The First Tax Hire: Your Strategic Bet on Tomorrow

Let’s say it out loud: hiring your first in-house tax professional isn’t just another HR task—it’s a fork in the road.

It’s the moment when you decide whether your company is going to keep reacting… or start building.

And here’s the hard truth: the longer you wait, the more expensive that decision becomes.

The Pipeline is Shrinking. And It’s Not Coming Back.

Across North America, the tax talent pool is drying up. In the U.S., accounting graduates—the backbone of tax hiring—are down 7.8% year over year. In Canada, accounting recruiters are calling it what it is: a long-term trend, not a temporary blip.

Why does this matter?

Because for decades, companies treated tax as a task. Outsource it. Spread the work out to the finance team. Automate it. Worry about it when the CRA or IRS knocks. But that playbook no longer works in a world where complexity is growing, and talent is shrinking.

So the question is: Are you ready to make a strategic hire?

Three Signs You’re Already Late

1. You’re spending more on outside advisors than you should.

If your external tax bills keep going up, you’re not saving money—you’re renting expertise. Every hour billed is an hour of knowledge walking out the door. The in-house, tax professional will dive deeper, find opportunities for better planning and savings— and you turn that cost into an asset. Your asset.

2. Your finance team is distracted by tax.

When your CFO or controller is buried in compliance—managing T2s, 1120s, or sales tax returns—they’re not doing the work only they can do: growing the business, managing capital, building strategy. A tax professional takes that off their plate, does it better—and is likely to find opportunities to save money that are missed by the finance team.

3. Growth is making your life harder, not easier.

New markets, new products, new geographies—they all come with new tax rules. U.S. sales tax nexus. Canadian GST/HST thresholds. Cross-border filings. If complexity is slowing you down, it’s time to build a function that keeps pace.

Don’t Hire a Task Manager. Hire a Tax Architect.

When most companies make their first tax hire, they think about today’s needs:
“Who can get this year’s filing done?”
But if you’re serious about building for the future, you need more than a technician. You need an architect—someone who can design your entire tax function from the ground up.

Here’s what to look for:

Credentials that matter – In the U.S., a CPA, EA, or JD. In Canada, a CPA or JD with specialized tax experience. These aren’t just letters—they come with the authority to represent your company before tax authorities.

A systems thinker – Ask how they’d build the tax process from scratch. Do they describe a workflow, or just a to-do list? You want someone who builds infrastructure, not just puts out fires.

Technology fluency – Your tax tech stack matters. The right hire will know how to choose and implement tools that reduce risk, save time, and scale with your business. This isn’t about buying software—it’s about building capability.

Strategic vision – Tax doesn’t live in a silo. It touches pricing, supply chain, M&A, legal structure, and more. Your hire should be someone who sees tax as a lever, not just a liability.

Integrate Early. Leverage Often.

Hiring the right person is just step one. Step two? Bring them into the business. Early.

Don’t isolate your tax professional. Instead:

• Involve them in strategic planning.
• Invite them to product launch meetings.
• Loop them in on M&A conversations from day one.

Why? Because tax is full of opportunity—if you spot it early enough.

A siloed tax department is a cost center. An integrated one is a profit center and a value multiplier.

Your Move

The world is not getting simpler. The talent pool is not getting deeper. And the longer you wait, the harder this hire becomes.

So, are you going to wait for a crisis? Or are you going to place a bet on building something smarter?

Hire the architect.

Give them tools.

Let them build the future of tax inside your company—before someone else hires them to build it for theirs.

Because in a world full of risk, your smartest move is the one you make before you have to.

Smart decisions don’t shout.

At Foxwood Tax Search, we help organizations see around corners.
No pitch. Just a focused, free consultation to figure out what kind of tax expertise makes sense—right now, for where you’re headed.

Because the best time to build the foundation was yesterday.
The second-best? Before your competitors do.

Key Sources:
AICPA | Canada Revenue Agency | Internal Revenue Service