Sales Specialist – Applications & AI

About the role

This role sells Application Managed Services and AI offerings at Ensono, owning bookings targets, prospecting new application and AI conversations, and partnering with Account Executives and Client Partners on account plans. It suits a quota-carrying enterprise technology seller with at least 7 years of experience, including 3 years selling application services and direct experience selling AI, data or intelligent automation solutions.

What you'll do

• Own and deliver quarterly and annual bookings targets for Application Managed Services and AI, across overlay opportunities and self-sourced pipeline.
• Prospect for and open application and AI conversations with C-level, application and business unit leaders, including in accounts without existing application or AI services.
• Partner with Account Executives and Client Partners on account plans that expand Ensono's role into application, data and AI layers.
• Lead deal strategy from first conversation through contract, including qualification, solution shaping, business case and close.
• Use focused entry engagements such as application observability reviews, AI-assisted code assessments, data-readiness assessments and AI proofs of value to convert into recurring managed services.
• Forecast accurately, keep CRM current, and report pipeline health, risks and upside to leadership.
• Act as a trusted adviser on running, modernizing and improving critical applications across mainframe, cloud and hybrid estates, and how AI can improve them.
• Translate technology outcomes into business terms that CIOs, CFOs and business leaders will fund.
• Facilitate discovery conversations, workshops and assessments with technical, operational and executive stakeholders.
• Position AI-enabled operations, including predictive incident detection, AI-driven root cause analysis, intelligent change-risk scoring and automated remediation, as part of Ensono's application run model.
• Position AI Managed Services and connect consulting opportunities to ongoing recurring services.
• Build business cases, ROI models and commercial proposals, including SLA- and outcome-based structures.
• Address responsible AI, security, data governance and regulatory considerations with clients in highly regulated industries.
• Orchestrate Solution Architects, AI and data specialists, delivery leaders and partners to design deliverable and profitable solutions.
• Lead solution positioning, proposal development, pricing discussions, presentations and contract negotiations.
• Work with hyperscaler and AI technology partners on joint account planning, co-selling and partner-funded programs.
• Raise application and AI fluency across the sales organization through enablement and mentoring.
• Bring client feedback, competitive intelligence and win/loss insights back to portfolio, product and AI teams.
• Partner with marketing and portfolio teams on campaigns that build application and AI pipeline.
• Support strategic growth initiatives and other responsibilities as assigned.
• Actively identify barriers to customer success and help develop strategies that improve client outcomes.
• Advocate for client needs while balancing business objectives and operational realities.
• Use AI in own selling, including account research, meeting preparation, proposal development and pipeline analysis, and share what works with the team.
• Drive client conversations by leading with the client's business outcomes, particularly around AI, and work with the internal Ensono team to design a solution.
• Maintain an informed view of client priorities, competitive activity, and the fast-moving AI and application services market.
• Mentor sellers on how to find and qualify opportunities.

What you'll need

• Bachelor's degree from a four-year college or university or equivalent work experience.
• Experience within a managed services provider, consulting organization, systems integrator, or technology services company.
• A consistent record of meeting or exceeding quota on complex, multi-year services deals, including self-sourced opportunities.
• Direct experience selling AI, data or intelligent automation solutions (such as generative or agentic AI use cases, AIOps, or data platforms supporting AI), and the ability to explain what made those deals succeed beyond the pilot stage.
• Working knowledge of how modern applications are built, run and supported, including SDLC, Agile, CI/CD, ITIL-based service management, observability and SRE practices.
• Familiarity with cloud platforms including AWS, Microsoft Azure, and Google Cloud.
• Proven ability to engage and influence senior executives, including CIOs, CTOs, CFOs and business unit leaders, and to build business cases tying technology investment to financial and operational outcomes.
• Experience in a sales specialist, overlay, or solution sales role, with proven ability to influence without direct authority across a matrixed organization.
• Strong verbal, written, presentation and executive communication skills, with strong analytical and problem-solving ability.
• Personal fluency with AI tools in day-to-day work and curiosity to keep pace with a fast-moving market.
• Proficiency with CRM tools, Microsoft Office applications, and sales enablement platforms.
• Experience selling application services such as application managed services, application modernization, application development and support, or DevOps/SRE services, for at least 3 years.
• 7+ years of quota-carrying enterprise technology sales experience.

Nice to have

• Experience selling application services or modernization for mainframe or other legacy platforms alongside cloud.
• Experience selling AIOps, observability or AI-enabled IT operations services.
• Familiarity with emerging AI engineering practices such as specification-driven development, AI agent orchestration and workflow design, and Model Context Protocol (MCP) server architectures.
• Familiarity with data governance, data mesh, data warehousing and data virtualization.
• Experience structuring SLA-, XLA- or outcome-based commercial models.
• Experience selling into regulated industries such as financial services, insurance, healthcare or the public sector.
• Experience working with large enterprise and mid-market clients and participating in large, strategic, multi-service transformation programs.
• Relevant certifications in cloud, AI, application or managed services technologies.
• Experience with data, AI and infrastructure-stack selling as part of managed services, and experience participating in large transformation programs.

Benefits listed by Ensono

• Unlimited paid days off
• Three health plan options
• 401(k) with company match
• Dental, vision, short and long-term disability, life and AD&D coverage, and flexible spending accounts
• Family forming benefit including fertility coverage and adoption/surrogacy reimbursement
• Paid childbearing and paternal leave
• Education reimbursement, student loan assistance or 529 college funding
• Sabbatical leave
• Wellness program
• Flexible work schedule
• Role-based sales incentive plan
• Associate Equity Appreciation Program equity grant

Tools & skills mentioned