Senior Director, Sales

At Upland Software, you’ll find smart, creative teams who love working together to deliver value for our customers, and a global culture of growth and possibility. Our operating model has always supported remote work—and as we keep growing and evolving our workplace, that won’t change. We’re passionate. We’re proactive. We take pride in our work, and we love a good challenge. Sound like you?

About Upland & BA Insight

At Upland Software, you’ll find smart, creative teams who enjoy working together to deliver value for our customers. We’re passionate, proactive, and proud of our work, and we love a good challenge.

BA Insight is Upland’s AI-powered enterprise search and data connectivity platform. It helps large, complex enterprises unlock information trapped across siloed applications and make that content securely available to enterprise search, generative AI, intelligent assistants, and Copilot experiences across Microsoft, AWS, and other technology environments. As enterprises move from experimenting with AI to putting it into production, BA Insight addresses a critical challenge: connecting AI platforms to the trusted enterprise information needed to deliver relevant, useful answers.

Upland is seeking a Senior Director of Sales to lead the go-to-market execution for BA Insight. This is a hands-on leadership role for someone who can build and coach a high-performing enterprise sales team while helping shape pipeline strategy, strategic deals, ecosystem relationships, and overall market execution.

This candidate will lead a team expected to include 4-6 quota-carrying Account Executives and 2 Solutions Consultants, while indirectly influencing the SDR team supporting BA Insight. The role will report to the General Manager of the business unit. They will also have a dotted-line relationship to the BA Insight product-line leader to ensure close alignment across Sales, Product, and Marketing. This role is currently US based and to be located in the eastern (preferred) or central time zones.

Primary Responsibilities

• Lead the BA Insight sales organization, coaching and developing AEs and Solutions Consultants, and collaborating with partner resources to consistently achieve quarterly and annual revenue objectives.
• Own sales execution and operating discipline, including territory planning, pipeline creation, deal inspection, qualification, forecasting, and Salesforce hygiene.
• Coach complex enterprise opportunities, helping sellers navigate multi-stakeholder buying processes, executive alignment, business cases, evaluations/POCs, and commercial negotiations.
• Build pipeline alongside the Demand Generation team, partnering on ABM programs, events, campaigns, target-account strategies, messaging, and marketing investments tied to measurable pipeline and revenue outcomes.
• Influence and align SDR execution, establishing clear qualification standards, messaging, target-account priorities, and SDR-to-AE handoffs.
• Develop the Microsoft and AWS ecosystem, working with the Partner Manager to expand relationships, develop co-sell motions, generate partner-influenced pipeline, and position BA Insight within enterprise AI initiatives.
• Partner across the business, working closely with BA Insight Product, Marketing, Customer Success, Services, and KCM leadership to align market strategy, product direction, customer needs, and sales execution.
• Maintain strong market awareness across AI, enterprise search, data connectivity, knowledge discovery, competitive offerings, and evolving enterprise technology priorities.
• Serve as an executive sponsor on strategic opportunities and establish strong relationships with senior customer and partner executives.

Requirements

• 10+ years of enterprise SaaS sales experience, including experience leading sales teams.
• Success managing teams of quota-carrying AEs and associated presales/technical resources.
• Consistent track record of achieving or exceeding revenue targets while developing sales talent.
• Experience selling complex enterprise solutions through multi-stakeholder buying processes involving business, IT, security, procurement, and executive leadership.
• Strong command of pipeline management, forecasting, quota models, sales economics, and Salesforce.
• Experience with value-based and MEDDICC-style selling, multi-threading, executive engagement, business-case development, and complex negotiations.
• Executive presence and the ability to credibly engage CIO, CTO, data, AI, and business leaders.
• Excellent leadership, communication, presentation, and organizational skills.
• Ability to lead through both direct authority and influence across Sales, SDR, Marketing, Product, and partner organizations.
• Willingness to travel as needed to customers, partners, and industry events.

Desired Skills

• Experience leading a team comparable in size and scope.
• Direct experience working within the Microsoft and/or AWS ecosystems, including partner, alliance, or co-sell motions.
• Experience collaborating closely with Demand Generation and SDR teams to build qualified enterprise pipeline.
• Experience with enterprise search, knowledge discovery, data connectivity, generative AI enablement, or adjacent enterprise software categories is a plus.
• Experience with enterprise search/AI providers (e.g. Glean, Coveo) and/or familiarity with Microsoft 365, Azure AI, Microsoft Copilot, AWS, Amazon Bedrock, Amazon Q, or related enterprise AI technologies is also a plus.
• Previous formal sales methodology training and strong customer and partner references.
• Bachelor’s or university degree preferred.

Why This Role?

Enterprise AI is creating enormous demand for secure, relevant access to organizational information, but much of that information remains trapped across disconnected applications and repositories. BA Insight helps solve that problem by connecting enterprise information to the AI, search, assistant, and Copilot experiences organizations are investing in today.

This is an opportunity to lead a focused enterprise sales organization at the intersection of AI, enterprise search, data connectivity, and the Microsoft and AWS ecosystems, while helping build the repeatable go-to-market engine for BA Insight.

Upland Software (Nasdaq: UPLD) is the intelligence layer that unifies and contextualizes enterprise knowledge, content, and data, turning isolated information into actionable outcomes for every human and agent. More than 1,100 enterprise customers rely on Upland's deep domain expertise to unlock the full value of their AI and agent-driven operating models, driving measurable outcomes across customer experience, employee productivity, and regulatory compliance. For more information, visit www.uplandsoftware.com.