In this episode of Growing Your Firm, brought to you by Jetpack Workflow, host David Cristello sits down with Tyler Winn, the founder and CEO of Cirrus Payroll

Tyler shares his journey of falling into the payroll business in 2012 and subsequently building a seven-figure firm that specializes in processing payroll for small businesses. 

Alongside running Cirrus Payroll, Tyler operates a coaching business for accountants called Payroll Profits (Formally, Winning with Payroll), where he debunks the myth that payroll services are inherently unprofitable and unpleasant to manage. 

He discusses the benefits of separating payroll services from an existing accounting firm, which can lead to a symbiotic relationship between the two entities and provides opportunities for cross-marketing services. 

The episode aims to help accounting firms understand how they can grow by incorporating payroll services and leveraging them as a strategic tool for expansion.

What you’ll learn

The listener will learn about techniques for growing the payroll arm of an existing firm, marketing payroll services to small businesses, making payroll profitable and exciting, opportunities in the payroll services market, and strategies for scaling up a payroll company within an existing accounting firm.

Guest Bio

Tyler Wynn is a distinguished figure in the payroll industry, renowned for his innovative approach to a field that many in the accounting sector tend to avoid. As the founder and CEO of Cirrus Payroll, Tyler has carved out a niche for himself by transforming the payroll process into a profitable and desirable service line for small businesses. 

His journey into the world of payroll began in 2012, and since then, he has successfully scaled Cirrus Payroll into a seven-figure firm that specializes in providing payroll services to businesses with one to forty-nine employees.

Tyler’s professional background is rooted in public accounting, having started his career with Deloitte, where he gained invaluable experience in the industry. 

His transition from working for a prestigious firm to entrepreneurship was driven by a desire to create a business that not only excelled in service delivery but also provided a much-needed solution to the small business market. His decision to focus solely on payroll services was a strategic move that set him apart from competitors who often view payroll as a cumbersome and low-margin task.

Under Tyler’s leadership, Cirrus Payroll has become synonymous with accuracy and responsiveness, two critical factors in the payroll industry. 

He has instilled a culture of relentless focus on customer service, ensuring that his team responds to client inquiries with impressive speed and efficiency. This dedication to service has allowed Cirrus Payroll to compete effectively against larger firms and has positioned the company as a preferred provider for businesses seeking a more personalized payroll experience.

In addition to his role at Cirrus Payroll, Tyler is also the founder of Payroll Profits, a coaching business and community for accountants. Through this platform, he shares his passion for payroll and educates other accountants and bookkeepers on how to debunk the myth that payroll is inherently unprofitable and burdensome. 

His philosophy is that with the right approach and pricing strategy, payroll can be a lucrative and enjoyable aspect of an accounting practice.

Tyler’s ethos revolves around the belief that specialization and premium pricing are key to building a successful payroll business. He advocates for accountants to either fully commit to offering payroll services or to outsource them if it’s not their area of passion. 

His strategy of creating a separate sister company for payroll services has proven to be an effective model for accounting firms looking to expand their offerings without diluting their brand or core services.

As a thought leader in the payroll space, Tyler’s insights and strategies have resonated with many in the accounting community. His approach to business growth, customer service, and niche specialization has not only led to the success of Cirrus Payroll but has also inspired other firm owners to reconsider the potential of payroll services within their own practices. 

Tyler Wynn’s story is a testament to the power of focus, dedication, and a willingness to challenge the status quo in the pursuit of entrepreneurial success.

Detailed Synopsis

Firms dedicated to expanding their payroll services can reap substantial benefits from establishing a separate entity focused solely on payroll. 

This strategy enables them to capitalize on existing client relationships while simultaneously exploring new opportunities within the payroll market. Here’s a closer look at why and how this approach can be highly effective:

Separate Branding and Focus

Creating a sister company for payroll allows firms to cultivate a unique brand identity centered around payroll expertise. This specialized branding positions the new entity as an authority in payroll solutions, making it more attractive to potential clients seeking dedicated payroll services.

Leveraging Existing Clientele

Firms with an established client base in accounting have a ready market for their payroll services. Introducing payroll through a distinct company provides clients with a comprehensive solution for their needs, enhancing client retention and satisfaction by broadening the service offering.

Marketing Flexibility

A standalone payroll company affords the flexibility to market its services to a wider audience, including small businesses that may not need full accounting services but are in search of payroll solutions. This strategy opens up a new revenue stream and allows the firm to target a market segment specifically seeking payroll expertise.

Symbiotic Relationship

The accounting firm and its sister payroll company can enjoy a mutually beneficial relationship. As the payroll company acquires new clients, there’s an opportunity to introduce them to the accounting services of the sister firm. 

Conversely, the accounting firm can refer clients in need of payroll services to the sister company, fostering a cycle of referrals that promotes growth for both entities.

Insights from the Podcast

In a podcast episode, the host speaks with Tyler Winn, founder and CEO of Cirrus Payroll, about the advantages of separating payroll into its own company. 

Tyler explains that this separation allows the firm to serve existing accounting clients with payroll services while also reaching out to businesses that are exclusively looking for payroll providers. 

He describes this as a “beautiful symbiotic relationship” where each company contributes to the other’s growth.

In conclusion, for firms intent on growing their payroll services, launching a separate sister company can be a strategic move that leverages their existing client base and independently pursues new payroll market opportunities.

Premium Pricing for Payroll Services: A Path to Quality and Responsiveness

In the competitive payroll services landscape, pricing strategies are pivotal in defining service quality and a firm’s success. Tyler Wynn, founder and CEO of Cirrus Payroll, discusses the importance of premium pricing not just as a revenue strategy but as a foundation for delivering superior service.

Investing in Quality Staff

A premium pricing model enables a firm to hire the industry’s best talent. Tyler underscores the need to price services sufficiently high to encourage growth and reinvestment in the business. 

This approach attracts top talent, including experienced professionals seeking remote work opportunities, as Cirrus Payroll does. Superior staff leads to superior service, creating a virtuous cycle that benefits both the firm and its clients.

Enhanced Responsiveness

Tyler highlights responsiveness as a key competitive edge. Cirrus Payroll prides itself on an average response time of about 20 minutes to client inquiries, a stark improvement over the days-long waits some clients endure with larger providers. 

This responsiveness is made possible by the premium pricing model, which supports a dedicated and efficient support team. Tools like Hiver, a Gmail extension Cirrus Payroll uses, help monitor and enhance response times, ensuring clients receive prompt and effective support.

Competitive Advantage

The synergy of quality staff and enhanced responsiveness gives firms like Cirrus Payroll a significant competitive advantage. Clients dissatisfied with larger providers’ service levels appreciate the personalized and swift attention from smaller, premium-priced firms. This advantage helps retain and attract clients who desire a better payroll service experience.


Tyler Wynn’s premium pricing strategy for payroll services shows that firms can excel by prioritizing quality and responsiveness. Investing in the right staff and resources enables firms to offer a service level that distinguishes them from the competition, leading to a successful and profitable payroll service.

Building relationships with other firms seeking to divest their payroll services is a strategic move that can significantly contribute to a payroll business’s growth. 

As discussed in the podcast episode, many accounting firms provide payroll services as part of their offerings but may lack passion or profitability in this area. These firms often view payroll as a necessary component of being full-service but may not have the expertise or desire to manage it effectively.

Tyler Wynn shares how he has successfully expanded his payroll business by partnering with firms that have strategically decided to stop offering payroll services. He notes that most firms dabble in payroll out of obligation to offer a full range of services. However, they may reach a point where the hassle of managing payroll is no longer worth it, particularly when a key staff member responsible for payroll departs.

At this juncture, these firms must decide whether to invest more in payroll or offload the service. This is where relationship-building is key. 

By presenting his company as a specialized and dependable payroll provider, Tyler has been able to acquire clients from firms eager to remove payroll from their list of services. 

He mentions that some firms are even willing to transfer their payroll clients at no cost, simply to relieve themselves of the burden.

For firms aiming to grow their payroll business, Tyler suggests the following strategies:

  1. Identify Firms Looking to Offload Payroll Services : Engage with local accounting firms, establish relationships, and offer a solution to their payroll challenges.
  2. Offer a Seamless Transition : Ensure these firms that their clients will continue to receive top-notch payroll services, which helps maintain their reputation while they concentrate on their core offerings.
  3. Capitalize on Remote Work : Utilize the trend of payroll companies bringing staff back in-house as a recruitment tool. Offering remote work can draw talent from competitors and serve as an attractive proposition for firms considering outsourcing payroll.
  4. Create a Separate Payroll Entity : For accounting firms serious about payroll, Tyler recommends forming a separate sister company with distinct branding and marketing. This enables the firm to provide payroll services to existing clients and attract new clients looking solely for payroll, who can then be introduced to other accounting services.
  5. Focus on Responsiveness and Service Quality : Stand out by providing quick and precise responses to client inquiries, which can give you a competitive edge over larger, slower firms.

By adopting these strategies and emphasizing the unique value of specialized payroll services, firms can effectively expand their payroll business and establish a profitable new revenue stream.


[00:02:42] Competitive landscape in payroll.

[00:06:06] Building a better payroll service.

[00:08:53] Investing in customer support.

[00:11:48] Payroll business growth strategies.

[00:15:37] Building relationships with firms.

[00:19:16] Hiring process insights.

[00:20:44] Connecting on LinkedIn for networking.

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