Skip to content
ToolUpJobs
Menu
For contractors, shops and trade businesses

Keep your best crew. Keep more of what you build.

Benefits that keep journeymen and foremen from walking to the competitor down the road, planning that cuts the owners' taxes, and protection for the business. Handled for you, in English or Spanish, coordinated with your CPA.

Get a free benefits reviewSee all services

For office managers, HR and controllers

Less time chasing paperwork. Fewer empty spots on the crew.

You keep the trucks moving and payroll right. We take benefits enrollment and renewals off your desk, help you keep good people, and give you something worth bringing to the owner.

  • We handle the benefits workEnrollment, renewals, new-hire setup and crew questions, in English or Spanish.
  • Easier hiring, fewer quitsPerks you can put in job ads, plus screened temp workers when someone leaves.
  • Something in it for youRetention bonus plans for key staff, including office and project managers.
  • Easy to take to the ownerAfter your free review, we send a one-page summary you can share. You get the credit.
Get a free benefits reviewSend this to the owner

Crew benefits · For your team

Benefits that keep good tradespeople on your crew.

The big outfits offer benefits. Now you can too, at a cost you control, with enrollment and paperwork handled for you.

  • Group health insuranceIncludes ICHRA

    Plan design and carrier shopping for small and mid-size contractors, including level-funded plans and ICHRA reimbursement options.

  • Dental, vision and disability

    Low-cost add-ons crews value, including short-term disability for time off the job.

  • Group life and accident coverage

    Basic group term life for every employee, plus voluntary accident and life coverage they can buy.

  • Benefits managementLess work for you

    Enrollment, renewals, new-hire setup and employee questions handled for you, in English or Spanish.

  • 401(k) and Safe Harbor plans

    Set up or fix a 401(k) with profit sharing, keep fees down and pass nondiscrimination testing.

  • Tax-free training and certification helpRarely offered

    Up to $5,250 a year per worker for welding, electrical, HVAC or CDL training, tax-free to them.

See the crew benefit spotlights

Owner wealth and tax planning · For owners and partners

Keep more of what the company earns.

A 401(k) was built for employees, not for profitable contractors and shop owners. These are the strategies that cut taxes today and build a real retirement and exit.

  • Cash balance pension plansOwner favorite

    Put away far more than a 401(k) allows, often several times as much for owners in their 40s to 60s, with a tax deduction for the company. Works alongside your 401(k).

  • Traditional defined benefit plansOwner favorite

    A guaranteed retirement benefit the company funds. Best for owners who want the largest deductible contributions and have a small office staff.

  • Leadership compensation planning

    Salary and distribution mix, deferred compensation, executive bonus plans and retention plans that keep your foremen and project managers.

  • Leadership tax reduction strategies

    Entity structure, reasonable compensation, retirement plan design and equipment timing, coordinated with your CPA.

  • Succession, exit and ESOP planning

    Sell to a buyer, a partner, your key employees or the whole crew through an ESOP, and plan how your wealth passes to your family.

See the owner planning spotlights
Spotlight · Crew benefits

Two benefits most contractors have never been offered.

Keep your crew

ICHRA: health benefits without a group plan

Many contractors either overpay for a group plan or offer nothing and lose good people. An Individual Coverage HRA (ICHRA) is a third option most local agents never mention, and it works well for crews that change size with the season.

How it works

  • You set a fixed monthly allowance, for example $400 per employee.
  • Each worker picks their own individual health plan, and you reimburse them tax-free up to that amount.
  • You know your exact cost every month. No surprise renewals and no minimum participation rules.
  • Set different amounts for eligible employee classes, subject to ICHRA class and minimum-size rules.
Keep your crew

Tax-free training and certification help

You can't hire enough certified welders, electricians and CDL drivers, so grow your own. Federal law (Section 127) lets the company pay up to $5,250 a year per employee for eligible training, tuition and student loans, tax-free to them and deductible for you.

How it works

  • We set up a written educational assistance plan for your company.
  • Pay for eligible welding certs, electrical or HVAC courses, CDL school or trade school tuition.
  • Helpers become journeymen on your crew, not someone else's.
  • Advertise it in every job post: "We pay for your certifications."

Only at ToolUpJobs

We fill the crew, then help you keep it.

Screened workers when you need them, plus benefits that make them stay, with bilingual enrollment in English and Spanish. One team that knows your business.

Request workers
Spotlight · Owner planning

Where the biggest tax savings and decisions are.

Owner planning

Cash balance pension plans

A 401(k) caps what you can save each year. A cash balance plan adds a second, much larger contribution the company can deduct, and the limit rises as you get older. Most advisors don't offer them because they need an actuary behind them. We do.

How it works

  • Keep your 401(k). The cash balance plan sits on top of it.
  • Owners in their 40s to 60s can often put away several times what a 401(k) allows.
  • Your crew receives a contribution too, based on plan design and applicable testing requirements.
  • For owner-operators with a small office staff, a traditional defined benefit plan can allow even more.
Owner planning

Succession, exit and ESOP planning

Many contractor owners plan to retire in the next ten years with no plan for who takes over. Selling to an outside buyer is one option. Selling to your key people, or to the whole crew through an employee stock ownership plan (ESOP), is one most small advisors never bring up.

How it works

  • Know your number: a valuation estimate and what you'd keep after tax.
  • Compare paths side by side: outside sale, sale to a partner or key employees, or an ESOP, which can carry significant tax advantages for the seller.
  • Partners: a buy-sell agreement actually funded with life insurance, plus key person coverage.
  • Plan 3 to 5 years ahead: pension contributions, entity structure and estate planning before the sale.

Risk protection · For the business

Protect the business and the people who run it.

A trade business runs on a few key people, trucks and equipment. An injury, a death or one bad claim can stop it. These policies keep income, partners and the company protected.

  • Most needed

    Life and disability income insurance

    Protect your income if you can't work, with key person coverage and buy-sell funding so partners can keep the business running.

  • Accident and short-term disability for crews

    Workers' comp generally covers work-related injuries and illnesses. These policies can help with covered off-job injuries or illnesses.

  • Key person and buy-sell funding

    If an owner or your best foreman dies or is disabled, the company has the cash to carry on or buy out a partner's share.

  • Through P&C partners

    Contractor business insurance

    General liability, commercial auto, tools and equipment coverage, and surety bonds, reviewed together.

Spotlight · Protection

The two gaps we find most often.

Protect your crew

Accident and short-term disability for crews

Tradespeople get hurt, and not always at work. Workers' comp generally doesn't cover a weekend injury or a non-work-related illness, and most crew members can't go a month without a paycheck.

How it works

  • Short-term disability replaces part of a worker's pay while they recover from a covered off-job injury or illness.
  • Accident coverage pays cash for covered events like fractures, ER visits and hospital stays.
  • Offer them employer-paid, or as low-cost voluntary benefits your crew can buy.
Protect the business

Contractor business insurance, reviewed together

Liability with one agent, trucks with another and equipment with a third means gaps, overlaps and surprise premiums. We review the whole picture through licensed property and casualty partners.

What we review

  • General liability and umbrella coverage, including what your contracts require.
  • Commercial auto for trucks, vans and trailers.
  • Tools and equipment (inland marine) coverage on and off the job site.
  • Surety and license bonds so you can bid on more work.
  1. Step 1

    Free review

    Send your current benefits, retirement plan and insurance summaries. We look for gaps and savings, and handle the legwork.

  2. Step 2

    A one-page summary

    Options side by side: cost, tax savings and what your crew receives. Easy to share with the owners.

  3. Step 3

    Set up and look after it

    Enrollment, plan administration and yearly reviews, coordinated with your CPA.

Get a free benefits review

A 30-minute call with a licensed advisor. Office managers and HR can start without the owners; we'll send a one-page summary to share. No cost and no obligation.

(555) 010-0199
  • Licensed insurance and retirement advisors
  • We work with your CPA and attorney
  • Companies of 1 to 500 employees
  • Se habla español
Interested in (choose any)

Crew benefits

Owner planning

Protection

Insurance, retirement plan and property and casualty services are offered through licensed, independent partner firms. Securities and advisory services, where offered, are provided by appropriately registered representatives. ToolUpJobs and its partners do not provide tax or legal advice; tax strategies are carried out with your CPA and attorney. Plan contribution limits depend on IRS rules, plan design and your employee census. Educational assistance benefits are subject to IRS Section 127 requirements. ESOP transactions require independent valuation and legal counsel.

Common questions

I'm the office manager. Does the owner need to be on the first call?

No. Most reviews start with the office manager or HR. We review what you have now and send a one-page summary you can share with the owners.

Can training help really be tax-free?

Yes. Under Section 127, a company can pay up to $5,250 per employee per year toward eligible tuition, courses and student loans, tax-free to the employee. The 2025 tax law made the student loan part permanent. It requires a written plan and compliance with eligibility rules.

Does ICHRA work for seasonal or variable-hour crews?

Often, yes. Different allowances may be available for permitted employee classes, subject to class rules and any applicable minimum class sizes. We check the rules for your crew before you switch.

Is my company too small for a pension plan?

Often not. Owner-operators and shops with a handful of employees use cash balance and defined benefit plans. What matters most is steady profits, the owners' ages and how many employees you have.

Is an ESOP only for big companies?

No, but suitability depends on profitability, company value, employee count and transaction costs. We help you compare it with selling to a buyer or to key employees.

Do I have to use ToolUpJobs for workers?

No. Many companies use one service and not the other. If you use both, one team knows your business and your crew.

Do you replace my CPA or insurance agent?

We work with your CPA and attorney, who handle tax filings and legal documents. For business insurance, we can review alongside your current agent or quote through our partners.

Short on workers too?

We send screened tradespeople and laborers, with bilingual leads when your crew needs them.

Request workersGet a free benefits review