Role commences as Director of Finance with path to Vice President of Finance within first 6 - 12 months

About KnowHow

KnowHow is a privately held, high-growth AI software company that provides workforce knowledge infrastructure for large, distributed service organizations. Our mobile AI platform is used by hundreds of U.S. and Canadian property restoration companies to onboard, train, and guide frontline employees with consistent, standards-based “how-to” knowledge, delivered in their preferred language.

By centralizing institutional knowledge and embedding it directly into daily operations, KnowHow helps employers reduce training friction, lower supervisory burden, and scale confidently amid labor shortages and increasing operational complexity.

KnowHow is on pace to exceed $8M CAD of ARR by YE 2026, and achieved its first cashflow positive and net income positive months in Q4 2025.

Role Summary

We are seeking an experienced, entrepreneurial and highly skilled Vice President of Finance to join our executive team. The ideal candidate will be a trusted ‘right-hand’ to the CEO, to provide oversight over all finance, accounting and reporting aspects of our business. In addition, the VP Finance will play a pivotal role in corporate strategy, fundraising and shareholder activities, as well as overseeing core operations, driving performance, and inspiring loyalty and performance from the team.

Key Responsibilities

Financial Leadership:

Oversee and manage all reporting financial and accounting systems, ensuring compliance and accuracy.
Lead the annual audit and quarterly reporting process, ensuring timely and accurate completion.
Track and manage subscription revenue, ensuring alignment with company goals, overseeing contract management.

Strategic Partnership

Work closely with the CEO on corporate strategy, fundraising efforts and shareholder activities.
Oversee quarterly and annual financial reporting requirements to Board of Directors and shareholders
Develop and implement financial strategies to support company growth and scalability.

Operational Excellence

Oversee core operations, ensuring efficient and effective processes.
Manage and inspire a high-performing finance and operations team.
Drive operational improvements to support the company’s strategic objectives.

Qualifications

Proven experience as a senior financial leader, ideally in a B2B SaaS environment.
Experience with SaaS metrics and financial modeling.
Demonstrated experience in fundraising and working with shareholders.
Strong understanding of accounting principles and financial regulations.
Exceptional managerial skills with a track record of inspiring and leading high-performing teams.
Excellent communication and interpersonal skills.
Experience as a senior strategic leader in a fast paced, growth oriented business environment.
Ability to work effectively with the Board of Directors and executive team.
Located in Calgary, Alberta, or anywhere in Canada (excluding Vancouver and Toronto).

Why Join KnowHow

Be part of a fast-growing and innovative, category-leading AI company.
Collaborate with a passionate and driven team.
Play a key role in shaping the future of the company.
Competitive compensation and benefits package.

If you are a strategic financial leader with a passion for innovation and a track record of driving growth, we want to hear from you. Apply today to join KnowHow and help us revolutionize the future of business with AI.

Learn more about the KnowHow Team: KnowHow Careers Page

Because this role will work closely with KnowHow’s CEO Leighton Healey, we’ve taken the time to have our CEO outline their ideal candidate in the format of a ‘Painted Picture’

The ideal candidate for the VP of Finance would describe themselves in this way:

I am a passionate results-driven business builder, with a track record of getting top performance out of my teams, while cultivating an employment experience that is second to none. I am a finance wiz, who thinks in spreadsheets. I love the B2B SaaS model, and I nerd out on SaaS metrics, viewing each metric as a value-driving gear in an intricate ‘money machine’.

People on my team know we play to win, I build cultures that are laser focused on honorable victories and hitting goals. I am relentless in ensuring company wide goals and priorities are crystal clear, I don’t let anything get in our way. I work hard to ensure my team is composed of top talent and that their teams each have the right people, in the right seats. I support the development of my people to be their best and to work hard to grow. I thrive on having full responsibility for operations, finance and revenue. Allowing the CEO to focus is important to me.

I am passionate about building strategic plans that translate into results – plans that allow me to lead the charge with focused execution, tight accountability and frequent celebration.

I have a track record of being a great partner for other senior leaders that report to me, I know how to balance relationships with accountability. I have the courage to push back, and know when to trust. I am willing and able to protect the company and the team.

I work best when I am partnered with a driven, values-rooted ‘Entrepreneur CEO’ with a large vision, a passion for the business and the team, who needs a strategic and execution partner to help figure out both the ‘How’ and the ‘Where’.

I want to play a major role in building a company that transforms industries for the better.

I value family, the outdoors, volunteering, laughter and winning. I know how to manage myself, and keep my emotional tank full so I can lead without needing the approval or affirmation of my reports. I’ve often thought about living near the Canadian Rockies, in Calgary, Canada.

Job Description: complement the CEO’s strengths in critical areas

Everything the company needs that the CEO, Leighton Healey, is great at

Vision casting, big picture thinking and ‘dot connecting’ opportunities & growth initiatives
Selecting strong team members, and supporting my managers to select and develop their teams effectively
Resourcing the team: problem solving, unsticking, allocating capital & resources
Setting, nurturing and safeguarding company culture, and supporting professional development initiatives to grow leaders
Strategic relationship building and brokering partnerships
Closing key strategic large accounts
Cash Flow and Burn management
Encouraging & Supporting Team Health
Investor & Shareholders: negotiation, data room management, legal & compliance matters, Board obligations (quarterly package, etc)
Breaking new ground into new markets
Being the face of the company in speaking and thought leadership

Everything the company needs that the CEO, Leighton Healey, is not great at

Managing ‘Day to Day’ (rhythms, routines, reporting)
Owning execution of strategic & business matters, working hand in hand with, and in support of, the CEO & Board. Maintaining integrity of company-wide performance 'scorecards and ‘dashboards’ including SaaS KPIs (example)
Operationalizing strategic initiatives: developing & executing plans, moving them ahead and reporting on progress, holding tension and accountability to follow through
Establishing and maintaining operational rhythms: spanning management meeting agendas to daily & weekly reporting across departments
Financial forecasting and budgeting; setting and managing a budget & forecast
Ensuring all team members have clear, tangible goals and are being held accountable by their supervisor to aligned targets
Cash Flow and Burn management
Encouraging & Supporting Team Health
Investor & Shareholders: negotiation, data room management, legal & compliance matters, Board obligations (quarterly package, etc)
Maximizing profitability, and ‘Valuation Driving’ key SaaS metrics (GRR, LTV, Payback Period, Rule of 40, etc)
Tax, audit, grants, SRED

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