recruiting, and onboarding new franchisees across the country.
Day to day, the Director, Franchise Development manages the full franchise sales process from initial inquiry through discovery, program walkthrough, Franchise Disclosure Document (FDD) review, and signed franchise agreement. This includes building and converting a strong pipeline of qualified franchise candidate's solo agents, book of business owners, career changers, and other franchise groups exploring diversification representing We Insure at industry conferences and franchise expos, and partnering with the Discovery and Deal Operations teams to keep the sales process moving efficiently.
This is a high visibility role for an experienced insurance and franchise sales leader who wants to play a lead part in scaling We Insure's franchise footprint nationally.
Key Responsibilities.
Franchise Sales & Deal Execution

Manage the full franchise sales process from initial inquiry and discovery through program walkthrough, Franchise Disclosure Document (FDD) review, and signed franchise agreement

Build and convert a strong pipeline of qualified franchise candidates, meeting or exceeding quarterly and annual development goals

Maintain deep knowledge of franchise program economics and clearly communicate investment, fees, and return potential to prospective franchisees

Guide prospective franchisees through a transparent, consultative sales process to help them evaluate whether We Insure is the right fit for their goals

Lead Discovery Day meetings and franchise presentations for prospective candidates

Relationship & Pipeline Development

Identify, recruit, and build relationships with prospective franchisees, including solo agents, book-of-business owners, career changers, and other franchise organizations exploring diversification

Represent We Insure at industry conferences, trade shows, and franchise expos to build brand awareness and generate qualified leads

Partner with the Discovery and Deal Operations teams, and with marketing resources, to optimize lead generation and pipeline conversion

Track and report pipeline health, conversion rates, and development velocity to senior leadership on an ongoing basis

Strategic Growth & Market Development

Develop and execute strategies for franchise market planning, territory development, and growth initiatives that support national expansion

Provide field-informed input on franchise sales strategy, positioning, and process improvements

Monitor industry trends and the competitive landscape to inform We Insure's franchise growth strategy

Partner with cross-functional teams to support a smooth transition from signed agreement into onboarding

Brand Representation

Act as a credible, experienced ambassador for the We Insure franchise opportunity, grounded in real industry background

Model We Insure's core values in every prospect interaction and public appearance

Nurture relationships with existing franchisees to support their continued growth and success within the network

Contribute to a transparent, respectful candidate experience that reflects We Insure's people-first culture

Qualifications.
Required Qualifications.

10+ years of experience in the insurance industry, ideally as an agency owner or top producer rather than solely in a corporate or carrier-side role

Direct experience in franchise sales or franchise development

Demonstrated ability to independently run a full, consultative sales cycle from first conversation through signed agreement

Preferred Qualifications.

Experience spanning both the insurance and franchising industries

Experience representing an organization at industry conferences, trade shows, or expos

A firsthand, credible track record building or owning an insurance business, rather than solely a hired-sales background

Our Values. The We Way.
At We Insure, Group our values shape how we work, how we lead, and how we grow together. They’re more than just words, they guide every interaction, every decision, and every customer experience.
We Way Reflects Our Commitment to.
We personalize protection at a price you can trust
We hustle to find opportunity
We care authentically
We thrive in ambiguity
We own our results
We have fun along the way
And—we’re just getting started

Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

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Executive
Technology & IT Business Development Human Resources Operations Sales Executive level full-time

Likely questions

  1. Tell us about work you have done that is close to the Director, Franchise Development role.
  2. How would you approach your first 30 days at PEAK6 Insurtech Services LLC?
  3. Which of Business Development, Human Resources and Operations have you used recently, and what did it help you achieve?
  4. How have you led people, improved a process, or made a hard decision in a previous role?
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Business Development, Human Resources and Operations.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Director, Franchise Development role because I can bring practical experience in Business Development, Human Resources and Operations, learn the team quickly, and contribute to the outcomes PEAK6 Insurtech Services LLC needs from this hire.

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