Regional Sales Director

Weekday AI•Kingdom City, MO

3d•$13,000,000 - $18,000,000•Remote

About The Position

We are looking for a high-calibre Business / Sales Leader to build and scale enterprise business across the US, UK, and European markets. This is an entrepreneurial, market-building role focused on creating demand, opening executive relationships, winning strategic accounts, and establishing the commercial foundation required for sustained regional growth. The ideal candidate will be an accomplished enterprise sales leader and rainmaker with a proven track record of originating and closing large technology and services engagements, particularly across AI, data, IT services, BPO/KPO, and technology-enabled operations.

Requirements

12+ years of enterprise B2B sales, business development, or business leadership experience across AI/ML, data, IT services, BPO/KPO, or technology-enabled services.
Proven track record of building and scaling significant technology or services businesses across US, UK, or European markets.
Demonstrated ability to create markets, generate demand, open executive doors, and originate large enterprise opportunities.
Strong track record of closing multi-million-dollar enterprise deals with complex sales cycles and multiple stakeholders.
Established relationships with senior decision-makers across large enterprises, AI/technology companies, GCCs, and hyperscalers.
Strong understanding of AI, data, technology services, and technology-enabled operations.
Ability to engage credibly with senior technical and business leaders and navigate complex enterprise buying processes.
Strong expertise in strategic account development, cross-selling, expansion, and long-term customer partnerships.
Proven ability to build and execute regional GTM and growth strategies with clear revenue ownership.
Strong commercial acumen with experience in pricing, negotiations, proposals, deal structuring, and commercial closure.
Ability to translate complex technology offerings into compelling business value and measurable outcomes.
Entrepreneurial mindset with the ability to operate independently, build from the ground up, and take ownership of regional growth.
Excellent executive presence, communication, negotiation, and relationship-building skills.
Strong collaboration skills with geographically distributed delivery, solutioning, and technical teams.
Ability to represent the organisation effectively with customers, partners, and senior industry stakeholders.

Nice To Haves

Willingness to travel extensively across the US, UK, and Europe as required.

Responsibilities

Own regional GTM, business development, revenue growth, and market expansion strategies across the US, UK, and Europe.
Build markets from the ground up by identifying target segments, opening executive relationships, creating demand, and establishing a strong sales pipeline.
Personally originate, develop, negotiate, and close large and complex enterprise technology opportunities.
Drive new-logo acquisition and establish strategic anchor clients within target markets.
Develop opportunities across AI Data, HITL, Model Evaluation, Trust & Safety, AI Operations, data services, and technology-enabled solutions.
Build and maintain trusted relationships with CXOs, AI/ML leaders, Data & Engineering executives, Procurement leaders, and business stakeholders.
Develop multi-million-dollar strategic accounts through expansion, cross-selling, upselling, and long-term partnership development.
Create account strategies and executive engagement plans for high-value enterprise customers.
Partner with India-based delivery, engineering, and solutioning teams to develop scalable and commercially compelling client solutions.
Translate complex technical capabilities into clear business value, outcomes, and commercial propositions.
Lead executive-level presentations, commercial discussions, negotiations, and deal closures.
Build strategic partnerships, alliances, and channel relationships to accelerate market access and regional growth.
Monitor market trends, competitive activity, customer needs, and emerging opportunities across AI and enterprise technology.
Develop accurate revenue forecasts, pipeline plans, account strategies, and regional growth initiatives.
Represent the organisation with strategic clients, technology partners, industry stakeholders, and the wider AI ecosystem.
Contribute to building the regional organisation, sales processes, operating model, and capabilities required for long-term scale.