The Executive Career Playbook

Looking for your next executive role but unsure where to start? At the senior level, a successful search requires more than updating your resume and applying online. In this conversation, we answer the questions executives are asking about: • Getting your resume in front of the right recruiters • Using LinkedIn to strengthen your visibility • Positioning yourself for executive opportunities • Purs...

AI was supposed to make the job search easier. But for most job seekers (and especially senior leaders), it is creating an entirely new set of challenges. AI-generated résumés, increased application volume, and automated screening are all making it harder for even highly qualified leaders to stand out. Listen till the end for a practical conversation about three ways AI is changing the executive j...

A potential layoff is not the time to wait and see. Learn five critical steps senior executives can take now to protect their career, strengthen their resume and LinkedIn presence, prepare for an executive job search, and negotiate severance and outplacement support. Facing uncertainty in your role? Book a complimentary call with D&S Executive Career Management and build your strategy before y...

Success doesn't protect you from burnout. In this candid conversation, Debra Boggs and Lesley Hunter explore the hidden mental health challenges many high performers face but rarely discuss. From perfectionism and burnout to vulnerability, resilience, and redefining success, they share practical insights for executives, senior leaders, and ambitious professionals navigating demanding careers. Whet...

Join board positioning expert Debra Boggs, CEO of D&S Executive Career Management, for a tactical and practical workshop. You will leave with a draft of your own board value statement, ready to use in networking conversations, warm introductions, and with board chairs and Nom/Gov committees. This episode is for senior executives actively pursuing their first board seat, or looking to expand th...

This episode explains why well‑qualified executives often get no response or rejections when applying online, covering common issues like being perceived as overqualified, making a career pivot, job scope changes, internal referrals, and the rise of mass applicants driven by AI. Practical takeaways include focusing on strategic networking, positioning your unique value, preserving confidence durin...

You've spent decades building your career. Leading teams. Driving growth. Solving complex business challenges. So why aren't the right opportunities turning into interviews? The reality is that AI can help you write a resume, but it can't define your value. It can't tell your story. And it can't position you as the leader a company needs right now. In this episode of The Executive Career Playbook,...

Corporate board opportunities rarely go to the most qualified executive. They go to the executive who is visible, positioned correctly, and connected to the right decision-makers. In this session, Debra Boggs shares the strategies executives use to secure corporate board seats, strengthen board readiness, build board visibility, and position themselves as valuable contributors in the boardroom. Yo...

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:...