The Problem: Hiring Fast Without Written Expectations

Hiring fast without clear written expectations feels light speed – right up until it turns into chaos. At that point, it is no longer “moving fast,” but rather managing uncertainty around roles, compensation, and ownership while trying to keep the business moving forward.

The Big Idea: Early Hires Shape Saskatchewan Startups More Than Founders Expect

In the Saskatchewan startup ecosystem, early hires shape a company more than founders often expect. Legal documents set expectations, include role clarity, compensation clarity, confidentiality obligations, and ownership of what gets built.

The Process

Step 1 – Have Employment Contracts Signed Before the First Day of Work

The cleanest rule is also the simplest: documents should be signed before the first day of work.

When contracts are signed late, two things tend to happen:

1. Leverage shifts, because the individual is already working; and
2. Risk increases, because promises and expectations become harder to prove.

Step 2 – Is This Hire an Employee or Contractor? What Canadian Startups Need to Know

Misclassification is not just a technical issue. It can trigger tax, benefits, and employment law problems, often at exactly the wrong time, such as during fundraising or when closing significant customer contracts.

Step 3 – Equity Incentives in Canadian Startups: Avoid Over‑Granting Early

One of the most common early‑stage mistakes is over‑granting equity too early, particularly when someone is wearing an impressive title.

A common market approach includes:

• Equity vesting over four years
• A one‑year cliff
• Monthly vesting thereafter

This structure helps protect the company from short‑term participation while rewarding individuals who stay and contribute to building the business.

Step 4 – Milestone Vesting in Startups: Objective and Measurable

Milestone vesting can work well when milestones are objective, such as:

• Closed revenue
• Signed customer contracts
• Shipping clearly defined deliverables

It tends to fail when milestones are subjective, such as:

• “Build an MVP”
• “Make the product great”
• “Get traction”

If two reasonable people could disagree on whether a milestone has been achieved, it is not a milestone–it is a dispute waiting to happen.

Step 5 – Building Minimum Viable People Infrastructure in Early‑Stage Startups

Even small companies should have basic onboarding processes and baseline policies, particularly as the team grows beyond a handful of people. This is not corporate theatre. It is risk control.

Startup Hiring Checklist: What to Implement in the Next 7 Days

• Implement a standardized new‑hire package, including offer terms, confidentiality and IP assignment, invention agreements, and compensation terms.
• If equity is offered, adopt a simple vesting standard (four years with a one‑year cliff) and document approvals properly.
• Prepare a one‑page “Equity 101” overview so candidates understand what they are being offered.
• If milestone vesting is used, select only objective milestones that can be clearly demonstrated.

This article, Hiring Employees in Canadian Startups: Legal Risks Saskatchewan Founders Should Know is part of a series relating to the Technology & High Growth Startup in Saskatchewan, written by Saskatoon Partner, Joe Gill. Follow McKercher LLP on LinkedIn to be notified when the next article in this series is published. This post is for information purposes only and should not be taken as legal opinions on any specific facts or circumstances. Counsel should be consulted concerning your own situation and any specific legal questions you may have.

About the Author

Joseph A. Gill is a partner in the McKercher LLP Saskatoon office. He is the Prairie's go-to technology and startup lawyer, having assisted hundreds of prairie startups from formation and beyond. He works with founders throughout the startup life cycle through growth, scale, and exit. Joe was named a 2025 Lexpert Rising Star - Leading Lawyer Under 40 in Canada. This prestigious national award recognizes exceptional young lawyers who demonstrate leadership, innovation, and community impact.

About McKercher LLP

For 100 years, McKercher LLP has grown deep roots across Saskatchewan, serving the community from offices in Saskatoon and Regina. As one of the province’s largest and most established full-service law firms, we proudly follow a client-first philosophy as we provide legal services and real solutions for the people who rely on us.

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