Sales Trainer (AI Enablement)
- Role: Sales Trainer, Phase 2 (AI Enablement)
- Engagement: External contractor, on-site
- Location: Pristina, Kosovo — on-site
- Dates: Mon 17 Aug – Fri 25 Sep 2026 (6 weeks)
- Teaching days: 2 days per week, 1-2 hours per day
- Reports to: Olivia, Program Lead
- Works with: The AI Trainer (technical)
- Comp: Negotiable — propose a number and we'll discuss from there
The program, in brief
The Outsorcy AI Academy prepares people for the SDR role. In Phase 1, interns learn core sales skills, while Phase 2 focuses on carrying out that work with AI. By the end of the program, interns are expected to operate as AI-enabled SDRs who can manage AI-driven sales workflows independently, produce roughly double the output at about half the cost of a rep who is not AI-enabled, and be ready for placement.
Phase 2 centers on practical SDR training. Each intern manages one simulated book of accounts that expands every week — first it is built and scored, then outreach is run on it, then replies are handled, and finally the full process is managed and reviewed for the capstone. Compared with Phase 1, this phase mirrors the real job more closely: longer office days, a short instructional block each day, and most of the time spent actively working the book.
What you'll own
You will be responsible for the sales side of the program. Phase 2 is led by two external trainers: an AI trainer who creates the tools and workflows, and you, who take what is built each week and show interns how to use it in real selling situations. Your focus covers the SDR craft — research and targeting, angle creation and outreach, replies and objections, and pipeline management — all carried out with AI available.
- Lead the twice-weekly sessions and co-teach Week 6 together with the AI trainer.
- Guide interns through practical work on their book, with most of each day devoted to hands-on application rather than lecture.
- Provide feedback on their sales execution — including targeting, messaging, and call handling — so they improve from week to week.
The Week 4 readiness check-in and the tracking of interns' reply and meeting numbers are not part of your scope; those are handled by the program lead and Blake. Your responsibility is the teaching and coaching.
How the two trainers split
The AI trainer (technical) covers how to create the tools and workflows, including agentic loops, integrations, and the prompt library. Your role is to teach how to use what has been built to perform the SDR job. The schedule will be fixed so you can organize your week in advance. The AI trainer leads 2 days each week, you lead 2 days each week, and both of you jointly run Week 6. You are not expected to build any AI infrastructure yourself.
What you'll teach
Your sessions are structured week by week:
1 · Working with AI
- Tuesday: Move from doing the work manually to operating it with AI, using AI as an assistant on real SDR tasks.
- Thursday: Evaluate AI output on real tasks and learn when to rely on it versus when to step in directly.
2 · Research & Targeting
- Tuesday: Focus on fit versus timing — identifying which signals show an account is worth working now and defining the ICP for the book.
- Thursday: Work through the list by validating signals against reality, prioritizing the top accounts, and defending each account choice.
3 · Writing Outreach
- Tuesday: Develop the angle — the main reason an account should care now — and use AI to generate and choose it.
- Thursday: Maintain quality at volume by editing output to a human standard and keeping a person involved in the send.
4 · Handling Replies
- Tuesday: Work on replies and objections, qualification, and deciding where AI should be removed from the loop for the live call. Mon is Labor Day — no session.
- Thursday: Check-in day is run by the program lead / Blake, not by you.
5 · CRM & Pipeline
- Tuesday: Manage the book inside the CRM, with clean logging treated as part of the role.
- Thursday: Read the funnel with AI to identify the leaking stage and the highest-leverage fix.
6 · Capstone
- Tuesday: Co-teach throughout the week with the AI trainer.
- Thursday: Support interns as they run the full motion end to end and present it; certification follows.
What we're looking for
- Real SDR or sales experience. You have done the work yourself and can coach others in prospecting, outreach, reply handling, qualification, and pipeline discipline.
- Comfortable using AI day to day. You already work with tools such as ChatGPT or Claude, a CRM, and sequencing tools. You do not need to build these systems — that is the AI trainer's role — but you should be comfortable working with them. Familiarity with automations, agentic loops, prompt generation, and AI system maintenance is needed.
- A real coach. You can give clear feedback, lead a room of interns through applied work, and assess whether someone can run the motion to the expected standard.
- Comfortable on-site. This is a practical, in-room assignment for six weeks rather than a lecture series. Expect to be in the office up to 5 hours per week.
What success looks like
By 25 September, your interns should be able to run the full sales motion on their book — research, outreach, replies, and pipeline — using AI effectively and with sound judgment about when to use it. The wider objective of the program is to produce AI-enabled SDRs who generate roughly double the output at half the cost; your contribution is to make sure the underlying sales craft is strong. You will be evaluated on teaching and coaching, not on the interns' numbers.
Logistics & comp
- The role is on-site in Pristina, Kosovo, for the full six weeks (Mon 17 Aug – Fri 25 Sep 2026). Mon 7 Sep is Labor Day, so there is no session that day.
- The engagement is an external contract.
- Compensation is negotiable, and you are expected to propose a number for discussion.
Sales Trainer (AI Enablement)
- Role: Sales Trainer, Phase 2 (AI Enablement)
- Engagement: External contractor, on-site
- Location: Pristina, Kosovo — on-site
- Dates: Mon 17 Aug – Fri 25 Sep 2026 (6 weeks)
- Teaching days: 2 days per week, 1-2 hours per day
- Reports to: Olivia, Program Lead
- Works with: The AI Trainer (technical)
- Comp: Negotiable — propose a number and we'll discuss from there
The program, in brief
The Outsorcy AI Academy prepares people for the SDR role. In Phase 1, interns learn core sales skills, while Phase 2 focuses on carrying out that work with AI. By the end of the program, interns are expected to operate as AI-enabled SDRs who can manage AI-driven sales workflows independently, produce roughly double the output at about half the cost of a rep who is not AI-enabled, and be ready for placement.
Phase 2 centers on practical SDR training. Each intern manages one simulated book of accounts that expands every week — first it is built and scored, then outreach is run on it, then replies are handled, and finally the full process is managed and reviewed for the capstone. Compared with Phase 1, this phase mirrors the real job more closely: longer office days, a short instructional block each day, and most of the time spent actively working the book.
What you'll own
You will be responsible for the sales side of the program. Phase 2 is led by two external trainers: an AI trainer who creates the tools and workflows, and you, who take what is built each week and show interns how to use it in real selling situations. Your focus covers the SDR craft — research and targeting, angle creation and outreach, replies and objections, and pipeline management — all carried out with AI available.
- Lead the twice-weekly sessions and co-teach Week 6 together with the AI trainer.
- Guide interns through practical work on their book, with most of each day devoted to hands-on application rather than lecture.
- Provide feedback on their sales execution — including targeting, messaging, and call handling — so they improve from week to week.
The Week 4 readiness check-in and the tracking of interns' reply and meeting numbers are not part of your scope; those are handled by the program lead and Blake. Your responsibility is the teaching and coaching.
How the two trainers split
The AI trainer (technical) covers how to create the tools and workflows, including agentic loops, integrations, and the prompt library. Your role is to teach how to use what has been built to perform the SDR job. The schedule will be fixed so you can organize your week in advance. The AI trainer leads 2 days each week, you lead 2 days each week, and both of you jointly run Week 6. You are not expected to build any AI infrastructure yourself.
What you'll teach
Your sessions are structured week by week:
1 · Working with AI
- Tuesday: Move from doing the work manually to operating it with AI, using AI as an assistant on real SDR tasks.
- Thursday: Evaluate AI output on real tasks and learn when to rely on it versus when to step in directly.
2 · Research & Targeting
- Tuesday: Focus on fit versus timing — identifying which signals show an account is worth working now and defining the ICP for the book.
- Thursday: Work through the list by validating signals against reality, prioritizing the top accounts, and defending each account choice.
3 · Writing Outreach
- Tuesday: Develop the angle — the main reason an account should care now — and use AI to generate and choose it.
- Thursday: Maintain quality at volume by editing output to a human standard and keeping a person involved in the send.
4 · Handling Replies
- Tuesday: Work on replies and objections, qualification, and deciding where AI should be removed from the loop for the live call. Mon is Labor Day — no session.
- Thursday: Check-in day is run by the program lead / Blake, not by you.
5 · CRM & Pipeline
- Tuesday: Manage the book inside the CRM, with clean logging treated as part of the role.
- Thursday: Read the funnel with AI to identify the leaking stage and the highest-leverage fix.
6 · Capstone
- Tuesday: Co-teach throughout the week with the AI trainer.
- Thursday: Support interns as they run the full motion end to end and present it; certification follows.
What we're looking for
- Real SDR or sales experience. You have done the work yourself and can coach others in prospecting, outreach, reply handling, qualification, and pipeline discipline.
- Comfortable using AI day to day. You already work with tools such as ChatGPT or Claude, a CRM, and sequencing tools. You do not need to build these systems — that is the AI trainer's role — but you should be comfortable working with them. Familiarity with automations, agentic loops, prompt generation, and AI system maintenance is needed.
- A real coach. You can give clear feedback, lead a room of interns through applied work, and assess whether someone can run the motion to the expected standard.
- Comfortable on-site. This is a practical, in-room assignment for six weeks rather than a lecture series. Expect to be in the office up to 5 hours per week.
What success looks like
By 25 September, your interns should be able to run the full sales motion on their book — research, outreach, replies, and pipeline — using AI effectively and with sound judgment about when to use it. The wider objective of the program is to produce AI-enabled SDRs who generate roughly double the output at half the cost; your contribution is to make sure the underlying sales craft is strong. You will be evaluated on teaching and coaching, not on the interns' numbers.
Logistics & comp
- The role is on-site in Pristina, Kosovo, for the full six weeks (Mon 17 Aug – Fri 25 Sep 2026). Mon 7 Sep is Labor Day, so there is no session that day.
- The engagement is an external contract.
- Compensation is negotiable, and you are expected to propose a number for discussion.
