CMO Confidential: Dick Satterfield | Could I, Would I, Should I Leave? - A Career Management Discussion

Podcast: CMO Confidential
Host: Mike Linton
Guest: Dick Satterfield
Date: December 30, 2025

Episode Overview

In this insightful episode, Mike Linton welcomes Dick Satterfield, a veteran executive recruiter and career advisor, to discuss the intricacies of career management for senior marketers and executives. The conversation centers on the crucial questions professionals should ask themselves—Could I, Would I, Should I Leave?—when considering a career move. With decades of experience at Satterfield Renzenbrink Associates and a deep understanding of executive transitions, Dick offers practical frameworks, tactical advice, and a no-nonsense approach to navigating one of the most high-stakes roles in the C-suite.

Key Discussion Points & Insights

1. Defining Success and Happiness in Your Career

(02:23–03:39)

• Dick emphasizes the importance of evaluating whether you are both successful and happy in your career.
• Key considerations for happiness: company culture, people you work with, scope of responsibilities, and work-life balance.
• Success is subjective but typically involves achieving personal goals, working for desirable companies, being compensated well, and having the desired responsibility.

Notable Quote:

“There are a lot of successful business people that aren’t happy. There are a lot of happy business people that aren’t successful. So if you happen to be successful and happy, you’re very lucky.” — Dick Satterfield (02:23)

2. Measuring Career Progression—It’s About Promotions

(04:09–05:42)

• Recruiters primarily assess candidates based on the pace and frequency of promotions, not merely titles or resume bullet points.
• Real promotions involve increased responsibility, not just title inflation or minimal staff additions.

Notable Moment:

“When we look at resumes, we don’t look to see what their accomplishments were. We look to see how often they were promoted.” — Dick Satterfield (04:17)

3. When Is It Too Early or Too Late To Leave? (“Could I?”)

(06:00–09:10)

• Too early to leave: if you’re still learning and being challenged.
• Too late to leave: if moving disrupts your family significantly, especially geographically, or if you’re too anchored in your current role.
• Dick’s commuting checklist: definable timeframe, same time zone, direct flight.
• Staying in a role too long can signal a lack of ambition or flexibility.

Notable Quote:

“If you’re currently working for a good company, you’re working for a pretty good boss, but, most importantly, you’re still really learning, it’s probably too early to leave.” — Dick Satterfield (06:35)

4. The Realities of Making a Move—When and How (“Would I?”)

(10:46–15:16)

• The best leverage is when you’re still employed; seek to move to a job, not just away from your current one.
• Structured networking process:
  • Make a target list of companies (control geography).
  • Identify influential contacts and get warm introductions.
  • Build relationships with search professionals and recruiters, especially those who placed your peers.
  • Dedicate at least 30 minutes a day to your job search.

Notable Quotes:

“If you’re going to make a move, try very hard to do it while you’re employed because you have so much more leverage.” — Dick Satterfield (11:14)
“We are all better editors than we are creators. When you give people a list, it makes it so much easier to engage.” — Dick Satterfield (13:57)

5. Navigating Job Transitions and Handling “In Between” Periods

(15:36–17:11)

• If unemployed (“in transition”), same job search process applies, but dedicate more time.
• Importance of keeping your spouse/partner informed during a job hunt—your identity and theirs are intertwined.
• Don’t beat yourself up if your next role after a long tenure isn’t perfect; focus on remaining attractive for future opportunities.

6. Evaluating a Job Offer (“Should I?”)

(17:11–20:46)

• The key question: “Am I poised to succeed in this new role?”
• Always interview with the intention of getting the offer—even if you’re not sure you’ll take it.
• Interviewing is a two-way street; pay attention to the decision-making speed and ask managers: “What does success look like at 3, 6, and 12 months?”
• Probe for real power dynamics: Who controls budgets? Who approves creative?

Notable Quotes:

“The single biggest thing you should be thinking about, am I poised to succeed in this new role? … Is this new job really optimizing what I am good at? That is the single biggest thing that you should do.” — Dick Satterfield (17:52)
“If your interviewing process … just lingers and lingers, then you better know that when you join the company, it’s going to take them a while to make decisions.” — Dick Satterfield (20:08)

7. Counter-Offers: Why They Rarely Work

(21:14–22:36)

• 85% of people who accept counter-offers are gone within a year.
• Counter-offers are typically a stopgap for the company and rarely address underlying issues.

Notable Quotes:

“You never know how much they love you until you want to leave.” — Dick Satterfield (21:14)
“85% of people who accept counteroffers are gone within a year.” — Dick Satterfield (21:29)

8. Negotiating Severance and Perks

(23:00–24:00)

• The best—and often only—time to negotiate severance is before you start a new role; get it in writing.
• Recruiters often help facilitate these negotiations.
• If you’re asked to sign a non-compete, ensure severance is included.

9. The Biggest Career Management Mistakes

(24:21–25:08)

• Failing to actively manage your career or set goals.
• Aspiring to jobs that overemphasize your limitations.

Notable Quote:

“The biggest mistake people make when managing their career … They don’t manage their career, they don’t think about it.” — Dick Satterfield (24:21)

10. Special Considerations for Marketers

(25:13–25:52)

• The market has shifted: marketing is now viewed more as an expense than an investment.
• Present yourself as a businessperson first, marketer second—highlight top-line growth and cost-cutting contributions.

Notable Advice:

“You’re not a marketing person. You’re a business person who happens to be in marketing.” — Dick Satterfield (25:43)

11. Final Practical Advice

(26:12–27:02)

• Always return recruiters’ calls—even if you’re not interested—to build long-term relationships.
• Don’t wait to engage with your network or recruiters until you need them; nurture those links continuously.

Notable Quote:

“Return every phone call that you get from a recruiter. … Don’t ignore recruiters until you need them. Call them when you don’t need them.” — Dick Satterfield (26:47)

Memorable Moments & Quotes

• “We are all better editors than we are creators. When you give people a list, it makes it so much easier to engage.” — Dick Satterfield (13:57)
• “You never know how much they love you until you want to leave.” — Dick Satterfield (21:14)
• “If your interviewing process … just lingers and lingers, then you better know that when you join the company, it’s going to take them a while to make decisions.” — Dick Satterfield (20:08)
• “You’re not a marketing person. You’re a business person who happens to be in marketing.” — Dick Satterfield (25:43)

Important Timestamps

• Success vs Happiness Framework: 02:23–03:39
• Career Progression (Promotions): 04:09–05:42
• When to Leave/Not Leave: 06:00–09:10
• How to Build Options and Network: 11:12–15:16
• Evaluating Offers and Interview Red Flags: 17:11–21:14
• Counter-Offers: 21:14–22:36
• Negotiating Severance: 23:00–24:00
• Biggest Mistakes in Career Management: 24:21–25:08
• Advice for Marketers: 25:13–25:52
• Final Practical Advice: 26:12–27:02

Tone and Style

The conversation is candid, practical, sometimes humorous, but always direct. Both Mike and Dick display seasoned, “in the trenches” wisdom without sugar-coating the challenges executives face—especially in marketing. The overall message: Be intentional, proactive, and realistic about your career moves, and don’t be afraid to ask hard questions or build genuine professional relationships.

A must-listen for marketing leaders, aspiring executives, and anyone facing a pivotal career decision in today’s fast-moving business world.