Director of Sales

Job Summary:

Gallery Systems is a global leader in collections management software, serving the museums, galleries, and cultural institutions that preserve and share the world's cultural heritage. As part of Volaris Group within Constellation Software (TSX: CSU), we are accelerating our investment in AI, deepening our product portfolio, and expanding our global reach to support the cultural sector's evolving needs.

We are seeking a strategic, hands-on Director of Sales to lead our global sales organization. Reporting to the General Manager / CEO, you will own sales strategy and execution across our Cultural Heritage and Art Business segments, lead a team of Sales Managers, and partner closely with Marketing, Product, the Innovation Hub, and Customer Success to deliver measurable revenue growth. You will be the executive voice of the customer in our go-to-market motion, and the face of Gallery Systems in our most strategic global opportunities.

The ideal candidate is a global sales leader who grows revenue through proactive, value-based, consultative selling — and who measures success not only in revenue, but in the institutions, collections, and audiences our work makes possible. This is a fully remote role with competitive benefits, long-term equity participation through the Constellation Software employee stock ownership plan, and access to the broader Volaris Group leadership network. Passion for the cultural sector is essential.

Job Description:

About Gallery Systems

Gallery Systems, part of Volaris Group within Constellation Software (TSX: CSU), is a global leader in collections management software solutions, serving museums, galleries, and cultural institutions worldwide. Our customers are largely mission-driven non-profits operating with constrained budgets and outsized impact — we are accelerating our work today by investing in AI, deepening our product portfolio, and expanding our global reach.

The Role

We are seeking a strategic, hands-on Sales Director to lead our global sales organization. This is a fully remote, global role reporting to the General Manager / CEO; you will own sales strategy and execution, lead a team of Sales Managers, and partner closely with Marketing, Product, the Innovation Hub, and Customer Success to deliver measurable revenue growth. You will be the voice of the customer in our go-to-market strategy and the face of Gallery Systems in our most strategic global opportunities. This role is best suited to a sales leader who measures success not only in revenue, but in the institutions, collections, and audiences our work makes possible — passion for the cultural sector is essential.

Who we’re looking for

Gallery Systems is looking for a global sales leader who grows revenue through proactive, value-based, consultative selling — and earns the deep domain trust our customers expect. The ideal candidate brings sales leadership credentials in cultural heritage or art business (commercial galleries, auction houses, and dealers); where domain depth is limited, we will prioritize a leader with the curiosity and humility to acquire it quickly. Our portfolio spans both an enterprise platform and a SaaS offering with distinct buyer profiles and commercial models; the ability to lead and coach a team across both is essential. You will be measured by global revenue growth, executive-level customer relationships, and Gallery Systems’ position as the strategic platform of choice for cultural institutions worldwide.

Your responsibilities at Gallery Systems

• Global Sales Strategy and Growth: Define and execute global sales strategy across the Cultural Heritage and Art Business segments, aligning go-to-market plans with the product roadmap and growth priorities. Lead growth across North America, Europe, and other international markets, adapting to local cultural, regulatory, and procurement norms.
• Lead and Develop the Sales Team: Manage, coach, and develop a team of regional and segment Sales Managers. Build a culture of disciplined account planning, proactive customer engagement, and value-based selling — equipping the team to articulate measurable customer outcomes in every conversation.
• Strategic Account Engagement: Engage senior institutional decision-makers — Directors, CIOs, COOs, Trustees, and Gallery Principals — and build executive-to-executive relationships, account-based programs, and customer advisory structures that support long-term partnership.
• Solution and Innovation Selling: Partner with the Product team and the Innovation Hub — Gallery Systems’ internal AI research and product incubation team — to bring new capabilities to market. Lead early adopter programs and customer co-creation initiatives that strengthen Gallery Systems’ position as the sector’s forward-looking technology partner.
• Field Presence and Industry Engagement: Set the expectation — and personally model — active presence at industry events, customer institutions, and partner forums. Drive a culture of high in-market customer engagement across the sales organization.
• Revenue, Pipeline, and Performance Discipline: Own global bookings, ARR, net revenue retention, new-logo revenue, and quota attainment — driving disciplined execution through pipeline health, win/loss analysis, stage conversion, and consistent forecast cadence.
• AI in the Sales Motion: Champion AI tool adoption across the sales organization — for prospecting, account research, proposal development, competitive intelligence, and enablement — as a core part of how Gallery Systems operates.
• Cross-Functional Leadership: Partner with Marketing, Product, Customer Success, the Innovation Hub, and Operations to ensure alignment across the full customer lifecycle — from demand generation through deployment and renewal.
• Salesforce and Sales Operations Discipline: Drive rigorous CRM hygiene, account planning, and discovery documentation. Use Salesforce and AI-driven insights to direct targeted campaigns, account-based motions, and renewal and expansion activity.
• Ethical and Compliant Selling: Ensure all global sales activities comply with applicable privacy and procurement regulations (including GDPR, CASL, and public-sector tender requirements) and Volaris Group and Constellation Software ethical standards.

Your qualifications, experience and personal attributes

• Bachelor’s degree required. An advanced degree is an asset but not required — demonstrated sales leadership results take priority over academic credentials.
• 10+ years of B2B software sales experience, with at least 5 years in sales leadership roles managing distributed, multi-region/international teams.
• Demonstrated success leading complex, long-cycle enterprise software sales — including six- and seven-figure deals, multi-stakeholder buying committees, and public-sector procurement — with measurable improvement in pipeline generation, win rates, and forecast accuracy.
• Experience selling value-based solutions in premium-positioned markets, winning on outcomes rather than price, including AI-enabled or emerging technology.
• International sales leadership experience, with practical understanding of cultural, regulatory (including GDPR), and procurement differences across global regions.
• Strong executive presence with the ability to engage senior institutional buyers, and excellent communication, coaching, and team-building skills.
• Genuine passion for the cultural, museum, heritage, or art sectors — and the institutions and communities they serve.
• Proficiency in Salesforce (or equivalent CRM), modern sales engagement platforms, and AI-driven sales tooling.
• Willingness to travel extensively and maintain high in-market presence, including direct involvement in strategic opportunities.

Preferred Assets

• Direct domain experience in cultural heritage, museums, galleries, art business, or adjacent cultural and nonprofit software verticals.
• Familiarity with Volaris Group, Constellation Software, or comparable buy-and-hold vertical software portfolio operating models — understanding how these businesses prioritize retention, operational discipline, and long-term customer value over growth-at-all-costs.
• Familiarity with collections management, digital asset management, loan management, condition reporting, or related museum and gallery workflows.
• Formal sales methodology training or certification — MEDDIC/MEDDPICC or Challenger preferred.
• Multilingual capability (especially French, German, Spanish, or Italian) for international market engagement.
• Experience working closely with Marketing in an account-based, demand-driven motion.
• Track record of building executive-to-executive selling programs and customer advisory boards.

What Gallery Systems offers you

Gallery Systems is part of Volaris Group, which has completed hundreds of vertical market software acquisitions and has never sold a business — this is a company, and a career, built to last. As a Volaris Group portfolio company, you gain access to a global network of software leaders, cross-portfolio mentorship and leadership development programs, and genuine opportunities to grow within the broader Volaris and Constellation Software ecosystem over time. Work with world-renowned museums, galleries, and cultural institutions across the globe, in a fully remote role with competitive benefits — including flexible vacation and time-off, 401(k), an Employee Assistance Program, and health, dental, vision, and life insurance.

A note on compensation:

This role offers mission-driven work and a genuine quality of work life — 100% remote, flexible time off, and access to Volaris Group leadership development. It also includes long-term equity participation through the Constellation Software (TSX: CSU) employee stock ownership plan; CSU has compounded shareholder value for over 20 years as a publicly traded company, making the ESOP a meaningful long-term wealth-building vehicle, not a token line item. Total compensation includes base salary and performance-based variable tied to global revenue outcomes. We are transparent that cash compensation reflects our customer base — cultural and non-profit institutions — and is positioned below commercial enterprise software benchmarks. This is the right fit for a sales leader for whom customer impact, equity upside, and quality of work are meaningful parts of total reward.

Gallery Systems is an equal opportunity employer. We encourage all qualified individuals to apply. You will receive consideration for employment without discrimination based on age, race, color, religion, national origin, ancestry, sex, sexual orientation, gender identity, disability, marital or domestic partner status, or any other characteristic protected by law.

Ready to apply?

If this role resonates — the mission, the customers, the work — we’d love to hear from you.

Worker Type:

Regular

Number of Openings Available:

1