Senior Account Executive

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? 

RightAnswers is Upland’s AI‑powered knowledge management platform used by large, complex enterprises to speed troubleshooting, standardize processes, and elevate customer and agent experiences. It’s KCS v6 verified and offers flexible AI options—including “bring your own AI”—plus 30,000+ pre‑packaged Knowledge‑Paks to accelerate time‑to‑value. If you thrive on selling strategic, multi‑stakeholder solutions and want to shape how enterprises operationalize AI in the contact center and service desk, this role is for you. 

You’ll step into a category with clear product‑market fit and active go‑to‑market momentum—marketing has increased organic reach and engagement, and sales pipeline productivity has been trending upward—giving you strong air cover to build and close net‑new, enterprise‑scale deals.

Primary Responsibilities 

• Own the full enterprise sales cycle from territory planning and prospecting to multi‑threaded discovery, executive alignment, business case creation, commercial negotiation, and close.


• Create qualified pipeline via a mix of targeted outbound, event follow‑up, ABM plays, and collaboration with SDRs/Marketing; rigorously track progress in Salesforce with clean hygiene and forecast accuracy.


• Lead consultative discovery with Operations, Support, CX, and IT stakeholders to uncover knowledge/workflow gaps, AI enablement requirements, and success metrics; translate into solution roadmaps and win themes.


• Build compelling value cases (TCO/ROI, KPI impact on FCR, AHT, CSAT, adoption) and navigate legal, security, and procurement to remove friction and accelerate agreements.


• Orchestrate resources (Solutions Consulting, Product, Services, Customer Success, Marketing, and Partners) to run tailored demos, POCs/pilots, and reference calls that de‑risk complex programs.


• Partner‑led growth: align with channel and alliance partners to expand reach within target accounts and co‑sell into strategic opportunities.


• Land and expand: secure initial wins and drive expansion across use cases (agent assist, self‑service, knowledge creation/governance) and adjacent teams/regions.


• Be the voice of the customer back to Product and Marketing—especially around AI authoring, integration patterns, and KCS practices—to influence roadmap and content.

Requirements 

• Proven enterprise hunter/closer with consistent achievement against new‑logo and expansion targets selling B2B SaaS into complex, multi‑stakeholder environments.


• Fluent in value‑based, MEDDICC‑style selling, multi‑threading, and executive storytelling; expert in running structured evaluations/POCs and building hard‑dollar business cases.


• Domain familiarity with Knowledge Management, Contact Center, Service Desk/ITSM, or adjacent CX/EX workflows (e.g., Salesforce, ServiceNow, Zendesk, ITIL/KCS).


• Credible on AI—able to discuss AI authoring vs. retrieval/search patterns, data governance, and integration choices (embedded AI vs. BYO‑AI) with technical and business leaders.


• Operational rigor: exceptional pipeline discipline, forecasting accuracy, and command of Salesforce and sales collaboration tools.


• Excellent communication (written, verbal, and presentation) with the executive presence to influence VP/C‑level stakeholders.


• Travel as needed to customers, partners, and events.

Desired Skills 

• Experience selling into large, complex enterprises in high‑tech or financial services (our core ICP).


• Knowledge of KCS practices (certification a plus) and exposure to knowledge governance/curation programs.


• Familiarity with CCaaS/CRM/ITSM ecosystems (e.g., Genesys/NICE/Five9; Salesforce/ServiceNow).


• Comfort collaborating with partners and alliances to source/influence pipeline and co‑sell into strategic accounts.

Why this role? 

You’ll sell a differentiated, AI‑forward solution that enterprises already trust, backed by a roadmap doubling down on AI for content authoring/governance and flexible integration into customers’ tech stacks—exactly where the market is headed. You’ll have strong marketing tailwinds and clear ICP focus, with the ability to shape outcomes for marquee brands

Upland Software is an Equal Employment Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status or other legally protected status.