Sales Manager

PaintScout is building the operating system that helps professional painting contractors run stronger, more confident businesses. We create tools that make their work easier, their days smoother and their companies more profitable. That mission guides everything we do.

We're looking for a Sales Manager to lead our sales team: coaching our Account Executives, guiding our Partnerships channel, and building the playbooks, training, and systems that help the team do the best work of their careers. Thousands of painting contractors use PaintScout every day, and we want to help many more. Help us get there.[1] [2]

This is a coach role. Your challenge: build a world class sales team that hits ambitious targets, upholds our values, and looks after our customers and each other.

How we sell

We think long term, meaning we sell solutions. Our team qualifies what a painting contractor actually needs and sells the solution that fits, even when that means a smaller plan, or telling them we aren't the right choice today. The relationship with our contractors is of utmost importance, we honor it in everything we do. We'd rather lose a sale than win it the wrong way.

As Sales Manager, you're the person who champions that standard, especially when targets are tight. You hold the team accountable for how they sell, not only whether they hit their goals. You build it into everything the team uses: discovery that uncovers real needs, demos that show the fit, honest pricing conversations, and handoffs that start every customer with clear expectations that we meet.

We’ll measure it that way too. Close rate and sale size matter, but so do early retention, downgrades, and whether each customer got the plan that fits their business.

Leading a team that wins together

We want a sales team, not a group of people flying solo. A teammate’s win needs to be a team win, and you’ll build the habits and structures that makes the team hit ambitious targets together:

In a team that wins together, you'll see AEs:

● Learn from sales together. Wins and losses get reviewed as a team, so knowledge is spread across the team, empowering each teammate.

● Share what works. A great discovery question, a sharp answer to an objection, or a call worth hearing goes into the playbook.

● Coach each other. Teammates listen to each other's calls and give honest, useful feedback.

● Look after each other. When someone's out, teammates pick up their follow-ups and demos so the contractor's experience stays the same.

● Uphold our values. The standard is a shared one, and teammates champion it for each other even when targets are tight.

Variable comp is designed to support these mindsets and behaviours. You'll run it day to day and help shape where it goes next, with pay that rewards selling within our values and onboarding customers who stay. Your own comp has an element tied to team performance, not individual deals.

From an in-practice standpoint, you will:

● Coach our AEs through 1:1s, call reviews, and sales strategy, and grow early-career reps into confident sellers and future leaders.

● Lead our Business Development rep in running the Partnerships channel: recruiting value-aligned referral partners and making sure every referral gets a great experience.

● Build the team's sales assets in GitBook: playbook, discovery and demo frameworks, objection library, and new-AE training.

● Own pipeline health/forecasting in HubSpot, and make the numbers meaningful to the team.

● Run the sales month-end: performance review, accurate variable comp, and quota recommendations.

What we're looking for

● A track record of success in consultative sales, ideally SaaS sold to small business owners

● Experience coaching, training, or leading sales reps, formally or informally

● The credibility to step into a complex sale or relationship and handle it well, with a teaching mindset

● A builder's mindset: you've created playbooks, training, or process that resulted in useful outcomes

● Experience running variable comp or incentive programs, and a strong sense of how they shape a team's behaviour in line with values

● Comfort with sales data and CRM reporting (HubSpot experience is a plus)

● A solutions-based approach to selling, and the integrity to protect it when targets are tight

Experience in the painting, construction, trades, or home services industries is a bonus, but not required. The ability to correspond (speak and write) in Spanish is an advantage.

What we offer

● Competitive base salary plus a bonus tied to team performance

● Three weeks’ vacation

● Health benefits

● Hybrid work from our Calgary office (TWTh in office, MF remote)

● A growing, profitable company that makes decisions for the long term

● A motivated team ready to be coached

● Real ownership: the chance to build our sales playbooks, training, systems, and how we reward the team

Why PaintScout?

We're not trying to build software for every small business. We're focused on one industry, painting, and we want to build the best software in the world for the contractors who work in it.

If you want to build a sales team that contractors trust, help team members grow, and play a meaningful role in where PaintScout goes next, we'd love to meet you.

Company Overview

Please visit https://www.paintscout.com for more information