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Summer Westerbur

FounderKairos Insurance Group Cannabis Division

New York, NY

Member Since March 2023


Public Speaking
New Business Development


Summer Westerbur, CEO of Kairos Insurance Group Cannabis Division, celebrated 19 years of running her own insurance agency in January. The boutique employee benefits firm was one of the first agencies to work with cannabis business owners in Colorado and has expanded nationwide. Summer is co-founder of Simcha, a kosher CBD/CBG company, bringing Boulder-grown kosher CBD to the Jewish community. A serial entrepreneur, she is in the process of opening a woman-owned retail dispensary in the Northeast. She serves on the Tri-state Regional Board of Cannabis Chamber of Commerce, bringing her cannabis experience in Colorado to the emerging regulated markets in the Northeast. She is a regular speaker at U.S. and international cannabis conferences. She is passionate about seeing the end of the drug war. Summer and her son travel obsessively, visiting a dozen countries or more each year knowing that a real education and perspective is only available to those who take the time to understand the world around them.

Published content

Understanding the Regulatory Greenscape in 2024


Anticipation among cannabis industry legal and policy experts is high, with many expecting rescheduling and foreseeing substantial implications.

11 Key Steps Business Leaders Can Take to Meet Their 2024 Goals

expert panel

Your team needs a clear plan of action if they’re going to help you succeed. Individuals aren't the only ones setting resolutions for the new year. Throughout the month of January, even business leaders are reviewing their major goals for the year, setting timelines and creating plans for how to achieve them. Without such plans, business leaders aren’t likely to see success, as it takes intentional effort from them and their teams to accomplish the potentially challenging tasks they’ve set before them.  To ensure you’re setting you and your business up for success in 2024, taking the following 11 steps can be a good place to start. Here, Rolling Stone Culture Council business leaders each suggest one thing their fellow business leaders can do to ensure they meet their goals for 2024 and beyond.

Breaking Barriers: Pioneering a Consumer-Centric Approach to Cannabis Products and Market Expansion


In the evolving landscape of the cannabis industry, it has become evident that a paradigm shift is needed to overcome the current struggles and capture new consumers.

12 Essential Tips for Hiring the Right Talent in the Early Stages of a Startup

expert panel

Ensure the success of your startup by following these 12 tips to build the best possible team through effective hiring practices. Building a successful startup requires assembling a team of talented individuals who can contribute to its growth and navigate the challenges of the early stages. However, hiring the right people for a startup can be a daunting task. It requires a strategic approach to identify individuals who not only possess the necessary skills but also align with the company's vision and culture. Below, Rolling Stone Culture Council members shared some essential tips for bringing on the right people to help grow a startup in its early stages. These insights will empower entrepreneurs to make informed hiring decisions that lay a solid foundation for long-term success. 

11 Low-Cost Strategies for Acquiring and Retaining New Customers

expert panel

From building key relationships to traditional marketing strategies, there are many low-cost ways to attract new customers. In today's highly competitive market, acquiring and retaining new customers is a top priority for any business. However, many businesses struggle with the costs associated with marketing and advertising efforts to attract new customers. Fortunately, there are low-cost strategies businesses can implement to acquire and retain new customers without breaking the bank. These strategies not only help businesses save money, but they are also highly effective in building brand awareness, increasing customer engagement and driving sales. Below, Rolling Stone Culture Council members share 11 low-cost strategies any business can implement to acquire and retain new customers.

How Companies Can Demonstrate Their Commitment to the Environment

expert panel

With a business strategy centered around sustainability, brands can attract consumers and increase their bottom lines. As sustainability becomes a prominent topic of discussion, environmentally conscious consumers are actively seeking out companies that align with their values. Because of this increasing concern for environmental issues among consumers, businesses are now recognizing the need to show their dedication to eco-friendly practices. Below, Rolling Stone Culture Council members share practical steps businesses can take to demonstrate their commitment to the environment and eco-friendly policies. From incorporating sustainable materials in their products to implementing energy-efficient measures in their operations, these efforts not only benefit the planet but also have a positive impact on their bottom line.

Company details

Kairos Insurance Group Cannabis Division

Company bio

Launched in Colorado, Kairos Insurance Group has expanded to include the majority of states that legalized adult-use cannabis. Kairos focuses on providing affordable employee benefits packages to cannabis retail dispensaries, grows, and product manufacturers. Summer understands the unique challenges facing the cannabis industry and works with business owners to decrease cost and increase benefits. Employee turnover is above average in the cannabis industry; designing an attractive benefits package retains key employees. A boutique independent agency, Kairos quotes employer's benefits plan at renewal.



Area of focus

Employee Benefits
Health Insurance

Company size

2 - 10