Career Transition Council

A Discussion with Don Weintraub, September

False Assumptions That PE-Backed Executives Make in Phase One of the Job Search Process

The Career Transition Council is a group of current and former PE-Backed Executives. We meet every two weeks to support one another with advice, counsel, introductions, best practices and more. Occasionally outside experts help guide discussions on pre-planned topics. Our most recent expert speaker was @DonWeintraub.

Don is Founder and CEO of his own company, Your Work in Progress. YWiP provides an array of services including Executive Career Coaching and Collateral; Executive Recruiting; Business Optimization Consulting and Sales Effectiveness Assessments; and Training. Don is a Trusted Advisor to executives across multiple industries and functions.

Don suggests that executives carefully think through four distinct phases of their career transitions:

  • Phase 1: Being Prepared and Compelling; Leading to Being Found

  • Phase 2: Continuing to Impress and Advance in the Search Process

  • Phase 3: Negotiating the Job Specifics; Getting a Written Job Offer

  • Phase 4: Saying Yes, Onboarding; Succeeding Early and Often

This article will focus on the misperceptions that PE-Backed Executives often make when it comes to Phase One.

Introduce a New Product or Service (You) to Your Target Customers (Hiring Decision Makers)

As you consider your career transition as a process, it may be helpful to envision the process as if you were marketing a new product or service. If you were, you would want to explain the problem or the need which you are solving, with an effective value proposition and clear proof points to a targeted customer base. To pull this off (introducing yourself as a new product or service), you will need to know yourself, understand the needs of your customer base (hiring decision makers) and how to market yourself effectively to them, and understand the competition and how they are presenting themselves.

Conduct Competitive Analysis

Research how your competitors (PE-Backed executives with a similar role/functional expertise serving the same industry, in a similar size range) are marketing themselves. Compare your LinkedIn profile to the competition. Determine which profiles you admire, appreciate, and respect and take note of the reasons. Chances are, what catches your eye is not the specific skills, knowledge and experience, but rather the storyline and how they present themselves.

Develop Your Storyline

Rather than selling someone strictly, literally on your accomplishments and experiences (which they can easily see if they read your resume), try selling them on your unique story. A story is typical about a main character (you) whom the audience wants to cheer for, who faces a major obstacle. Your story could be about the problems that you were hired to solve in a previous role. You are the hero of your story; you saved the day by doing something that the Company was doing wrong, not doing, or not doing well enough. Your story needs to include the details of how the hero resolved the dilemma or problem. You will want some proof points – numbers or metrics or measures of your success. In addition, the lessons that you learned from that experience are valuable because they serve as opportunities for you to be vulnerable and establish connections with other human beings, and also
allow you to say how you grew as a person from the experience.

Your uniqueness, as presented through your story, makes you authentic. Think about three elements: 1.) What you are uniquely best in class at. 2.) What you love to do or what you love in general. 3.) How you can create value for companies. Now, combine those three. Think of a Venn Diagram, with those three interlaced circles. Where they overlap, is where you should focus. And this is helpful narrative for your story! To the extent that story conveys how you can solve problems for a very targeted, relevant hiring decisionmaker, you have an effective value proposition!

Formatting Your Messaging

In addition to the value proposition and storyline messaging, it is important to consider the format of this message. Readers skim from the top down and look for something worthwhile that catches their eyes. It is important to grab the attention of those members of your target market who actually find you or take the time to read about you.

For resumes, start at the top with Your Name, obviously, but also use a phrase that enables the reader to understand your uniqueness and compelling value proposition. Next, cite a role or function or purpose that you can provide well. Third, offer bullets describing your unique value and accomplishments, with metrics or numbers indicating success. Fourth, offer up to 20 keywords (not phrases), in bullet-point format, in three or four columns.

Below that, rather than using generic headings, such as Experience, use the available real estate in your resume to tell your unique story. For example, why were you hired in the past. Being hired is a story about problem-solving. Then explain how you solved that problem during your time in that role. And provide elaboration in terms of metrics.

For most people, a two-to-three page resume is better than a longer resume in part because you are able to demonstrate an ability to refine and focus. It makes sense to go back only about 20 years, in most cases.

On LinkedIn, there are ways to optimize your collateral to be discovered, at the top of the pile, based on how LinkedIn, for example, utilizes key words and algorithms. For example, use keywords directly under your name, separated by a bar.

Below the keywords, use Accomplishments. Provide a list of bullets, with metrics, or numbers, or words that demonstrate tangible successes. Be specific and cite metrics and numbers, but not so specific that the reader has a hard time relating to you or thinking actively about you in terms of solving their unique need.

Plan for the Dream Job; But Be Prepared for Second Best Until the Dream Job Comes Along

Timing is everything. Define your ideal next job, taking into consideration your personal Venn diagram of 1.) Best in class skills. 2.) Things you love. 3.) How you create value for companies. Based on that definition, develop a list of perfect jobs, however, decide in advance on some other options that would make sense for you, given the constraints of timing. In other words, it makes sense to be in control of your destiny by ideating on the parameters of a less desirable job, one that you would take, but acknowledge is not ideal. Those employed often have an easier time finding a next job than those. In addition, it does provide you with a sense of being in control; it provides immediate income, and time to wait for the ideal opportunity to come along. Make yourself available for your ideal next job on an ongoing basis, while you are doing a job that is slightly less than ideal. Examples may include interim roles, fractional work, serving as a consultant or industry expert, being a board member or an Operating Partner temporarily.

In conclusion, focus on making your collateral more story-like and less of a list. Make it easy to read and relatable. And remember, this is merely your first Phase. Again, these are the four phases that Don advises on:

  • Phase 1: Being Prepared and Compelling; Leading to Being Found

  • Phase 2: Continuing to Impress and Advance in the Search Process

  • Phase 3: Negotiating the Job Specifics; Getting a Written Job Offer

  • Phase 4: Saying Yes, Onboarding; Succeeding Early and Often

Reach out to Don directly for help on any of these phases. Don ended the discussion with the Career Transition Council by volunteering to review collateral such as resume or cover letter or LinkedIn profile, gratis, for PE-Backed executives. Don can be reached at

For more information on The Career Transition Council, contact Kit Lisle at

Leave a Reply

Your email address will not be published. Required fields are marked *