Director, Enterprise Sales

Who Are We

Over the past 16 years, Afinitis patented technology has paired customers and contact centre agents in real time based on how well they are likely to interact, leading to better experiences across the entire customer journey. As our products evolve, it is our mission to retain and grow revenue by creating repeatable AI-driven solutions that transition from high-touch managed services to product-led growth. Afiniti operates throughout the world and has driven billions of dollars of precisely measurable AI value for our telecommunications, banking, insurance, healthcare, and travel customers. To learn more, visit www.afiniti.com.

Our Vision

Afinitis vision is to lead the contact centre industry by delivering innovative AI solutions that uniquely enhance customer lifetime value and operational efficiency, earning us the trust of leading consumer companies worldwide.

Our Ways of Working

At Afiniti, how we work is just as important as what we achieve. Our Ways of Working are ten guiding principles that define the standards and behaviors we hold ourselves accountable to every day. They push us to act with urgency and discipline to innovate with data and facts and to always see our work through the eyes of our clients. These principles are not abstract values - they are actionable commitments that shape daily decisions, strengthen collaboration, and ensure we deliver outcomes that matter. Together, they encourage us to be intentional in how we prioritize and execute, to confront challenges directly, and to embrace the richness of our global community with respect and openness. By living these principles consistently, we build a culture that is ambitious, respectful, and relentlessly focused on meaningful impact.

The Role

Role Title: Director Enterprise Sales Location: Washington DC, US (Remote) Reports To: SVP Head of Sales

About the Role

We are seeking a high-performing Enterprise Sales Director to drive revenue growth across low-enterprise and upper mid-market segments. This role is responsible for identifying qualifying and closing new business opportunities while expanding and nurturing relationships within existing accounts. As a senior individual contributor, you will own the full sales cycle across all of Afiniti product offerings - from strategic prospecting through deal closure - leveraging a solution-selling approach to position Afiniti AI-driven solutions as transformative business enablers. You will engage key decision-makers, develop compelling value propositions, and convert interest into high-quality pipeline opportunities. A core focus of the role is proactive enterprise engagement, generating demand among prospective customers, securing strategic meetings, and building a robust pipeline aligned with Afinitis go-to-market priorities. You will collaborate closely with Sales Engineers, Marketing, and Growth Leadership to execute targeted account strategies, refine messaging, and deliver coordinated outreach campaigns.

Key Deliverables

• Drive new revenue across enterprise and upper mid-market accounts through proactive prospecting and demand generation
• Open and expand accounts generating pipeline via outbound activity, events, partner engagement, and BDR collaboration
• Identify, engage, and qualify high-value prospects leading complex consultative sales cycles with executive stakeholders
• Develop and execute strategic account plans aligned with go-to-market GTM priorities
• Partner cross-functionally with Sales Engineering, Marketing, Growth, Product, and Customer Success to ensure seamless deal execution and onboarding
• Build long-term client relationships focused on expansion, retention, and long-term partnership
• Lead pilot entry validation and conversion into contracted and expansion revenue
• Consistently exceed sales targets, delivering exceptional client experiences
• Track and deliver against success metrics, including new logo, ARR, pipeline coverage, forecast accuracy, pilot conversion, and expansion revenue
• Represent the company at industry events, conferences, and executive briefings
• Own an assigned industry segment or territory across enterprise and upper mid-market accounts
• Establish repeatable pipeline motions and industry positioning within assigned segment
• Orchestrate internal and external stakeholders to advance complex opportunities from initial engagement through close

Who You Are

Qualifications:

• Bachelors degree in Business, Marketing, Technology, or a related field, or equivalent practical experience
• 8-12 years of progressive experience in B2B technology sales with a significant focus on enterprise and strategic accounts
• Demonstrated success selling complex, high-value solutions with long multi-stakeholder sales cycles
• Proven ability to consistently exceed revenue targets and close seven-figure enterprise deals
• Strong experience in consultative solution-based selling methodologies (e.g., MEDDPICC, Challenger, SPIN, Sandler)
• Experience working with CRM platforms (e.g., Salesforce, HubSpot) and advanced pipeline management tools

What Were Looking For

• Proven success in enterprise and upper mid-market B2B technology sales, consistently exceeding revenue targets
• Strong executive presence, communication, and negotiation skills, with the ability to influence C-suite and senior stakeholders
• Demonstrated ability to lead complex, multi-stakeholder consultative sales cycles
• Strategic data-driven mindset with disciplined pipeline management, forecasting accuracy, and CRM hygiene
• Strong commercial acumen, including deal structuring, pricing strategy, and contract negotiation
• Deep expertise in agentic AI, conversational AI, and contact center technologies, contact center operations, and how AI is and can be used
• Ability to build trusted executive-level relationships and act as a strategic advisor
• Track record of closing high-value, multi-year agreements and driving long-term partnerships
• Strong cross-functional collaboration across Sales, Marketing, Product Engineering, and Customer Success
• Ability to provide actionable market and customer insights to inform product roadmap and GTM strategy
• Experience building industry presence, developing repeatable sales playbooks, and leveraging partners, SIs, and advisors

Required Experience

• Extensive experience in enterprise and mid-market B2B SaaS or enterprise technology sales
• AI and Contact Centre technology
• Strong background in solution-based consultative selling with complex products and long sales cycles
• Deep understanding of enterprise procurement processes and buying committees
• Consistent overachievement against annual and quarterly revenue targets
• Proven ability to build VP- and C-level relationships within strategic accounts

Compensation

• Total OTE up to $290,000
• Base performance-based incentives