Sales Instructor / Trainer (B2B/SaaS, confident with AI) at Skills U

About Skills Union

Skills Union combines workforce technology and training delivery to help employers, universities and governments achieve measurable, long-term employment outcomes. Our work spans three areas: talent strategy, industry-aligned training, and technology. We design programmes mapped to real job roles and the AI capabilities employers now expect, then deliver them at scale across institutions, regions, and delivery models.

This role sits within our training delivery practice. It is an onsite role based in Australia. You must have the right to work in Australia. Freelance and contract positions are available.
 

About The Role

We are looking for a commercially sharp Technical Sales Enablement Trainer to deliver training programs that equip our channel partners with the skills to effectively identify, qualify, and convert opportunities for OpenAI Codex and OpenAI's frontier AI platforms.

This role is designed for someone who combines deep sales methodology expertise with enough technical fluency to credibly position AI products in enterprise conversations. You should be comfortable teaching partner sales teams how to build ideal customer profiles for AI adoption, develop buyer personas across technical and business stakeholders, run effective discovery conversations that surface AI readiness and pain points, qualify leads using structured frameworks, handle objections specific to enterprise AI procurement, and articulate the value of Codex and frontier AI platforms in terms that resonate with CTOs, engineering leaders, digital transformation heads, and senior business decision-makers.

The ideal candidate does not need to be a deep AI researcher, but must understand the Codex and frontier AI value proposition well enough to train partners on positioning, use-case mapping, and commercial storytelling. You should be able to translate sales strategy and methodology into clear, practical learning experiences that help partners improve pipeline quality, shorten sales cycles, increase win rates, and build lasting client relationships around AI adoption.

 

Key Responsibilities:

• Training Delivery: Deliver high-quality, engaging workshops and training sessions for channel partner sales teams covering customer qualification, persona development, discovery techniques, objection handling, value selling, and pipeline management — all in the context of selling OpenAI Codex and frontier AI platform adoption.
• Customer Qualification Frameworks: Teach partners how to apply structured qualification methodologies (such as BANT, MEDDIC, CHAMP, or SPIN) to assess prospect fit for AI adoption, including technical readiness, organisational appetite for AI, buying authority, budget alignment, and decision timelines.
• Ideal Customer Profile & Persona Development: Guide partners through defining ideal customer profiles for Codex and frontier AI adoption, including firmographic indicators (industry, company size, engineering team maturity, existing tech stack) and building detailed buyer personas across technical decision-makers (CTOs, VP Engineering, platform teams), business decision-makers (COOs, digital transformation leads), and influencers (product managers, senior developers, L&D leaders).
• Discovery & Needs Analysis: Train partners on how to conduct effective discovery conversations that uncover AI-relevant pain points such as developer productivity bottlenecks, software delivery speed, knowledge work inefficiencies, manual workflow overhead, and innovation capacity — and connect these to Codex and frontier AI capabilities.
• Value Proposition & Use-Case Mapping: Help partner teams articulate the value of OpenAI Codex (AI-assisted code generation, debugging, test writing, code review, codebase exploration, delegated coding tasks) and frontier AI platforms (reasoning models, multimodal capabilities, agentic workflows, retrieval, automation) in practical business terms. Teach partners how to map specific client pain points to relevant AI use cases.
• Client-Facing Facilitation: Lead training sessions with confidence for mixed audiences, including partner sales representatives, account managers, solutions consultants, business development leads, and senior commercial leaders.
• Curriculum Customisation: Adapt training content, role-plays, case studies, and exercises to suit each partner's market, vertical focus, sales maturity, and the types of clients they serve.
• Sales Simulations & Role-Plays: Design and facilitate realistic sales scenarios, mock discovery calls, qualification exercises, and pitch simulations centred on selling AI adoption to enterprise buyers with varying levels of technical sophistication and AI readiness.
• Objection Handling for AI Sales: Equip partners to handle common objections specific to enterprise AI procurement, including concerns around data privacy, security, intellectual property, hallucination risk, ROI uncertainty, integration complexity, workforce displacement fears, and organisational change readiness.
• Consultative Discovery: Work with partner stakeholders to understand current sales capabilities, performance gaps, market positioning, and desired commercial outcomes before and during delivery.
• Learner Support: Guide learners through hands-on activities, provide real-time coaching during role-plays, and help participants build confidence in positioning AI products in live selling environments.
• Assessment & Feedback: Evaluate learner progress through exercises, call reviews, pipeline audits, and reflections. Provide clear recommendations for ongoing skill development and sales process improvements after training.
• Sales Tools & Technology: Introduce best practices for using CRM systems, sales engagement platforms, pipeline tracking tools, and AI-assisted selling tools to support qualification and follow-up workflows.
• Continuous Improvement: Stay current with OpenAI product updates, Codex capabilities, frontier model releases, evolving enterprise AI buyer behaviour, and partner enablement best practices. Continuously improve course materials and delivery based on learner feedback and commercial results.

Required Skills & Qualifications:

• Sales Methodology Expertise: Deep working knowledge of established sales qualification and discovery frameworks such as MEDDIC, BANT, SPIN Selling, Challenger Sale, CHAMP, Sandler, or Solution Selling. Ability to teach these frameworks in practical, applied contexts rather than purely theoretical terms.
• Experience: Minimum 3–5 years of experience in B2B sales, sales enablement, sales training, channel/partner enablement, revenue operations, or related commercial roles — ideally with exposure to selling technology, SaaS, developer tools, or enterprise software. A track record of either carrying a quota or directly enabling teams who do.
• Technical Product Fluency: Sufficient understanding of AI platforms, developer tools, and software development workflows to credibly train partners on positioning OpenAI Codex and frontier AI capabilities. You do not need to be an engineer, but you must be able to speak confidently about use cases, value drivers, and technical buyer concerns.
• Qualification & Pipeline Skills: Demonstrated ability to teach structured lead qualification, opportunity scoring, pipeline hygiene, and deal progression. Comfortable coaching teams on how to disqualify early, prioritise high-value opportunities, and maintain forecast accuracy.
• Buyer Persona & ICP Development: Experience building or teaching others to build ideal customer profiles and multi-stakeholder buyer personas grounded in real market data, customer research, and commercial strategy — particularly for technology or platform sales involving both technical and business buyers.
• Discovery & Consultative Selling: Strong ability to model and teach effective discovery conversations, including open-ended questioning, active listening, pain-point mapping, stakeholder mapping, and needs-to-solution alignment.
• Objection Handling & Negotiation: Skilled at teaching techniques for handling common sales objections, reframing value, navigating procurement processes, and closing with confidence — particularly in enterprise technology and AI contexts.
• Communication & Facilitation: Outstanding verbal and written communication skills. Comfortable leading engaging, interactive workshops for audiences ranging from junior sales reps to senior commercial leaders.
• Coaching & Feedback: Proven ability to observe sales behaviours, provide constructive real-time coaching, and deliver actionable developmental feedback in group and one-on-one settings.
• Commercial Acumen: Able to connect sales skills training to measurable business outcomes such as pipeline growth, conversion rate improvement, average deal size, sales cycle reduction, and partner revenue contribution.
• CRM & Sales Tool Literacy: Familiarity with CRM platforms (e.g., Salesforce, HubSpot) and sales enablement tools. Ability to teach partners how to use these tools to support qualification workflows and pipeline visibility.
• Adaptability: Comfortable working across different partner organisations, industries, and sales maturity levels. Able to adjust training depth, examples, and pace to meet diverse learner needs.
• Instructional Design Awareness: Ability to design or co-design exercises, role-plays, case studies, and assessment rubrics. Experience creating learner-facing materials such as playbooks, cheat sheets, and quick-reference guides is a plus.

Other Skills:

• Excellent English communication skills, both verbal and written. 
• Strong executive presence and confidence when working with corporate clients.
• Ability to support learners from mixed backgrounds, including business users, junior developers, senior engineers, and transformation teams.
• Comfortable delivering in-person, hybrid, and online workshops.
• Strong customer service orientation with a focus on learner experience and client outcomes.
• Ability to collaborate well within a diverse, cross-cultural team environment.

Qualifications:

• A diploma or degree in business, marketing, communications, psychology, education, or a related field is preferred. 
• Equivalent professional experience in B2B sales, sales management, sales enablement, or commercial training will also be considered. 
• Prior experience training partner or channel sales teams, running sales workshops, or supporting go-to-market enablement programs is highly desirable — particularly in technology, SaaS, developer tools, or enterprise AI contexts. 
• Certifications in sales methodologies (e.g., SPIN, Sandler, Challenger, MEDDIC) or instructional design will be a strong advantage.

This role is crucial for helping channel partners move beyond general AI enthusiasm into disciplined, high-quality selling. The Sales Enablement Trainer will equip partner teams not only with a clear understanding of what OpenAI Codex and frontier AI platforms can do, but with the commercial skills to identify the right buyers, ask the right questions, qualify opportunities effectively, and articulate AI value in terms that resonate with both technical and business decision-makers. By building partner confidence and sales capability, this role directly accelerates enterprise AI adoption and drives sustainable revenue growth across the partner ecosystem.

The Four Agreements (how we show up and hold each other accountable):

• Be Impeccable With Your Word. Speak with integrity. Say only what you mean. Avoid using the word to speak against yourself or to gossip about others. Use the power of your word in the direction of truth and love.
• Don't Take Anything Personally. Nothing others do is because of you. What others say and do is a projection of their own reality, their own dream. When you are immune to the opinions and actions of others, you won't be the victim of needless suffering.
• Don't Make Assumptions. Find the courage to ask questions and to express what you really want. Communicate with others as clearly as you can to avoid misunderstandings, sadness and drama. With just this one agreement, you can completely transform your life.
• Always Do Your Best. Your best is going to change from moment to moment; it will be different when you are healthy as opposed to sick. Under any circumstance, simply do your best, and you will avoid self-judgement, self-abuse and regret.

Rules of Engagement

• Be On Time - Respect other people’s time
• Be Present - Active listening, phones off and away
• Effective Meetings - Always have a POAD: Purpose, Outcomes, Agenda, Decisions.
• Diversity & Inclusion - All voices represented, All voices heard
• Take a Stand - Hold ourselves and each other accountable

Skills Union is an equal opportunities employer and actively encourages applications from all backgrounds.