AI Sales Engineer

ConnectWise is an industry and Global leading software company with over 3,000 colleagues in North America, EMEA and APAC. As a community-driven software company dedicated to the success of technology solution providers, our suite helps over 45,000 of our partners manage their businesses better, sell more efficiently, automate service delivery, and remotely control technology so they can consistently deliver amazing customer experiences.

Our company is powered by our connections, our colleagues, and our community. And, we accept all kinds.

Game-changers, innovators, culture-lovers—and humankind.

We invite discovery and debate. We recognize key moments as milestones.

We see you and value you for your unique contributions. Our inclusive, positive culture lays the foundation to ensure every colleague is valued for their perspectives and skills, giving you the choice of how YOU make a difference.

Curious? Read this opportunity to learn how YOU can make a difference at ConnectWise!

General Summary:

The AI Sales Engineer is a highly skilled, consultative technical sales professional responsible for driving new business and expanding existing accounts through expertise in artificial intelligence, automation, and data-driven solutions. This role evaluates customer needs, identifies opportunities for AI adoption, and demonstrates how our AI platform and services deliver measurable business value. AI Sales Engineers articulate the company’s value proposition, provide technical guidance throughout the sales cycle, and relay customer insights to influence future product development. They leverage deep technical knowledge of AI/ML technologies, automation workflows, and data infrastructure to support sales efforts, generate pipeline, and ensure successful customer onboarding and implementation.

Essential Duties and Responsibilities:

• Represent both the technical and functional aspects of our AI platform, automation tools, and integrated partner solutions, clearly articulating how they address customer challenges.

• Deliver high-impact technical demonstrations, product walkthroughs, and presentations tailored to both technical and business audiences.

• Lead proof-of-concepts (POCs) and pilot engagements that showcase the value of AI models, automation workflows, and data-driven insights.

• Translate customer requirements into scalable AI solution designs, including model selection, data integration, workflow automation, and deployment considerations.

• Develop and execute standard or customized POCs, trials, and sandbox environments to help prospects evaluate AI capabilities.

• Work independently or collaboratively with sales teams to position AI solutions in a consultative manner, guiding customers through capability assessments and ROI analysis.

• Prepare and contribute to technical RFP/RFQ responses, including architecture diagrams, integration plans, and security documentation.

• Serve as a key technical resource for revenue teams by providing product expertise, training, coaching, and ongoing support.

• Maintain a strong understanding of AI sales methodologies, including objection handling, business case development, and technical deal qualification.

• Stay current on AI/ML technologies, LLM advancements, automation frameworks, and industry trends through continuous learning.

• Maintain excellent CRM hygiene by documenting all activities, technical notes, and engagement details throughout the presales cycle.

Knowledge, Skills, and/or Abilities Required:

• 3+ years of experience as a Pre-Sales Engineer, Solutions Architect, or Technical Consultant supporting AI, ML, automation, or data-driven products.

• Proven track record in technical sales with the ability to identify opportunities, influence stakeholders, and drive complex technical evaluations.

• Strong understanding of AI/ML concepts, including model training, inference, vector databases, data pipelines, and prompt engineering.

• Working knowledge of cloud platforms (Azure, AWS, GCP), APIs, data integration, and automation frameworks.

• Familiarity with LLMs, generative AI, RAG architectures, and enterprise AI deployment patterns.

• Ability to evaluate competitive AI solutions and articulate strengths, weaknesses, and differentiators.

• Experience working with MSPs, VARs, technology service providers, enterprise IT, or AI-focused solution partners.

• Excellent communication and interpersonal skills with the ability to simplify complex technical topics.

• High energy, curiosity, adaptability, and a collaborative mindset.

• CRM experience (Salesforce or equivalent).

Working Conditions:

• Professional office or remote work environment.

• Occasional extended hours to meet deadlines, support customer evaluations, or attend events.

• Fast-paced atmosphere within a rapidly evolving AI technology landscape.

• Travel of 20% or more may be required.

ConnectWise is an Equal Opportunity Employer, dedicated to building a diverse and inclusive workforce and providing a workplace free from discrimination and harassment. ConnectWise provides equal employment opportunities to all employees and applicants without regard to race, ethnicity, color, religion, age, sex (including pregnancy), sexual orientation, gender, gender identity or expression, ancestry, national origin, citizenship status, physical or mental disability, genetic information, military/veteran status, marital status, familial or parental status, or any other characteristic or status protected by applicable federal, state and local laws.

The statements above are intended to describe the general nature and level of work being performed by individuals assigned to this job. Other duties may be assigned as needed. Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions of the job and/or to receive other benefits and privileges of employment. If you need a reasonable accommodation for any part of the application and hiring process, please contact us at [email protected] or 1-800-671-6898.