Experienced HR Team

We have over 145 years of HR experience, from manager, programmer, system designer, CEO, sales, more so we know how everything comes together which makes us the perfect partner to connect your applications together.

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Dianna Sheppard


People who know Dianna say, “she is a person who inspires people and organizations to accomplish more than they ever thought was possible.”

She is doggedly passionate about the “clear mission at hand” and employs accountabilities tactics with intense focus on “process efficiency and breakdown risk mitigation”.

With over 20 years of experience in various sales, management, operational and marketing roles, Dianna has a demonstrated ability in unique product positioning, problem solving and building motivated teams, both on the explosive growth and the downsize sides. She has effectively worked on both the buy and sell side of acquisitions/divestitures.

Before joining CloudMills, Dianna was the President/CEO of a $30M company offering strategic Human Resource Solutions including: Recruiting, Health Insurance/Benefits/Workers’ Compensation, and Strategic Planning. She’s also served as Founding Partner and Board Member of CogNet HRO and Sr. Vice President of the strategic team at Ceridian.

Bennett M. Reddin


Bennie is every HR officer’s dream come true. He can have a conversation with a payroll clerk or board member and everyone walks away satisfied with having gained valuable knowledge.

A technologist at heart, with a true passion for revolutionizing information delivery to transform HR into corporate innovation catalysts, Bennie frequently contributes this vision to HR strategy and technology publications. Consulting directly to client enterprises, he helps them lay the strategic and technological foundations for emerging innovation in HRIS.

Bennie has designed and continues to architect HRIS to meet the needs of 21st century enterprises. He comes to CloudMills with 25 years of HRIS expertise ranging from early PC-based HR systems through current Service Oriented Architectures. He has engineered and deployed several HR and Payroll architectures for service bureaus and ERP vendors, improving toolsets and practices for implementation in the process. As founder of TiltingWindmills (the predecessor to CloudMills), he has participated in numerous strategic technological initiatives for corporate HR, injecting Human Capital vision and value into executives’ focus.

Bradley Rhine


Those who work with Bradley say “he is relentlessly driven to provide high quality, creative solutions to complex business challenges…and can ‘sling code’ when circumstances require.”

In addition to executive business functions, he maintains a deep understanding of system, database, and network internals with emphasis on contemporary, “always on” cloud-based services. He continues to deliver hands-on technical contributions, using open source technologies in areas that include financial, human resources, payroll and benefits. His philosophy is one of “rigor without frills” – paying close attention to the essential details without becoming enmeshed in overly ornate processes.

Bradley’s expertise spans multiple realms including front-end applications, security infrastructure (including SSO), relational database design and data transformation, data analytics, network protocols, server operating systems and HA/DR/BC. Bradley’s past experiences architecting, building, and supporting operational SaaS applications provide a practical perspective on the real-world challenges of complex, multi-system integration chains.

Laura LaValley

VP of Client Services

Laura is the face of CloudMills and voice of our clients. Those who have worked with her all have the same comment “she’ll get the job done with a smile on her face!”

Using her broad experience in software and hardware implementation, project management, software solutions consulting, sales team administration, problem solving and new product launch, Laura fits in very well with all clients.

Laura’s career experience ranges from very large multi-national companies, deploying start-up business units, mid-sized companies and even to small service providers. She has served as the Director of Business Launch and Director of Sales Administration at Fidelity Investments, Director of Sales Support at Advantec, VP of Product Specialists, Organizational Readiness Analyst, and Implementation Project Manager at Ceridian.

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