Skip to main content

Evaluate & Negotiate Your Startup Offer

Evaluate & Negotiate Your Startup Offer

Offered by Colin B.

Product Lead at Poolside | Scale Your Startup Career Strategically

Boston University Questrom School of Business Logo

Studied at Boston University Questrom School of Business

Poolside Logo

Works at Poolside

Description

Have a startup offer and aren’t sure whether it’s actually a good one? In this session, we’ll evaluate the company, opportunity, compensation, equity, and career upside together — then build a strategy for negotiating the offer if there’s room to improve it. Before or during the session, we’ll work through areas such as: - Cash compensation: Base salary, bonus/OTE, sign-on bonuses, benefits, and how the package compares with your alternatives. - Startup equity: Option or RSU grants, strike price, 409A valuation, preferred valuation, vesting, dilution, and how to think about the potential value of your equity. - Company health: Funding, revenue/growth metrics, runway, investors, customer traction, burn, and the questions worth asking before you join. - Role quality: Scope, title, reporting structure, team, influence, promotion potential, and whether the actual job matches what was sold during interviews. - Career upside: Whether this company and role will increase your future market value — not just what it pays today. - Risk assessment: Leadership, turnover, product-market fit, funding risk, unrealistic growth expectations, and other warning signs. - Negotiation strategy: What to push on, where you have leverage, how much to ask for, and how to frame the conversation professionally. - Your specific decision: We’ll ultimately answer the most important question: Would I take this offer if I were in your position? If appropriate, we can also compare multiple offers or your startup offer against staying in your current role.


What you'll get from this package

A clear assessment of whether the startup itself appears healthy and promising.

A better understanding of what your compensation and equity are actually worth.

A structured view of the risks and upside of taking the job.

An assessment of how the opportunity fits your longer-term career trajectory.

A list of any outstanding questions you should ask before signing.

Specific compensation or equity areas worth negotiating.

A recommended negotiation strategy and target.

A much more confident accept / negotiate / decline decision.


More packages from Colin

Custom hourly · $79/hr

Get help with Competitive Analysis, Resume Review, and .

Colin also coaches for Build with AI, Career Coaching, and Product Management. View all.


Colin B.

Offered by Colin B.

Joined September 2026

Product Lead at Poolside | Scale Your Startup Career Strategically

I've worked across almost every stage of technology company, from 9-person IT shops to MongoDB and AWS, before leaving Big Tech to join Poolside as employee #47. At Poolside, I experienced the startup journey firsthand: rapid growth, building teams and products from scratch, changing roles as the company evolved, working directly with executives, and ultimately navigating a major strategic transaction and company restructuring. I can help people evaluate startup opportunities beyond the headline salary or company hype: stage and runway, equity and dilution, role scope, founder quality, career upside, compensation, risk, and whether joining actually makes sense for where you want your career to go. I'm particularly useful for people deciding whether to leave a larger company for a startup, comparing multiple offers, negotiating startup compensation, or trying to understand what working at an early-stage company is really like.

Experience level: Director

$125

1h–2h of coaching