This is a set of ideas, advice, and questions I put together for several friends that have asked for advice in how to structure their job search and negotiate/evaluate offers. This is primarily geared toward those seeking exec roles in startup or growth-stage companies, but elements might be useful for all kinds of job searches. I’ve been sending it out more frequently so I wanted to share it here for anyone that it might help!

Starting your search

Have a specific role/company in mind
* You can’t just be looking for “a great role at a great company”
* Get specific about the job title, industry, company size
* People will only be able to help if they can put you in a box

Know your story
* Have a quick-quick bio you can tell/give people
* Give your specific target (above)
* Talk about why that target is important to you
* Be aware of potential objections (“you haven’t done this before”)
* Prepare potential responses for each of these
* Look for unique pat experiences that make you “perfect”

Know your value prop
* Have a clear idea of how you’ll add value in the role/company you want
* Nobody wants an executive that will “do what they’re asked”
* Ideally you tie this value to “enterprise value” (more rev, more profit, faster growth)
* You should have a plan and a reason why you’re better than others

Get in touch with recruiters but don’t count on them
* Recruiters are very “title focused”
* If you aren’t changing titles, they can be helpful
* If you’re changing titles/roles probably not…
* Get in touch with top recruiters and share “updates” every 6 weeks

Say “yes” a lot, but communicate honestly
* Go on every interview, take every meeting… why not!
* Don’t exaggerate your interest to potential employers
* Share accurate timetables, requirements, comp expectations, etc.

Target specific companies
* Based on your specific role/company profile pick 5-10 “ideal” companies
* Know your value prop for each one and why you’re excited about them
* If you can’t find enough companies, your target might be too narrow

Work the funnel
* I wrote each company name down on a sticky note and made a kanban
* “Targeted”, “Introduced”, “Discussing”, “Selected as Candidate”, “Negotiating”, “Hired”
* Every day, I worked on moving cards forward in the funnel
* If you get too many “no’s” then add more companies to the top

Expect the process to take a while – be patient
* Hiring execs takes a lot of bandwidth and comes with lots of risk for the company
* Nobody hires execs when everything is fine…
* Expect the role to have been previously neglected or occupied by a bozo
* Exiting/demoting a predecessor can be tricky
* Creating budget for an expensive new hire can be tricky
* Executive roles often require board approval and exec team consensus

Evaluating / negotiating an offer

Things to know about the role:
* Will you like what you’re doing?
* Will you be good at what you’re doing?
* Does what you’re doing move your career in the right direction?
* Do you have a clear idea of “what is success”?
* Who will you depend on to be successful?
* Will you have what you need to be successful? (Budget, autonomy, support)

Things to know about the company:
* How does this company affect your career “story”?
* Do you think, “this is brilliant” wrt the business model/idea?
* Is this a “need to have” for customers or a “nice to have”?
* Is the plan straightforward and achievable or a “tricky bank shot”?
* Is the problem they’re solving big enough and interesting to you?
* Is there an exit strategy? If so what is it?
* Where is the company strongest?
* Where is the company weakest?

Things to know about the industry:
* Are there external trends that will grow the industry?
* What competition will you face from incumbents/upstarts?
* Which adjacent industries are affected by this business?
* Will those other industries want to help or hinder this business?
* What are new technologies that could put your industry at risk?
* What are potential regulations that could put your industry at risk?
* What are other potential trends that could put your industry at risk?

Things to know about your boss and the team:
* Do you negotiate well together (respectfully, productively)?
* Are their expectations aligned with yours?
* Do you like their personal style?
* Do you respect them?
* Do you want to spend time with them?
* Do you feel like you can learn from them?
* How is the culture and team that they built?

Things to know about the investors/board:
* What is the funding history of the company?
* How capital intensive is the business? How much runway is there?
* Any red-flags like down-rounds or founder drama?
* Are there “name brand” investors in the company?
* What value would the CEO say the investors bringing to the table?
* Where do board voting rights sit? Who’s really in charge?
* What is the investment thesis of the folks in charge?
* How does that thesis line up with the CEO’s strategy?
* What is the relationship of the CEO and the board?

Things to know about the offer:
* Is the cash comp fair/sufficient (assume there’s no equity)
* How are bonus targets set? Has management achieved in the pat?
* Is the equity comp fair/sufficient (look for comps)?
* How is the cap table set up (who gets paid first)?
* What is your strike price, what are others’ strike prices, what’s current value estimate?
* How quickly does your equity vest?
* What happens in a change of control?

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