Evaluate & Negotiate Your Startup Offer
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's included
- 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.
Meet your expert
Colin B.
Product Lead at Poolside | Scale Your Startup Career Strategically
I've spent my career at the intersection of technology, customers, and product, from small IT consulting firms to MongoDB, AWS, and most recently Poolside, where I joined as the company's first Solutions Architect and later moved into Product leadership. At Poolside, I helped build the global Solutions Architecture organization from 0 to 7 before identifying an opportunity around sovereign AI, building the first prototype myself, and ultimately leading the resulting product line. Over roughly 14 months, we grew it to ~$3M ARR and 40+ deployments across enterprise, government, and highly regulated environments. I've made several career transitions myself, from IT consulting → Sales Engineering → Solutions Architecture → Product, and I've interviewed extensively across startups and large technology companies. I have an MBA from Boston University and particularly enjoy helping people think through career positioning, technical interviews, compensation, startup opportunities, and how to move between technical, product, and customer-facing roles. I'm also an active builder. Outside of work I've launched my own AI-powered market analytics SaaS and built an open-source agent harness. For anyone looking to understand or build with AI, I'm happy to work hands-on across LLMs, agents, cloud architecture, product strategy, and turning an idea into something real.
