Remote Chief of staff Jobs in North York, ON

COMPANY SUMMARY

Sapling Financial Consultants is a management consulting firm, founded in 2015. What started as an idea from a kitchen table has turned into a trusted advisor serving clients across North America. Headquartered in Toronto, Ontario, with a newly opened satellite office in Atlanta, Georgia, Sapling is supported by a team of 30 professionals, delivering high-quality financial modelling, due diligence, interim FP&A and data analytics solutions tailored to mid-market companies, private equity firms, investment banks, search funds and independent sponsors, infrastructure and electricity developers, as well as entrepreneurs.

More than half of Sapling’s clients are based in the U.S., reflecting its expanding geographic footprint and growing reputation in management consulting. The firm continues to scale its capabilities, invest in new talent and maintain flexibility in response to shifting market conditions. During periods of economic uncertainty, Sapling has consistently demonstrated steady growth. The firm has been recognized repeatedly for its excellence, being awarded the CanadianSME National Business Award for Best Professional Service in 2023, receiving Ragan’s 2025 Workplace Wellness Award in the category of Learning & Development – Wellness Initiatives, as well as being ranked among Canada’s Top Growing Companies by The Globe and Mail’s Report on Business Magazine for two years in a row.

POSITION SUMMARY, DUTIES AND QUALIFICATIONS

Position Summary

We are looking for an ambitious Chief of Staff, ideally with a strong record of building great teams and people leadership experience in either management consulting or the professional services industry.

Our guiding principle is We Live for A+. If you are someone who strives for excellence, not because you have to, but because you take pride in doing great work and enjoy seeing how far you can go, then Sapling might be exactly where you belong.

As a Chief of Staff, you will work at the intersection of scaling the business, performance management and guiding cross-functional initiatives that drive our firm’s growth objectives forward. You will work to ensure strong performance, motivating and enabling our team to become the best possible.

We are a boutique consultancy that differentiates itself from the big firms with best-in-class work and a strong functional expertise, and we have no interest in diluting our brand. Working through complex problem-solving with various teams is essential, and you will need to find a balance between hands on work and maintaining oversight of follow-up and accountability to ensure all initiatives are delivered to our high-quality standards.

For this role, we are looking for someone with initiative, competitive drive, and an ability to stay focused on results despite changing conditions. This is a fast-paced role, so the ability to learn very quickly and thoroughly under changing circumstances is very important. This is a high-visibility, high-impact role that blends strategic thinking with operational execution and requires exceptional communication, analytical, and organizational skills.

We’re looking above all for someone with a longer-term outlook who wants to join like-minded people in building a wildly successful company founded on that principle of creating high-impact value for clients. Ultimately, you will play a large role in a small but growing team with big ambitions for the future.

Our company is on a hybrid model, with the entire team in-office (Yonge/Sheppard) Tuesdays and Wednesdays, and the balance of days at home. Our hybrid model is a reflection of the independence that our team is entrusted with in completing their work.

Responsibilities

• Drive the recruitment of senior talent while overseeing a rigorous, high-quality hiring process for junior team members.
• Monitor individual and team performance, proactively support the development of high-potential team members, and help design retention strategies that keep top talent engaged and growing.
• Support the CEO, Partners, and Senior Leaders in defining and executing the strategic roadmap across various teams.
• Oversee and coordinate cross functional projects such as launching new product lines or setting up a new office, (HR, sales, consulting, marketing), etc.
• Navigate sensitive employee matters and resolve HR challenges with discretion and judgment, leveraging outside legal counsel where needed.
• Identify process inefficiencies and implement solutions that scale.
• Provide executive coaching support, including preparation for high-stakes presentations and client engagements.
• Facilitate reflection and learning, helping to identify blind spots and growth opportunities.
• Support leadership development through feedback, frameworks, and strategic perspective.
• Act as sounding board for complex decisions and organizational challenges.

Skills & Qualifications

• Bachelor’s degree or Master’s degree
• 10+ years of full-time progressive professional experience in our field or a similarly high-performing field, with 2+ years of leadership experience, either leading people or managing projects. Whether you come from operations, consulting, HR or something else is less important than your versatility and willingness to tackle challenging, cross-disciplinary problems.
• Proven experience working with C-level executives on strategic planning, execution, and communication.
• Experience in project management and coordination of cross-functional teams, managing project timelines and budget, and ensuring projects meet their objectives.
• Ability to lead with a positive attitude and approach challenges head-on.
• Strong dedication to the team and excellent work ethic, as well as enthusiasm about going above and beyond to ensure our clients achieve their business goals.

APPLICATION DETAILS

• Start Date: ASAP
• Location: Toronto
• Application Materials:
• Resume
• Non-AI Cover Letter focusing on your career achievements and goals and how they apply or translate to this role.
• Answering a couple of questions on our online form.

We do not use AI to review your application. When it is reviewed, it is reviewed by a human being, likely a senior one, at Sapling. This reflects the care with which we do all our work. At Sapling, you are a person in whose growth we are deeply vested - you are not a number, and not data for a large language model

Sapling Financial Consultants is an equal opportunity employer.