Oregon
The first hire
in Notes
Somewhere past the point where the work stops fitting into the available hours, a sole proprietor starts thinking about a first employee. The jump from zero to one is the largest single step a small business takes, and most of the size of it is administrative.
At zero employees the business is one person's time. At one employee it is an employer, which means a federal employer identification number, state registration, payroll withholding, unemployment insurance, workers' compensation coverage, wage and hour rules, a pay period, a record retention obligation and a written policy or two. Oregon layers several state requirements on top of the federal ones, including paid leave and sick time rules that reach down to small headcounts.
All of that is a reason to know the cost before making an offer, because the salary is somewhere between seventy and eighty-five percent of what the person costs.
One number is worth working out before anything else. Take the hours you want to hand over, multiply by the wage it takes to get somebody competent in this market, add a third for the employer costs, and compare the result against what you bill in those same hours. If the comparison is close, the role is a cost rather than capacity and it needs a different design. Most first hires that work are either the administrative half of the owner's week, which is cheap to cover and expensive to keep doing yourself, or a second pair of billable hands in a business already turning work away.
The intermediate steps people skip
The gap between doing everything yourself and hiring somebody full time is wide, and it contains several arrangements that are easier to reverse.
- A contractor for a discrete, bounded piece of work. Worth being careful here. The test for whether somebody is genuinely a contractor turns on control and independence, and getting it wrong is expensive in back taxes.
- A staffing agency placement, which costs more per hour and carries the employment relationship for you while you find out whether the role is real.
- Part time, ten to fifteen hours, which triggers most of the same administration at a size where a mistake is survivable.
- Buying back your own hours. A bookkeeper for four hours a month returns more usable time to many owners than a part time assistant for ten.
The last one is the most common right answer and the least satisfying, because it feels like a retreat from growth.
The first employee also changes what the owner does all day. Time that went into the work goes into deciding what the work is, checking it, and answering questions about it. Owners who liked their business because they liked doing the work often find the first year after the first hire unpleasant, and some of them go back to one person on purpose. That is a legitimate outcome, and it is worth deciding on deliberately rather than discovering.
Timing matters more than most owners expect. Hiring into a busy month feels obvious and goes badly, because training somebody takes the hours you do not currently have. The month to hire in is the quiet one before the busy one, which means deciding roughly a quarter ahead of the point where it feels urgent. Owners who wait for the pain usually hire in the worst available week and then conclude the person was wrong for the job.
Before advertising, write down what the person is responsible for, as a list of outcomes you will stop handling yourself. Owners who cannot finish that list usually discover three months in that they hired somebody to help, which describes a feeling rather than a role, and the arrangement ends badly for reasons nobody can name afterwards.
A sequence that keeps people out of trouble: talk to whoever does your taxes before you write the job description, get workers' compensation coverage quoted before you make the offer, and set the pay period and the payroll mechanism up before the first day rather than during the first week. The Oregon Employment Department and the state's Bureau of Labor and Industries both publish plain guidance for first-time employers, and a small business development centre advisor will walk through the order at no cost. The information is easy to find. The part people skip is reading it before the offer instead of after.