The Executive Career Playbook

You have spent years building an exceptional career. You have led teams, driven revenue, navigated change, and delivered results at the highest levels. And now, you are ready for something different. But here is the question most senior leaders wrestle with: How do I make a significant career pivot without appearing to start over, take a step back, or lose the credibility I have spent decades buil...

At the executive level, interviewing is not about proving you can do the job. It is about demonstrating that you already think like the person they need. That distinction changes everything about how you prepare, how you show up, and how you close. In this episode, Michelle Merritt and Debra Boogs will talk you through the strategies that help senior executives command C-suite conversations, not j...

What do senior recruiters look for when reviewing an executive resume or LinkedIn profile, and what makes them stop scrolling? Join Debra Boggs, D&S CEO and Matilda Cole, Lead Coach and 20-year executive recruiting veteran, for a candid conversation that takes you behind the curtain of the executive hiring process. Matilda has worked inside Fortune 500s, private equity firms, and FAANG compani...

You have a strong executive track record. You’ve led teams, driven results, and influenced organizations at the highest level. So why does landing your first board seat feel like cracking a code nobody handed you? In this episode, we'll walk you through exactly how to position yourself for your first paid board opportunity, including what boards are actually looking for, how to build your board na...

You negotiated hard for your last role… or did you? Most executives leave between $50,000 and $200,000 on the table in every compensation negotiation, not because they lack leverage, but because they don't know how to use it. In a job search, the offer isn't the finish line. It's the starting line. Join Michelle Merritt and Ezra Singer for a candid, tactical conversation designed specifically for...

This is a career strategy conversation built specifically for C-suite and senior leaders who want to lead, not react. The talent and HR community is buzzing about SHRM 2026 but here is the question most people are not asking: What did it mean for the executives sitting on the other side of the hiring equation? Join Michelle Merritt for a focused 30-minute debrief on the biggest lessons, themes, an...

You have done everything right. Strong career. Impressive title. Real results. And yet, the executive job search feels like shouting into a void. Applications go unanswered. Conversations stall. Opportunities seem to materialize for everyone but you. Here is what most executives figure out too late: the traditional job search playbook does not work at the senior level. Applying to posted roles, wa...

Join Michell Merritt for an essential conversation about advancing your board career beyond your first appointment. Whether you're currently serving on one or two boards and ready to expand your portfolio, or preparing for your inaugural board seat, this session delivers the strategic framework you need. What You'll Learn: -How to leverage your current board experience to attract premium opportuni...

How Senior Leaders Successfully Pivot Join Debra and Michelle for a conversation about making strategic career pivots as a senior or C-suite executive. Whether you're considering a move to a different industry, transitioning from corporate to private equity, exploring a portfolio career, or positioning yourself for your next C-suite role, this session will provide you with practical frameworks and...

The executive search landscape has shifted dramatically. What worked even 18 months ago may now work against you. In this candid conversation, Debra Boggs sits down with Amber Schleinkofer, President & Strategic Talent Partner at AS Talent Advisors, LLC, to pull back the curtain on what actually matters when recruiters are evaluating C-suite candidates today. You'll discover: -How AI and autom...

Get ready for an honest conversation about networking at the executive level. Whether you're exploring new opportunities, pursuing board roles, or strengthening your professional relationships, this session cuts through the noise to deliver practical strategies that work for senior leaders. What We'll Cover: - Why traditional networking advice falls flat for executives (and what actually works) -...

Is your LinkedIn profile working for you or against you? If you're a C-suite executive or senior leader exploring opportunities, your profile needs to do three things simultaneously: Maintain professional discretion with your current role Signal availability to the right people (recruiters, board committees) Demonstrate thought leadership and expertise Most executives nail one. Maybe two. But all...

Join us for an eye-opening conversation about the real cost of leaving money on the table as Debra Boggs sits down with our D&S Chief Strategy Officer Michelle Merritt to discuss her compelling chapter "The $2.8M Lesson" from the newly released book Empathy Impact: The Wild Effects of Kindness in Action. In this episode Michelle Merritt shares the true story behind the $2.8M figure and reveals...

Landing a senior leadership role with a private equity or venture capital-backed company requires a fundamentally different interview approach than traditional corporations. These organizations operate under unique pressures, timelines, and success metrics that directly impact how they evaluate executive talent. Join Michelle Merritt & Debra Boggs in this episode designed specifically for seni...

The corner office isn't the only path forward. More executives are building portfolio careers: combining board seats, fractional C-suite roles, and consulting work into strategic income streams. The reality? Year one often generates 40-60% of prior W-2 comp but the upside is flexibility, control, and monetizing your expertise on your terms.   Join Debra Boggs and Michelle Merritt as they dive into...

The best time to prepare is before you need it. If your materials aren't ready, you'll miss the window. You want the confidence that comes with being ready. Join Michelle Merritt and Debra Boggs as they talk about building a comprehensive, action-ready executive career portfolio that positions you to capitalize on opportunities the moment they arise. This session is for you if you want to be prepa...

Join Debra Boggs and Michelle Merritt as they discuss the strategies and tactics to shorten the distance between where you are now and the job you want to be in. Listen in and take control of your next opportunity.   Subscribe to our newsletter: https://sai1k.share.hsforms.com/2q3qZvHrGTmWhDwaxJCl3gA   Learn more at our website: https://www.dscareermanagement.com   Book a call with us today here:...

The executive talent landscape is shifting faster than ever. AI expectations are reshaping hiring criteria. Generational transitions are opening C-suite doors. Board opportunities are at unprecedented levels. The skills that got you where you are now may not be the ones that get you where you want to be in the future. Join Debra Boggs and Ascentria Search Partners’ Ken Schmitt for a focused 30-min...

We've had the same conversation with dozens of C-suite executives lately: "I've been trying to land a board seat for two years and I'm not getting anywhere. Here's the thing, being qualified for a board and being positioned to land one are two completely different challenges. And most executives are solving the wrong problem. If 2026 is your year to land a board seat, we need to talk about what ha...

For executives navigating career transitions or pursuing board appointments, courage isn't optional. It's the differentiator between settling and strategic advancement. In this conversation with Debra Boggs, Christopher O.H. Williams, NACD.DC, author of C.O.U.R.A.G.E.: 7 Choices for Living a Life Without Regret, draws from his leadership roles at Nike, Adidas, Goldman Sachs, and as the first presi...

Compensation negotiations in 2026 demand a different playbook. Join Debra Boggs and Michelle Merritt for 30 minutes of straight talk on what it takes to secure the package you've earned. This session is for you if: You're a C-suite executive or senior leader planning a move, expecting a promotion, or ensuring your current compensation reflects your actual value. Walk away with a clear strategy to...

This episode is your roadmap to finding opportunities in today’s hiring landscape, not the one from 5 years ago.   Work with D&S (Executive Search Support): https://www.dscareermanagement.com/   Visit us at: https://www.dscareermanagement.com/ to learn how we can help you stand out, stay visible, and move your career forward.   Book a call with us today here: https://meetings.hubspot.com/cpoff...

The Shocking Truth: A recent IT Manager posting received 1,600 applications. Your odds of getting hired? Worse than becoming a NASA astronaut.   When companies face this tsunami of applications, they don't review them all. They tap their network or hire a recruiter to start over. Your perfect resume? Never even opened.   Join Debra Boggs, CEO, and Michelle Merritt, Chief Strategy Officer of D&...

Executive recruiters can be your secret weapon in landing your next leadership role, but most marketing executives don't know how to leverage these relationships effectively. Join Debra Boggs for a candid conversation with David Honig, one of the top marketing executive recruiters in the business, as they pull back the curtain on what really happens in executive search, and how you can position yo...

    How to Maintain Hope and Confidence During Your Executive Career Transition   The average executive search now spans 6-9 months. If you're feeling the weight of an extended transition, you're not alone, and more importantly, you're not broken. Our panel has guided over 3,000 executives through successful transitions, and they're here to share what actually works. Our experts reveal the #1 ment...