EverPro: Director, Planning and Insights, Invoicing (Remote, Ontario/Canada)

EverCommerce; Canada; Remote; CAD 180,000 - 200,000; Full time

Job summary

A leading software company is seeking a Director, Planning & Insights to shape growth strategies and lead a team of professionals. This senior leadership role focuses on strategic planning, competitive analysis, and program execution, providing flexibility to work remotely within Canada. Ideal candidates have extensive experience in strategy and team leadership, with strong analytical capabilities. The compensation target ranges from $180,000 to $200,000 CAD annually, plus variable compensation.

Benefits

Flexibility to work remotely or in-office

Robust health and wellness benefits

Professional development learning allowance

RRSP/TFSA with company match

Generous paid time off

Employee Stock Purchase Program

Qualifications

• 7+ years of experience in strategy consulting, corporate strategy, or product strategy.
• Strong analytical skills with expertise in business modeling, market analysis.
• Demonstrated success in B2B SaaS or fintech/payments.

Responsibilities

• Lead annual and quarterly OKR and strategic planning processes.
• Manage and coach a high-performing team of strategy professionals.
• Oversee commercial insights, performance analytics, and reporting.

Skills

Analytical skills

Leadership experience

Strategic planning

Education

BS/BA

MBA or equivalent advanced degree

Job description

Position Summary

The Director, Planning & Insights is a senior leadership role reporting directly to the GM, Invoicing. You will lead the team responsible for strategic planning, commercial insights, customer and competitive analysis, and program execution. This role is central to shaping our growth agenda and ensuring the business operates with clarity, rigor, and alignment.

You will guide and coach a team that includes a Strategic Planning Manager, Commercial Insights Lead, Business Performance Analyst, and Program Manager. Together, your group will deliver the strategic frameworks, insights, and execution support that enable leadership and cross-functional teams to make informed decisions and achieve ambitious goals.

Key Responsibilities

• Strategic Planning & Alignment: Lead annual and quarterly OKR and strategic planning processes.
• Strategic Planning & Alignment: Develop frameworks for initiative evaluation, resource allocation, and prioritization.
• Strategic Planning & Alignment: Drive cross-functional alignment across product, marketing, operations, and customer-facing teams.
• Insights & Intelligence: Oversee commercial insights, performance analytics, and reporting.
• Insights & Intelligence: Build competitive intelligence programs to anticipate market shifts and competitor strategies.
• Insights & Intelligence: Translate customer research into actionable recommendations for product and go-to-market.
• Strategic Analysis & Business Consulting: Lead deep dives into product-market fit, pricing, expansion, and growth opportunities.
• Strategic Analysis & Business Consulting: Partner with leadership to build business cases for new initiatives.
• Strategic Analysis & Business Consulting: Act as a strategic advisor to the GM and senior leadership team.
• Team Leadership & Development: Manage and coach a high-performing team of strategy, insights, and program professionals.
• Team Leadership & Development: Foster a culture of analytical rigor, strategic thinking, and collaboration.
• Team Leadership & Development: Ensure clarity of goals, roles, and deliverables across the team.
• Program Orchestration: Facilitate leadership offsites, planning sessions, and cross-functional initiatives.
• Program Orchestration: Monitor strategic execution and track progress against goals.
• Program Orchestration: Drive visibility into business performance through reporting and insights.

Qualifications

• 7+ years of experience in strategy consulting, corporate strategy, or product strategy, including 2+ years in people leadership roles.
• Strong analytical skills with expertise in business modeling, market analysis, and financial evaluation.
• Demonstrated success leading strategic planning and operational alignment in B2B SaaS or fintech/payments.
• Proven track record of managing and developing high-performing teams.
• BS/BA required; MBA or equivalent advanced degree strongly preferred.

Personal Characteristics

• Strategic thinker who simplifies complexity and inspires clarity.
• Strong communicator and facilitator who builds consensus across diverse stakeholders.
• Team-oriented leader who empowers and develops talent.
• Analytical problem-solver who thrives in ambiguity and drives action.
• Passionate about leveraging strategy and insights to drive business growth.

Where: Remote Ontario/Canada

The EverCommerce team is distributed globally, with teams in the U.S., Canada, the U.K., Jordan, New Zealand, and Australia. This role can be based anywhere in Canada – if you’re close to one of our offices, we can set you up in-office or you can work 100% remotely. Please note that you must be eligible to work without sponsorship to qualify for this position, and this role will require travel to our Corporate Headquarters in Denver, Colorado, or to other office locations around North America.

Benefits & Perks

• Flexibility to work where/how you want within your country of employment – in-office, remote, or hybrid
• Robust health and wellness benefits, including an annual wellness stipend
• Continued investment in your professional development through learning allowance
• RRSP/TFSA with company match
• Annual wellness stipend
• Flexible and generous paid time off
• Employee Stock Purchase Program

Compensation

The target base compensation for this position is $180,000 to $200,000 CAD plus a variable compensation per year in most Canada locations. EverCommerce considers factors such as scope and responsibilities of the position, candidate’s work experience, candidate’s work location, education/training, key skills, internal peer equity, external market data, as well as market and business considerations when making compensation decisions.

EverCommerce is an equal opportunity employer and we value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender identity, sexual orientation, age, marital status, veteran status, or disability status. We look forward to reviewing your credentials and getting to know more about your experience!