Untethered Phoenix

Founder

General welding supply corp

Manager

Executive Assistant

Customer Service Representative

New York Home Health Care Equipment

Process Improvement Coordinator

Sleep Division Coordinator

Medical Gases Inc

I get it. Something in your past is holding you back. I've been there 😏

The weight of experiences, challenges, and setbacks can feel like a anchor ⚓ keeping you from moving forward. But here's the thing—I stopped letting those obstacles define me, and you can too!

Hi, I'm Samantha Sierra, but you can call me Sam. I've walked the path of transformation 🚶‍♀️ Faced my own share of struggles, and understand how it feels when the past seems like a barrier to progress. However, I've also experienced the power of turning adversity into a gift, evolving into someone who embodies resilience, trustworthiness, and emotional intelligence 🔥

Now, imagine this: breaking free from the chains of your past and rewriting your narrative. That's where I come in as your personal mindset coach 💪 I've been where you are, and I've also been where you want to go. Together, we'll navigate the challenges, tapping into your inner strength to create a future that reflects the very essence of the Phoenix Mindset 🧠

Ready to rise above and embrace positive change? Head to my featured section and setup a chat! Let's see if we can set your inner Phoenix free 🔥

Your past doesn't doesn't define your future. You do 💜

Samantha Sierra

bswift

Building stronger channel partnerships across the country!

Vice President of Channel Partnership Sales

Health & Voluntary Benefits Association (HVBA)

I am dedicated to advancing the HVBA's mission in our industry by setting higher standards for the distribution of voluntary benefits, grounded in integrity and a commitment to education. While I take pride in my contributions, I believe that true success comes from our collective efforts. Together with other industry leaders, we can unlock incredible value and demonstrate the power of our dynamic community. Join us for an upcoming event—it’s an experience that promises to inspire and connect us all!

Advisory Board Member

Rock Enrollment

In my role, I focus on financial and strategic initiatives to help establish a new brand for Rock Enrollment within the benefit community. Together with the talented technology team, we innovate and enhance our SaaS benefits platform to serve the needs of brokers and carriers across the US. By combining our technological advancements with industry expertise, we strive to create a brand identity that truly resonates with our audience.

I also contribute to the development of retention strategies that aim to:

- Strengthen connections with HR partners through our REfresh HR experiences.
- Promote a modern and diverse product mix through our SaaS benadmin and year-round REstore.
- Elevate educational resources for employee understanding and buying confidence.
- Enhance relationships between brokers, carriers, and the workforce.

My role revolves around sales and strategy and is focused on collaboration and innovation. I’m thrilled to work alongside such a talented team whose diverse perspectives spark new ideas and solutions. We’re building a dynamic environment to serve the future of the workforce.

Chief Strategy Officer, Employee Benefit Broker Channel

Life Time Inc.

I embarked on an exciting opportunity to blend my passion for sports with my entrepreneurial spirit by building a solid community around pickleball. This venture allowed me to tap into my love for fostering communities while focusing on health and well-being, all while balancing it as a passion project alongside my other commitments.

Collaborating with an outstanding pickleball team and some of the best facilities in the city, we crafted a dynamic program tailored specifically for the Birmingham market. Our approach included everything from innovative leagues and engaging skills clinics to thrilling tournaments, ensuring we catered to players of all skill levels. The feedback from the community was overwhelmingly positive, reflecting the powerful impact we had in fostering a vibrant sports environment.

As I honed my own skills as a player, I gained invaluable insights from Life Time about providing holistic benefits solutions that truly meet the needs of both employers and employees. This period not only sharpened my abilities but also positioned our facilities as a hub for special events in the employee benefits sector, including several well-executed tournaments.

Highlighting this journey, I had the honor of being sponsored by Joola, a respected leader in the pickleball industry. This experience reinforced my commitment to wellness and community building, demonstrating that even during a transitional phase, I was actively creating something meaningful and impactful.

Part-Time Pickleball Pro

Springboard Benefits

With the help of a fantastic team, I successfully built the company from the ground up, transforming it into a thriving organization with hundreds of thousands of users. By conceptualizing and driving the adoption of a complex, powerful, and personalized SAAS software platform, I enhanced the health and benefits ecosystem by providing innovative solutions that set new industry standards.

* Built company from start-up stage to hundreds of thousands of users by conceptualizing and driving adoption of complex, powerful, and personalized SAAS software platform for the benefit of the entire health and benefits ecosystem.

Under my leadership, we achieved the prestigious honor of graduating from an elite group of selected "Signature" program companies at the Advanced Technology Development Center (ATDC) at the Georgia Institute of Technology. This milestone not only validated our business model but also opened doors to invaluable networking and growth opportunities.

* Scaled the company to achieve graduation from an elite group of selected "Signature" program companies at Advanced Technology Development Center (ATDC) located at Georgia Institute of Technology in midtown Atlanta.

My substantial fundraising experience has been a cornerstone of our success. Through strategic business planning and leadership during multiple investment rounds, I effectively communicated our compelling vision for growth, resonating with investors and securing the capital vital for expansion.

* Significant fundraising experience and business planning strategies gained through my time at ATDC, as well as led multiple investment rounds while driving vision for growth.

As an entrepreneur, I served as the company's acting president and senior officer from its inception to my exit. This role enabled me to cultivate a deep understanding of the operational landscape and foster a resilient organization capable of thriving in a dynamic market.

Chief Sales Officer, Executive Board Member

- Spearheaded the design of a dynamic SAAS platform and effectively led a talented software development team to create core, voluntary, and lifestyle plans. This initiative empowered individuals to obtain, access, and optimize their health and benefit programs during their initial enrollment and throughout significant life events.

- Guided product development and digital strategy with a focus on sales and growth, successfully delivering hundreds of solution-oriented product demonstrations. I took pride in leading clients from solution awareness through to successful contract closure.

- Developed and implemented an internal program to transition legacy software systems to a proprietary platform, integrating robust fintech billing solutions. This initiative, though a team effort, significantly streamlined our processes.

- Fostered a cross-functional, empathetic working environment as a team leader, collaborating closely with every department in the company. I was always ready to support licensed benefit coaches when my expertise was needed.

- Built meaningful relationships with some of the world's largest life and health insurance carriers and brokers, simplifying product distribution to workplace settings. 

- Championed user adoption of the platform and advanced our analytics approach, creating a stronger offering that genuinely served the needs of HR executives and employees alike.

- Formulated an e-commerce strategy aimed at increasing user engagement over time, recognizing that continuous improvement is key to success.

Chief Product Officer

DirectPath

In my role, I spearheaded nationwide employee benefit broker relations and development, immersing myself in the intricacies of business growth with national brokers in metropolitan areas catering to 1,000+ employee organizations. My time was marked by coast-to-coast travel, allowing me to forge invaluable connections and build an extensive network with industry leaders across the country.

I worked closely with HR executives, CFOs, and brokers, devising innovative open enrollment solutions that not only met but exceeded client expectations. My commitment to cultivating enduring broker and partner relationships ensured a seamless flow of collaboration and success.

Leveraging my deep expertise in the employee benefits industry, I was instrumental in developing both new and existing insurance carrier partnerships. This not only enhanced the market relevance of HRIS and enrollment technology systems but also positioned our offerings at the forefront of the industry.

Executive Vice President, Business Development, National Brokerage Channel

Cobbs Allen

- Managed a significant profit center as the managing producer, leading a team of over 20 dedicated benefit professionals in navigating all strategic issues related to our employee benefits division.
- Designed innovative self-insured employer solutions for both large public and private companies, enhancing their competitive employee benefit programs with a deep understanding of the healthcare system, claims management, voluntary benefits, and wellness solutions.
- Curated impactful programs and cost-saving strategies that have successfully saved employers millions of dollars, showcasing a commitment to financial efficiency.
- Collaborated closely with a talented internal team of benefit experts to foster a supportive culture centered on client-focused customer service, always striving for excellence.
- Honored as one of Birmingham Business Journal's "Top 40 Under 40", recognized for my leadership and passion for Employee Benefits.
- Proudly served as the first female board member, breaking barriers and paving the way for future leaders.
- Skillfully managed vendor relationships, ensuring beneficial partnerships that enhance our service offerings.
- Represented Assurex Global and Marsh Berry Agency, building strong connections within the industry.
- Recipient of the coveted Grizzly Award, recognizing outstanding performance and top producing performer across all offices and all business units to include: P&C, Surplus Lines, Personal Lines, Wholesale and Employee Benefits

Executive Vice President, Employee Benefits Practice Leader, Executive Board Member

*Passionate, nationally licensed employee benefits insurance professional responsible for serving clients with expertise in holistic workplace wellness, benefit budgeting and procurement as well as financial implications and stewardship. 
*Drove personal revenues to over $1M annually with support of dynamic account management team and other seasoned staff and leadership. 
*Top Sales Leader Achievement Award: honored with the highest annual "Grizzly" Award for Top Company Performer
*Led educational efforts for professional development to further understand industry nuances and stay ahead of benefit trends. 
*Consistently invited to participate in industry think tanks and leadership roundtables.

Employee Benefits Consultant/Producer

Just For Feet

*Ran recruiting and benefit enrollment efforts for extremely fast-growing National organization. 
*Responsible for procuring and executing recruiting software to keep up with high inflow of resumes across the country. 
*Built process flow between HR and Recruiting leadership teams to manage employee benefit communications and open enrollment materials. (this is where I first developed a passion for breaking free from status quo enrollments)
*Led weekly new hire and benefit orientation meetings at corporate office to include 1000+ new hire. 
*Worked closely with Marketing and Operations to execute Grand Opening events across the country. These events included car give-aways and hosting many celebrity athletes on in-store basketball courts to drive awareness of the company's "experience" approach to shopping!

Recruiting Lead

Co-Founder @ Rock Enrollment! Exponentially Elevating 🚀 the Value of Employee Benefits! WE ARE HIRING!

Transformational Benefits & Insurtech Leader | Building Bridges in Benefits | Passionate About Connecting People & SolutionsI

I’m a connector who thrives on uniting people, ideas, and technology to reshape the benefits and Insurtech industry. With over a decade of leadership and deep expertise, I’ve driven transformative change by forging strategic partnerships that empower brokers, carriers, and point solution providers to deliver innovative, employee-centric benefits. 

My strength lies in understanding the workforce’s evolving needs and leveraging cutting-edge solutions to make benefits more impactful, accessible, and human

I’ve led high-impact initiatives, including scaling a SaaS benefits platform to nearly a quarter of a million users and generating over $1B in annual premiums, partnering with 9 of the top 10 U.S. brokers. 

As the first female executive board member at Cobbs Allen, a Top 40 Under 40 honoree, and a graduate of Georgia Tech’s prestigious ATDC Signature Program, I’ve championed cost-saving programs, AI-driven platforms, and mentorship to drive industry innovation. My passion for building relationships fuels collaboration and creates a lasting impact.

Outside the office, I’m all in for college sports (a little Roll Tide and a lot of Hotty Toddy!), dominating pickleball, and hunting for unique vintage treasures. With a husband, five (almost adult) kids keeping life vibrant, I bring the same energy to connecting people in both my professional and personal worlds. Let’s link up to create something extraordinary—whether it’s revolutionizing benefits or swapping stories about the perfect nostalgic office find.

taplio

The Battle

Samantha Sierra

Amy☕️ Mansfield Nelli

Followers

Posts

Engagements

Likes

Ready to grow your LinkedIn presence?