Payroll has a peculiar talent for vanishing. When it works, the money arrives, the ledger closes and everybody gets on with Friday. When it falters, the invisible machinery becomes the only thing anybody can see. Michael Young has built his career around that abrupt change of focus. His answer is neither a cheerful robot nor a nostalgic stack of paper. It is good software with a telephone nearby.
Young is the co-founder and CEO of ConnectPay Payroll Services, the Massachusetts company he started with Paul Altavena after the pair had already spent decades in business together. ConnectPay serves the sort of employer that rarely appears in glossy enterprise-software advertising: the landscaper, the dental practice, the auto shop, the company with ten or twenty-five employees and no dedicated HR executive waiting in a glass office.
These owners, in Young’s phrase, are “chasing their passion.” Then they choose a name, make a logo and discover that enthusiasm comes bundled with tax filings, deductions, reporting deadlines and rules that keep changing. A paycheck may look simple to its recipient. Behind it is a compact treaty among an employer, an employee, a bank and several levels of government. Young’s business lives in the clauses.
A family tree with customer service in the roots
Long before ConnectPay had a platform, Young had an operating model. In the late 1970s, his mother became the first woman to start and run a State Farm insurance agency. He remembers her taking up the period’s new technology from the day she opened. The machines mattered because they helped her clients and gave her young business an edge. Adoption was not theatre. It was service.
Her father had supplied the previous chapter. In his early twenties, Young’s maternal grandfather became, at the time, the youngest person awarded a General Motors dealership. Cars then could arrive from the factory with more character than reliability. When one proved to be a lemon, he would sometimes take it back at a loss rather than let a customer carry the mistake. The arithmetic hurt. The relationship survived.
“My mom learned it from her dad, and I learned it from both of them.”Michael Young
The lesson is unfashionably durable: take the useful tool, then stand behind the outcome. Young would eventually apply it to a financial transaction that repeats every week or two and permits very little improvisation. In payroll, a founder does not get points for being nearly right. A successful pay run is ordinary by design.
After studying at Niagara University from 1982 to 1986, Young entered operations and investment at SafeSite Records Management. It was the beginning of a long working partnership with Altavena, described in 2024 as having lasted thirty-eight years. That duration matters. Their later division of labor at ConnectPay did not emerge from a hurried founder-matching exercise. Young led the company as CEO while Altavena, as president, eventually concentrated on mergers and acquisitions. Familiarity became infrastructure: each knew the other’s judgment well before the first ConnectPay client or acquisition arrived.
Software for the work; people for the question
Young and Altavena founded ConnectPay in 2008, with operations commonly dated from 2009, after Young had led Advantage Payroll Services and earlier worked as an operating executive and investor at SafeSite Records Management. The new company’s choice was to occupy the ground between large corporate processors and do-it-yourself tools. It would automate the work without asking the customer to become a payroll scholar.
The distinction sharpens when a rule changes or a number looks wrong. “People love our software,” Young has said, but when a transaction the size and consequence of payroll turns into a question, they want to call, receive an answer and feel protected. A help desk can be measured as cost. ConnectPay treats it as part of the product.
The model is “connected” in another sense. Payroll sits in the center of a small firm’s professional circle, beside its accountant, bookkeeper and other advisers. ConnectPay does not insist on replacing those relationships. Its platform is designed to coordinate them. That is a subtle kind of ambition: become the hub without pretending every spoke belongs to you.
This also explains Young’s attention to local knowledge. A small business often has one person doing three jobs and an owner doing the fourth at night. Giving that team a named expert is less dramatic than unveiling a feature. It is also more useful at 4:45 on payroll day.
The deal is an event. Integration is a habit.
ConnectPay’s growth brought a different question: how do you buy local payroll providers without sanding away the qualities that made their customers loyal? The company began setting up a systematic answer in 2016, when it combined the founders’ offices with its software provider. Altavena moved his attention fully toward finding acquisition candidates. From 2017 through early 2023, ConnectPay completed 27 deals.
The revenue movement was considerable, from $2.8 million annually to a $20 million run rate reported in 2023. Yet the reusable asset was the sequence beneath it. ConnectPay developed a template covering sourcing, diligence, negotiation, discovery, team welcome, secure data conversion, product migration, client communication and the first live cutover. Afterward came efficiency work, growth and a retrospective.
The addition loop / simplified
That last move deserves ink. A retrospective turns every acquisition into tuition for the next one. It acknowledges that a plan can be standardized while the people entering it remain particular. ConnectPay converts clients to its own payroll software, gaining the efficiency of one platform. It also searches for cultural and customer fit before the papers are signed.
The company frequently calls acquisitions “additions.” Corporate language can be wallpaper, but this word imposes a useful idea. The incoming operation adds clients, employees, local memory and relationships. It does not arrive as an empty revenue cell. By March 2025, ConnectPay had completed 37 acquisitions in eight years.
The operating balance
The percentages above are an editorial illustration, not company metrics. The point is the shape: technology and procedure create capacity, while local trust makes that capacity acceptable. Remove any leg and the stool develops a comic lean.
A family asset, protected every pay period
Young’s language returns repeatedly to protection. When a small company succeeds, he argues, it often becomes a family’s largest asset. Payroll is not the glamorous part of that asset. It is the recurring proof that the business can meet an obligation to the people who make it run. Compliance, in this reading, is less a bureaucratic fog than a guardrail around somebody’s livelihood.
That view also carried Young beyond ConnectPay. He has served the Independent Payroll Providers Association as president emeritus and government affairs lead, representing the practical concerns of independent processors in public-policy discussions. His work earned the association’s Business Excellence Award in multiple years.
Young’s public career traces a remarkably consistent line: operations and investment at SafeSite, leadership at Advantage Payroll, then the founding and expansion of ConnectPay. The industries and company names changed. The recurring problem was how to make a complex service dependable.
In 2025, Smart Business Dealmakers named Young a Dealmaker of the Year. He joined a conference discussion on building effective capital stacks, a suitably financial title for someone whose company had spent years making acquisitions repeatable. That same year, ConnectPay entered the Inc. 5000 at No. 2,667, with 157 percent growth over three years.
Awards and rankings provide convenient punctuation. They are not quite the sentence. The sentence is written every payday, in thousands of small businesses whose owners would rather think about customers, craft and tomorrow’s work. ConnectPay’s job is to let payroll become invisible again.
“We live and breathe American small business and the communities they serve.”Michael Young
Standardize the handoff, personalize the promise
There is a neat tension in Young’s playbook. ConnectPay standardizes aggressively where variation creates risk: one platform, a defined conversion path, explicit decision rights and a review after each deal. It preserves variation where uniformity would destroy value: the local expert, the trusted adviser, the person who knows why this customer is calling.
Founders in any service business can borrow that split. Write the checklist for what happens behind the curtain. Keep a name and a voice in front of it. Let technology handle repetition, but do not force it to perform reassurance. Machines are excellent at arithmetic and notably poor at saying, with earned confidence, “We have it.”
Young learned the principle from an insurance agent willing to master new tools and a car dealer willing to absorb a loss. He and Altavena turned it into a payroll company, then an acquisition system, then a national organization that still speaks in the vocabulary of Main Street. The phone remains nearby. On a quiet Friday, nobody needs it. That is part of the design.