Account Executive- AI and Automation

Quandary Account Executive

Quandary helps organizations solve complex operational challenges through AI, automation, operational consolidation, low-code platforms, integrations, and technology-enabled services. We work with teams that are outgrowing manual processes, disconnected systems, fragmented workflows, and legacy tools, helping them build smarter, more scalable ways to run their business.

We are growing our Core business and are looking for a full-cycle Account Executive who can create new relationships, open new opportunities, and help companies modernize operations through AI, automation, and operational consolidation.

About The Role

We are hiring an outbound-focused Account Executive to drive net-new growth for Quandary's Core AI, automation, and operational consolidation business.

This is a hunter role. You will be responsible for identifying target accounts, starting conversations from scratch, developing partner-led opportunities, and running complex B2B sales cycles from prospecting through close.

The initial go-to-market wedge for this role is AI, automation, and operational consolidation. You will focus on companies struggling with manual workflows, disconnected applications, spreadsheet-driven processes, repetitive work, poor visibility, and teams that know they need better automation but do not have a clear path to implement it. From there, you will position Quandary as the partner that can help automate, integrate, consolidate, and modernize the systems that run the business.

This is not a transactional hardware, printer/copier, office equipment, or commodity technology sale. Our clients need a seller who can understand operational pain, identify where AI, automation, and consolidation can create business value, and bring in the right technical and delivery resources at the right time.

What You'll Do

• Build and manage your own outbound pipeline focused on net-new logo acquisition
• Prospect into target accounts using phone, email, Linked In, events, referrals, and partner relationships
• Lead with AI, automation, and operational consolidation pain points such as manual work, repetitive processes, disconnected systems, workflow bottlenecks, reporting gaps, and teams outgrowing their current tools
• Own the full sales cycle from prospecting and discovery through proposal, negotiation, and close
• Work inbound and partner-sourced opportunities from Quickbase, Workato, Dialpad/Broadvoice, advisor relationships, and other ecosystem partners
• Run discovery with executives, operations leaders, IT leaders, and department stakeholders
• Position Quandary's services around business value, automation outcomes, operational consolidation, efficiency, visibility, scalability, and transformation
• Sell core solution areas including AI-enabled workflows, business process automation, low-code applications, systems integration, operational consolidation, and reporting, with opportunities to expand into CCaaS/UCaaS-adjacent workflows where appropriate
• Navigate complex, variable use cases where the solution is not the same every time
• Bring in solution engineers, delivery leaders, and internal subject matter experts to support scoping and feasibility
• Collaborate with leadership on messaging, talk tracks, target accounts, partner strategy, and go-to-market execution
• Maintain accurate pipeline, activity, and forecasting in Salesforce
• Ensure clean handoffs from closed deals into delivery and account management

What We're Looking For

• Proven success in full-cycle B2B sales, especially in AI, automation, SaaS, low-code, integration, consulting, or complex technology-enabled services
• A true outbound hunter mindset, with comfort creating conversations from scratch
• Experience selling to executives, operations leaders, IT leaders, and department stakeholders
• Strong discovery skills and the ability to connect operational pain to automation, consolidation, and business impact
• Ability to sell solutions that are not identical every time and adapt across multiple business use cases
• Comfort selling AI, automation, workflow modernization, operational consolidation, systems consolidation, or business process transformation initiatives
• Ability to…