Marketing Team Hiring And Talent

---
name: marketing-team-hiring-and-talent
description: "Guidance for B2B marketing leaders on how to hire, structure, onboard, and retain marketing teams — covering role sequencing, interview techniques, candidate evaluation, and org design. Trigger when a user is making a hiring decision, building a team from scratch, evaluating candidates, or diagnosing team performance issues."
version: "2026-04-20"
episode_count: 37
---

# Marketing Team Hiring and Talent

## Overview
This skill covers how B2B marketing leaders should approach hiring, team structure, candidate evaluation, onboarding, and talent retention. All practices are sourced exclusively from guests on the Exit Five podcast. Do not supplement with general hiring advice not represented here — gaps in coverage are intentional.

---

## Role Sequencing: Who to Hire and When

**Hire a product marketer as your first marketing role.** Positioning, messaging, competitive intelligence, and product strategy alignment are the foundational work that makes all downstream tactics (paid, content, events) more effective. This role is often overlooked because it's not immediately measurable in pipeline terms, but it creates the narrative that makes everything else work. (Source: Dave Gerhardt, Episode #219)

**When moving from Head of Content to Head of Marketing, hire a product marketer as your first direct report.** This creates minimal overlap with your existing strengths (top-of-funnel thought leadership) and fills the gap in messaging and positioning. Look for someone who can simplify complex product stories while maintaining brand personality. (Source: Jess Cook, Episode #266)

**Hire a marketer who can write, not a writer who will learn marketing later.** A marketer with writing skills understands the full content lifecycle — creation, distribution, optimization — from day one. Once that foundation is in place, hire specialized writers to support them. (Source: Dave Gerhardt, Episode #200)

**Prioritize hiring a GTM engineer as one of your first three to five marketing hires.** This person should focus on building efficient systems for content creation, customer feedback loops, AI integration, and workflow automation from the start rather than waiting until the team is larger. (Source: John Short, Episode #271) *(Note: this is contested — see Where Experts Disagree)*

**Hire your first ops person after achieving product-market fit and a repeatable sales process.** At that stage, an ops person can instrument your funnel, anticipate where the plan will break as you scale, and embed a data-driven culture. Hiring ops too early wastes the hire; hiring too late means you've already built bad habits. (Source: Sean Lane, Episodes #274 and #187)

**Scale marketing team size based on marketing budget, not company ARR.** If your marketing budget is under $10 million, expect the VP of Marketing to do much of the work themselves — webinars, campaign execution, list building. At $10M+ in marketing budget, you can justify a full CMO with specialized teams and supporting agencies. Below that threshold, hiring multiple specialists and agencies creates unsustainable cost structures. (Source: Jason Lemkin, Episode #142)

**When hiring your first events person, prioritize candidates with hospitality industry experience combined with customer success or sales background.** This combination ensures they understand both operational excellence and how events fit into the broader revenue picture. (Source: Natalie Taylor, Episode #306)

**When expanding into a new geographic market, hire at least two people: a local marketer and a local salesperson.** The marketer creates native content tailored to local nuances — not translations of existing content. The salesperson should already have an existing network in that market. (Source: Max Van Den Ingh, Episode #161)

---

## Proving Functions Before Hiring

**Before hiring a dedicated full-time person for a new marketing function, first test whether that function works for your business.** Run it as part of someone's existing job, validate that it drives results, and only then hire a dedicated person. Every hire is a bet; only place bets on things you've already validated. (Source: Sylvia Lepoidevin, Episodes #283 and #199)

**Do the role yourself before hiring someone to do it.** Spend time executing the function solo or with a contractor on a part-time basis first. This gives you clarity on what success looks like, prevents expensive hiring mistakes, and ensures the new hire inherits a role with clear processes and expectations rather than a blank slate. (Source: Dave Gerhardt, Episode #169)

**Before committing to a full-time hire for a new function, run experiments for a quarter using existing resources.** This allows you to understand the actual workload, learn what capabilities are needed, and validate that the function is worth the investment. It also gives you a better scorecard for measuring the eventual hire's performance. (Source: Dave Gerhardt, Episode #138)

**Prove a function works before hiring a specialist to own it.** Once you've proven the function generates results, you can hire a specialist with confidence and better interview questions. This reduces hiring risk and ensures you're not making a bad investment. (Source: Dave Gerhardt, Episode #143)

*(Note: the "prove before hiring" principle is contested for certain foundational roles — see Where Experts Disagree)*

---

## Candidate Evaluation and Interview Techniques

### Structured Interview Frameworks

**Implement a structured hiring process based on the 'Who' method.** Walk through a candidate's last three jobs in detail, asking what they were proud of, what they could have done better, and why they left each role. Write down all answers and share with the hiring team so others don't repeat the same questions. Soften it by explaining upfront that you'll be asking structured questions. (Source: Jeff Hardison, Episode #335)

**Use deep probing follow-up questions to assess motivation and thinking patterns.** When a candidate gives an answer, ask "tell me more," "how," "what," and "where else did that show up?" This reveals how someone thinks and what drives them, which is more predictive than stated accomplishments. Get specific on past work — tools used, metrics, outcomes — to verify depth of knowledge. Inform candidates upfront that you'll be drilling deep. (Source: David Kline, Episode #138)

**Before posting a job, identify five people you would ideally hire for the role and have conversations with them.** Use the commonalities you discover to design the actual job description and candidate profile. This ensures you're hiring for the right attributes rather than filling a generic role, and it builds your recruiting pipeline by starting conversations with potential candidates early. (Source: David Kline, Episode #138)

**When hiring a marketing leader, give them a take-home exercise using a neutral third-party company — not your own — to evaluate positioning, branding, messaging, and campaign execution.** This avoids information asymmetry. Have them spend a few days on-site workshopping the analysis with your team. Compensate them for the work as a paid project, not free labor. (Source: Pranav Piyush, Episode #259)

**When hiring AI Creative Producers, evaluate candidates on two criteria: portfolio (showing creative taste and past work) and a take-home challenge where they produce a full video in 30 minutes using AI tools.** This compressed timeline filters for people who understand both creative direction and AI tool fluency. (Source: Luke, Episode #345)

### Revealing Fit and Alignment

**Ask candidates to describe their nightmare scenario.** Ask: "In six months, if you were to join our company, what would be a nightmare situation where you'd be like, oh my gosh, I can't believe I left my job?" Their answer reveals whether they'll actually be happy in your current situation doing the things you need them to do. (Source: Jeff Hardison, Episode #335)

**Show product marketing candidates a list of core PMM activities and ask them to stack rank what they like doing most to least.** Use their ranking to determine if they're a good fit for the specific role. If you need someone to work heavily with sales, they should rank sales enablement high. If you need someone focused on research and experimentation, they should rank research highly. This prevents hiring mismatches where a talented PMM is unhappy because they're doing work they don't enjoy. (Source: Jeff Hardison, Episode #335)

**When interviewing for a VP of Marketing or CMO role, ask the CEO to force-rank their top three marketing priorities.** This reveals whether the CEO has a clear vision for marketing and whether your strengths align with their needs. If the CEO's priorities don't match your expertise or passion, it's a sign of poor fit. (Source: Jason Lemkin, Episode #207)

**Use force-ranking to uncover true priorities in executive interviews.** Ask executives to force-rank priorities rather than list them. Force-ranking reveals what people actually care about versus what they think they should care about, and prevents vague answers that don't expose real trade-offs. (Source: Jason Lemkin, Episode #207)

**Evaluate candidates based on clear career narrative and intentional moves, not just tenure.** Ask candidates to articulate their big vision and how each role supported it. A clear, intentional narrative is a stronger signal than tenure length; lack of a coherent story is a red flag regardless of how long someone stayed at each company. (Source: Sylvia Lepoidevin, Episodes #283 and #199)

**Hire marketing leaders whose strengths match your company's current needs, not generic titles.** Identify the top 2-3 things your company needs marketing to accomplish right now, then hire someone whose passion and expertise align with those specific needs. A brand-focused marketer will fail at a company that needs demand generation, and vice versa. (Source: Jason Lemkin, Episode #207)

**Before accepting an early-stage marketing role, honestly assess whether you're willing to do hands-on execution work.** Many marketers claim they want early-stage roles but are unwilling to do the actual work (webinars, email campaigns, list building, HubSpot execution). If you're not willing to do this work yourself, don't take the job. (Source: Jason Lemkin, Episode #142)

---

## Sourcing and Recruiting

**Have the CMO directly message candidates on LinkedIn with a simple, direct message** (e.g., "I'm hiring this role") rather than relying solely on recruiting team outreach. This generates significantly higher response rates than recruiter-initiated contact. The message from a prospective direct manager carries more weight and signals seriousness. (Source: Sylvia Lepoidevin, Episodes #283 and #199)

**Recruit ops talent from specialized ops communities rather than general job boards.** These communities are where strong ops practitioners hang out, ask questions, and share knowledge. Posting there gives you access to a concentrated pool of actively engaged practitioners. (Source: Sean Lane, Episodes #274 and #187)

**Leaders should dedicate approximately 25% of their time — roughly 10 hours per week — to recruiting and nurturing relationships with potential future hires, even when not actively hiring.** This includes coffees, lunches, and networking to build a pipeline of talent. The best leaders maintain this discipline consistently, which allows them to have their pick of top talent when a role opens. (Source: David Kline, Episode #138)

**To calibrate whether you need to upgrade a team member, go meet five peer-level professionals in that function without a formal job opening or interview process.** Just have coffee and ask yourself: if I had someone at this level, would my life change? If yes, consider making a move. If no, keep your current person. This is a low-friction way to assess whether a capability gap is real or whether you're experiencing loyalty bias. (Source: Dave Kellogg, Episode #342)

---

## Evaluating Specific Candidate Types

**When hiring ops people, look for candidates who are "adaptively excellent."** They can take context from previous experiences and thrive in new environments without hand-waving or faking. They should understand foundational elements deeply and apply them creatively to new situations. Also prioritize inherent curiosity and a competitive drive to solve problems. As an unconventional signal, candidates who enjoy crossword puzzles tend to excel in ops roles. (Source: Sean Lane, Episodes #274 and #187)

**When hiring designers, prioritize curiosity — what they think about outside of work, what content they consume, what they find aesthetically compelling — over portfolio depth or years of B2B experience.** A designer with 1,000 B2B websites in their portfolio may produce nothing fresh. Seek designers inspired by work outside the B2B space. Assess this by asking what they're curious about and what motivates them creatively. (Source: Dmitry Shamis, Episode #238) *(Note: this is contested — see Where Experts Disagree)*

**When hiring for community roles, prioritize subject-matter expertise over community management experience.** A person who understands your audience can learn community management skills on the job, but a community manager without subject-matter expertise will struggle to create meaningful content and connections. (Source: Dave Gerhardt, Episode #320)

**When you lack domain expertise, hire subject matter experts as brand advocates or evangelists rather than as full-time specialists.** This can be done part-time or as contractors. Pair this with internal editorial oversight to maintain quality control. (Source: Kevin White, Episodes #286 and #179)

**When an influencer or creator demonstrates strong performance in a creator program and shows genuine product value, consider hiring them into a relevant full-time role.** This eliminates ongoing creator fees, ensures they continue evangelizing authentically, and brings their audience credibility and distribution into the company. This works best when the influencer's expertise aligns with an actual team need. (Source: Kevin White, Episode #179)

**When hiring for AI video teams, prioritize generalist creatives who understand direction, cinematography, and copy over specialists in single disciplines.** The ideal candidate understands the full creative workflow and can move from idea to execution without needing to hand off to multiple specialists. (Source: Vicente, Episode #345) *(Note: this is contested — see Where Experts Disagree)*

---

## Team Structure and Org Design

**Structure your team around business functions and goals, not job titles.** Start by identifying the key functions and goals your business needs to accomplish, then hire people who can own those functions. Avoid defaulting to traditional org charts or industry benchmarks. Allow roles to evolve as the business grows rather than locking people into rigid titles. (Source: Dave Gerhardt, Episode #143)

**As a marketing leader, hire strong functional leaders and ask them detailed questions rather than trying to be expert in every discipline.** When you don't understand something, ask the leader to explain it simply, then ask follow-up questions about the underlying logic. Trust them while advocating for them. (Source: Priscilla Barolo, Episodes #302 and #193)

**As a CMO, deliberately hire VPs and specialists who are smarter than you in specific functional areas rather than hiring junior people you can manage.** Acknowledge gaps in your expertise openly to your team and ask for master classes from your specialists. This creates a stronger overall marketing organization and prevents the CMO from becoming a bottleneck. (Source: Maura Rivera, Episode #301) *(Note: this is contested — see Where Experts Disagree)*

**Use a portfolio approach when building a leadership team.** Hire 1-2 world-class experts in critical areas (your blind spots, strategic priorities, or areas where you lack depth), then hire high-potential people in other roles and invest heavily in their development through mentorship, training, and support. (Source: Peter Mahoney, Episode #128) *(Note: this is contested — see Where Experts Disagree)*

**Invest in hiring talented designers relative to company size.** Design is one of the few areas where AI still struggles to produce work that stands out. A strong design team allows you to obsess over details and build a distinctive brand while competitors rely on generic AI-generated creative. (Source: Tom Wentworth, Episode #304)

**When scaling a small team, hire senior peers who can operate independently rather than junior staff requiring management.** Prioritize hiring someone at or near your level of seniority who understands your communication style and won't require extensive training or one-on-ones. This preserves your ability to move fast without the overhead of coaching. (Source: Dave Gerhardt, Episode #205)

**Hire and develop multi-threaded marketers who can execute across integrated tactics, not siloed specialties.** A multi-threaded marketer understands how content, paid media, lifecycle marketing, and events interconnect and can execute across these areas. This is especially valuable in AI-first companies where you need fewer people doing more. (Source: Kady Srinivasan, Episode #276) *(Note: this is contested — see Where Experts Disagree)*

**Actively avoid hiring people in your own image.** Deliberately hire for diversity of thought, background, and skill. Consciously check whether you're gravitating toward people who think like you, come from similar backgrounds, or have similar skill sets. Homogeneity leads to groupthink and repeated mistakes. (Source: Peter Mahoney, Episode #128)

**Hire a strong chief of staff who can tell you when you're overstepping your role or diving too deep into execution.** The chief of staff serves as both an operational enabler and a boundary-setter, preventing the CMO from bungee-jumping into work that should be delegated. This relationship requires trust and directness. (Source: Peter Mahoney, Episode #128)

---

## Hiring Standards and Decision-Making

**Before hiring someone, ask: Am I confident I need this role for 2-3 years?** If the need is only 12-18 months, bring in a specialist, consultant, or outsource instead. Recognize that hiring someone means asking them to commit a third of their life to your organization. This high bar prevents over-hiring and forces discipline in headcount decisions. (Source: Peter Mahoney, Episode #202)

**Treat hiring and layoffs with equal seriousness.** When you hire someone, you're responsible for a third of their life and half their waking hours — that's a significant commitment requiring a high bar. When you must reduce headcount, do it decisively and with clear business rationale. (Source: Peter Mahoney, Episode #128)

**Do not hire someone who is skilled but culturally misaligned, even under pressure to fill a role quickly.** Cultural misalignment will not improve over time — people do not change after hire. Red flags during interviews (e.g., scarcity mindset, unwillingness to help outside their job description, poor interpersonal fit) are predictive of future problems. It is better to stay understaffed than to hire someone who will create friction. (Source: David Kline, Episode #138)

**Before hiring to solve an overwork problem, first audit your current work to eliminate unprofitable or low-value activities.** Examples include raising prices on unprofitable customers, reducing meeting frequency, or eliminating unnecessary processes. Only hire after you've streamlined and confirmed the need is real. (Source: David Kline, Episode #138)

**When building teams, prioritize hiring people with extreme strengths in specific areas rather than people who lack obvious weaknesses.** Use strengths-based frameworks (like StrengthsFinder) to identify what each person is uniquely good at, then structure the team so those strengths compound. (Source: Matt Devincentis, Episode #260)

---

## Onboarding and Retention

**For senior hires, expect the new hire to spend 3-6 months primarily shadowing and learning rather than producing work.** This allows them to absorb context, build relationships, and understand the organization deeply. While high-performing hires will naturally start taking on work, the expectation should be learning-focused. This prevents setting them up for failure and leads to steeper performance trajectories. (Source: David Kline, Episode #138)

**During onboarding, ask team members how they want to be managed, how they prefer to receive feedback, and what challenges they face.** Use this information to tailor your management approach. This early conversation signals that you care about their preferences and creates a foundation for psychological safety. (Source: Dan Cmejla, Episode #134)

**When joining a new company or team, interview every person on your marketing team and cross-functional partners using consistent questions.** Collect verbatim comments, then analyze them for patterns. Bucket findings into categories like problem areas, strengths, and areas of uncertainty. This gives you a data-driven view of the team's state. (Source: Tara Robertson, Episode #188)

**Regularly review compensation for your top 1-2 performers and proactively offer raises or bonuses before they ask or leave.** Recognize that the easiest way for an employee to get a 20-30% raise is to change jobs; retention through competitive compensation is more cost-effective than external hiring. Ensure compensation decisions are tied to clear role levels and salary bands so raises feel systematic rather than arbitrary. (Source: Dave Gerhardt, Episode #131)

---

## AI Tools and Team Adoption

**Create a dashboard to identify which team members are using AI tools most actively.** Recruit these power users as evangelists by asking them to record demos and share their workflows with the broader team. Bottom-up adoption driven by peer examples is more effective than top-down training, as team members get excited seeing someone like them successfully building with AI. (Source: Drew Pinta, Episode #346)

**Teach junior marketers from day one that AI is part of their operating system, not an optional tool.** Emphasize that success requires being more curious and strategic than AI itself — reading widely, building reference points, questioning outputs, and knowing which tool to use for which task. The goal is to shift from "finding information" to "discerning and questioning." (Source: Jennifer Cannizzaro, Episode #267)

---

## Diagnosing Underperformance

**When someone is underperforming, work through four diagnostic questions in order:**
1. Do they have the resources and tools needed?
2. Have they received adequate training and context?
3. Do they have the skill (ability) to do the job?
4. Do they have the will (motivation) to do the job?

Start with will before skill because if someone doesn't want the job, training won't help. If they have both skill and will but are still struggling, consider whether an external hire could catch up in 3-6 months — if yes, it may be time to move on rather than continue investing. (Source: David Kline, Episode #138)

---

## Where Experts Disagree

### 1. Should you prove out a marketing function before hiring a dedicated person, or hire early to build the function?

**The dominant position — prove before hiring (5 supporters):**
Sylvia Lepoidevin (Episodes #283 and #199), Dave Gerhardt (Episodes #143, #169, and #138) all argue that before hiring a dedicated full-time person for a new marketing function or channel, you should first test and validate that the function works for your business. Run it yourself or with existing resources, confirm it drives results, and only then hire a specialist. Lepoidevin explicitly stated that every hire is a bet and you should only place bets on things you've already validated. Gerhardt shared a personal example: he spent 2 years doing content himself, then 1.5 years with a contractor, before hiring a full-time content person.

**The dissenting position — hire foundational roles early (1 supporter):**
John Short (Episode #271) argues that for certain roles — specifically GTM engineers — you should hire early, ideally as one of the first three to five marketing hires, rather than waiting to prove out the function. Building efficient systems for content creation, customer feedback loops, AI integration, and workflow automation from the start sets the foundation for scalable operations.

**Support summary:** 5 vs 1

**Context dependency:** John Short's advice is specifically about GTM engineers as a systems-building role, which could be seen as a different category than channel-specific hires. However, the core question of whether to hire before or after validation is the same, making this a genuine disagreement in philosophy even if the specific role differs.

**Trend note:** The lone dissenter (John Short, August 2025) is more recent than most of the "prove before hiring" advocates, potentially reflecting a newer view that AI-era team building requires earlier infrastructure investment. However, one data point is insufficient to call a trend.

**Why it matters:** Hiring before validating a function wastes budget and sets up the new hire for failure; but waiting too long to hire foundational roles can mean building on a weak operational foundation — the sequencing decision has real cost implications.

---

### 2. Should you hire marketing specialists or generalist multi-threaded marketers?

**Position A — hire generalists and multi-threaded marketers (2 supporters):**
Kady Srinivasan (Episode #276) argues that multi-threaded marketers who understand how tactics interconnect are more valuable than specialists, especially in AI-first companies where you need fewer people doing more across content, paid, lifecycle, and events. Vicente (Episode #345) makes a parallel argument specifically for AI video teams: prioritize generalist creatives who understand the full creative workflow over specialists in single disciplines like motion graphics.

**Position B — hire deep specialists smarter than you (3 supporters):**
Maura Rivera (Episode #301) recommends hiring VPs and specialists who are smarter than you in demand gen, marketing ops, analytics, etc., and asking for master classes from them rather than managing junior generalists. Peter Mahoney (Episode #128) advocates a portfolio approach that explicitly values deep specialists in critical functions. Jason Lemkin (Episode #142) argues against hiring generalist marketers and expecting them to excel at everything — instead, match the person's specific superpower (brand, demand gen, product marketing, growth) to the company's immediate need.

**Support summary:** 3 vs 2

**Context dependency:** The generalist argument is strongest for small AI-first teams or early-stage companies where headcount is constrained, while the specialist argument applies more to scaling teams with budget for dedicated functional leaders. However, both camps are making broader team-building philosophy claims, so there is genuine disagreement on the default hiring approach.

**Why it matters:** The choice between generalists and specialists shapes org design, hiring criteria, and how marketing teams scale — getting this wrong means either hiring people who can't execute across the full funnel or hiring specialists who create silos and handoff friction.

---

### 3. Should you weight credentials and prestigious backgrounds heavily when hiring marketers?

**Position A — de-emphasize credentials, value hustle and non-traditional backgrounds (2 supporters):**
Jeff Hardison (Episode #335) explicitly argues against over-weighting school or prestigious company backgrounds, citing the example of an NPR hire with no tech experience who could be an amazing hire with the right instincts. Look for hustle, creativity, and ability to figure things out. Dmitry Shamis (Episode #238) makes a parallel argument for designers: a designer with 1,000 B2B websites in their portfolio may produce nothing fresh; prioritize curiosity and outside interests over portfolio depth or years of B2B experience.

**Position B — weight demonstrated public expertise and reputation (2 supporters):**
Jess Cook (Episode #266) recommends prioritizing candidates who have built their own audience and reputation publicly, as they can become evangelists and amplify marketing efforts. Dan Cmejla (Episode #134) recommends recruiting talent at the intersection of excellence and public content creation, looking for candidates with existing followings or content portfolios.

**Support summary:** 2 vs 2

**Context dependency:** The "public presence" advocates (Jess Cook, Dan Cmejla) may be specifically addressing content and brand roles where public visibility is itself a job requirement, while the "hustle over credentials" advocates (Jeff Hardison, Dmitry Shamis) are speaking more broadly about product marketing and design. The disagreement partially dissolves if you account for role type, but both camps are making general hiring philosophy claims.

**Why it matters:** Overweighting credentials screens out high-potential non-traditional candidates, while ignoring demonstrated public expertise may mean missing candidates who bring built-in distribution and credibility — the right filter depends on what the role actually requires.

---

## What NOT To Do

**Don't hire based on title or past success alone.** A VP of Marketing who succeeded at a brand-focused company will fail at a company that needs demand generation. Match the person to the actual job, not the job title. (Source: Jason Lemkin, Episode #207)

**Don't accept surface-level answers in interviews.** Small talk and gut feeling are not a hiring process. Use structured questions and follow-up probing to understand how candidates actually think and what drives them. (Source: David Kline, Episode #138; Jeff Hardison, Episode #335)

**Don't hire someone who is culturally misaligned, even if skilled and even if you're under pressure to fill the role.** Cultural misalignment will not improve after hire. Red flags during interviews are predictive of future problems. (Source: David Kline, Episode #138)

**Don't hire people in your own image.** Homogeneity in thought, background, and skill leads to groupthink and repeated mistakes. Consciously check for this bias. (Source: Peter Mahoney, Episode #128)

**Don't hire to solve an overwork problem before auditing whether low-value work can be eliminated first.** Hiring is not the only solution to capacity constraints. (Source: David Kline, Episode #138)

**Don't hire a community manager without subject-matter expertise in your audience's domain.** They will struggle to create meaningful content and connections regardless of their community management experience. (Source: Dave Gerhardt, Episode #320)

**Don't hire a specialist for a new marketing function before validating that the function works for your business.** (Source: Sylvia Lepoidevin, Episodes #283 and #199; Dave Gerhardt, Episodes #143, #169, #138) *(Note: contested for certain foundational roles — see Where Experts Disagree)*

**Don't hire a writer and expect them to figure out marketing strategy later.** Hire a marketer who can write, not the reverse. (Source: Dave Gerhardt, Episode #200)

**Don't claim you want an early-stage role if you're unwilling to do hands-on execution work.** The CEO will be doing the work themselves anyway, and you'll be miserable. (Source: Jason Lemkin, Episode #142)

**Don't rush senior hires into production.** Expecting a C-level or high-impact hire to produce immediately rather than spend 3-6 months learning sets them up for failure. (Source: David Kline, Episode #138)

**Don't rely solely on recruiter outreach when hiring.** CMO-direct LinkedIn messages generate significantly higher response rates. (Source: Sylvia Lepoidevin, Episodes #283 and #199)

**Don't hire incrementally without justification.** Before hiring, ask whether you need this role for 2-3 years. If not, use a specialist, consultant, or outsource instead. (Source: Peter Mahoney, Episode #202)

**Don't attempt to hire A+ proven leaders across all functions simultaneously.** Use a portfolio approach instead: world-class experts in critical areas, high-potential developers elsewhere. (Source: Peter Mahoney, Episode #128)

---

## Sources

| Episode | Guest | Date |
|---------|-------|------|
| #346 | Drew Pinta | 2026-04-13 |
| #345 | Vicente | 2026-04-09 |
| #345 | Luke | 2026-04-09 |
| #342 | Dave Kellogg | 2026-03-31 |
| #335 | Jeff Hardison | 2026-03-05 |
| #320 | Dave Gerhardt | 2026-01-12 |
| #306 | Natalie Taylor | 2025-11-24 |
| #304 | Tom Wentworth | 2025-11-17 |
| #302 | Priscilla Barolo | 2025-11-10 |
| #301 | Maura Rivera | 2025-11-06 |
| #286 | Kevin White | 2025-09-29 |
| #283 | Sylvia Lepoidevin | 2025-09-18 |
| #276 | Kady Srinivasan | 2025-08-25 |
| #274 | Sean Lane | 2025-08-18 |
| #271 | John Short | 2025-08-07 |
| #267 | Jennifer Cannizzaro | 2025-07-24 |
| #266 | Jess Cook | 2025-07-21 |
| #260 | Matt Devincentis | 2025-06-30 |
| #259 | Pranav Piyush | 2025-06-26 |
| #238 | Dmitry Shamis | 2025-04-17 |
| #219 | Dave Gerhardt | 2025-02-13 |
| #207 | Jason Lemkin | 2025-01-02 |
| #205 | Dave Gerhardt | 2024-12-26 |
| #202 | Peter Mahoney | 2024-12-16 |
| #200 | Dave Gerhardt | 2024-12-09 |
| #199 | Sylvia Lepoidevin | 2024-12-05 |
| #193 | Priscilla Barolo | 2024-11-14 |
| #188 | Tara Robertson | 2024-10-28 |
| #187 | Sean Lane | 2024-10-24 |
| #179 | Kevin White | 2024-09-26 |
| #169 | Dave Gerhardt | 2024-08-22 |
| #161 | Max Van Den Ingh | 2024-07-25 |
| #143 | Dave Gerhardt | 2024-05-23 |
| #142 | Jason Lemkin | 2024-05-20 |
| #138 | David Kline | 2024-05-06 |
| #138 | Dave Gerhardt | 2024-05-06 |
| #134 | Dan Cmejla | 2024-04-22 |
| #131 | Dave Gerhardt | 2024-04-11 |
| #128 | Peter Mahoney | 2024-04-01 |