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Published 2023-05-08

Operations Specialist

Type of job: Remote
Country: Canada
City: Toronto
Company: Willful

Description of the offer

Are you looking to join an enthusiastic mission-driven startup? At Willful we’re known for bringing the crucial but overlooked task of estate planning out of the shadows and into the same conversation as insurance, financial planning and filing your taxes. While end-of-life planning is a very sensitive subject, our mission at Willful is to use technology and empathy to make the process as simple and painless as possible. It’s a great day at Willful when a customer finishes their will and writes to tell us “Hey, that was kind of fun!”

Our user-friendly design has caught the attention of major publications such as The Globe and Mail, The Toronto Star, Global News, Betakit and has struck a deal on Dragons’ Den. Willful has been approached for partnerships from industry leaders in banking, insurance and employee benefits, and we have active partnerships with Wealthsimple, CIBC, Meridian Credit Union, and other leading Canadian companies.

Every adult needs a will and should have an emergency plan in place for their own peace of mind and to help guide their loved ones. Transforming estate planning to give people an accessible, dependable and affordable option is the fuel that drives us every day. We’ve helped thousands of customers create their wills and Power of Attorney documents since launch, and now we’re looking to hire an Operations Specialist to help us continue on our mission.

What does it mean to be an Operations Specialist at Willful?

As an Operations Specialist at Willful, you will be responsible for managing and coordinating the daily operational activities at the fastest-growing legal tech company in Canada. In this role you will report to the Chief Operating Officer. Your primary objective will be to handle a variety of human resources, finance, and operational tasks to ensure the business runs smoothly. These activities will include performing administrative duties, assisting with project management, defining processes, enabling educational opportunities, and organizing events.

To be successful you will: 

  • Assist with the management of daily operational activities;
  • Perform administrative tasks such as booking travel, scheduling meetings, etc.;
  • Arrange and assist with the onboarding of new employees;
  • Manage projects by building project plans, assigning tasks, and tracking progress;
  • Document and maintain HR, financial, and operational processes and procedures;
  • Assist with monthly financial reporting;
  • Plan and organize virtual and onsite, events, training, and employee engagement activities.

You’re a perfect fit for the role if you are: 

  • Highly organized: You’re a successful individual contributor who is organized and detail-oriented. You are able to prioritize effectively and manage multiple deliverables simultaneously. You know how to organize your day to be successful and prioritize the right activities to meet the company’s goals. You pride yourself on accuracy and full completion of tasks.
  • Excellent communicator: You clearly and effectively communicate with internal team members and external vendors, contractors and consultants. You build strong rapport with all stakeholders.
  • Outgoing: You are open, friendly and responsive. The company culture and the people you work with are very important to you. You actively engage with team members and contribute positively to building an inclusive culture that people want to be a part of.
  • Solution oriented: You quickly and easily resolve problems and identify solutions. You don’t just default to the status quo – you are always looking for better, more efficient ways of accomplishing tasks and goals.
  • Entrepreneurial: You’re entrepreneurial, are confident making decisions, take ownership of your work, and you don’t hesitate to roll up your sleeves with a “let’s get it done” attitude. Willful is a small team, so we’re looking for a team member that can execute tactics in a pinch.
  • Motivated by impact and growth: You want to make a difference at scale, creating positive outcomes for hundreds of thousands of Canadians.

Do you have the right experience and expertise?

  • Experience in operations, office management, or project management, preferably with a startup or small company;
  • Excellent organizational and time management skills;
  • Proficiency in software tools such as GSuite, Notion, Slack and Asana;
  • Ability to prioritize and manage multiple deliverables simultaneously;
  • Excellent problem-solving skills;
  • Excellent communication skills, both written and verbal;
  • Formal expertise/education in human resources is a bonus.

We’re building a diverse team

Willful is an equal opportunity employer. We celebrate our inclusive work environment and welcome members of all backgrounds and perspectives to apply. We are committed to providing reasonable accommodations and will work with you to meet your needs.  We have a commitment to diverse hiring, and are proud to say that over 50% of our team, and 50% of our C-level executives, are women.

Remote working environment

We’re looking for the person to join our team so this role isn’t limited by geography and will be 100% remote. The only requirement is that you must be legally able to work in Canada. You will be required to attend in-person company retreats twice per year.


May 2023 (flexible)


  • Competitive compensation;
  • Participation in employee stock option plan;
  • Sun Life benefits plan including health, dental, and vision;
  • Choice of $500 annual perk: a health spending account (HSA) or $500 annual RRSP contribution through Wealthsimple for Employees;
  • An annual mental wellness budget;
  • Educational opportunities to hone your skills or learn a new skill;
  • Shortened summer hours, extra long weekends, and company-wide “recharge” days off in December in addition to your vacation time;
  • Competitive parental leave policy;
  • Flexible work hours to accommodate both work and home life;
  • Opportunities for coaching and mentorship;
  • Fun, inclusive quarterly team events (virtual) and bi-annual team-wide events (in person).

Interviewing at Willful:

  1. Phone screen with Amanda Perriccioli (Fractional EA for Willful)
  2. First interview 1 hour with Julia Wilkie (COO)
  3. Assignment and presentation with Julia Wilkie (CEO)
  4. Second interview 30 min with Willful team members
  5. Reference Check
  6. Offer

All recruiting activities including interviews and new hire on-boarding will be conducted virtually.

How to apply?

Click on the button to get the company email or employment application form.
Apply on home page

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