Cmo Role Definition And Career Navigation

---
name: cmo-role-definition-and-career-navigation
description: "Guidance for marketing leaders navigating the CMO role—defining scope, managing career transitions, onboarding into new positions, and avoiding common failure modes. Trigger when a user asks about CMO responsibilities, career advancement, new role onboarding, or marketing leadership development."
version: "2026-04-21"
episode_count: 31
---

# CMO Role Definition and Career Navigation

## Overview
This skill covers how marketing leaders should define the CMO role, navigate career transitions into and within senior marketing positions, onboard effectively into new companies, and avoid the most common failure modes. All practices are sourced exclusively from guests on the Exit Five podcast. Where guests disagree, those disagreements are surfaced explicitly rather than resolved artificially.

---

## The Three Jobs of the CMO

Recognize that the CMO role contains three distinct jobs, not one. Allocate time deliberately across all three:

1. **Run marketing** — Execute the plan, keep operations smooth, generate demand.
2. **Help your boss run the company** — Participate in CEO-level business decisions and strategy; think beyond the marketing function.
3. **Market marketing** — Proactively communicate internally what marketing does and why it matters. Treat this like a political campaign: hold town halls with sales, meet one-on-one with key stakeholders, and make the function visible and credible inside the organization.

Most CMOs spend 100–120% of their time on job one and neglect jobs two and three, which leads to failure. (Source: Dave Kellogg, Episode #342)

Separately, distinguish between **running marketing** (execution, keeping operations smooth) and **leading marketing** (setting direction, improving the function over time, adapting to market changes). Running is the baseline; leading is where you create strategic value. Prioritize leading and delegate running. (Source: Peter Mahoney, Episode #128)

---

## Defining the CMO Role Before You Accept It

**Align with the CEO's definition of marketing before accepting any CMO role.** The CEO's vision of what marketing should do will shape your mandate and what success looks like. Misalignment here is a primary cause of CMO failure. (Source: Megan Lueders, Episode #229)

**Evaluate CEO/founder marketing philosophy and leadership style fit.** Use a sports analogy: a Chelsea-style direct player will fail at Barcelona's possession-based system, even though both are successful. Ensure the company's marketing philosophy, pace, and approach match your strengths. This fit matters more than company prestige or compensation. (Source: Shane Murphy, Episode #173)

**Define the CMO role based on your strengths, not a generic job description.** The CMO mandate is not standardized the way CFO or COO roles are. Identify your core strengths (e.g., strategy, product marketing, communications) and build your marketing organization and priorities around them. Communicate clearly to the organization what marketing will be at your company. (Source: Kimberly Storin, Episode #229)

**Establish 3–4 non-negotiable criteria before beginning a CMO job search.** Examples: geography, company scale, product quality, portfolio complexity. Use these criteria to filter opportunities and avoid roles that create friction with your life circumstances or don't align with your strengths. (Source: Peter Mahoney, Episode #128)

---

## Transitioning Into the CMO Role

### The Mindset Shift from IC to Executive

**Recognize that the VP/CMO role is not an execution role—it is a strategic one.** As you move from individual contributor to VP level, your job shifts from executing the work to inspiring and leading people. Expect your task list to shrink significantly as you delegate execution. Use the freed-up mental space to think strategically: take walks, consume high-quality information, and generate bigger-picture ideas. (Source: Jessica Andrews, Episode #217; Matt Devincentis, Episode #260)

**Adopt a "first team" mindset.** Your executive leadership team is your primary accountability—your "first team." Your functional marketing team is your "second team." Success means understanding the broader business, building relationships with other executives, and contributing to company-level metrics and strategy—not just making marketing look good. (Source: Bill Glenn, Episode #328)

**Shift from departmental optimization to business stewardship.** The core distinction: marketing's job is to grow the business, not to execute marketing tactics. Measure success by business impact (NRR, customer expansion, time-to-value), not by activity (three webinars a week, two blog posts). Research suggests 60–70% of marketing activities would not be missed if they stopped. (Source: Sangram Vajre, Episode #299)

**When moving from a content or creative role to VP of Marketing, explicitly identify and build two key skill gaps:** (1) Metrics and reporting—learn to track what's working, build dashboards, and distinguish signal from noise; (2) Team leadership—managing a marketing team requires different skills than managing creative work. Partner with specialists (e.g., a RevOps lead) to build reporting infrastructure. (Source: Jess Cook, Episode #321)

**Assess honestly whether you're ready for the people management burden of a CMO role.** Before pursuing a CMO role, evaluate whether you enjoy coaching and mentoring people and whether you're prepared to have regular difficult conversations. Many people are drawn to CMO roles for the strategic work but become miserable because they underestimate the people management component. (Source: Mychelle Mollot, Episode #182)

**Understand that as a CMO, you cannot spend every day executing in your area of passion.** CMO roles require constant context-switching between strategic planning, team management, and occasional tactical execution. If your passion comes primarily from hands-on execution in one area, a CMO role may make you miserable. Assess this honestly before accepting the role. (Source: Mychelle Mollot, Episode #182)

*(Note: The question of how much hands-on execution a sitting CMO should maintain is genuinely contested — see Where Experts Disagree.)*

---

## Onboarding Into a New Marketing Leadership Role

*(Note: The appropriate length of the listening phase is genuinely contested — see Where Experts Disagree.)*

### Listening and Assessment

**Conduct a listening tour with both internal teams and external customers when joining a new company.** Focus on identifying internal subject matter experts who can serve as advocates. Understand the company's positioning, messaging, and what's actually working in the market. (Source: Kevin White, Episodes #286 and #179)

**When joining a new company, listen to the existing team before applying previous playbooks.** The team has been running the business successfully and knows it well. Understand the unique constraints and opportunities before prescribing solutions. (Source: Priscilla Barolo, Episode #302)

**Conduct structured interviews with your entire marketing team and cross-functional partners when entering a new role.** Use consistent questions, collect verbatim comments, and analyze for patterns. Bucket findings into problem areas, strengths, and areas of uncertainty. This gives you a data-driven view of the team's state. (Source: Tara Robertson, Episode #188)

**Assess the current state of go-to-market before applying any playbook.** Understand where demand is coming from, where the company is successful, what the mix of inbound vs. outbound looks like, who the customers are, and what the market opportunity is. Build strategy from that foundation. (Source: Kady Srinivasan, Episode #276)

**When taking over a new organization, spend time developing a mental picture of the future state before diving into structural decisions.** Resist the urge to immediately restructure. Only after a learning phase should you make structural decisions. (Source: Peter Mahoney, Episode #202)

### Building Credibility Early

**Leverage the new CMO window for organizational change.** When starting as a new CMO, you have a limited window—typically the first 3–6 months—where stakeholders expect and accept dramatic change. Use this window strategically to make structural changes, reorganizations, and difficult decisions that would be harder to implement later. (Source: Peter Mahoney, Episode #128)

**Build credibility by delivering quick wins tied to real business problems.** Identify low-hanging fundamental gaps (e.g., missing Salesforce fields, broken website pages, missing event infrastructure) and fix them quickly. Frame these as favors for stakeholders whose trust you need. This builds credibility faster than large initiatives and creates goodwill for larger strategic proposals later. (Source: Taylor Udell, Episode #190; Dave Gerhardt, Episode #133)

**Create a 30/60/90 plan with named phases to show leadership your thinking and build buy-in.** Use memorable codenames (e.g., Sponge for learning, Scaffolding for building systems, Ninja Kick for execution) to make the plan memorable and emotionally resonant. Present this early—even unsolicited—and reference it later when pitching budgets or major initiatives. (Source: Jess Cook, Episode #266)

**Structure your first 90 days as CMO in distinct phases:** (1) Listen and absorb—understand the current org, objectives, team strengths/weaknesses, and gaps; (2) Implement—build your first-line marketing leadership team, establish operating model and KPIs; (3) Stabilize—let the team get up to speed; (4) Look forward—shift to 6-month and 1-year planning. (Source: Kelly Hopping, Episode #255)

---

## Structuring the CMO Role for Ongoing Effectiveness

### Time and Schedule Management

**Separate your calendar into manager days (stacked meetings) and maker days (completely open for deep work).** Stack all internal meetings on specific days (e.g., Monday). Reserve other days (e.g., Wednesday and Friday) for uninterrupted thinking, writing, and strategic work. This prevents context-switching that kills creative productivity. (Source: Chris Walker, Episodes #281 and #211)

**Schedule regular 3–4 day breaks away from your workspace every 6 weeks.** During these breaks, avoid work but allow space for thinking and writing. The clarity generated upon return—solving problems that confused you for months—makes these breaks a business investment, not an expense. (Source: Chris Walker, Episode #211)

**Limit CMO direct reports to 3 to enable approximately 50% outward-facing time.** A structure with only 3 direct reports (e.g., VP of Integrated Marketing, Head of Demand Gen, and an individual contributor experimenter) allows the CMO to spend significant time on customer meetings, prospect meetings, and speaking at conferences, while strong internal leaders manage day-to-day operations. This requires hiring leaders who can make decisions without constant CMO input. (Source: Andrew Davies, Episode #195)

*(Note: The value of external visibility and personal brand-building for CMOs is contested — see Where Experts Disagree.)*

### Developing Functional Expertise You Don't Own

**Develop functional expertise in areas you don't manage directly through structured learning with functional leaders.** Schedule off-the-clock learning sessions. Ask them to teach you what metrics matter, what roadblocks exist, what questions you should ask to help them improve, and what good performance looks like. The goal is to be a good leader who understands the business, not to become a hands-on expert in every discipline. (Source: Kelly Hopping, Episode #255)

**Develop demand generation expertise by directly managing campaigns during staffing gaps.** Take on hands-on execution when a role is vacant or understaffed. Complement this with free certification courses (e.g., Marketo certifications) and regular one-on-ones with demand gen team members to ask why they make specific decisions. (Source: Jessica Andrews, Episode #217)

**Invest in continuous AI tool learning personally—don't delegate all AI learning to your team.** Personally invest time in learning new AI applications and tools. This keeps you sharp, helps you understand what's possible, and models the behavior you want from your team. (Source: Kelly Hopping, Episode #255)

**Evaluate new marketing tools through personal trial before recommending them to your team.** Take free trials yourself to filter out tools that look good on the surface but don't deliver in practice. Only recommend tools you've personally tested, and frame recommendations as informative suggestions rather than mandates. (Source: Kris Rudeegraap, Episode #159)

---

## Leadership Behaviors and Mindset

**Own the outcome, not the task.** Measure yourself and your work against business outcomes (revenue, pipeline growth) rather than marketing inputs (leads, website visits, content pieces). This mindset gets you a seat at the table with executives who care about revenue, not vanity metrics. (Source: Matt Devincentis, Episode #260)

**Represent company strategy to your team with full commitment, even if you privately disagreed with the decision.** You can disagree in the room with leadership, but once a decision is made, you own it fully when communicating to your team. Signaling doubt or reluctance to your team is a failure of leadership responsibility. (Source: Mychelle Mollot, Episode #182)

**Sleep on major decisions before acting.** When facing a significant decision, deliberately delay action by sleeping on it overnight. Waiting 24 hours creates space to reconsider and often reveals that decisions don't need to be made immediately. This is especially valuable in real-time communication environments (Slack, email). (Source: Dave Gerhardt, Episode #298)

**Lead authentically with your natural personality, and choose your environment carefully if it doesn't fit.** Don't try to be someone you're not as a leader. However, recognize that not every environment will value your style. Choose your company and team carefully so your authentic leadership style is appreciated rather than constantly fighting against the culture. (Source: Amrita Mathur, Episode #188)

**Understand your personality superpower and its corresponding kryptonite, then manage both consciously.** Your superpower is often linked to a kryptonite (e.g., being calm and unflappable is a strength but can make you seem emotionally distant). Identify this dynamic, communicate it to your team, and consciously work to mitigate the downside. (Source: Peter Mahoney, Episode #188)

**Prioritize communication in all directions as the core skill of marketing leadership.** Communication—outward to the company, inward to your team, and sideways to peers—is the most critical skill for marketing leaders. You must be able to communicate your strategy, priorities, and progress clearly to executives, your team, and cross-functional partners. (Source: Tara Robertson, Episode #188)

**When facing imposter syndrome about a specific marketing discipline, lean into project management.** Be the person who makes meetings happen, pulls the right people into the room, takes notes, creates tracking mechanisms, and ensures execution. You don't need to be the expert; you need to be the person who drives it forward. (Source: Priscilla Barolo, Episode #302)

**Invest in executive coaching as a non-negotiable leadership development tool.** High-performing leaders benefit from external coaching, similar to how elite athletes have coaches. A coach provides outside perspective, helps you see blind spots, and guides you through situations you haven't encountered before. This is especially valuable as you scale into VP and C-level roles. (Source: Matt Devincentis, Episode #260)

**Optimize for rate of learning and execution speed over short-term revenue targets in early-stage or uncertain environments.** When joining early-stage companies or facing high uncertainty, shift focus from revenue targets to learning velocity and execution speed. This reduces stress and enables faster iteration and better decision-making. (Source: Amrita Mathur, Episode #188)

**Trust your instincts when something looks wrong, even without perfect data.** Develop confidence to speak up when something doesn't look right, rather than deferring to data or others' opinions. This requires overcoming shyness about challenging the status quo. (Source: Peter Mahoney, Episode #188)

**Build skills through community connection and peer learning, not just by becoming an expert in everything yourself.** Actively network and build community relationships to learn from others who have deeper expertise in areas outside your core skills. (Source: Tara Robertson, Episode #188)

---

## Diagnosing and Avoiding CMO Failure Modes

**Identify which of eight CMO failure archetypes you may embody and apply targeted remediation:**

- **He Liquor** — Chokes in board meetings. Fix: Find a coach who understands both boards and marketing.
- **Vendor Whisperer** — Outsources all decisions to vendors. Fix: Build internal judgment and own your decisions.
- **Finger Pointer** — Defensive, blames others. Fix: Listen more and talk less.
- **Tasmania Devil** — Chaotic, unfocused energy. Fix: Slow down and communicate clearly.
- **Sneaker** — Gets undermined by other executives. Fix: Build direct relationships with the CEO to prevent being undercut.
- **Two Thirds** — Stays in a narrow functional lane and neglects the other two CMO jobs. Fix: Deliberately allocate time to helping the CEO run the company and marketing marketing internally.
- **Second Guesser** — Presents data that burns into decision-makers' minds without context. Fix: Always provide context alongside data.
- **Self Promoter** — Overexposed externally. Fix: Be transparent with CEO and CRO about external activities and frame them as professional development.

(Source: Dave Kellogg, Episode #342)

*(Note: The Self Promoter archetype and the broader question of CMO personal brand-building is contested — see Where Experts Disagree.)*

**Recognize that there is no universal marketing playbook.** Marketing success depends on context: company stage, size, budget, industry, CEO beliefs, and available talent. Rather than seeking a universal playbook, understand the fundamentals and adapt them to your specific constraints and opportunities. This requires judgment and intuition, not formula. (Source: Dave Gerhardt, Episode #316)

---

## Fractional CMO Operating Model

**Structure fractional CMO work similarly to a full-time role: set OKRs, run regular stand-ups, manage team alignment, and oversee agencies.** The key difference is efficiency—work fewer hours but deliver full-time value. (Source: Amanda Goetz, Episodes #244 and #158)

**Establish strict meeting hygiene as a fractional CMO.** Working 20 hours per week, you cannot afford to spend all hours in meetings. Set a structured operational cadence and manage it tightly. Without meeting discipline, you'll have no time for strategic work. (Source: Amanda Goetz, Episode #158)

**Begin fractional CMO engagements with a listening phase.** Introduce yourself, explain your background and why you're there, and make clear you're coming to listen first. Frame your role as helping the team feel less frustrated and make progress on their goals. Speak in the team's language. Ensure the CEO is aligned and supportive, and that feedback flows both ways. (Source: Amanda Goetz, Episode #158)

---

## Where Experts Disagree

### 1. Should CMOs stay hands-on with execution or fully delegate to focus on strategy?
**Support summary: 5 (delegate/strategy) vs. 3 (stay hands-on)**

**Position A — Delegate execution, focus on strategy:**
Kady Srinivasan (Episode #276), Mychelle Mollot (Episode #182), Jessica Andrews (Episode #217), Matt Devincentis (Episode #260), and Peter Mahoney (Episode #128) all argue that advancing to CMO requires deliberately letting go of day-to-day execution. Srinivasan states the CMO's job is to serve as the glue across product, sales, and customer success—not to execute. Mollot warns that CMO roles require constant context-switching and that passion for hands-on execution in one area will make you miserable in the role. Andrews describes the VP Marketing role as explicitly not an execution role. Devincentis frames the shift as moving from executing work to inspiring and leading people. Mahoney distinguishes "running marketing" (execution) from "leading marketing" (direction-setting) and argues leading is the CMO's primary job.

**Position B — Stay connected to execution:**
Chris Walker (Episodes #211 and #281) argues that CMOs and senior marketing leaders must remain involved in execution—attending events, reviewing creative, listening to customer feedback in real-time. He specifically warns that CMOs at $50M+ ARR companies who become purely political/administrative lose the ground truth about what messaging resonates. Kieran Flanagan (Episodes #318 and #257) argues the future CMO role will shift toward being a hands-on craftsperson and operator with a smaller team, reversing the trend toward CMOs becoming pure managers—enabled by AI reducing the need for large execution teams.

**Context dependency:** Flanagan's position is explicitly forward-looking (AI-enabled future state with smaller teams), while Walker's position is most applicable at $50M+ ARR companies where CMOs risk becoming purely administrative. The delegation camp tends to speak about the transition period from IC to CMO. However, the core tension—whether a sitting CMO should be personally executing work—is a genuine disagreement that persists even within similar company stages.

**Trend note:** The hands-on/craftsperson position is more recent (2025–2026, Episodes #257 and #318), while the delegation/strategy position spans 2024–2025. This may reflect an emerging AI-driven shift in thinking about the CMO role, but the sample is too small to confirm a clear trend.

**Why it matters:** A CMO who stays too hands-on may fail to provide strategic leadership and cross-functional alignment; one who fully delegates may lose the ground truth needed to make good strategic decisions. Getting this balance wrong in either direction is a common CMO failure mode.

---

### 2. How long should a new marketing leader spend listening before acting?
**Support summary: 5 (extended listening, 2–3 months) vs. 3 (quick wins alongside listening) vs. 2 (rapid listening, move fast)**

**Position A — Extended listening, 2–3 months:**
Peter Mahoney (Episode #202) explicitly recommends spending 2–3 months listening and learning before making structural changes. Tara Robertson (Episode #188) recommends a structured 90-day learning plan with the first 30 days dedicated entirely to learning. Priscilla Barolo (Episode #302) advises listening to the existing team's perspective before applying lessons from previous experience. Kady Srinivasan (Episode #276) recommends resisting the urge to immediately apply a previous playbook. Amanda Goetz (Episode #158) recommends beginning even fractional CMO engagements with a listening phase.

**Position B — Quick wins alongside listening:**
Dave Gerhardt (Episode #133) recommends shipping a small, visible win in week one or two of a new role to build credibility and generate momentum, rather than spending weeks purely listening. Jess Cook (Episode #266) recommends pursuing quick wins (e.g., adding a CTA button, writing a blog post) alongside strategic planning from the start. Taylor Udell (Episode #190) recommends identifying low-hanging fundamental gaps and fixing them quickly to build credibility faster than large initiatives.

**Position C — Rapid listening, move fast:**
Kevin White (Episodes #286 and #179) explicitly advises keeping the listening tour short—not 60 days—because CEOs won't accept a lengthy listening period and strategic decisions cannot be delayed. Prioritize speed over comprehensiveness.

**Context dependency:** The extended listening recommendation may apply more to large, complex organizations where structural changes have significant downstream effects. The rapid listening and quick-wins positions may be more appropriate for smaller companies or roles where the CEO expects fast impact. However, all guests appear to be speaking about marketing leadership roles generally, making this a genuine disagreement.

**Why it matters:** A new marketing leader who listens too long risks losing credibility and the window for change; one who acts too fast risks making poorly-informed decisions that damage relationships and strategy. The right balance directly affects whether a new CMO succeeds or fails in their first year.

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### 3. Should CMOs actively build a personal brand through external visibility?
**Support summary: 3 (personal brand as core strategy) vs. 1 (personal brand with caution)**

**Position A — Personal brand as core strategy:**
Dave Gerhardt (Episode #316) has built his entire career and the Exit Five community around the premise that marketing leaders should build personal brands and share their expertise publicly—treating external visibility as a core professional strategy, not a risk to be managed. Chris Walker (Episode #281) structures his entire schedule around producing strategic thought leadership content, treating external content creation as a core part of his professional role. Andrew Davies (Episode #195) recommends structuring the marketing org so the CMO has only 3 direct reports specifically to enable 50% of CMO time on outward-facing activities including speaking at conferences—treating external visibility as a core CMO function.

**Position B — Personal brand with caution:**
Dave Kellogg (Episode #342) identifies "Self Promoter" as one of eight CMO failure archetypes—being overexposed externally. He advises that self-promotion is possible but requires proactive communication with CEO and CRO, and must be framed as professional development, not personal branding. The risk: peers in sales will resent external visibility while they're grinding internally.

**Context dependency:** Kellogg is speaking specifically about CMOs at companies where they report to a CEO and have peers in sales who may resent external visibility. Gerhardt and Walker are speaking from the perspective of founders/independent operators where external visibility is unambiguously beneficial. The tension is most real for employed CMOs specifically.

**Why it matters:** An employed CMO who builds a high-profile personal brand without managing internal perceptions risks being seen as self-serving and damaging relationships with sales and the CEO—potentially accelerating their departure from the role.

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## What NOT To Do

- **Do not spend 100% of your time running marketing and neglect helping your boss run the company and marketing the marketing function internally.** This is a primary CMO failure mode. (Source: Dave Kellogg, Episode #342)
- **Do not immediately apply a playbook from a previous company without assessing the new company's unique context.** Every company has a unique go-to-market motion. (Source: Priscilla Barolo, Episode #302; Kady Srinivasan, Episode #276)
- **Do not accept a CMO role without explicitly aligning with the CEO on what marketing means at that company.** Misalignment on this is a primary cause of CMO failure. (Source: Megan Lueders, Episode #229)
- **Do not immediately restructure a new organization before completing a learning phase.** Reactive changes made without context damage relationships and strategy. (Source: Peter Mahoney, Episode #202)
- **Do not signal doubt or disagreement with a leadership decision to your team.** You can disagree in the room; once a decision is made, you own it fully. (Source: Mychelle Mollot, Episode #182)
- **Do not retreat into meetings as a senior leader.** Separation from execution and customer feedback makes it impossible to drive strategy effectively. (Source: Chris Walker, Episode #211)
- **Do not look for shortcuts—a single tool, platform, consultant, or tactic that will solve a marketing problem.** There is no one simple trick. Success comes from sustained, thoughtful work across multiple dimensions. (Source: Brian Kotlyar, Episode #118)
- **Do not try to be a generalist CMO if your strengths are specific.** Build your organization and priorities around your strengths and communicate clearly what marketing will be at your company. (Source: Kimberly Storin, Episode #229)
- **Do not push new tactical ideas to your team immediately after generating them.** Present them casually as suggestions and let the team decide whether to pursue them. (Source: Jessica Andrews, Episode #217)
- **Do not allow your personality superpower to become a liability.** Identify the kryptonite linked to your strength and consciously manage it. (Source: Peter Mahoney, Episode #188)
- **Do not measure marketing success by activity volume** (webinars run, blog posts published, social posts). Measure by business impact. (Source: Sangram Vajre, Episode #299)
- **Do not delegate all AI learning to your team.** Personally invest time in learning new AI applications to stay sharp and model the behavior you want. (Source: Kelly Hopping, Episode #255)

---

## Sources

| Episode | Guest | Date |
|---------|-------|------|
| Episode #118 | Brian Kotlyar | 2024-02-19 |
| Episode #128 | Peter Mahoney | 2024-04-01 |
| Episode #133 | Dave Gerhardt | 2024-04-18 |
| Episode #158 | Amanda Goetz | 2024-07-15 |
| Episode #159 | Kris Rudeegraap | 2024-07-18 |
| Episode #173 | Shane Murphy | 2024-09-05 |
| Episode #179 | Kevin White | 2024-09-26 |
| Episode #182 | Mychelle Mollot | 2024-10-07 |
| Episode #188 | Amrita Mathur, Peter Mahoney, Tara Robertson | 2024-10-28 |
| Episode #190 | Taylor Udell | 2024-11-04 |
| Episode #195 | Andrew Davies | 2024-11-21 |
| Episode #202 | Peter Mahoney | 2024-12-16 |
| Episode #211 | Chris Walker | 2025-01-16 |
| Episode #217 | Jessica Andrews | 2025-02-06 |
| Episode #229 | Megan Lueders, Kimberly Storin | 2025-03-20 |
| Episode #244 | Amanda Goetz | 2025-05-08 |
| Episode #255 | Kelly Hopping | 2025-06-16 |
| Episode #257 | Kieran Flanagan | 2025-06-23 |
| Episode #260 | Matt Devincentis | 2025-06-30 |
| Episode #266 | Jess Cook | 2025-07-21 |
| Episode #276 | Kady Srinivasan | 2025-08-25 |
| Episode #281 | Chris Walker | 2025-09-11 |
| Episode #286 | Kevin White | 2025-09-29 |
| Episode #298 | Dave Gerhardt | 2025-10-27 |
| Episode #299 | Sangram Vajre | 2025-10-30 |
| Episode #302 | Priscilla Barolo | 2025-11-10 |
| Episode #316 | Dave Gerhardt | 2025-12-29 |
| Episode #318 | Kieran Flanagan | 2026-01-05 |
| Episode #321 | Jess Cook | 2026-01-15 |
| Episode #328 | Bill Glenn | 2026-02-11 |
| Episode #342 | Dave Kellogg | 2026-03-31 |