Remote Pilot Jobs in Springfield, VA (NOW HIRING)

About Afiniti
​Who Are We?

Over the past 16 years, Afiniti's 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
Afiniti's 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’s product offerings —from strategic prospecting through deal closure—leveraging a solution-selling approach to position Afiniti’s 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 Afiniti’s 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.

What Will Be Your 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

• Bachelor’s 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 We’re 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
• Demonstrate deep expertise in agentic AI, conversational AI, and contact center technologies, contact centre 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
  

We believe that richness in diversity is a huge asset for Afiniti. We value both the similarities and differences in everyone who is a part of the Afiniti team. We believe that this diversity builds a stronger organization and is in keeping with the core values of our company. Our policy, therefore, is to provide equal employment opportunities for all applicants and employees without regard to race, color, religion, sex (including pregnancy, childbirth, related medical conditions, breastfeeding or reproductive health decisions), gender identity or expression, national origin, age, marital status, ancestry, physical or mental disability, sexual orientation, personal appearance, genetic information, family responsibilities, matriculation, political affiliation, military or veteran status, or any other category protected under applicable federal, state or local law.