Director, Enterprise Sales

Get roles like this by email

New Sales roles in Waterloo Region, mailed the morning after they appear, and The Weekly each Monday.

Change or stop it from any email.

We are seeking an accomplished Director, Enterprise Sales to lead the expansion and growth of our Enterprise business across you assigned region. This is a hybrid leadership position that combines strategic account management with team leadership—you'll maintain a personal book of high-value business while building and coaching a world-class sales organization.

You'll be responsible for developing market strategy, driving sustainable revenue growth, and establishing our company as a trusted enterprise solutions provider in the Malaysian market.

KEY RESPONSIBILITIES

Market Development & Strategic Planning

• Lead market entry planning and develop comprehensive go-to-market strategies aligned with Malaysian market dynamics and competitive landscape

• Create territory plans, target account lists, and market-specific business plans with measurable milestones

• Identify and prioritize target accounts and market segments; establish strategic partnerships and channel relationships

• Build brand awareness and establish strong company positioning within Malaysia and the region

• Develop scalable, repeatable sales processes tailored to market and organizational requirements

• Monitor competitive activity and conduct quarterly win/loss analysis; adjust strategies accordingly

Revenue Performance & Sales Execution

• Own regional Enterprise revenue objectives, growth targets, and forecasts

• Establish rigorous pipeline discipline

• Drive new logo acquisition and expansion opportunities within existing enterprise customers

• Balance team revenue performance with personal strategic account management

• Track key performance indicators: pipeline coverage, conversion rates, deal size, new logo acquisition, and sales cycle velocity

• Conduct weekly pipeline reviews, monthly forecasts, and quarterly business reviews with leadership

Sales Team Leadership

• Build, recruit, and mentor a high-performing team of enterprise sales professionals

• Establish team culture, clear expectations, goals, and performance metrics

• Lead hiring, onboarding, and training on products, processes, and market-specific knowledge

• Provide regular coaching, constructive feedback, and performance management

• Identify skill gaps and coordinate professional development; create individual development plans

• Implement consistent account planning and sales methodology across the team

• Develop emerging sales leaders within your organization

Enterprise Account Management

• Manage strategic enterprise accounts as the primary executive point of contact

• Generate new enterprise opportunities; identify, qualify, and develop compelling value propositions and ROI analyses

• Lead complex enterprise sales cycles (6-18 months) involving multiple C-suite stakeholders

• Negotiate and close complex deals exceeding USD 1 million; drive upsell and cross-sell expansion

• Execute account strategy and manage implementation oversight; conduct strategic account reviews and manage renewals

• Build and maintain strong executive relationships with CIOs, CTOs, and business leaders

Executive Relationships & Market Presence

• Build trusted relationships with C-level executives and key decision-makers

• Represent the company as a thought leader at industry conferences, events, and networking forums

• Serve as bridge between customer needs and internal product and delivery capabilities

• Provide market intelligence and customer feedback to senior leadership

• Collaborate with marketing, product, and delivery teams on account strategies and market requirements

REQUIRED QUALIFICATIONS

• Enterprise Sales Experience (10+ years)

• Proven track record of consistently achieving and exceeding annual sales quotas

• Extensive experience selling enterprise software, SaaS, cloud solutions, or digital transformation services to Fortune 2000 organizations

• Demonstrated success closing complex deals exceeding USD 1 million

• Proven ability to generate qualified pipeline and acquire new logos in competitive markets

• Experience managing complex, multi-stakeholder enterprise sales cycles (6-18 months)

• Established ability to sell to and build relationships with C-level executives

• Demonstrated success in market entry or new territory development

Team Leadership Experience

• Proven experience building and scaling enterprise sales teams in high-growth markets

• End-to-end people leadership capability (hiring, onboarding, coaching, performance management, development)

• Experience leading sellers through complex enterprise sales motions

Core Competencies

• Strong consultative selling methodology and enterprise sales expertise

• Excellent communication, negotiation, and executive presentation skills

• Ability to build and maintain long-term executive relationships

• Strong forecasting, account planning, and sales discipline

• High emotional intelligence with demonstrated coaching capability

• Problem-solving and issue resolution skills

• Comfort working in ambiguous, fast-paced environments

• Proficiency with Salesforce CRM

• Deep understanding of enterprise sales processes, value-based selling, and ROI development

• Cross-cultural awareness and comfort in international business environments

DESIRED QUALIFICATIONS

• Previous success expanding sales into new verticals, industries, or geographic markets

• Experience building scalable, repeatable sales organizations and processes

• Experience selling Network Observability, APM/DEM, Infrastructure Monitoring, Cloud Networking, AIOps, or Enterprise Networking solutions

• Experience with key vertical sectors: Hospitality/Resorts, Higher Education, Data Centers, AI Infrastructure, MSPs, or Smart Infrastructure

• Track record in ASEAN market development

• Bachelor's Degree in Information Technology, Business, or related field

WORK CONDITIONS

• Hybrid work arrangement

• Extended hours may be required to support customer engagement …