When One Job Becomes Three: A Fair Conversation About Pay in a Tough Market

Job Seekers By Editor Published on July 21

As wineries operate with leaner teams, many employees are taking on broader roles. Recognizing that change does not require ignoring the financial pressure employers are facing.

The wine industry is asking many businesses to do more with less.

Sales remain under pressure, operating costs have climbed, and wineries are making difficult decisions about staffing, production, facilities, and spending. Silicon Valley Bank’s 2026 State of the U.S. Wine Industry Report found that roughly half of wineries characterized 2025 negatively, although about one-third reported a positive year—an important reminder that conditions are difficult, but not identical, across the industry.

Recent winery closures, consolidations, and layoffs have made those pressures especially visible. When positions are eliminated or left unfilled, the work attached to them does not always disappear. It is often redistributed among the people who remain.

A marketing employee may inherit wine club communications and event planning. A tasting room manager may take on scheduling, customer service, inventory, and club retention. A production employee may become responsible for compliance, purchasing, or logistics. Someone who was hired to support one function can gradually find themselves accountable for several.

For employees, that can create a difficult question: At what point does being flexible and helping the business become a fundamentally different job?

For employers, the question can be just as difficult: How do you recognize a growing role when the business may not have room in the budget for a significant raise?

There is no universal answer. But avoiding the conversation entirely is rarely sustainable.

Two Things Can Be True at the Same Time

It is possible for a winery to be under legitimate financial pressure and for an employee’s role to have grown beyond what they were originally hired and paid to do.

Those realities do not cancel each other out.

Not every expanded workload is evidence that an employer is taking advantage of someone. Wine is seasonal, unpredictable, and often powered by small teams. Employees may occasionally need to cross departmental lines, help during harvest, cover a leave, support a major event, or respond to an unexpected staffing gap. That flexibility has always been part of working in the industry.

At the same time, “temporary” responsibilities can quietly become permanent. A few weeks of coverage can become a new department. Helping with wine club emails can turn into responsibility for retention and recurring revenue. Filling in after a departure can become ownership of the position without the title, authority, resources, or compensation that came with it.

The purpose of a compensation conversation should not be to accuse the employer of bad intent. It should be to acknowledge when the job has materially changed and decide what should happen next.

A Bigger Workload Is Not Always a Bigger Job

Before asking for a raise, it helps to separate being busier from taking on a higher-level role.

A particularly demanding month, a busy tasting room weekend, or additional administrative tasks may increase the volume of work without changing the position itself. A more substantial change usually involves greater ownership, complexity, accountability, or decision-making authority.

The U.S. Bureau of Labor Statistics evaluates the level of a job partly through factors including the knowledge required, the complexity and control involved, the nature of the employee’s professional contacts, and the working environment. In other words, the value and level of a position are determined by more than the number of items on a to-do list.

Employees considering a compensation conversation should ask:

  • Am I now responsible for results that were previously owned by someone else?
  • Have I taken ownership of a department, program, budget, revenue stream, team, or vendor relationship?
  • Am I making decisions that previously required a manager or more senior employee?
  • Have the additional duties continued long enough to become part of my regular job?
  • Would the company need to hire someone with a different or more senior skill set to replace the work I am now doing?
  • Has my role expanded while my original responsibilities have remained unchanged?

The last question is particularly important. Sometimes employees are not simply accepting a broader role. They are attempting to perform two complete roles simultaneously.

That is not only a compensation issue. It is also a prioritization and sustainability issue.

Start with a Role Review, Not a Demand

“Ask for a raise” can sound confrontational, especially when employees know their employer is cutting costs. A more productive approach is to request a review of how the role has changed.

That shifts the conversation away from personal frustration and toward the actual needs of the business.

An employee might say:

“Since the team changed, I’ve taken ongoing responsibility for wine club communications, customer service, and event coordination in addition to my original marketing role. I’d like to review how the position has evolved, make sure we agree on its priorities, and discuss whether my title and compensation still reflect its current scope.”

This wording does not assume the answer will be yes. It also does not minimize the work being performed.

The goal is to create a shared understanding of four things:

  1. What the employee was originally hired to do.
  2. What the employee is responsible for now.
  3. Whether those changes are temporary or permanent.
  4. What the organization can realistically offer in response.

Calling it a role review also gives the employer an opportunity to clarify expectations. A manager may not fully realize how much work has accumulated, particularly when responsibilities have been transferred gradually rather than through a formal promotion.

Bring Evidence, Not Just Exhaustion

Feeling overwhelmed may be the reason an employee initiates the conversation, but it should not be the entire case for a compensation adjustment.

The strongest discussion will focus on changes in scope and value.

Employees can prepare by documenting:

  • Major responsibilities added since their last compensation review.
  • Projects, functions, or accounts they now own.
  • Revenue they have generated or protected.
  • Memberships, customers, or accounts they have retained.
  • Processes they have improved.
  • Expenses, labor, or outside services they have helped reduce.
  • Employees or vendors they now supervise.
  • Specialized systems or skills they have learned.
  • Problems they are now expected to resolve independently.
  • The amount of time the expanded arrangement has been in place.

It may also help to compare the current role with relevant job postings and compensation data. The comparison should be based on actual responsibilities, geography, experience, and company size—not simply a more impressive title found online.

An employee does not need to arrive with a dramatic presentation or a threat to leave. A clear one-page summary of how the position has changed is often more useful than a long explanation of how hard they have been working.

Timing Matters, but It Should Not Become Permanent Avoidance

There are moments when asking for an immediate raise may be unrealistic. A company may have just lost a major account, entered a cash-flow crunch, announced layoffs, or frozen spending.

Nationally, employers are approaching compensation cautiously. Mercer’s survey of more than 1,000 U.S. organizations found that employers planned average 2026 merit increase budgets of 3.2 percent and total salary increase budgets of 3.5 percent, unchanged from the increases they reported for 2025. Those figures are not specific to wine, but they illustrate the broader limits many organizations are placing on salary growth.

Employees should consider the business context and choose their timing thoughtfully. But waiting for the company to face no financial uncertainty at all may mean waiting indefinitely.

A compensation conversation does not have to begin with a specific demand or end with an immediate decision. It can begin by formally acknowledging that the role has changed and establishing a process for addressing it.

The important thing is to avoid an undefined arrangement in which the employee is told, “We’ll revisit this when things get better,” with no criteria, timeline, or follow-up date.

When an Immediate Raise Is Not Possible

A salary increase may be the most direct response to a permanently expanded role, but it is not the only possible outcome.

Depending on the position and the winery’s circumstances, other options may include:

  • A smaller increase now with another review at an agreed-upon date.
  • A one-time bonus for absorbing a major project or temporary function.
  • An incentive tied to measurable sales, retention, efficiency, or performance goals.
  • A title change that accurately reflects the employee’s current level.
  • Additional paid time off or greater scheduling flexibility.
  • Employer-funded training, education, or professional certification.
  • Greater decision-making authority over the work the employee now owns.
  • Reassigning, automating, postponing, or eliminating lower-priority responsibilities.
  • A written compensation review triggered by a specific revenue, budget, or performance milestone.

Not every alternative has the same value. A new title can strengthen an employee’s career path, but it should not become a permanent substitute for compensation when the company is continuing to rely on higher-level work. A future review date is useful only when both parties understand what will be reviewed and when.

Sometimes the fairest answer is not to add compensation—it is to remove work.

If the company cannot pay one employee to perform three full positions, leadership may need to decide which responsibilities are actually essential. An employee should not be expected to maintain every previous priority while absorbing an eliminated role indefinitely.

What Employers Can Do When Budgets Are Tight

A manager does not need an open compensation budget to handle this conversation well.

The first step is simply to listen without treating the request as disloyal or ungrateful. Employees can appreciate having a job and still raise a legitimate concern about how that job has changed.

Employers can then evaluate the position honestly:

  • Which responsibilities were added?
  • Which are temporary?
  • Which have become central to the role?
  • Has the employee’s authority grown with their accountability?
  • Are the current expectations possible within a normal workweek?
  • Which original duties should be deprioritized?
  • Does the title accurately describe the work?
  • What would it cost to replace the employee’s combined responsibilities?

Clear communication matters because workload problems rarely remain confined to employee morale. Gallup identifies unmanageable workloads, unclear communication, lack of manager support, and unreasonable time pressure among the workplace factors most strongly associated with burnout.

An employer who cannot approve a raise should be direct about that reality without using the difficult market to end the conversation. A constructive response might sound like:

“I agree that your role has expanded, and I understand why you are asking for a review. We cannot support the full salary adjustment right now. Let’s identify which responsibilities are permanent, adjust your title, remove two lower-priority areas from your workload, and schedule a compensation review for October after we have the third-quarter results.”

That answer may not give the employee everything they hoped for, but it provides recognition, specificity, and a path forward.

“We can’t do anything” is a very different message from “We cannot do everything now, but here is what we can do.”

What Employees Should Listen for

A difficult answer is not necessarily an unfair answer.

An employer may genuinely be unable to offer more money at that moment. What matters is whether the organization acknowledges the situation and participates in finding a sustainable solution.

Positive signs include:

  • The manager takes the expanded responsibilities seriously.
  • The company is transparent about its constraints.
  • Priorities are adjusted rather than simply added.
  • Any future review includes a date and clear criteria.
  • Agreements are documented.
  • The employer is willing to consider alternatives.
  • The employee’s title, authority, goals, and compensation are reviewed together.

More concerning signs include repeatedly delaying the discussion without a plan, denying that the role has changed despite clear evidence, using recent layoffs to discourage any employee from speaking up, or continuing to add responsibilities while refusing to clarify priorities.

A single “no” does not always mean it is time to leave. But an indefinite expectation that someone will perform a materially larger job without recognition, resources, or a plan may provide important information about their future with the organization.

The Conversation Is Bigger Than a Raise

This is not a story about employees versus employers.

It is a story about an industry in transition, and the pressure which that transition has placed on both sides of the employment relationship.

Wineries need adaptable employees who understand more than one part of the business. Employees need organizations that recognize when adaptability has grown into ownership, leadership, and increased accountability. Employers may not always be able to respond with the full raise an employee requests. Employees may not always be able to continue carrying an unlimited workload while waiting for conditions to improve.

The most productive outcome begins with honesty.

A difficult market may explain why a role expanded without an immediate increase in pay. It should not require either side to pretend that the role has not changed.

When employers and employees can openly discuss responsibilities, priorities, compensation, and business constraints, the conversation does not need a winner and a loser. It can become an opportunity to design a role—and a working relationship—that is more realistic, transparent, and sustainable for everyone.