Job Description

Chief of Staff

Reports to:

CEO

Location:

Calgary, AB

About PaintScout

PaintScout is the leading software platform built specifically for painting contractors. What started as a tool to help one contractor sell jobs more easily has grown into a platform trusted by painting companies worldwide, supporting over

$1B in painting projects every year

.

Our mission is simple:

help painting contractors win more jobs, sell with confidence, and run more profitable businesses.

By transforming how contractors price, present, and close their work, we're not just streamlining operations--we're elevating an entire industry.

This is a pivotal moment at PaintScout. We're scaling rapidly, expanding into new product areas, and building the

central operating system for professional painting contractors.

Why This Role Matters

As Chief of Staff, you'll step into the heart of this journey--working directly with the CEO and leadership team to drive strategy, execution, and growth. This role is for someone who wants to be part of a

fast-growing SaaS company

with a massive market opportunity, where your work will directly shape the trajectory of the business and the future of an industry.

Key Responsibilities

Strategic Support & Alignment

Partner with the CEO to define and communicate company strategy, OKRs, and key initiatives. Track progress on strategic goals and provide clear reporting to leadership and the board. Research market trends, competitors, and customer insights to support strategic decisions.

Execution & Operations

Run the cadence of leadership meetings, quarterly planning, and board prep. Ensure cross-functional alignment across Sales, Marketing, Product, and Customer Success. Manage high-priority projects from inception to delivery, often stepping in to "unblock" progress. Improve internal processes to help the company scale efficiently.

Communication & Leadership

Act as a communication bridge between the CEO, leadership team, and broader organization. Draft executive communications, board updates, and investor reports. Provide decision-making leverage for the CEO by triaging issues, preparing briefs, and surfacing key insights. Build trust across teams by ensuring transparency and clarity on goals and priorities.

Special Projects

Lead new initiatives that don't neatly fit into existing teams (e.g., new product experiments, GTM pilots, partnerships). Own time-sensitive projects that require senior-level oversight without distracting functional leaders.

What Success Looks Like

Company strategy and CEO priorities are clearly understood and executed across the org. Leadership team is aligned and operating at a high level of accountability. The CEO's bandwidth is freed up to focus on vision, relationships, and growth. Cross-functional projects consistently hit deadlines and move the business forward.

Qualifications

5-10+ years of experience in SaaS, consulting, or high-growth tech (with exposure to strategy and operations). Proven track record in project management and executive-level communication. Strong analytical skills with the ability to turn data into clear insights. Comfortable working across all functions: product, engineering, sales, marketing, customer success. Highly organized, detail-oriented, and able to juggle multiple priorities in a fast-paced environment. Strong interpersonal skills: able to build relationships and influence without direct authority.

Bonus Points

Experience supporting a CEO or executive team directly. Background in SaaS go-to-market (sales, growth, or marketing). Familiarity with board and investor relations.
Job Type: Full-time

Work Location: In person