Senior Director, Sales

Upland Software • ,

1d • Remote

About The Position

Upland Software is seeking a Senior Director of Sales to lead go-to-market execution for BA Insight, Upland’s AI-powered enterprise search and data connectivity platform. BA Insight connects information across enterprise applications and makes it securely available to enterprise search, generative AI, intelligent assistants, and Copilot experiences.

This is a hands-on leadership role focused on building and coaching a high-performing enterprise sales team, shaping pipeline strategy, supporting strategic deals, developing ecosystem relationships, and driving market execution. The team is expected to include 4–6 quota-carrying Account Executives and 2 Solutions Consultants, with indirect influence over the SDR team supporting BA Insight. The role reports to the General Manager of the business unit and has a dotted-line relationship to the BA Insight product-line leader to ensure alignment across Sales, Product, and Marketing.

The position is US-based, with the eastern time zone preferred, or the central time zone. Travel is expected as needed to customers, partners, and industry events.

Requirements

• 10+ years of enterprise SaaS sales experience, including experience leading sales teams.
• Success managing teams of quota-carrying Account Executives and associated presales or technical resources.
• A consistent 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 engage credibly with CIO, CTO, data, AI, and business leaders.
• Excellent leadership, communication, presentation, and organizational skills.
• Ability to lead through direct authority and influence across Sales, SDR, Marketing, Product, and partner organizations.
• Willingness to travel as needed to customers, partners, and industry events.

Nice To Haves

• Experience leading a team comparable in size and scope.
• Direct experience in 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.
• Experience with enterprise search or AI providers such as Glean or Coveo, and/or familiarity with Microsoft 365, Azure AI, Microsoft Copilot, AWS, Amazon Bedrock, Amazon Q, or related enterprise AI technologies.
• Previous formal sales methodology training and strong customer and partner references.
• Bachelor’s or university degree preferred.

Responsibilities

• Lead the BA Insight sales organization, coaching and developing Account Executives and Solutions Consultants, and collaborating with partner resources to 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, supporting sellers through multi-stakeholder buying processes, executive alignment, business cases, evaluations and proofs of concept, and commercial negotiations.
• Build pipeline with the Demand Generation team by partnering on account-based marketing programs, events, campaigns, target-account strategies, messaging, and marketing investments tied to measurable pipeline and revenue outcomes.
• Influence and align SDR execution by establishing qualification standards, messaging, target-account priorities, and SDR-to-AE handoffs.
• Develop the Microsoft and AWS ecosystems with the Partner Manager by expanding relationships, developing co-sell motions, generating partner-influenced pipeline, and positioning BA Insight within enterprise AI initiatives.
• Work across BA Insight Product, Marketing, Customer Success, Services, and KCM leadership to align market strategy, product direction, customer needs, and sales execution.
• Maintain 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 build strong relationships with senior customer and partner executives.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed