Whispered Hiring

Nick Mehta, longtime CEO of Gainsight, dives into the intricacies of executive hiring and culture design. He reveals how defining clear expectations transforms the hiring process, especially for CMOs, and shares a vulnerability exercise that enhances team alignment. Nick discusses the pitfalls of hiring leaders without first defining their roles and explains the importance of generating instant 'wow' reactions from new executives. His methods, like back-channeling candidates and creating an 'org chart without names,' provide key insights for building effective leadership teams.

Building a 57,000+ LinkedIn following eliminated Kristi Faltorusso's recruiter dependency. One post now generates hundreds of qualified CS applicants while her network delivers pre-vetted referrals through direct outreach. But the deeper insight is how she completely rewired her hiring methodology after repeatedly failing to replicate playbooks across companies. Customer success roles are never portable. What worked at Series A fails at Series C. Leaders who scaled at Salesforce often can't operate in startups. She now evaluates candidates against 24-36 month company trajectories, filtering for grittiness before considering experience or quota achievement. Her interview process rejects stage gates and prescribed frameworks. She asks candidates to recall times they were "in over their head" and requests "a failure you're really proud of," separating those who own mistakes from those who point fingers. Before any offer, she dedicates a full session where candidates ask her anything. Their questions expose business acumen, reveal what broke at previous companies, and eliminate the assumption gaps that derail new hires within weeks. Post-hire, she meets daily with direct reports for the first 14 days, not for status updates, but to build trust and surface friction before it calcifies. Topics discussed: Building a 57,000-follower LinkedIn presence that replaced external recruiters through one-post sourcing and network referrals Why customer success playbooks and hiring profiles can't transfer between Series A and Series C stage companies Using marathon completions and multi-year personal commitments to assess grittiness independent of professional achievements The "tell me about a time you were in over your head" question that reveals self-awareness and problem-solving under ambiguity How "what's a failure you're really proud of" separates candidates who own outcomes from those who deflect responsibility Allocating a full interview session for candidate questions to surface concerns and eliminate misaligned expectations before offers Meeting daily with new direct reports for two weeks to establish trust rather than relying on structured 30-60-90 plans Conducting backchannel references with unprepared cross-functional colleagues instead of candidate-selected contacts 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 Whispered Hiring, Andy Mowat speaks with Ghazi Masood, CRO at Replit, about building GTM organizations in product-led growth environments. With experience scaling Auth0 through hypergrowth and acquisition, plus leading revenue at Retool, Ghazi breaks down how PLG hiring differs by role, why he rarely posts senior positions, and the back-channel timing that saves months of wasted interviews. His frameworks reveal how to spot enterprise readiness in a PLG funnel and the specific red flag that predicts sales leader failure. Topics discussed: The three roles where PLG experience actually matters when hiring: RevOps (must understand PQL/MQL interplay and marketing alignment), Head of Sales Development (needs experience transitioning inbound to outbound), and segment sales leaders building hybrid inbound/outbound machines for enterprise. How to evaluate whether a PLG company can successfully add SLG: look for enterprise employees already signing up individually. If someone at JP Morgan is using your product on a small team, that's your signal to swarm them and build intentional outbound around those product signals. Why BDR-to-AE progression works as an internal flywheel for SMB and mid-market, but strategic accounts (selling to Amazon, Netflix, Coinbase) typically require external hires. The gap is multi-threading, procurement navigation, and business value selling. Most internal candidates need more time before making that jump. Auth0's enablement approach during hypergrowth: role-based onboarding curriculum with pitch certifications where new hires had to get certified before hitting the field. This predicted who would perform and prevented the org from "missing a beat" while scaling 10x. Ghazi's senior hiring philosophy: work with people you've worked with before, or people one layer removed through trusted networks. If timing doesn't work with your first choice, ask them for referrals and back-channel those names. He also leverages VC talent teams, noting they maintain deep relationships with hundreds of CROs and conduct thorough vetting most companies underutilize. Why he back-channels senior candidates immediately rather than at final rounds. Early diligence saves time, but requires going to previous companies when candidates are still employed. If a bad reference surfaces, get the context. Everyone has one difficult peer or subordinate in their past. The interview approach that reveals sales readiness: ask candidates to walk through specific deals they've closed. Who was the decision maker? How did they navigate procurement? Strong candidates rattle this off instantly. He also prioritizes relationship and presence over paper credentials, noting he's hired people with less experience who outperformed because of how they'd present in front of customers. The red flag that signals a sales leader won't survive: when AEs stop inviting them to customer calls. Ghazi shares a specific example of a leader who couldn't grasp pricing methodology. The field team lost trust and started excluding them from deals. Once that credibility gap opens, it rarely closes. His approach to developing direct reports: dedicate one monthly 1:1 exclusively to career growth with zero business discussion. Ask where they want exposure (board meetings, new functions, specific skills) and actively create those opportunities. His stated philosophy: "You're only as successful as the team you build."   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 Whispered Hiring, Andy Mowat speaks with Jessica Chiew, Head of GTM Strategy & Operations at Canva, about her rigorous approach to hiring builders in product-led growth environments. Drawing from her experience scaling GTM operations at Asana and Canva, Jessica shares tactical frameworks for testing whether candidates can truly execute versus simply tell polished stories, structuring ops teams that span product and enterprise motions, and designing onboarding that delivers impact in the first 90 days. Her insights reveal how calculated vulnerability and continuous team evolution drive both individual performance and organizational velocity. Topics discussed: How to test for customer journey fluency in PLG environments by asking candidates to describe the journey at their previous company, then present a live scenario where 260 million MAUs already exist in your domain and watching whether they shift from MQL/SQL language to customer-centric thinking. The "rocks and rubble" test for builder mentality. True builders describe scenarios where multiple crises hit simultaneously (missing quarterly target, product launch, doubling headcount, losing office space) and frame it as energizing rather than overwhelming, versus managers who cite isolated quarterly challenges. Jessica's signature 30-minute interview structure starting with "I've read your professional background, can you quickly talk me through your story and path to today's conversation" where failure states include reading their resume back for 20 minutes or lacking intentionality about how to use limited time. The four to five layer questioning depth that reveals hands-on leadership. Starting with "what does the future of customer success look like?" then drilling through implementation details, measurement approaches, and roadblocks encountered until candidates either demonstrate project-level ownership or reveal they're reciting refined talking points. Why making yourself available during case study prep is a conversion predictor. Jessica offers her cell phone number for 30-minute prep calls, 20% of all candidates take her up on it, but 50% of successful hires do, simulating their actual working style and investment level before they join. The continuous team restructuring philosophy where Jessica constantly reevaluates scope and structure every six months as the business evolves, maintaining team trust through upfront vulnerability about business gaps, personal motivations, and explicitly asking for flexibility while keeping career growth top of mind. The four-element onboarding pack that drives first-90-day impact. A written narrative of business state and their role in it (not just verbal), explicit 30/60/90 expectations including quick wins, full repository of QBRs and dashboards for self-service, and a sequenced listening tour spreadsheet with every stakeholder meeting pre-planned by week. The portfolio staffing approach for balancing pattern recognition with execution capability. Mixing enterprise veterans with startup athletes across the team while testing experienced hires for builder traits through SQL proficiency as a proxy for hands-on work and ensuring they have startup experience somewhere in their background to prove they can operate without massive resources. 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

Heather Doshay, Founder of Waypoint Works and former VP of People at Webflow, shares her insights on identifying high-slope talent. She introduces the PEAKS framework—Persistence, Emotional grounding, Action, Knowledge, and Systems thinking—explaining how it identifies candidates capable of growth. Heather discusses avoiding 'shiny object syndrome' in hiring and favors pairing emerging talent with experienced advisors instead of opting for traditional hires. Additionally, she highlights the importance of emotional grounding and listening for verbal cues to spot candidates who may be burning out.

In this episode of How I Hire, Andy Mowat speaks with Melissa Rosenthal, Co-Founder at Outlever and former CRO at Cheddar and Chief Creative Officer at ClickUp, about her approach to vetting executive talent. Drawing from her transition from BuzzFeed creative leadership to sales leadership, Melissa shares how she vibe-coded a Lovable app that filtered 1,000 applicants to 20 candidates, why she requires minimum 10 back-channels before offers, and her view on growth leader tenure at scaling stages. Topics discussed: Why hiring VPs from ServiceNow-scale companies for startups consistently underperforms, and the profile with "really good success": candidates who've worked at enterprises but chose Series B/C startups, showing they grasp both corporate infrastructure and startup pace. The 15-minute "biggest project" question covering what the candidate did, team composition, individual roles, and outcomes, designed to expose ego when candidates position themselves as "the center and the hero" while gathering names for back-channeling. How Melissa and her co-founder vibe-coded a Lovable app in two days requiring candidates to answer two questions without previewing or redoing them, filtering 1,000 submissions down to 20 completions and three successful hires. The controversial growth marketing reality: "there's a tenure that exists within that role...you can probably get the most out of them for two years" before needing someone who's scaled your next stage, as finding leaders who've scaled 0 to 500M "is probably not really realistic." The minimum 10-person back-channel protocol for VP roles: five who worked adjacent, two superiors, and two peripheral colleagues, with "no offer until the back channel is complete" after learning from having to rescind previous offers. Why she will "never hire a fractional person" for VP roles at high-growth companies where she's "barely sleeping," as fractional means "they're not all in," though agencies work for tactical gaps once solid leadership exists. The "hardest thing you've gone through" question designed to "open up a world of like this person's gonna bare their soul," revealing resilience and EQ critical for all go-to-market roles she hires. Why most founder hires didn't work out: candidates aren't transparent despite clear "work life imbalance" warnings, "rotten leaders" who treat teams poorly, people "always in the car" suggesting outsourced work, requiring her "trust and respect" leadership approach. 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 Eric Gilpin, President GTM at G2, about his systematic approach to executive hiring built on 22 years of sales leadership at companies like Upwork and CareerBuilder. Eric shares his contrarian philosophy on recruiting directly from your customer base, his specific four-stage VP+ interview process that treats candidates as collaborators rather than supplicants, and why he maintains relationships with his next three hires before roles even open. His insights reveal how leveraging conversation intelligence tools and transparent back-channeling can transform executive hiring outcomes. Topics discussed: Why recruiting from your customer base provides a competitive moat. Eric actively evaluates every customer CRO and CMO he meets for potential fit, and uses Gong as a "cheat code" to review two years of recorded customer calls before initial conversations. The role design framework that prioritizes team capability gaps over individual credentials. Eric audits his entire leadership team for gaps in AI literacy, data-driven thinking, or emotional intelligence before defining what each new executive hire must bring to raise the bar across the organization. How Eric maintains an "always on" executive pipeline by knowing his next three VP+ hires right now despite all roles being filled. This eliminates reactive recruiting and prevents managers from hoarding talent due to lack of pipeline. The four-stage interview process for VP+ hires: 30-minute relationship call, context deck deep dive with 15 slides of non-public data, panel of no more than three people, then collaborative working session on real business problems where output gets used in actual kickoffs or strategy. Why executive search agencies are non-negotiable for senior hires despite cost. Agencies handle initial vetting so conversations focus on co-authoring roles, plus they maintain year-round relationships with passive candidates and access to unlisted opportunities in the private market. The outbound gap revealing selection bias in funnels. Despite 20 open roles generating thousands of monthly applicants, Eric receives only one quality outbound per month, yet he forwards every single one because the effort signals exactly what GTM roles require. The transparent back-channel approach where Eric tells candidates upfront "I'm going to poke around, you should too" and asks what's off limits. He never outsources this to recruiters to control market noise and hear context firsthand. Why cross-functional customer journey reviews must precede GTM hiring. Eric runs weekly reviews covering the entire funnel with every function present, tracking 90 days forward given G2's 66-day sales cycle plus 28-day speed to lead, ensuring aligned input metrics before making hires. 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 Wade Foster, Co-founder & CEO of Zapier, about his counterintuitive discovery that doing 20+ reference calls per executive finalist was the breakthrough that fixed his 50/50 executive hiring hit rate. Wade shares why he returned to approving every offer after watching standards slip, his specific reference questions that reveal culture fit across a decade of companies, and how he shifted from hiring impressive resumes to deliberately assembling executive teams with complementary behavioral traits. His insights reveal how auditing process thoroughness rather than overriding decisions, and treating references as puzzle piece collection rather than validation, can transform executive hiring outcomes. Topics discussed: Why Wade shifted from hiring "been there, done that" executives with strong logos to deliberately assembling teams where behavioral traits (bold risk-taking, operational soundness, communication/storytelling) are as intentionally distributed as functional representation, requiring brutal self-awareness about which CEO weaknesses to cover versus double down on strengths. The CEO offer approval framework with a sub-24-hour SLA that audits "did we probe where we needed to probe?" rather than evaluating the candidate directly, walking the fine line where hiring managers maintain ownership without "licking the cookie" and deflecting decisions upward to Wade. The 20+ reference methodology per executive finalist, deliberately collecting multiple managers, peers, direct reports, and founder/CEOs across companies spanning a decade, asking "compare to the best person you've worked with, rate them 1-10, and what closes the gap to 10?" to understand skill ceilings. How asking references "what will this person's biggest fans say and biggest critics say?" creates ammunition for subsequent reference calls where you can test provocative claims, forcing references to either confirm uncomfortable truths or vigorously defend the candidate when critiques don't match their experience. Why fully green references signal a red flag at the executive level, since effective leaders are necessarily "demanding plus supportive" which creates mixed feedback, and how asking about company culture fit ("what types thrived, what types didn't?") reveals whether your environment will set them up for success or failure. The mutual evaluation conversation where Wade brings all reference findings back to the finalist, explicitly naming strengths and growth areas, then encourages them to back-channel him as CEO too, framing it as "are we both signing up for each other's beautiful mess?" rather than hoping it works out. Why frontline managers who hire once yearly lack pattern recognition to spot "tiny yellow flags" worth pulling versus glossing over, and how Wade's high-volume hiring reps let him see threads that easily unravel candidates, justifying his process audit role despite it appearing like micromanagement. The "Zapier on Zapier" procurement gate requiring teams to attempt building on Zapier before buying point solutions, creating a specific product feedback loop when use cases fail, while maintaining honest judgment on clear exceptions like payroll processing that Zapier will never build. Using pre-interview automation to compile candidate briefs from application data, prior interview notes, and public internet presence, then post-interview feeding transcripts through rubrics to generate AI assessments that Wade compares against his own scorecard as a "rubber duck" to strengthen his evaluation. The philosophy that hiring decisions require maximum information surface area since you're "inevitably getting one tiny puzzle piece about this person," and while each piece contains bias and inaccuracy, collecting more pieces in aggregate washes out bias better than rejecting imperfect data sources. 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 Daniels, Chief Business Officer at Zensai, about his framework for building high-performing go-to-market teams. Drawing from his tenure as CMO at Matterport, WeWork, and leading Talent Solutions marketing at LinkedIn, plus his formative years at Salesforce and Box, Robin shares his three non-negotiable hiring attributes, why CMO hiring fails without archetype clarity, and how open-ended storytelling questions reveal candidate potential better than structured interviews. His insights reveal how elite talent networks compound across companies and why communication mastery separates effective leaders from domain experts. Topics discussed: The three non-negotiable attributes Robin tests at all levels: grit (proven resilience through market crashes or setbacks), aptitude (curiosity to solve ambiguous problems without clear answers), and passion (energy that transfers to teams as a force multiplier), and why these override credentials in scale-up environments. Why most CMO hires fail within nine months due to role clarity gaps between the two distinct archetypes: product marketing background (for competitive positioning and story problems) versus demand gen/revenue marketing background (for conversion and pipeline issues). Robin's signature interview question "Tell me about the most epic thing you ever did" and how 10-15 minute responses reveal level of thinking, team attribution ("we" versus "me"), self-awareness about failures, and ambition calibration. How one HP candidate's white paper story immediately signaled misaligned performance bars. The career compounding effect of high talent density nodes like Salesforce and Box. How Robin has hired the same core team members (Indy Send four times, Nicole Rogers three times) across multiple companies, and why every role adds a handful of inner circle relationships that become your long-term network. Why Robin invested in Stanford acting courses to master attention-holding through body language, voice modulation, and presence rather than following rigid presentation frameworks. How top communicators like Aaron Levie and Marc Benioff succeed by leaning into authentic quirks versus corporate polish. The "input plus output equals outcome" success formula and why the only controllable variable is how you show up to every interaction, regardless of external circumstances like flight delays or difficult conversations. How this mindset helped Robin navigate being laid off in April 2006 right before his son was born. How to modulate communication style across stakeholder functions because finance, engineering, sales, and customer-facing teams have fundamentally different worldviews. Why treating cross-functional partners identically guarantees friction in matrix environments and limits executive effectiveness. Why checklist-style interviews fail at executive levels by treating senior hires like junior candidates. How executive interviews should be bidirectional conversations focused on vision alignment and cultural fit after technical validation happens earlier in the funnel with direct reports. 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 Sylvia LePoidevin, CMO at Kandji and early marketing leader at Flowcast and Datafox, about her approach to building marketing teams that prioritize customer proximity over conventional playbooks. Drawing from 500+ interviews conducted over five years, Sylvia shares specific frameworks for structuring teams at different scales, evaluating senior talent through storytelling, and creating organizations where internal narrative matters as much as external messaging. Topics Discussed Why writing a company manifesto should precede all marketing activity. It defines why you exist and what will be different in 10 years because of your company. This isn't positioning, it's the existential story about what you're trying to change. The critical distinction: she'll join a company without a manifesto, but never one unwilling to write one. The "tastemakers vs. operators" framework for structuring lean marketing teams under five people. Tastemakers have film or journalism backgrounds and care about quality and storytelling with zero ego. Operators can take 17 disconnected tools and build them into a functioning engine. Pairing these profiles prevents AI commoditization by combining automation that scales with soul that differentiates. How the squad model solves the velocity problem in 30+ person marketing organizations by eliminating assembly-line handoffs. Cross-functional squads organized by domain (ABM, SEO, website conversion) include embedded designers and copywriters. Squad leaders own end-to-end execution including goal setting, quarterly planning in Asana, and resource allocation. The model is orthogonal to org structure. "Proximity over playbooks" as the defensible moat when AI commoditizes helpful content. When you understand your buyer's pain, daily problems, and context at a deep level, marketing strategy becomes obvious rather than theoretical. This customer intimacy fuels authentic storytelling that cuts through AI-generated, interchangeable content. Why internal storytelling matters more than data for getting budget and organizational support. Sylvia teaches her team that conviction and narrative about impact often move initiatives forward better than perfect data sets. Data becomes supporting evidence rather than the primary argument for executive buy-in. Why "What's your story?" separates self-aware leaders from professional personas in first interviews. She doesn't want job history, she wants life story, pivotal moments, and mistakes that shaped who candidates are today. This question immediately reveals whether someone can lead with the vulnerability required to create psychological safety for teams. The product marketer who reverse-engineered competitive positioning before the second interview by visiting Kandji's booth and every competitor booth at a conference, then synthesizing the positioning gap in an email. This delivered immediate value before hire, instant credibility with sales, and organizational buy-in before day one. The five interview mistakes from 500+ conversations: asking basic questions about her role easily found on LinkedIn, speaking in broad jargon without specifics about tools or workflows used, zero personal sharing that prevents feeling passion, resume and LinkedIn mismatches on dates or roles, and no clear articulated reason for leaving current or past roles. The "hire to the next level" strategy where her highest success comes from hiring senior managers into director roles rather than lateral moves. These candidates have something to prove and bring urgency to perform. When explaining departures, articulate what you're looking for in your next role to implicitly communicate what was missing without badmouthing previous employers. 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