Director of Sales

Gallery Systems • New York, NY

29d • Remote

About The Position

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.

Requirements

• Bachelor’s degree required.
• 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.

Nice To Haves

• 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.

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

Benefits

• Flexible vacation and time-off
• 401(k)
• Employee Assistance Program
• Health, dental, vision, and life insurance
• Long-term equity participation through the Constellation Software employee stock ownership plan

What This Job Offers

• Job Type: Full-time
• Career Level: Director