Whispered Hiring

In this episode of How I Hire, Andy Mowat speaks with Guy Yalif, Chief Evangelist at Webflow and former co-founder of Intellimize (acquired by Webflow), about his precision-engineered approach to executive hiring in marketing. Drawing from leadership roles at Twitter, Yahoo, and BrightRoll, plus an unconventional career path from aerospace engineer to CMO, Guy shares specific frameworks for evaluating senior marketing talent across product marketing, demand gen, brand, and comms. His insights reveal how to assess whether candidates genuinely understand AI tooling versus surface-level ChatGPT usage, why traditional case studies fail in 2025, and how to implement "SIM" interviews that actually predict on-the-job performance. Topics discussed: The four core marketing specialties framework for executive hiring: product marketing (messaging, positioning, value prop), demand gen (paid, organic, SEO), comms, and brand. Why clarifying a candidate's "wheelhouse" matters more than checking boxes, and ensuring they'll hire people better than themselves in weaker areas to round out the team. Why product marketing is the hardest marketing discipline to hire for: the feedback loop takes 6+ months to see if messaging shifts drive business impact, "great" looks deceptively similar to "good" during interviews, and the role splits into two distinct types (inbound/strategic versus outbound/launch execution) that use identical terminology. The "altitude assessment" interview technique: listen for whether candidates answer at market dynamics and business impact level versus spreadsheet mechanics level, then deliberately ask follow-up questions to force altitude changes and identify where they have genuine depth versus rehearsed talking points. How the "SIM" (simulated meeting) approach fixes broken case studies: give candidates ~1 week on a real scenario, explicitly tell them to use you as a resource ("ping me off hours, ask anything"), and judge the prep conversations as heavily as the final presentation to see how they synthesize, ask questions, and handle ambiguity rather than how well they prompt ChatGPT. The framework for assessing stage-readiness: look for experience at both large companies ("seen it done really well") and startups ("scrappiness and grit"), then test if their muscle memory matches your stage by listening for whether they describe slicing roles into multiple people (big company reflex) or being hands-on with zero direct reports (startup reality). The blind reference process that works: tell candidates upfront you'll contact people they didn't introduce, ask what's off-limits to protect their current job, then do 3-5+ references. When one reference is surprisingly negative, do 4-5 more to determine if it reveals a pattern or says more about that specific reference-giver. Why tracking consistency and variety of storylines separates real performers from interview performers: watch for candidates who tell the same story with different data to different interviewers (red flag), and assess whether they have multiple strong examples across situations or just one or two polished go-to stories indicating limited depth. The "magic wand" question that cuts through performance: "If you could craft the perfect next gig that had you happy to go to work every day, irrespective of this discussion, what's that job look like?" This surfaces genuine alignment, reveals rote regurgitation, or uncovers the one critical dimension they haven't voiced that might be a dealbreaker.   ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Ryan Westwood, CEO and founder of Fullcast and serial entrepreneur who previously scaled Simplist to over $600 million in revenue. Ryan reveals his systematic approach to M&A and executive hiring, including why he uses physical activities to assess mindset beyond polished interviews and maintains a multi-decade spreadsheet of talent observed in authentic contexts. His frameworks demonstrate how maintaining six executives with 10+ year tenure creates compound advantages in speed and decision-making. Topics discussed: Using physical activities to reveal authentic leadership beyond interviews: Why Ryan uses VR skydiving for acquisition target CEOs and walking or fly fishing for executive candidates. These contexts bypass the "professional interviewer" problem where senior leaders have refined responses across 25+ similar conversations. Ryan notes: "I will find without fail, I will learn very insightful things. I've never been on a walk in an interview process where I didn't pick up on really great nuggets that I never gathered in the interviews." The decisive integration framework for M&A success: After vetting the CEO, the critical success factor is decisive clarity on two variables: the CEO's specific role going forward and whether products will integrate. The failure zone is ambiguity or the "middle ground." If a CEO is tired after 15 years, that's acceptable if explicitly acknowledged upfront rather than pretending continued enthusiasm while the team detects misalignment through actions. The compounding advantage of hiring one executive at a time: Ryan has never hired more than one executive in a year time frame, maintaining six executives with 10+ year tenure. This creates asymmetric advantages: zero political dynamics, executives who proactively solve problems without CEO involvement, and bandwidth to deeply support the single new hire versus the typical scenario of simultaneously training four executives competing for attention. The board composition question that reveals company dynamics: Ryan walks through how to decode company risk, culture, and power dynamics by understanding board makeup (common vs. preferred seats, independents, investor types). The specific question to ask during interviews: "Tell me about the board you've constructed." This single question reveals more about a company's trajectory than hours of other diligence. The repeat executive diagnostic for vetting CEO quality: When evaluating offers, ask "How many people are repeat executives for you?" If a CEO built a unicorn but zero executives from their prior company joined their next venture, that's a signal about working relationship quality. Ryan's six long-term executives each received double-digit equity stakes, creating aligned economics beyond typical executive compensation. Maintaining a talent observation system across decades: Ryan keeps a spreadsheet of impressive operators observed in non-interview contexts: cubicle colleagues who stayed focused during company chaos, HR consultants who delivered executive-caliber presentations, people demonstrating character in everyday situations. This becomes the first hiring source because authentic behavior reveals more than performative interviews. The 50-page CEO Operating Rhythm document for accelerated onboarding: Ryan maintains a living document covering his complete operating philosophy, department-specific frameworks, decision-making preferences, and working style. New executives review relevant sections to compress the getting-to-know-you period from years to weeks. Supplement with daily check-ins initially, weekly video calls, and mandatory first-week meetings with all other executives who report observations back to Ryan. ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Robin Bordoli, CRO & CMO at Weights & Biases, about his engineering-informed approach to hiring senior GTM talent in AI-native companies. Drawing from his experience leading revenue organizations through IPO at Marketo and Jive, plus CEO roles at Nextroll and Figure 8, Robin shares his five-element pre-search system and how he applies optimal stopping theory to make mathematically rigorous hiring decisions. Topics discussed: Why VP of Field Engineering is the hardest GTM hire, requiring leaders who can manage four distinct technical roles (solution architects, pre/post-sales solution engineers, forward-deployed engineers) while balancing deep technical acumen with commercial instincts that most candidates spike one direction or the other. The mandatory five-element pre-search framework executed before meeting any candidates: JDs written from scratch with force-ranking criteria (specific program spend, pipeline targets, ARR stage), hunting grounds, minimum five sample profiles ranked against the JD, interview process with decider/inputs/socializers explicitly designated, and role-specific take home exercises. How to design AI-resistant take home exercises using open-ended scenarios (annual planning with constraints for demand gen, live sales positioning with 10 minutes prep for PMM) requiring 1-3 hours prep plus live presentation, where synthesis quality and trade-off articulation matter more than the artifact itself. The three-round interview structure optimized for 9-hour total candidate investment, with Round 3 socializers serving as the final gate where candidates can expose naivete about equity/board dynamics or reveal poor judgment through inappropriate requests. Why external recruiters provide three strategic advantages beyond sourcing: accessing passive candidates planning six-month professional exits, providing market intelligence on whether hundreds or five people fit specialized criteria, and creating trusted advisor dynamics where candidates reveal vulnerabilities they won't share internally. Applying optimal stopping theory (the 37% rule) to sequential hiring decisions: estimate total qualified candidates meetable in your timeline, interview the first 37% to calibrate on the strongest, then extend offer to the next candidate exceeding that benchmark. Three executive diagnostic questions that expose readiness: "What four adjectives appear in a word cloud from everyone who knows you well?" "Where were you the best and worst versions of yourself and why?" "What are your decision criteria and where does your current role fall short?" The counterintuitive onboarding framework that prevents executive failure: explicitly contract for 30-90 days where the only ask is listening and learning, while concurrently assigning a first project that's in their wheelhouse but requires cross-functional engagement to balance psychological safety with purposeful integration.   ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Julien Sauvage, CMO at Cordial, about building authentic hiring processes that cut through scripted interactions. Drawing from his experience scaling marketing at Salesforce, Gong, Clary, and Talend, Julien reveals why he starts every interview by saying "I hate interviews," how to identify storytellers within three sentences, and why the commoditized 30-60-90 day plan has become useless for evaluating senior talent. Topics discussed: How to assess storytelling and listening skills immediately: evaluating whether candidates create narrative contrast in warm-up questions versus flat responses, while ensuring they demonstrate empathy and active listening rather than constant pitch mode. Why you must build the plan and define outcomes before the org chart: using the create-capture-convert demand framework to color-code performance gaps, then determining whether to solve with programs or headcount rather than reflexively backfilling roles. The strategic outsourcing decision matrix: why PMM and brand require full-time employees who breathe company identity daily, while creative and MOPs can be outsourced when CEOs won't approve design headcount over campaign managers. The broken state of VP+ recruiting: receiving 3,000 applications for a senior manager role at Cordial, leading to targeted outreach through operator networks instead of posting senior roles that waste everyone's time. Why company pedigree matters and when to take risks: prioritizing candidates from high-growth companies over inflated titles at stagnant organizations, while recognizing when to make strategic bets like his jump from public company VP to three-person team at pre-unicorn Gong. Creating joyful interview experiences through radical authenticity: starting with "I hate interviews, let's not make this feel like one" to drop facades and enable real assessment of how candidates handle ambiguity. The go-to interview question for marketing leaders: "What's the riskiest bet you've taken?" to assess boldness, self-awareness, and ability to reflect on both wins and failures in a risk-averse industry. How to close candidates with brutal honesty: explicitly stating "there's no dream job" while painting the real challenges alongside opportunities, removing fluffy mission-driven narratives that candidates see through. Why the 30-60-90 day plan is dead: everyone uses GPT to generate identical plans, making it worthless for evaluation while emphasizing the need for balance between strategic thinking and delivering quick wins in the first six months. ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Tolithia Kornweibel, CEO of Beam Benefits, about her progression from CMO to CRO at Gusto before taking the CEO helm. Having scaled through Gusto's growth from 300 employees to its current size while managing both marketing and sales organizations, Tolithia shares why she deliberately operates without talent acquisition at Beam and how transparent communication about company challenges, including directing candidates to read negative Glassdoor reviews, actually strengthens hiring outcomes. Her approach challenges conventional wisdom, from eliminating 90-day plans to maintaining hands-on involvement from day one. Topics discussed: Why sales leadership remains the hardest GTM hire to get right, with success depending as much on organizational readiness to support transformation as finding the right person, and why it must show impact within one sales cycle. The "describe your perfect boss" interview technique that reveals collaboration style and independence spectrum positioning, with resistance to "micromanagement" serving as an immediate disqualifier for small company environments requiring altitude flexibility. How transition from Gusto's 70-person talent acquisition team to zero TA at Beam forced a shift to continuous networking and proactive relationship building, often having 3-4 hours of exploratory conversations before formal interviews. The deliberate use of job postings solely as shareable links for network distribution, acknowledging that at VP level and above, submitted applications are essentially unusable due to volume and AI-generated noise. Why keeping interview panels to 4 people maximum (2 decision makers, 4 total) while encouraging candidates to request additional stakeholder access serves as both efficiency measure and positive signal of thoroughness. The mixed value of Gusto's hiring committee structure requiring conviction ("if it's a soft yes, it's a no") for values alignment, while creating educational tax for GTM leaders needing to justify hires to engineering-heavy committees. The case against 90-day plans for senior hires: "Your half-informed decision is probably better statistically than anything we were coming up with before" because senior leaders are hired specifically to drive immediate change. Why senior leaders must become "mildly dangerous" with AI tools quickly, not for innovation but to implement brilliant basics, validate ideas rapidly, and create psychological safety for their teams' experimentation in an AI-transformed landscape. ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Manny Medina, Co-Founder & CEO of Paid (an AI agent monetization platform), about dismantling the traditional SaaS hiring playbook that helped define his previous company, Outreach. After scaling Outreach to over 1,000 employees and hundreds of millions in revenue, Manny reveals why he's now refusing to hire senior executives and instead building Paid with a radical junior-first, contractor-heavy approach. His contrarian insights challenge twenty years of VC-backed wisdom about org structure, talent evaluation, and the fundamental economics of building software companies in the AI era. Topics discussed: Why the era of templated org structure playbooks is dead: Manny challenges the assumption that every SaaS company needs the standard SDR → AE → CSM structure, arguing companies should question whether these roles should even exist rather than automatically copying what worked elsewhere. Mission charts over org charts at Paid: Instead of traditional reporting structures, Paid organizes around specific revenue missions (self-serve for agent builders, SaaS companies selling agents, enterprise) with teams aligned to outcomes rather than titles or hierarchies. The "AI first, then contractor, then person" hiring framework: This progression allows maximum flexibility to correct inevitable hiring mistakes while testing whether roles can be automated before committing to full-time headcount. Why "no breath is better than bad breath" thinking is dangerous: Manny learned that hiring mediocre talent lowers the bar for future hires and signals to existing team members they can coast, creating a gradual slide from A-players to B-plus teams. The power of forward deploy engineers learning directly from customers: Putting junior talent in front of customers accelerates their learning curve and business acumen faster than any internal training, while costing a fraction of senior hires. How aggressive negotiation reveals future management headaches: When candidates push too hard on compensation during offers, it often predicts they'll renegotiate every 60 days, turning one-on-ones into advocacy sessions rather than productive work discussions. Hiring mistakes aren't permanent if you stay close: By personally onboarding everyone and maintaining proximity to new hires in the first 30-60 days, you can quickly spot mismatches between talent and role requirements, then course-correct before damage compounds. ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Alina Vandenberghe, Co-CEO of Chili Piper, about building high-performing remote teams through radical transparency and unconventional talent development. Over 10 years of scaling Chili Piper into a leading demand conversion platform, Alina has developed contrarian approaches to executive hiring, from requiring GTM leaders to pass technical competency tests to sharing complete financial data during interviews. Her insights reveal how treating internal promotion as the default path, rather than external hiring, creates both stronger leadership and better cultural alignment. Topics discussed: Why Chili Piper opens their entire data room to all employees, including cash runway, churn rates, and board decks, and how this transparency enables SDRs to develop executive-level thinking and grow into VP roles within the company. The "electrons and protons" framework for role optimization: identifying energy-giving versus energy-draining tasks for each employee, then strategically deploying fractional specialists and AI agents to handle the draining work while maximizing individual impact zones. How to evaluate remote work readiness beyond the resume: screening for intrinsic motivation through storytelling passion, why office experience is non-negotiable for junior hires, and the correlation between self-directed learning and remote success. The technical competency requirement for all GTM executives, including testing CMOs and CROs on JSON and JavaScript understanding, to ensure they can credibly engage with RevOps buyers and technical stakeholders. The three-part framework for evaluating departure stories: verifying honesty through back-channel references, assessing ownership versus blame mentality, and gauging compassion toward their current employer as a predictor of future behavior. Why leading with questions rather than data during executive interviews reveals strategic thinking: asking candidates what metrics they need rather than presenting your board deck shows how they prioritize and think about the business. The paradox of building a fully remote company while prioritizing in-person recruiting at industry events, using stage presence and dinner interactions as leading indicators of cultural fit and relationship-building ability. The intensive onboarding approach where new executives spend multiple days at Alina's home, observing founder-mode operations firsthand and understanding how personal mission integrates with business execution, plus explicitly communicating where founder support ends and external mentorship begins. ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Patty DuChene, SVP of Marketing and Growth at Sendoso, about her systematic approach to inheriting and rebuilding teams post-acquisition. Drawing from her experience scaling from first sales hire at bootstrapped Wrike to leading teams through high-growth trajectories, Patty shares her 45-day team diagnostic framework, her contrarian stance against case studies, and why she deliberately targets hospitality veterans and returning parents for revenue roles. Topics discussed: The JD forensics methodology for new leaders—systematically auditing every team member's original job description against their actual time allocation through self-assessment, revealing scope creep patterns where critical functions (like demand gen) were consuming 40% instead of planned 10% of bandwidth. Why deliberately posting senior roles publicly functions as a behavioral screen for leaders who retain entrepreneurial hunger—specifically filtering for executives willing to navigate competitive application processes rather than waiting for recruiters to approach them passively. The acquisition integration playbook of cataloging competitor intimidation factors first—identifying specific capabilities that created competitive anxiety, then reverse-engineering those strengths into role definitions and team gaps for the combined entity. Google's empirical finding that three 45-minute interviews predict role fit regardless of seniority level, making organizations requiring 6+ interviews or extensive case studies symptomatic of executive indecision rather than thoroughness. Non-traditional talent arbitrage strategies targeting hospitality professionals (bartenders managing 2am crowd control translate directly to cold-calling resilience) and returning parents (daily EQ testing with children builds exceptional people leadership capabilities that surface in management roles). Two behavioral interview questions that bypass resume screening: Asking "What are you most proud of?" without clarification to assess self-direction versus approval-seeking, and "What's the last thing you taught someone?" to evaluate knowledge transfer capabilities essential for cross-functional influence. The strategic onboarding framework of pre-structured cross-functional stakeholder meetings with specific agendas, enabling new hires to understand each leader's decision-making triggers and craft compelling change narratives from day one. The 45-day confidence litmus test for senior hires—executives who haven't begun making autonomous decisions by this milestone typically indicate fundamental issues with executive presence that compound over time, requiring immediate intervention or replacement. ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

In this episode of How I Hire, Andy Mowat speaks with Mike Weir, CRO of Finalis and former CRO of G2, about his tactical approach to executive hiring at inflection points. Mike shares the specific methodologies he uses to assess leadership gaps when joining early-stage companies, restructure inherited hiring processes mid-flight, and design roles that prevent the expensive cycle of executive turnover. His contrarian insights on posting strategy, interview control dynamics, and pre-emptive problem solving reveal how intentional hiring decisions compound organizational velocity. Topics discussed: Why head of revenue operations is the critical first hire within 30 days of any CRO joining: Serving as brain trust for business fundamentals while functioning as organizational ambassador who keeps leadership accountable to cross-functional stakeholders and long-term planning. The precise methodology for inheriting in-process executive searches: How Mike evaluates existing candidates without prior team bias, uses the interview process to calibrate expectations with peer leadership, and reshapes job requirements mid-search when business needs shift. The bright-line rule for executive recruitment: C-suite roles never get posted due to competitive intelligence risks and requirement customization needs, while VP-level roles always get posted to access talent pools beyond homogeneous networks—with specific tactics for managing high-volume applications. Strategic role architecture decisions: When to hire Chief Sales Officer versus full-stack CRO based on company stage and CEO capacity, including the trade-offs of having the CEO become the final go-to-market decider and required operational depth this demands. The "business conversation litmus test" for senior leadership interviews: If candidates cannot engage in strategic dialogue about real company challenges and offer substantive questions within the first interaction, they lack the executive presence required for autonomous leadership roles. Mike's pre-structured onboarding methodology: A meticulously mapped 3-week schedule with defined meeting agendas for peer introductions, foundational knowledge transfer, and strategic context—designed to accelerate time-to-impact while securing early wins before complex problem inheritance. The preemptive talent management approach: Why Mike negotiates difficult personnel decisions and active performance issues before new executive hires start, preventing them from absorbing political damage and relationship capital loss in their first 90 days. Technical assessment frameworks for executive hiring: Using real business scenarios and current decision points as case studies to evaluate thinking processes, stakeholder engagement approaches, and decision-making frameworks rather than theoretical responses. ABOUT YOUR HOST:  Andy Mowat has built GTM engines for top companies throughout his career. He led Revenue Operations and Demand Gen at four unicorns, including scaling from $10M to $100M ARR at both Upwork and Culture Amp, and helping guide Box and Carta through IPO scale. With a passion for connecting people, Andy has advised executives on their careers for years and launched Whispered to make searching for executive roles less intimidating.  Learn more about about Whispered: www.whispered.com Interact with AI Andy: www.whispered.com/whisper-search

Kyle Norton, CRO at Owner.com and a former sales leader at Shopify, shares his expertise in systematic hiring processes for high-velocity sales environments. He reveals his 'hire 18 months ahead' framework that helped scale Owner.com and discusses how traditional sales performance metrics can mislead hiring decisions. Leveraging Kahneman's principles, he emphasizes structured evaluations to minimize bias. Additionally, he advocates for quarterly hiring analyses to refine talent assessment and improve overall accuracy in hiring.