Regional Sales Director, Canada

GitLab · Remote · Canada

Open 2 days

New Business + Account Growth: you win new customers and grow existing ones.

Base: Not disclosed
OTE: Not disclosed
Posted: 3d ago

Still open · checked 6h agoon GitLab's careers page

Apply on GitLab →

The job

What you'd do

Lead and coach a team of salespeople selling GitLab's software to large Canadian companies across many industries. You'll set sales plans, hit revenue targets, and hire new team members.

What you'd sell

Helps software teams build, test, and ship code safely

When a software team has to get new code out the door, they usually have to build it, test it, and check it for security before customers can use it. The problem is, if those steps live in different tools or get skipped when deadlines loom, bugs and security holes reach customers. GitLab keeps writing, testing, and security checks for code in one place, so teams can ship better, safer software faster.

In plain English, from their own job posts. Something wrong? Tell me · More Developer & IT tools companies →

Who you'd sell to

Not stated in the posting.Ask: “Who's the economic buyer, and who else is in the deal?”

Where deals come from

Not stated in the posting.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Shares 1 of 5. Mentions territory. Ask about quota, attainment, deal size and sales cycle.
Time on market: Open 2 days.
Company hiring: 28 sales roles open, hiring at a steady pace. Ask how many reps they hired last year and how many are still there.

Red lights

Pay. No pay listed at all.

Green lights

None spotted.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
2.
What are the base and the OTE for this role?
No point investing hours before you know the number.
3.
Who's the economic buyer, and who else is in the deal?
Selling to a CFO and selling to a developer are different jobs.
4.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
5.
Where does pipeline come from: inbound, SDRs, or me?
Tells you how much of your week is prospecting versus selling.

Before You Apply

Find out where you fit, and where you don't, before you hit submit.

Why I built it this way ↓

Most résumé tools try to make you look like a match. I'd rather help you find out if you are one.

Nothing made up.
Nothing goes on your résumé that you didn't do. If a line would need a number you didn't give me, I ask. I don't guess. On Braun Board it's checked in code, not just promised.
Curiosity before conclusions.
If the job wants something your résumé doesn't show, I ask before I assume. Plenty of sellers have done the thing and just never wrote it down.
Sorting, not selling.
Some jobs won't line up with what you've done. Finding that out before you apply isn't a loss. It's an hour back, spent on a job that fits.
No score.
A match score tells you how well you copied their words. It doesn't tell you whether you'd be good at the job, or happy there.

It's the same way I teach selling. We don't control who says yes. We do control where we spend our time, and whether everything we say is true.

Josh

1 Is the job worth it?

Ask hard questions. Too much is left unsaid. Make them answer before you invest.

No pay listed at all.

Might be worth asking about this before you spend an hour on a tailored résumé.

See the full Braun Read

2 Where you fit

Upload once, see where you fit on any job.

What people say about working at GitLab ↓

Got an offer from GitLab? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Rather talk it through? Call or text me: 954-695-0844 (text)

Full posting

GitLab is the intelligent orchestration platform for DevSecOps. GitLab enables organizations to increase developer productivity, improve operational efficiency, reduce security and compliance risk, and accelerate digital transformation. More than 50 million registered users and more than 50% of the Fortune 100* trust GitLab to ship better, more secure software faster. The same principles built into our products are reflected in how our team works: we embrace AI as a core productivity multiplier, with all team members expected to incorporate AI into their daily workflows to drive efficiency, innovation, and impact. GitLab is where careers accelerate, innovation flourishes, and every voice is valued. Our high-performance culture is driven by our values and continuous knowledge exchange, enabling our team members to reach their full potential while collaborating with industry leaders to solve complex problems. Co-create the future with us as we build technology that transforms how the world develops software. *Fortune 500® is a registered trademark of Fortune Media IP Limited, used under license. Claim based on GitLab data. Fortune 100 refers to the top 20% ranked companies in the 2025 Fortune 500 list, published in June 2025. Fortune and Fortune Media IP Limited are not affiliated with, and do not endorse products or services of GitLab. As the Regional Manager, Sales for Canada, you’ll lead a high-performing team of Account Executives to grow adoption of GitLab’s AI-powered DevSecOps platform across industries and customer segments, helping Canadian organizations plan, build, secure, and ship software faster across the entire software development lifecycle. You’ll be responsible for managing software sales, bookings, and revenue, while building strong relationships with new and existing customers who rely on GitLab to increase developer productivity, improve operational efficiency, and reduce security and compliance risk. You’ll hire and develop top talent, set clear territory and market strategies, and ensure your team’s sales plans align with GitLab’s overall growth goals. In your first year, you’ll focus on building a strong team culture, deepening our presence with leading Canadian organizations, and consistently meeting or exceeding performance objectives in a fast-paced, open source software and SaaS environment. Must be located in Canada What you’ll do - Lead, coach, and motivate a team of Account Executives covering Canada to deliver software sales, bookings, and revenue results - Drive territory and market planning by analyzing market dynamics, customer needs, and competitive trends to identify and execute on growth opportunities across segments and industries - Develop and own accurate sales forecasts, territory management plans, and growth strategies that align to GitLab’s overall revenue goals - Establish, track, and report on key performance metrics for the team, and take action to address gaps and improve outcomes - Collaborate closely with Renewals, Marketing, Sales Operations, and other cross-functional partners to manage pipeline health, renewal performance, and deal execution - Recruit, hire, and onboard top sales talent while investing time weekly to build and maintain a strong pipeline of potential future hires - Create a high-performing, inclusive, and positive team culture through regular coaching, clear expectations, and ongoing development - Educate and enable your team on GitLab’s product, pricing, AI-powered DevSecOps positioning, and the industry, privacy, and regulatory factors that matter to Canadian customers What you’ll bring - 7-10 years of progressive experience in field sales, sales operations, and sales management in an open source software, DevOps, or similar software-as-a-service environment - Demonstrated success leading and developing account-focused sales teams in a commercial or enterprise segment, including hiring, coaching, and performance management - Experience selling to large commercial and enterprise organizations, with a willingness to “roll up your sleeves” and participate directly in selling activities when needed - Proven track record of meeting or exceeding performance objectives (revenue targets, pipeline targets, etc.) - Experience building and executing go-to-market strategies across multiple segments or industries, including regulated ones - Ability to exercise effective judgment, sensitivity, and creativity as needs change, and to thrive in a fast-paced environment with a challenging workload - Strong relationship-building, negotiation, and presentation skills, including executive-level written and verbal communication and the ability to mentor others - Alignment with GitLab’s values and a genuine passion for open source, with openness to candidates who bring transferable leadership experience from adjacent software markets - Ability to travel if needed and comply with the company’s travel policy Remote-Global How GitLab Supports Full-Time Employees - Benefits to support your health, finances, and well-being - Flexible Paid Time Off - Team Member Resource Groups - Equity Compensation & Employee Stock Purchase Plan - Growth and Development Fund - Parental Leave Please note that we welcome interest from candidates with varying levels of experience; many successful candidates do not meet every single requirement. Additionally, studies have shown that people from underrepresented groups are less likely to apply to a job unless they meet every single qualification. If you're excited about this role, please apply and allow our recruiters to assess your application. Country Hiring Guidelines: GitLab hires new team members in countries around the world. All of our roles are remote, however some roles may carry specific location-based eligibility requirements. Our Talent Acquisition team can help answer any questions about location after starting the recruiting process. Privacy Policy: Please review our Recruitment Privacy Policy. Your privacy is important to us. GitLab is proud to be an equal opportunity workplace and is an affirmative action employer. GitLab’s policies and practices relating to recruitment, employment, career development and advancement, promotion, and retirement are based solely on merit, regardless of race, color, religion, ancestry, sex (including pregnancy, lactation, sexual orientation, gender identity, or gender expression), national origin, age, citizenship, marital status, mental or physical disability, genetic information (including family medical history), discharge status from the military, protected veteran status (which includes disabled veterans, recently separated veterans, active duty wartime or campaign badge veterans, and Armed Forces service medal veterans), or any other basis protected by law. GitLab will not tolerate discrimination or harassment based on any of these characteristics. See also GitLab’s EEO Policy and EEO is the Law. If you have a disability or special need that requires accommodation, please let us know during the recruiting process.

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