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  • Shawn Lankton

Startup Exec Search Advice

Updated: Apr 23

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 past 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 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 bring 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 past?

  • 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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