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UPSKaiLL

A 24/7 career coach that builds a learning path to your next role.

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EducationFreemiumWe checked the prices on upskaill.ai on 27 Sep 2026.

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What is UPSKaiLL?

A 24/7 career coach that builds a learning path to your next role.

Who is UPSKaiLL best for?

UPSKaiLL is best for people in Canada and the US moving into a new role who want an AI coach and a learning plan.

  • Career changers

    A coaching conversation maps your skills against 55,000+ roles and shows which ones you are already close to and which gaps matter most.

  • People eyeing new AI-era jobs

    It tracks 300+ emerging roles, such as AI security engineer or battery storage technician, that older job data does not list yet.

  • Self-paced learners

    Each learning journey mixes lessons, flashcards, mind maps and projects, with difficulty that adapts to how you are doing.

  • Active job seekers

    It filters 160M+ postings down to your target role, location and work preferences and links to each employer's application.

How much does UPSKaiLL cost?

UPSKaiLL starts with a 7-day free trial that needs no card, then Pro costs $29 a month and Ultra $59 a month in the US, or $22 and $44 a month billed yearly.

Pro$29Per month
  • 25 AI career coach conversations a month
  • Coaching interview, skills analysis and a personal learning journey
  • Career matching and job search
Ultra$59Per month
  • Unlimited AI career coach access
  • More new learning journeys and revisions each month
  • Advanced career analytics and priority support

These are US prices in US dollars; in Canada Pro is $34 CAD and Ultra $74 CAD a month. Billed yearly, Pro is $22 and Ultra $44 a month in the US ($26 and $55 CAD in Canada). The 7-day trial needs no card, ends without a charge if you do not pick a plan, and is limited to one per person. Taxes are extra where they apply. Full pricing on upskaill.ai. We checked these prices on .

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What are the best UPSKaiLL alternatives?

One tool on Recaply does UPSKaiLL's job.

Questions about UPSKaiLL

What is UPSKaiLL?

A 24/7 career coach that builds a learning path to your next role.

Who is UPSKaiLL for?

UPSKaiLL is best for people in Canada and the US moving into a new role who want an AI coach and a learning plan.

Is UPSKaiLL free?

No, UPSKaiLL is a paid subscription, but it starts with a 7-day free trial that needs no card. The trial includes coach conversations and a Career Snapshot of your best-fit roles; if you do not pick a plan, it ends and nothing is charged.

How much does UPSKaiLL cost?

UPSKaiLL's paid plans are Pro at $29 per month and Ultra at $59 per month.

What are the best UPSKaiLL alternatives?

The closest alternatives on Recaply are COACH by CareerVillage.

Where can I try UPSKaiLL?

On its official website, upskaill.ai.

Does UPSKaiLL offer refunds?

Usually not. UPSKaiLL does not refund a billing period once it has started, except where the law requires it, after a billing error or in exceptional cases, and you must ask within 14 days of the charge. You can cancel at any time and keep access until the paid period ends.