Helping small businesses compete through collective buying power!
Exectras began with a question that most small business owners often ask themselves: how can we compete with larger firms that always seem to have better access, lower costs, and stronger benefits? For Joe Cherry, CEO and Founder of Exectras, this was not just a question but a challenge worth solving.
Cherry had watched the payments industry shift into a space where profits overshadowed service. The rapid rise of the internet and ISO channel created an environment where short-term gains mattered more than long-term expertise. Many new players entered without the knowledge or experience to guide business owners properly. The result was striking. Customer attrition rose as high as 30 percent, leaving many small businesses feeling unsupported.
While speaking at associations, Cherry repeatedly heard the same pain points from owners of small firms. Insurance plans were often priced out of reach. Payment processing felt like a constant battle with hidden costs. Employee benefits seemed reserved for larger corporations with stronger bargaining power. These frustrations revealed a clear imbalance in the market.
That gap sparked the idea for Exectras. Instead of allowing small businesses to face these challenges alone, what if they could pool their strength? By using the principle of collective buying power, Cherry realized there was a way to bring balance back to the system. Small companies could access resources and savings that were once thought to belong only to big players.
Today, Exectras is built on that foundation. Its model is centered on restoring real value to an industry that had lost touch with the people it was meant to serve. For small business owners, this means practical access to affordable insurance, fair payment processing, and employee benefits that support growth rather than drain resources.
Cherry’s vision has given small businesses a path to compete with confidence. What started as a frustration voiced in countless conversations has grown into a company designed to answer that need. For Exectras, restoring value is not just a mission statement. It is the heart of everything the company does.
The Origin Story
Exectras began with Joe Cherry’s observation that the payments, insurance, and benefits industry had shifted from service and value toward margin chasing and commoditization. The internet and ISO channel expansion had allowed many inexperienced players to offer low-cost solutions with weak customer retention.
Small business owners were unable to access the same advantages larger firms enjoyed, such as group insurance, favorable payment processing, and meaningful employee perks. Cherry’s response was to use collective buying power to negotiate better pricing and improved benefits, and to deliver them fairly to small and mid-sized businesses.
From that foundation the company Exectras was born, with a mission to restore value, reduce cost, improve benefits, attract and retain talent, and overturn poor service norms.
Business Model: Collective Buying Power
What distinguishes Exectras is scale. It aggregates the needs and trust of over 800,000 businesses and many associations. This reach allows the company to engage with major institutions such as Chase, Liberty Mutual, Gallagher, and Paychex, securing Fortune 500 pricing for smaller firms.
Even businesses with only one to five employees, typically excluded from group insurance, can qualify through Exectras’s larger pool which satisfies insurer thresholds. This model translates directly into reduced costs, better benefit terms, and a value proposition that grows with scale.
Exectras positions itself as a Costco for businesses, leveraging aggregate purchasing, partnering with leading providers, and extending those advantages directly to members.
Core Offerings: Payments, Memberships, Partnerships
Exectras operates across three interlocking domains: payments, memberships, and partnerships.
In payments, the company provides in-person, online, and integrated transaction solutions, POS systems, ACH, and smart terminals.
Through membership programs such as Exectras 360 Health, 360 Business Services, and 360 Employee Benefits, businesses gain access to world-class employee benefits including virtual primary care, prescription coverage, wellness programs, and behavioral health—often included at no additional cost.
On partnerships, Exectras works with associations, ISOs, integrated software vendors, franchises, and referral partners. Partners extend reach, while Exectras delivers discounted services and benefits. These offerings connect seamlessly: a business joins as a member, gains payment solutions and benefits, and through partners accesses deeply discounted operational services.
Innovation in Employee Benefits
One of Exectras’s signature innovations is Exectras 360 Health. This program provides far more than telehealth. Members and their families access virtual primary care, a choice of doctors, health history tracking, referrals, and behavioral and mental health support.
Additional features include prescription drug discounts, wellness initiatives, identity theft protection, and financial wellness programs. At an average of $17 per month per employee, Exectras delivers benefits typically reserved for large corporations at a cost small businesses can manage.
The result is stronger employee retention, loyalty, and morale. In industries like hospitality, where insurance is often prohibitively expensive, businesses can now offer competitive packages without heavy financial strain. This has become a clear differentiator, as many competitors either under-offer benefits or structure them inefficiently.
Simplicity Without Compromise
Exectras balances two important demands: simplicity for clients and strong levels of security, sophistication, and reliability. The company developed myExectras, a membership portal also available as a white-labeled solution for partners, along with mobile apps for iOS and Android.
Members can access payments, benefits, and business tools in one place. On payments, Exectras ensures smooth integration across online, in-person, POS, and text-to-pay channels. Businesses therefore avoid the complexity of piecing together multiple providers.
Security is central, with cloud-based storage, minimal collection of personally identifiable information, continuous monitoring, and round-the-clock support across time zones. The guiding philosophy is to always serve the member’s interest first, shaping decisions on contracts, transparency, pricing, and partner relationships.
Measurable Impact
The impact of Exectras is visible in numbers. Industry attrition in payment and benefits services often ranges between 20 to 30 percent, while Exectras reports a rate of less than 2 percent.
Members also report substantial financial savings, with some businesses saving more than 90,000 US dollars annually, and others exceeding 10,000 US dollars monthly depending on size and cost structure. For many, these savings preserve margins, create capacity for reinvestment, and strengthen cash flow.
Equally important, employee benefits improve staff retention and reduce turnover costs. Trust is reinforced through low churn, credible partnerships, and tangible value to employees, which in turn fuels referrals and partner expansion.
Anchors Behind Growth
Exectras is guided by experienced leadership. Joe Cherry, Founder and CEO, brings more than 30 years in sales and leadership. He has built strong institutional relationships, negotiated major contracts, and continues to drive the mission.
The executive team includes Shawn Dalton (Senior Vice President, strategic vision and go-to-market), Michael Gargano (COO, overseeing operations, HR, and membership support), John Coolbaugh (CFO), and Kasey Alexander (Vice President of Partner Relations). Each brings expertise in payments, insurance, and partnerships, creating a well-rounded offering.
The leadership culture emphasizes transparency, service, and integrity. Cherry reinforces the value of relationships, often stating that relationships are everything. This focus has built a foundation for trust and sustainable growth.
Forward Look
Exectras continues to expand with initiatives designed to deepen member value. One planned feature is offering every employee of every member a complimentary 10,000 US dollar life insurance policy, signaling care and differentiation.
The company is also introducing an as-earned wage card that allows employees immediate access to about 70 percent of wages already earned rather than waiting for payday.
Growth continues through the partnership model with associations, ISVs, and ISOs. Exectras is also moving into underserved sectors such as small businesses, restaurants, and hospitality, where employee benefits have long been inaccessible. Innovation in mobile tools, application experience, and payment flexibility will remain central.
The vision is to build not just a payments or benefits provider, but a complete ecosystem where operations, talent management, cost control, and wellness converge. If achieved, this could reset expectations for what small and mid-sized businesses should demand.
