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Career Stategy

Updated: Jun 21

People often focus just on the next role instead of thinking strategically about their career.  Our Whispered playbooks provide tactics but we also wanted to share a resource to guide how you think about your career beyond just this next job.


This article is written for GTM (Sales, Marketing, CS, RevOps..) leaders but can apply broadly to anyone thinking strategically about their career.


Have a strategy

Don’t just take the most interesting / highest-paying job.  Think about where this job will lead you.  

  • Have a career thesis that guides your career

  • It is good to specialize and define a clear niche rather than stay a generalist

  • You don’t want to end up with a custom job search for the rest of your career because you take ambiguous roles

  • Do you have clarity on the long-term strategy for your career and what C-Level role you are building to

  • Have you thought about how your career builds beyond W2 work and what your Career 2.0 might look like?


Think about the core skill set you are building and how that will translate to other companies:

  • What additional skills will you need to build to grow to a C-level leader in that function

  • What buyers do you know how to sell to

    • PLG is very different than enterprise

    • We often suggest avoiding selling to doctors / lawyers / teachers

    • Can you sell other products to the same buyer at other companies


Leverage this thinking to help you build your target list of companies.


Pick the right companies

“If you consistently make poor choices in companies, it does reflect badly on you.”  Top VC Talent Partner 

There definitely are times to take a chance on what could be a breakout company.  Whispered can help you find and network into these companies, especially if you can define a target company list.


But if you always go early-stage and don’t have a hit (IPO, significant M&A exit), you will find you’ll struggle later in your career.  Be conscious of the logos on your resume:

  • Consider taking a #2 role at a bigger logo

  • If you have a success, then that gives you the ability to take a calculated risk and go earlier stage with your next company

  • Ideally you will have a few companies in your career where large groups of talented people work alongside you (think “PayPal” mafia;).   If you don’t have these nodes yet, think of ways to join larger companies where you can build these deeper networks.  Whispered offers another opportunity to build relationships with top executives


“For most people, working at a large, established company will provide more value than targeting startups. This is because as a professional, you will receive: a) better brand recognition, b) grow a larger network c) receive better benefits d) generally, have greater job stability.”  Alan Stein, Kadima Careers

When taking a risk on a company and going earlier stage, do your research and come with questions vs. just letting them evaluate you:


Think about where a company is in its lifecycle vs. just picking it because it has a sexy name:

  • If you pick a company with a good name that is no longer breaking out, your career may stall because growth slows

  • If you are going to a PE-backed company, think about where it is in their investment cycle (article to come)


Think about how pigeon-holed you want to be (i.e. do you want to be know for just a specific industry)   Consider taking a role in a new/tangential industry to make sure you aren’t pigeon-holed.

“While all these are great questions… don’t be too picky/have too many requirements.  Ask all the questions but have a narrow set of 2-3 criteria to guide your decision on which role / company to take.”  Whispered Member

Expand within a company


One of the best places to grow your experience / scope and try new roles is in your current company (see our article on pivoting your career).  To execute this well:


Be thoughtful on tenure

Job hopping can negatively impact your career.  Be really thoughtful about leaving:

  • One short stint in a row is fine but 2 or 3 can be a killer

  • If you need to get a good-tenure role on your resume be really thoughtful about which company you pick.  Leverage Whispered insights and backdoor references here

  • When you do leave… leave right and think about references


Build your brand and your network

You can’t just wait for jobs to find you.  You have to build your brand and your network.  Here are some tactics we often coach people on:

  • Write - you will be shocked at how much it can open up for you.  See some podcasts from people who have had their career trajectory changed by writing

  • Get on podcasts - you learn how to articulate your visions and help others understand how you think

  • Learn how to network - don’t just network when you need a job, always be networking

  • Advise other great leaders - engage companies you love and start helping them.  You’ll be surprised at how it grows your network

“Define your personal brand. What are you great at? What do you stand for? Articulate this clearly to yourself so you can communicate it -- directly and indirectly -- to others.”  Rusty Gaillard, Executive Coach

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