Enterprise Sales Director

About the role

You will own the end-to-end enterprise sales cycle for strategic customers in a primary capacity, acting as the trusted advisor and key relationship owner from initial discovery through expansion. You will leverage deep industry expertise and market knowledge to identify high-value opportunities and shape solutions that address complex business problems for our enterprise clients. This role requires you to build and maintain long-term executive relationships, earning trust and credibility with senior stakeholders at each engagement. You will analyze competitive landscapes and market dynamics to position our AI platform effectively and differentiate our value in a crowded market. You will collaborate seamlessly with cross-functional teams to ensure flawless execution and delivery, aligning customer expectations with our product capabilities. You will use data and insights to drive strategic decisions, forecast performance accurately, and continuously refine your approach to exceed revenue targets. You will champion the Sierra values in every interaction, demonstrating integrity, customer obsession, and craftsmanship in all you do.

Key facts

What you'll do

• Research and identify high-potential enterprise accounts through targeted market analysis, industry research, and strategic networking to build a robust pipeline.
• Develop and execute tailored outbound and inbound strategies that align with buyer intent, creating personalized engagement plans for priority accounts.
• Lead discovery sessions and executive-level conversations to uncover critical business challenges, quantify value, and define compelling needs.
• Architect and deliver customized value propositions and business cases that clearly articulate ROI, risk mitigation, and strategic alignment for C-suite stakeholders.
• Manage multi-threaded deal negotiations, resolving objections and aligning contract terms, pricing, and commercial structures with customer requirements.
• Coordinate closely with legal, finance, and product teams to streamline contract finalization, ensuring terms reflect mutual benefit and long-term partnership goals.
• Utilize AI-powered sales tools to automate research, synthesize call insights, and enhance forecasting accuracy, enabling more time for strategic selling.
• Track and analyze pipeline metrics, conversion rates, and deal velocity to identify bottlenecks and optimize performance continuously.
• Collaborate with marketing to develop compelling narratives, proof points, and case studies that reinforce our position as an industry leader.
• Mentor junior sales representatives by sharing best practices, providing feedback, and fostering a culture of excellence and continuous learning.
• Partner with customer success to ensure smooth onboarding, adoption, and ongoing satisfaction, laying the foundation for expansion.
• Monitor competitive activity and market shifts, feeding insights back to product and leadership to inform roadmap and positioning decisions.
• Drive the end-to-end commercial process, from initial outreach to contract signing, ensuring alignment with governance and compliance standards.
• Own quarterly and annual forecasting for assigned accounts, providing transparent updates and rationale for pipeline changes.
• Proactively identify cross-sell and upsell opportunities, developing plans that deepen engagement and maximize customer lifetime value.

Requirements

• 6-8 years of experience in an enterprise customer-facing sales role, identifying and closing large accounts with a proven track record.
• Enterprise experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals with consistent success.
• Exceptional verbal and written communication abilities, demonstrating clarity, persuasion, and professionalism in all interactions.
• Strong analytical mindset with the ability to analyze market trends, identify opportunities, and make data-driven decisions that impact growth.
• Demonstrated prospecting and lead generation skills, having identified and targeted potential enterprise clients through research, networking, and cold calling.
• Experience navigating complex enterprise buying committees and influencing multiple stakeholders across technical and business functions.
• A history of building and maintaining long-term C-level and executive-level relationships in fast-growth technology environments.
• Comfort working in ambiguous, fast-paced situations while upholding the highest standards of integrity and accountability.
• Familiarity with CRM tools, sales automation platforms, and data visualization dashboards to track performance and forecast accurately.
• Willingness to travel within the US for key customer engagements, partner meetings, and industry events as required by business needs.

Nice to have

• Familiarity with the AI landscape, key players, and emerging trends that can inform strategic selling approaches.
• Experience selling AI, cloud, or enterprise software solutions to mission-critical environments.
• Background in coordinating with product and engineering teams to translate customer feedback into actionable insights.
• Track record of mentoring and developing other sales professionals through coaching and collaborative best practices.

Practical notes

US-based role with remote flexibility; candidates must be able to work from a US location and align with core operating hours. Travel within the United States may be required for strategic customer visits, partner meetings, and industry events. This role is not eligible for visa sponsorship at this time. The position reports to the leadership team and is expected to contribute to quarterly and annual sales targets with measurable outcomes.