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Break Into AI - Create Your Career Transition Plan

Break Into AI - Create Your Career Transition Plan

Offered by Colin B.

Product @ Poolside | Strategic Career Development for Tech Professionals

Boston University Questrom School of Business Logo

Studied at Boston University Questrom School of Business

Poolside Logo

Works at Poolside

Description

Want to move into AI but aren't sure where your existing experience fits? You don't need to become an ML researcher to build a career in AI. Companies increasingly need product managers, solutions architects, engineers, forward deployed engineers, technical GTM leaders, consultants, and operators who understand how to apply AI to real problems. In this session, we'll take your existing experience and create a realistic strategy for repositioning your career toward AI. We'll work through: - Your current profile: Your experience, technical skills, domain expertise, strengths, gaps, and career goals. - AI career landscape: Which roles exist and which ones actually make sense for your background. - Role selection: Whether you should target AI product, solutions architecture, FDE, engineering, technical GTM, strategy, or another path. - Gap analysis: What you're currently missing — and which perceived gaps actually aren't important. - AI knowledge: Which concepts and technologies you should understand for your target roles without wasting months studying unnecessary material. - Hands-on experience: Projects you can build to demonstrate practical AI experience even if your current employer isn't giving you that opportunity. - Positioning: How to reframe your existing experience so recruiters and hiring managers understand why it's relevant to AI. - Resume & LinkedIn direction: What should become more prominent, what should be de-emphasized, and which keywords or experiences matter. - Company targeting: Which types of AI companies and stages are likely to value your particular background. - Job-search strategy: How to overcome the classic problem of needing AI experience to get a job that gives you AI experience. - Concrete roadmap: What to do over the next several weeks or months to become a substantially stronger candidate. This is particularly useful for people coming from software, cloud, solutions architecture, sales engineering, product, consulting, enterprise technology, or adjacent technical backgrounds.


What you'll get from this package

A clearer picture of where you fit within the AI job market.

A shortlist of roles that make sense for your background.

An honest assessment of your biggest skill and experience gaps.

A prioritized learning plan focused on what actually matters.

Ideas for practical AI projects that can strengthen your candidacy.

Recommendations for repositioning your resume and professional story.

A strategy for identifying companies where your existing experience is an advantage.

A concrete roadmap for making the transition rather than simply “learning more AI.”


Colin B.

Offered by Colin B.

Joined September 2026

Product @ Poolside | Strategic Career Development for Tech Professionals

I've spent 12+ years in technology and have made many of the career transitions I now enjoy helping others navigate: IT consulting → Sales Engineering → Solutions Architecture → AI → Product leadership. Along the way I've worked everywhere from 9-person companies to MongoDB and AWS, joined Poolside as an early employee, built a global Solutions Architecture team from 0 to 7, and eventually moved into Product leadership. I've hired and interviewed candidates, built hiring processes and interview loops, negotiated compensation, and gone through extensive interview processes myself across Big Tech and startups. I'm particularly well suited to helping people break into or advance within technical, Product, Solutions, cloud, and AI careers. Whether you're choosing between opportunities, repositioning your experience for a career change, preparing for interviews, improving your resume, or negotiating an offer, my goal is to give you practical advice from someone who has actually been on both sides of the table.

Experience level: Director

$125

1h 30m of coaching