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?