Head of Direct Sales (North America & EMEA- remote work)

TuxCare Inc.; Toronto; Remote; CAD 180,000 - 240,000; Full time

Benefits offered by this job

Fully remote work with flexible hours

24 days vacation + 10 holidays

Unlimited sick leave

Private medical insurance

Job summary

TuxCare Inc. seeks a Head of Direct Sales to lead our North America and EMEA direct sales efforts from a fully remote position. You will coach Enterprise Account Executives, shape deal strategies, and drive new and renewal revenue across global markets.

You will collaborate with Marketing, Product, Finance, and Revenue Operations to optimize go-to-market motions and customer value, while traveling as needed to accelerate key opportunities.

Qualifications

• Experience leading direct sales teams for enterprise software.
• Proven record of achieving revenue targets across large territories.
• Hands-on coaching of account executives and renewals.

Responsibilities

• Set and execute the direct sales strategy across North America and EMEA, turning revenue goals into clear priorities for the team.
• Lead, coach, and develop Enterprise Account Executives, Account Executives, renewals, and sales development members.
• Collaborate with reps on active deals to uncover needs, communicate business value, and craft proposals.
• Support complex opportunities with tailored packaging and terms.
• Drive revenue from new business, account growth, and renewals with a healthy pipeline.

Skills

Direct sales

Enterprise sales

MEDDPICC

Forecasting

Negotiation

Deal coaching

Communication

Team leadership

Job description

TuxCare offers a portfolio of security solutions for Linux and open-source software aimed at enterprise organizations. With TuxCare, enterprises can automate live vulnerability patching, minimize downtime, keep their applications secure and compliant, and get support from a team that knows Linux security best – covering the most popular Linux distributions, end-of-life systems, programming languages, and much more.

We’re looking for a Head of Direct Sales to lead TuxCare’s direct sales organization across North America and EMEA. Reporting to the Chief Revenue Officer, you will lead a distributed team responsible for new customer acquisition, growth within existing accounts, and renewals.

This is a hands-on sales leadership role. Our solutions, including SecureChain and Extended Lifecycle Support for RHEL-based Linux alternatives (ELS for RLA), call for thoughtful discovery, tailored proposals, and flexible deal structures. You’ll coach the team through live opportunities, help shape complex deals, and build a sales approach grounded in each customer’s security and business needs.

Responsabilties:

• Set and execute the direct sales strategy across North America and EMEA, turning revenue goals and territory plans into clear priorities for the team.
• Lead, coach, and develop Enterprise Account Executives, Account Executives, account management, renewals, and sales development team members.
• Work closely with sales representatives on active deals, helping them uncover customer needs, communicate business value, and develop effective proposals.
• Support complex and strategic opportunities, including customer conversations, negotiations, and requests for tailored packaging or terms.
• Drive performance across new business, account growth, and renewals while maintaining a healthy pipeline and accurate forecasts.
• Review sales results and win/loss trends to identify coaching opportunities and improve the team’s approach.
• Build strong relationships with strategic customers and identify opportunities to grow TuxCare’s presence in both regions.
• Partner with Marketing, Revenue Operations, Product, and Finance to improve go-to-market execution and resolve customer needs.
• Hire, onboard, and develop sales talent across North America and EMEA.
• Represent TuxCare at relevant industry events and provide regular performance and forecast updates to the CRO and executive team.

• Proven experience leading direct sales teams across North America and EMEA, with a strong record of achieving revenue targets.
• Required: Direct sales or sales leadership experience in software supply chain security, software composition analysis (SCA), application security, or DevSecOps. Candidates must have sold enterprise solutions in this sector; experience selling general IT or infrastructure software alone does not meet this requirement.
• Hands-on experience selling solutions to buyers concerned with software vulnerabilities, end-of-life systems, compliance, or open-source security.
• Strong deal-coaching and value-selling skills, including experience with tailored product packaging and dynamic pricing.
• The ability to turn technical challenges into a clear business case for both technical and executive stakeholders.
• Experience managing new customer acquisition, account growth, and renewal motions.
• Strong forecasting, pipeline management, negotiation, and presentation skills.
• A coaching style that combines support, clear expectations, and accountability.
• Familiarity with MEDDPICC or a comparable enterprise sales qualification methodology.
• Willingness to travel as needed.

What's in it for you?

• A strong focus on professional development with opportunities for learning and growth:
• Interesting and challenging projects,
• Mentor and other knowledge-exchange programs;
• Fully remote work with flexible working hours, that allows you to schedule your day and work from any location worldwide;
• Paid 24 days of vacation per year, 10 days of national holidays, and unlimited sick leaves to ensure you maintain a healthy work-life balance;
• Compensation for private medical insurance;
• Co-working and gym/sports reimbursement;
• The opportunity to receive a reward for the most innovative idea that the company can patent, fostering a culture of creativity and innovation.