Regional Sales Director

Regional Sales Director (Player/Coach)

IT Service Management (ITSM), IT Operations

New York, Boston or Surrounding Areas

Remote

$175K Base / $175K OTE Options & Package

We're partnering with an ambitious, high-growth SaaS business looking to appoint a Regional Sales Director to spearhead expansion across the US Northeast.

This is a true player-coach opportunity for an experienced enterprise seller that can lead from the front and grow the team through success. We are looking for someone who loves being in the field, closing complex deals, building strategic relationships, and helping shape the future of a growing business.

You'll take ownership of a defined territory, driving new business acquisition across large enterprise organisations while contributing to go-to-market strategy, sales process development, and future team growth.

What You'll Be Doing

• Building and executing a territory strategy focused on enterprise account acquisition

• Developing and managing a strong self-generated pipeline

• Leading complex sales cycles from discovery through to negotiation and close

• Engaging with senior stakeholders, including C-suite executives

• Creating compelling business cases and ROI-driven value propositions

• Managing multiple stakeholders across IT, Procurement, Finance, Legal, and Executive teams

• Contributing to sales playbooks, messaging, and best practices as the business scales

• Acting as a senior commercial leader and role model within a high-performance culture

• Delivering accurate forecasting and pipeline reporting

What We're Looking For

• 8 years of proven success selling complex enterprise SaaS solutions into Fortune 500 and large corporate organisations across the US

• Strong focus on new business acquisition, enterprise prospecting, and closing complex opportunities

• Solid background within IT, IT Service Management (ITSM), IT Operations, Service Desk environments, or the broader ServiceNow ecosystem

• Ability to engage credibly with IT and ITSM leaders from day one

Track Record

• Consistent quota over-achievement in enterprise sales environments

• Proven experience managing and closing complex, multi-stakeholder five and six-figure enterprise deals

• Demonstrated ability to navigate long sales cycles and executive-level decision-making processes

Sales Expertise

• Deep understanding of consultative and value-based selling methodologies such as MEDDPICC, Challenger Sale, SPIN, or similar frameworks

• Ability to build pipeline independently and create opportunities through strategic prospecting

• Experience succeeding in high-growth or scaling businesses where processes, structures, and playbooks are still evolving

Technical Acumen

• Strong ability to understand and communicate both technical and commercial concepts

• Skilled at translating IT and ITSM challenges into measurable business outcomes, ROI, and strategic value

• Comfortable engaging both technical and non-technical stakeholders throughout the sales process

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